Phytochemicals¶

Last updated 2026-04-08 by Dr John Elfick

Terpenes are polymers of isoprene, (C₅H₈)n, and may also be called Terpenoids or Isoprenoids. source

Phytochemicals¶

Phytochemicals are plant-based bioactive compounds that are produced by plants for their protection, (Greek phyto 'plant').

Nutritionists suggest giving children a diet containing the 5 different-coloured phytochemials.

1. Purple / blue phytochemicals in | Beetroot | Red cabbage | Eggplant | contain anthocyanins.

3. Orange / yellow phytochemicals occur in carrots, contain carotenoids, betacarotene, and lutein.

4. Green phytochemicals in green vegetables, contain carotenoids, indoles and saponins.

5. Brown / white phytochemicals, e.g Illicin in garlic, and bananas and potatoes are a source of potassium.

Brown rice contains many differetn phytochemicals.

Isoprene¶

Isoprene, (2-methyl-1,3-butadiene), C₅H₈, CH₂=C(CH3)−CH=CH₂, C₅H₈ source

C₅H₈ in a molecule is called an isoprene unit, so 8 isoprene units = 8 X C₅H₈ = C₄₀H₆₄. source

A terpene is an unsaturated hydrocarbon molecule with the chemical formula, C₁₀H₁₆. source

A tetraterpene, (tetra terpene), = 4 terpenes, 4 X C₁₀H₁₆ = C₄₀H₆₄. source

Carotenoids have the chemical formula C₄₀H₆₄, so carotenoids are tetraterpenes. source

Hemiterpenes, 1 isoprene unit, C5H8¶

Hemiterpenes, 1 isoprene unit, C₅H₈ source

Isoprene, C₅H₈, CH₂=C(CH3)CH=CH₂ source

Isoprenol, C₅H₁₀O source

Isovaleric acid, C₅H₁₀O₂ source

Prenol, C₅H₁₀O source

Monoterpenes, 2 isoprene units, C10H16¶

Monoterpenes, 2 isoprene units, C₁₀H₁₆ source

Monoterpenoids are modified monoterpenes.

Sesquiterpenes, 3 isoprene units, C15H24¶

Sesquiterpenes, 3 isoprene units, C₁₅H₂₄ source

Sesquiterpenes and sesquiterpenoids

Sesquiterpenes, occur in essential oils

They stimulate glands and liver, anti-allergenic, antispasmodic, anti-inflammatory, acyclic or monocyclic or dicyclic, or tricyclic

They can be isolated from their natural sources by distillation with steam or by extraction, purified by vacuum fractional distillation or by chromatography.

Diterpenes, 4 isoprene units, C20H32¶

Diterpenes, 4 isoprene units, C₂₀H₃₂ source

Diterpenoids

Diterpenoids are derivatives of diterpenes.

Sesterterpenes, 5 isoprene units, C25H40¶

Sesterterpenes, 5 isoprene units, C₂₅H₄₀ source

Sesterterpenes, (C14 Sesterterpenes, five isoprene units), occur in insect waxes, fungi products, phytotoxins, insect gascardic acid.

Azafrin, C₂₇H₃₈O₄, a sesterterpenoid. source

Triterpenes, 6 isoprene units, C30H48¶

Triterpenes, 6 isoprene units, C₃₀H₄₈ source

Triterpenes and triterpenoids

Polyterpenes, many isoprene units, (C5H8)n¶

Polyterpenes, many isoprene units, (C₅H₈)n source

Polyterpenes contain a long chain of thousands of C₅H₈ isoprene subunits in milky latex sap. source

Rubber

Gutta-percha

Aromatic acids¶

Aromatic acids containing a carboxyl group (-COOH) attached to an aromatic ring, e,g, benzoic acid, C₆H₅COOH source

Benzoic acid, C₆H₅COOH source

Gallic acid, C₇H₆O₅ source

Ellagic acid, C₁₄H₆O₈ source

Hydroxycinnamic acid, C₉H₈O₃ source

Caffeic acid, C₉H₈O₄ source

Chlorogenic acid, C₁₆H₁₈O₉ source

Cinnamic acid, C₉H₈O₂ source

Ferulic acid, C₁₀H₁₀O₄ source

Coumaric acid, C₉H₈O₃ source

Saturated cyclic acids

Glycyrrhizic acid, C₄₂H₆₂O₁₆ source

Eculetin, C₉H₆O₄ source

Esculin, C15H16O9br>

Tetrapyrroles¶

Chlorophyll, C₅₅H₇₄MgN₄O₅+2 source

Haeme

Flavonoids¶

Flavonoids are 3-ring phenolic compounds with a double benzene ring with OH groups attached to a 3rd benzene ring by a single bond, C6-C3-C6.

Almost all fruits, vegetables, herbs and spices contain flavonoids.

See diagram 16.3.4.2. Flavonoids, (flavone, flavonol, riboflavin, flavonoid, anthocyanin).

See diagram. Flavonoid basic structure, ( 6-3-6 skeleton)

Plant pigments, are based on flavone or similar to flavone, C₁₅H₁₀O₂, including anthocyanins. source

Vasodilating actions, antioxidant, anti-allergenic, has anti-inflammatory and antiviral properties.

Colour, flavour and aroma for many foods and are found in fruits and vegetables, tea, red wine, cacao and some nuts.

Flavonoids are polyphenolic compounds, secondary metabolites, blue-pigments.

Flavonoids antioxidants, prevent the bad LDL cholesterol from forming oxidized LDL, which forms plaques in arteries.

Neoflavonoids¶

Dalbergin, occurs in Dalbergia, C₁₆H₁₂O₄ source

It occurs in (Dalbergia miscolobium) and (Dalbergia nigra).

Flavonols¶

Flavonols have a 3-hydroxyflavone backbone, with the phenolic –OH groups in different positions.

Flavonols occur in green leaves, fruits and grains.

Fisetin, C₁₅H₁₀O₆ source

Flavonol glycosides

Galangin, C₁₅H₁₀O₅ source

Kaempferol, C₁₅H₁₀O₆ source

Isorhamnetin, C₁₆H₁₂O₇ source

Myricetin, C₁₅H₁₀O₈ source

Pachypodol, C₁₈H₁₆O₇ source

Quercetin, C₁₅H₁₀O₇ source

Rhamnazin, C₁₇H₁₄O₇ source

Rhamnetin, C₁₆H₁₂O₇ source

Flavonol glycosides¶

Hyperoside, C₂₁H₂₀O₁₂ source

Icariin, C₃₃H₄₀O₁₅ source

Myricitrin, C₂₁H₂₀O₁₂ source

Rutin, C₂₇H₃₂O₁₆ source

Quercitrin, C₂₁H₂₀O₁₁ source

Flavones, (condensed tannins)¶

Flavones, (condensed tannins)

Flavone ketone derivatives are yellow glycoside plant pigments, and are used as dyestuffs.

Flavones occur in leaves, flowers and fruits.

Flavones:

Flavone, C₁₅H₁₀O₂, is a small molecule simplest member of the class of flavones. source

It occurs in (Camellia sinensis) and is a nematicide.

Acacetin, dihydroxyflavone, C₁₆H₁₂O₅ source

Apigenin, C₁₅H₁₀O₅ source

Baicalin, C₂₁H₁₈O₁₁ source

Galangin, trihydroxyflavone, C₁₅H₁₀O₅ source

Herbacetin, pentahydroxyflavone, C₁₅H₁₀O₇ source

Luteolin, C₁₅H₁₀O₆ source

Sinensetin, C₂₀H₂₀O₇ source

Tangeretin, C₂₀H₂₀O₇ source

Flavanols, (Flavan-3-ols)¶

Flavanols, (Flavan-3-ols)

1. Monomers - catechin, occurs in chocolate, cinnamon, red wine.

Epigallocatechin gallate

2. Dimers and polymers, occurs in chocolate, cinnamon.

3. Proanthrocyinidins - Flavon-3-ol polymers

4. Theaflavins

Theaflavin, C₂₉H₂₄O₁₂ source

Theaflavin-3-gallate

Butin

Hesperetin, C₁₆H₁₄O₆, occurs in lemon, orange source

Hesperidin, (aglycone hesperetin)

Naringin

Naringin 4'-0-glucoside, C₃₃H₄₂O₁₉, Flavanone Glycoside source

Narirutin, C₂₇H₃₂O₁₄, flavanone-7-0-glycoside, Flavanone Glycoside, occurs in Orange juice. source

Poncirin

Silibinin

Sinensetin

Flavan-3-ols (Flavanols), subgroup of Flavonoids, derivatives of Flavans Flavonols, most common, flavonoids, (Hesperetin. Icariin, Kaempferol, Myricetin, Naringenin, Quercitin)

Subgroup of Flavonoids, e.g. Catechin, C₁₅H₁₄O₆, occurs in chocolate, cinnamon, red wine source

Four categories: 1. Flavan-3-ols, 2. Flavan-4-ols, 3. Flavan-3,4-ols. isoflavan-4-ols

1. Flavan-3-ols, flavanols (NOT "Flavonols"!)

They occur in fruits and vegetables, e.g. apples, apricots, berries, cherries, grapes, nectarines, peaches, pears, plums, and Swiss chard.

They occur in nuts, e.g. almonds, cashews, hazelnuts, pecans and pistachios.

They occur in green, black and oolong teas, cacao, red and white wine.

Catechol

Leucanthocyanidin, C₁₅H₁₄O₃, from enzymes, occurs in many plants, e.g. (Zea mays) source

Catechins white tea, green tea, black tea, grapes, wine, apple juice, cocoa, lentils, black-eyed peas

Theaflavin | Theaflavin-3-gallate | Thearubigins | occur in black tea.

Catechins white tea, green tea, black tea, grapes, wine, apple juice, cocoa, lentils, black-eyed peas

2. Flavan-4-ols

Flavan-4-ols are colourless compounds that form red pigments in maize and sorghum.

Apiforol, C₁₅H₁₄O₅, a tetrahydroxyflavan, occurs in eastern honey bee, (Apis cerana). source

Luteoforol, C₁₅H₁₄O₆, a pentahydroxyflavan, occurs in (Sorghum bicolor), and pome fruits. source

3. Flavan-3,4-ols, Leucanthocyanidins

Leucanthocyanidin, C₁₅H₁₄O₃, from enzymes, in many plants, e.g. (Zea mays). source

Rutin hydrate, C₂₇H₃₀O₁₆.xH2O, poly flavonoid source

4. Theaflavins (TF), antioxidant polyphenols, occur from flavan-3-ols during "fermentation" of tea leaves, to produce black tea.

Theaflavin, C₂₉H₂₄O₁₂, occurs in (Camellia sinensis). source

Theaflavin-3-gallate, Theaflavin 3, C₄₃H₃₂O₂₀, occurs in (Camellia sinensis). source

Theaflavin 3,3'-di-O-gallate, C₄₃H₃₂O₂₀, occurs in (Camellia sinensis). source

Flavanones, dihydroflavones¶

Flavanones, dihydroflavones

Flavanones occur in citrus fruits.

Anthocyanins¶

Anthocyanins [Greek (ánthos) 'flower' (kuáneos) 'dark blue'], anthocyans, flavonoids, vacuolar pigments red to black, blueberry, raspberry

Anthocyanins cause the blue, purple, red, and orange colours of some flowers, leaves and fruits, e.g. berries, red cabbage, purple sweet potato.

Anthocyanidins are natural dyes, coloured pigments, antioxidative, antimicrobial activities, improve visual and neurological health.

Anthocyanidins are anthocyanin aglycones.

Anthocyanins are glycosides of anthocyanidins, e.g. Cyanin is a cyanidin glucoside.

Anthocyanins, glycosides, C₁₅H₁₁O + (glycosides of anthocyanidins), red, blue and purple flavonoids source

They occurs in cell sap, natural antioxidants (blueberry, boysenberry, black raspberry, black currant pigments), and in cyanidin chloride, C₁₅H₁₁ClO₆. source

Food additive E163 Anthocyanins (from grape skins, red cabbage, flowers), (colour. red to violet)

Anthocyanins are water-soluble plant pigments of the flavonoid class, antioxidants.

They are glycosides that on hydrolysis yield coloured aglycones, called anthocyanidins.

Anthocyanidin molecule + sugar, anthocyinidin glycosides are called anthocyanins.

Anthocyanins cause most of the red, purple and blue colours.

They occur in vacuoles of outer layers of plant cells as signalling colours.

They occur in black currant, blueberry, blackberry, red cabbage, black plum, radish, rasberry, apple, eggplant, grapes, pears, red onions, hazelnuts, pistachios.

Anthocyanins are water-soluble flavonoids in berries, grapes, apples, plums, cabbage, and most natural colorants.

Anthocyanins help to prevent cardiovascular and neurodegenerative diseases.

Cyanidin, delphinidin, malvidin, peonidin, petunidin, are the most common anthocyanins.

Some anthocyanins:

Aurantinidin, C₁₅H₁₁O₆ source

Aureusidin, C₁₅H₁₀O₆ source

Bracteatin, C₁₅H₁₀O₇ source

Butein, C₁₅H₁₂O₅ source

Cyanidin, anthocyanidin cation, C₁₅H₁₁O₆⁺ source

Delphinidin, anthocyanidin chloride, C₁₅H₁₁ClO₇ source

Malvidin, malvidin chloride, C₁₇H₁₅ClO₇ source

Peonidin, O-methylated anthocyanidin, C₁₆H₁₃O₆⁺ source

Petunidin, O-methylated anthocyanidin, C₁₆H₁₃O₇⁺ source

Pelargonidin C₁₅H₁₁O₅ source

PelargoninC₂₇H₃₁O₁₅ source

Anthoxanthins¶

Anthoxanthins, (flavones and flavonols) are water-soluble, white to yellow flavonoid pigments, and antioxidants.

They occur in potatoes, cauliflower, onions, parsnips, and bananas.

Anthoxanthins cause bright white colour of food in acid medium, and yellow in alkaline medium.

Colour in flower petals depends on the soil minerals.

Quercetin, C₁₅H₁₀O₇. source

Catechins¶

Catechins, flavonoids, the name comes from catechu, (Mimosa catechu), (Acacia catechu)

Catechin, C₁₅H₁₄O₆, has four catechin isomers: source

Two trans isomers called [(+)-catechin and (-)-catechin], the most common catechin isomers.
Two cis isomers called [(+)-epicatechin and (-)-epicatechin]

(+)-Catechin and (-)-epicatechin occur in food plants.

(-)-Epicatechins and their derivatives occur in green tea.

Catechin 7-O-beta-D-xyloside, C₂₀H₂₂O₁₀, is a monosaccharide derivative of catechin. source

Catechinic acid, C₁₅H₁₄O₆, is a flavan-3-ol, colourless, bioflavonoid, tannin, antioxidant, anti-viral, anti-bacterial. source

Catechin is in catechu, the astringent tannin-rich extract of acacia, in green tea, in cocoa, in vinegar, in catechu, in black grapes, in fava bean, in black tea.

Catechins occur in woody plants, willow catkin, (Salix haemostatic), (Potentilla fragarioides), (Salix capra), (Cinnamomum kotoense), and (Begonia nantoensis).

Catechins occur in many plant species of white tea, green tea, black tea, grapes, apple, cocoa, lentils, black-eyed peas.

Catechins are polyphenolic antioxidants, which support plant growth, and are used for treating obesity.

Catechin is used to treat liver diseases, e.g. hepatitis, possible radical scavenger, but excess treatment causes haemolysis and renal failure, skin rashes.

Dark chocolate and red table wine contain high concentrations of catechins and their compounds.

Catechins are water soluble polyphenols and antioxidants that are easily oxidized

Catechin sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them.

Catechin in green tea prevents viruses from adhering to cell walls and causing harm.

Catechin reacts with toxins created by harmful bacteria and harmful metals such as lead, mercury, chrome, and cadmium.

Catechin hydrate, C₁₅H₁₆O₇, C₁₅H₁₄O₆.xH2O, polyphenolic antioxidant, Chinese medicine, antioxidant, free radical scavenger, suppresses DNA strand breaks. source

The black tea oxidation process reduces catechin in black tea.

(+)-catechin, Cianidanol, C₁₅H₁₄O₆, antioxidant flavonoid, occurs in woody plants. source

Green tea is made from fresh, unfermented tea leaves where the oxidation of catechin is minimal, and so are antioxidants.

Racemic catechin is used to study seed germination and plant invasion.

Green tea, (Camellia sinensis), Theaceae

Catechin gallate, C₂₂H₁₈O₁₀ source

Catechin hydrate, C₁₅H₁₆O₇ source

Epicatechin, (EC), Flavonoid, C₁₅H₁₄O₆ source

ECG Epicatechin gallate (ECG), Flavonoid, C₂₂H₁₈O₁₀. source

EGC Epigallocatechin, Bioflavonoid, C₁₅H₁₄O₇. source

EGCG Epigallocatechin gallate, Bioflavonoid, C₂₂H₁₈O₁₁ source

Catechin gallate¶

Catechin gallate, , C₂₂H₁₈O₁₀, catechin 3'-O-gallate, is an ester, a polyphenol a flavan, bioflavonoid, green tea extract, antioxidant, and free radical scavenger. source

It may be used to treat breast cancer.

It occurs in (Camellia sinensis), and in (Rheum palmatum).

Catechin hydrate¶

Catechin hydrate, C₁₅H₁₆O₇, C₁₅H₁₄O₆.xH2O, polyphenolic antioxidant, Chinese medicine, antioxidant, free radical scavenger. source

It suppresses DNA strand breaks.

Epicatechin¶

Epicatechin, C₁₅H₁₄O₆, (EC), a flavonoid, is a catechin, tannin, flavan-3-ol, and antioxidant. source

It occurs in green tea, cocoa, black grapes, kola nut, peach, fava bean, woody plants, cacao bean, and in green tea.

Epicatechin gallate¶

Epicatechin gallate, C₂₂H₁₈O₁₀, (ECG), is a flavonoid, occurs in green tea, buckwheat, grapes, and in rhubarb. source

Epigallocatechin¶

Epigallocatechin, C₁₅H₁₄O₇, (EGC), is a bioflavonoid, flavan-3-ol, a catechin, antioxidant, and food component. source

It occurs in almond, broad beans, and green and black tea.

It occurs in St John's wort, (Hypericum perforatum).

Epigallocatechin gallate¶

Epigallocatechin gallate, C₂₂H₁₈O₁₁, tea catechin, (EGCG), is a bioflavonoid, antineoplastic agent, and a phenolic antioxidant. source

It is an ester of hydroxy group of epigallocatechin and gallic acid.

It inhibits cellular oxidation, and prevents free radical damage to cells

It occurs in green and black tea, (Camellia sinensis), and is the most abundant catechin in green tea.

Dietary fibre¶

Dietary fibre is the edible parts of plants or carbohydrates, resistant to digestion and absorption in the small intestine.

Dietary fibre includes non-starch polysaccharides, oligosaccharides, resistant starch, and lignin.

Dietary fibres are not digested by the human digestive enzymes.

They may be are broken down by fermentation activities of the gut microbiota in the large intestine.

Dietary fibre is a recommended component for a healthy diet, but the mechanism for preventing human ailments is not clearly understood.

Pectin¶

Pectin, (C₆H₁₀O₇)n, (β-D-Galactopyranuronic acid)n, is a heteropolysaccharide in the cell walls of plants. source

It is composed of linked methylated polygalacturonic acid units.

Pectin is a safe food substance.

Starchy endosperms resist digestion in the small intestine, but are broken up and fermented in the large intestine to feed the gut bacteria.

Resistant starch is a soluble, fermentable fibre in wholegrain cereals and legumes, and repeated cooked rice, and potatoes.

It passes through the small intestine undigested, to also feed the gut bacteria in the colon.

Starch = Amylose (linear glucose molecules) + Amylopectin (glucose molecules).

Arabinoxylan has a backbone of d-xylose units (C₅H₁₀O₅), linked by β (1→4) glycosidic bonds. source

16.1.9 Pectin

4.3.2 Pectins and pectinases

Pectins, E440, Emulsifiers, food additives

16.5.8, Tests for pectin in jelly and jam

Lignin

Hemicelluloses

Hemicelluloses¶

Araloside, C₄₇H₇₄O₁₈ source

Glucosinolates¶

Glucosinolates, mustard oil glycosides, are from sugar + amino acid, and contain S and N.

Glucosinolates + enzyme hydrolysis by thioglucosidases → mustard oil glycosides, when plant cells are damaged or chewed. source

Glucosinolates are the precursors to isothiocyanates, and occur mostly in family Brassicaceae

If cruciferous plants are consumed without processing,the myrosinase enzyme will hydrolyze the glucosinolates.

However, if cooked before consumption, myrosinase is inactivated and glucosinolates are absorbed through the gastrointestinal mucosa.

List of glucosinolates:

Epiprogoitrin, C₁₁H₁₉NO₁₀S₂ source

Glucoalyssin, C₁₃H₂₅NO₁₀S₃ source

Hydroxyglucobrassicin, C₁₆H₂₀N₂O₁₀S₂ source

Methoxyglucobrassicin, C₁₇H₂₂N₂O₁₀S₂ source

Neoglucobrassicin, C₁₇H₂₂N₂O₁₀S₂ source

Progoitrin, C₁₁H₁₉NO₁₀S₂ source

Sinalbin, C₃₀H₄₂N₂O₁₅S₂ source

Sinigrin, C₁₀H₁₆KNO₉S₂ source

Hydroxybenzaldehydes¶

Hydroxybenzaldehydes are phenolic aldehydes, e.g. 4-Hydroxybenzaldehyde, C6H4OH(CHO), a benzaldehyde, C₆H₅CHO, with a hydroxy group at position C-4. source

| 4-Hydroxybenzaldehyde, C₇H₆O₂ | Gallic aldehyde, C₇H₆O₄ | Anisaldehyde C₈H₈O₂ | source

| Protocatechuic aldehyde, C₇H₆O₃ | Syringaldehyde, C₉H₁₀O₄ | Vanillin C₈H₈O₃ | source

Hydroxybenzoic acids¶

Note. "hydroxybenzoic acid" may refer to different compounds.

| Sanguiin H-6, C₈₂H₅₄O₅₂ | Syringic acid, C₉H₁₀O₅ Valoneic acid dilactone, C₂₁H₁₀O₁₃ | source

| Vanillic acid, C₈H₈O₄ | Salicyclic acid, C₇H₆O₃ | source

3-hydroxybenzoic acid, C₇H₆O₃, in gut microfauna source

4-hydroxybenzoic acid, C₇H₆O₃ → esters → parabens, (esters of para-hydroxybenzoic acid) source

trihydroxybenzoic acid Gallic acid, C₇H₆O₅, hydrolysable tannin, pseudotannin source

Benzoic acid, C₆H₅COOH, C₇H₆O₂ source

Ellagic acid, C₁₄H₆O₈ source

Hydroxycinnamic acids

Hydroxycinnamic acids¶

Cinnamic acid occurs in cinnamon, aloe.

Ferulic acid occurs in oats, rice, artichoke, orange, pineapple, apple, peanut, açaí oil.

Indoles¶

Indole, C₈H₇N, Amine source

Indole, aromatic, in coal tar, fused benzene and pyrrole rings, toxic if ingested

It is formed from amino acid: | Tryptophan

It has a flowery smell at very low concentrations, but in human faeces intense faecal odour, in Jasmine oil, in Orange blossom.

Ergotamine, indole derivative

Five member heterocycles: 16.2.19

Indole-3-acetic acid, indole acetic acid, IAA

Indole-3-butyric acid, Indolebutyric acid, IBA

Indole-3-acetonitrile

Indole-3-carbinol

Indole alkaloids, indolizidine group: 16.6.4

Indole, C₈H₇N, C₆H₄CCNH₃, 1H-indole, an indole, an aromatic heterocycle, (benzene ring + pyrrole ring), occurs in Daphne. source

Indole-3-carbinol occurs in cabbage, kale, brussels sprouts, rutabaga, mustard greens, broccoli.

3,3'-Diindolylmethane, C₁₇H₁₄N₂, "DIM", an indole, occurs in broccoli family, brussels sprouts, cabbage, kale, Brassica oleracea, Arundina graminifolia. source

Iridoids¶

Iridoids are cyclic monoterpenoids

See diagram: Iridoid molecules

The iridoid Iridomyrmecin, C₁₀H₁₆O₂, occurs in Iridomyrmex ants, in (Actinidia polygama). source

Isoflavonoids Phytoestrogens¶

Isoflavonoids are flavonoid phenolic compounds.

Isoflavone, C₁₅H₁₀O₂, the simplest isoflavone, a soy phytoestrogen, and a commercial dietary supplement. source

It occurs in soy, peanut, green peas, chick peas and alfalfa.

Glycitein, C₁₆H₁₂O₅, an isoflavone, a phytoestrogen, it occurs in soy, Glycine max source

Isoflavonoids occur mostly in Papilionoideae subfamily of family Fabaceae

Some are physoalexins which form compounds to attack fungus or are activated when the host plant contacts a parasite.

Isoflavonoids are used in dietary supplements.

Isoflavonoid toxins include biliatresone.

List of isoflavonoids Isoflavones

Also: Isoflavanones, Isoflavans, Pterocarpans, Rotenoids

BetavulgarinC₁₇H₁₂O₆ source

Daidzein, C₁₅H₁₀O₄ source

Formononetin, C₁₆H₁₂O₄ source

Isoflavones¶

Isoflavones, C₁₅H₁₀O₂, occur almost only in legumes, oestrogenic activity, e.g. Psoralea, soybeans, and pistachios source

Isoflavones are related to isoflavonoids, phytoestrogens and antioxidants, soy isoflavones may prevent breast cancer, only in legumes.

Isoflavones almost only occur in Fabaceaelegumes, soybeans, and in pistachios.

Isoflavones is are related to isoflavonoids, phytestrogens and antioxidants.

Soy isoflavones may prevent breast cancer

Isoflavone, C₁₅H₁₀O₂, the simplest isoflavone, it lessens coronary heart disease, atherosclerosis, type II diabetes mellitus, breast / prostate cancer. source

Isoflavone is used in oral over-the-counter dietary supplements and pistachios.

Soybean and pistachios are rich in dietary isoflavones, soy phytoestrogen, 1-2 mg/gram.

Isoflavones are a type of isoflavonoid, phytoestrogen polyphenolic compounds, and are the major flavonoids, in legumes, especially soybeans.

The main precursor molecule for isoflavone biosynthesis is the flavanone naringenin, C₁₅H₁₂O₅. source

Red clover, (Trifolium pratense), contains the most isoflavones of any plant.

Isoflavones are similar to estradiol, beta-estradiol, 17beta-estradiol, C₁₈H₂₄O₂, in chemical structure. source

A high dietary intake of phytoestrogens may lower rates of cancers, cardiovascular problems, and menopausal problems.

However, isoflavones may be endocrine disruptors and have negative influences on the state of health of some populations, e.g. Greek people.

The isoflavone Formononetin caused reproductive malfunction, "clover disease”, in Australian sheep grazing on Subterranean clover (Trifolium subterraneum).

Astragalosides, C₄₁H₆₈O₁₄ source

psoralen), (flavone alkaloids: ficine, vochysine)

See: Vestitol.

List of isoflavones

Astragaloside C₄₁H₆₈O₁₄ source

Betavulgarin C₁₇H₁₂O₆ source

Daidzein, C₁₅H₁₀O₄ source

Formononetin, C₁₆H₁₂O₄ source

Genistein, C₁₅H₁₀O₅ source

Lignans¶

Lignans C₂₅H₃₀O₈, an ethyl carboxylate source

Lignans are plant polyphenols derived from phenylalanine, and are phytoestrogens

Lignans occur in flax, sesame, sunflower, pumpkin seeds and body fluids of humans and animals.

Bacteria occuring in the human colon convert lignan precursors to lignans.

Lignans are related to the lignins occuring in plant cell walls and are found mainly in woody tissue.

Lignin, is a disodium disulphonate, C₁₈H₁₃N₃Na₂O₈S₂ source

Lignans: Justicidin A, Steganacin

Sesamin, a lignan. C₂₀H₁₈O₆ source

Sesamol C₇H₆O₃ source

Podophyllotoxin, a lignan, C₂₂H₂₂O₈ source

Glepidotin, a trihydroxyflavone, C₂₀H₁₈O₅ source

Matairesinol

Stilbenes¶

Stilbene, trans-stilbene, C₆H₅CH=CHC₆H₅ is a diarylethene polyphenol. source

Stilbenoids are derivatives of Stilbene and the products of heartwood formation occurs in trees.

Stilbenoids, (C6–C2–C6), the hydroxylated derivatives of stilbene

Deoxykaempferol, trihydroxy flavone

16.5.6.0

href="../topics/topic16c.html#16.2.2.2H">Apiole, C₁₂H₁₄O₄ source

Pallidol a tetracyclic stilbenoid, C₂₈H₂₂O₆ source

Phyllodulcin, a hydroxybenzoic acid, C₁₆H₁₄O₅ source

Piceid stilbenoid glucoside

Resveratrol a stilbenol, C₁₄H₁₂O₃ source

Rhaponticin, stilbenoid glucoside, C₂₁H₂₄O₉. source

Polyphenol flavonoids¶

| Catechol | Geosmin | Chrysoeriol

| EGC Epigallocatechin | Kaempferol | Luteolin

| Naringin | Quercetin | | Tangeritin

Porphyrins, Haeme¶

Porphyrins, Haeme

Porphyrins refers to any of a group of compounds containing the porphyrin structure of four pyrrole rings connected by methine bridges.

It occurs in a cyclic configuration with usually metal side chains attached, e.g. with iron to form heme.

Porphyrin chelates include haeme, occurs in haemoglobin, bonded to iron (II) ion, and chlorophyll bonded to Mg (II) ion.

Haeme, (Heme), Haemoglobin, (Hemoglobin), is the protein that carries oxygen in the blood and causes the red colour of blood.

Haeme A is a cytochrome oxidase ligand complex, C₄₉H₅₆O₆N₄Fe, a tetradentate ligand. source

The most common type is Haeme B, C₃₄H₃₂O₄N₄Fe. source

The haeme component of the protein haemoglobin has four iron porphyrins.

Porphyrins occur in iron-containing cytochrome pigments, and in mitochondria in plants, animals and bacteria.

Is used for oxidative phosphorylation, electron transport system, and ATP production.

See diagram 16.3.5.01. Porphyrin, Porcine

For oxidative phosphorylation, electron transport system, and ATP production.

Xanthones¶

Xanthone, C₁₃H₈O₂, xanthenone, 9H-Xanthen-9-one, is prepared from phenyl salicylate, C₁₃H₁₀O₃. source

It is an insecticide ovicide.

It is used to prepare xanthydrol to determine urea levels in blood.t

The parent compound of xanthone derivatives called xanthones or xanthonoids are fluorescent.

It occurs mainly in Gentianaceae and Gutterferae roots and leaves.

List of xanthones

Athyriol C₁₄H₁₀O₆, occurs in the fern (Athyrium mesosorum). source

Bellidifolin C₁₄H₁₀O₆, anti-heptotoxic, mutagenic, occurs in (Gentiana lutea). source

Gambogic acid C₃₃H₄₄O₃, occurs in gamboge the gum resin of (Garcinia hamburgyi). source

Gentisein, C₁₃H₈O₅, occurs in (Garciniama lutea). source

Gentisin C₁₄H₁₀O₅, occurs in (Garcinia lutea). source

Gartanin C₂₄H₂₇O₁₀, antifungal, antibacterial, occurs in (Garciniama). source

Mangiferin C₁₉H₁₈O₁₁, Aphloid, Chimonin, Euxanthogen, widespread occurrence with Isomangiferin, occurs in (Mangifera indica). source

Mangostin C₂₄H₂₆O₆, mainly occurs in Garciniama. source

Morellin C₃₃H₃₆O₇, antibiotic, occurs in (Garcinia morella). source

Norathyriol C₁₃H₈O₆, tuberculostatic, occurs in Garciniama. source

Swertianin C₁₄H₁₀O₆ source

Flavan and flavone¶

Flavan, C₁₅H₁₄O, 2-Phenyl-3,4-dihydro-2H-1-benzopyran, the simplest member of the flavans, occurs in (Broussonetia papyrifera). source

Flavone, C₁₅H₁₀O₂, 2-phenychromen-4-one, the simplest member of the flavones, it occurs in (Camellia sinensis), and in (Anaphalis lactea). source

(Casuarina glauca) is an actinorhizal plant producing root nitrogen-fixing nodules, because it is infested by Frankia bacteria, containing flavans.

1. Flavanols, (NOT "Flavonols"!)

Flavanols occur in:

fruits and vegetables, e.g. apples, apricots, berries, cherries, grapes, nectarines, peaches, pears, plums, Swiss chard,

nuts, e.g. almonds, cashews, hazelnuts, pecans and pistachios,

green, black and oolong teas, cacao, red and white wine.

Catechin, C₁₅H₁₄O₆ source

Epicatechin, (EC), Flavonoid

ECG Epicatechin gallate (ECG), Flavonoid

Epigallocatechin (EGC), bioflavonoid

Epigallocatechin gallate (EGCG), bioflavonoid

Catechol, C₆H₆O₂, a phenol source

Leucanthocyanidin, C₁₅H₁₄O₃, from enzymes, occurs in many plants, e.g. (Zea mays). source

Rutin hydrate, C₂₇H₃₀O₁₆.xH2O, poly flavonoid source

Phenols¶

Phenols, Phenolic acids, Phenolics, Polyphenols

1. Phenol crystals, C₆H₅OH, Highly toxic by all routes, lung irritant, corrosive to skin source

Phenol solution < 1%, Not hazardous

Phenol red, C₁₉H₁₄O₅S: 28 (indicator) source

Phenol, phenolic, is a derivative of an aromatic hydrocarbon where a hydroxyl group is attached to a benzene ring.

Phenolic compounds occur occurs in seeds, grape skins occurs in citronella, clove oil, dicoumarin, eucalyptol, ubiquinone, urushiol and extracted from oak barrels.

Prepare carbol xylol solution: 1.4

Phenols are compounds having one or more hydroxy groups attached to a benzene ring, C₆H₆, or other aromatic hydrocarbon, e.g. 2-naphthol, C₁₀H₈O source

A phenolic is a derivative of an aromatic hydrocarbon. where a hydroxyl group is attached to a benzene ring.

Phenolic compounds occur in seeds, grape skins and and are extracted from oak barrels, in citronella, clove oil, dicoumarin, eucalyptol, ubiquinone, urushiol.

Prepare carbol xylol solution. 1.4.

Phenol red, C₁₉H₁₄O₅S. 28 (indicator) source

Naturally occuring phenols, by number of carbon atoms.

Phenolic compounds

Simple phenols

C6 Benzoquinone, C₆H₄O₂ source

C6 Catechol, C₆H₆O₂ source

Polyphenols

C7 Phenolic acids

C8 Tyrosol

C9 Hydroxycinnamic acids

C9 Caffeic acid

C9 Ferulic acid

C10 Napththoquinones

C13 Mangiferin

C14 Stilbenes and Stilbenoids

C15 Flavonoids

C15 Emodin

C16 Quercetin

C18 Lignans, C₁₈H₁₈O₂ source

C20 Sesamin, a lignan. C₂₀H₁₈O₆ source

C30 Lignin, C₁₈H₁₃N₃Na₂O₈S₂ source

C76 Tannic acid, C₇₆H₅₂O₄₆ source

Phenols, phenolics

Phenol, carbolic acid, the simplest phenol, C₆H₅OH source

Phenol, Carbolic acid¶

Phenol, Carbolic acid

Phenol, C₆H₅OH, carbolic acid, the simplest of the phenols, aromatic organic compound, corrosive, acute toxic source

Phenyl group (−C₆H₅) + hydroxy group (−OH), volatile white crystalline solid, mildly acidic, cause chemical burns or numbs source

Phenol crystals, C₆H₅OH, Highly toxic by all routes, lung irritant, corrosive to skin source

Phenol solution < 1%, Not hazardous

Phenol-indo-2, 6-dichloro phenol

Phenol fuchsin, carbol fuchsin

Phenols, group. (OH-C)

It is colourless to white solid when pure, liquid commercial product, distinct sweet odour, does not react with water.

It is used to make phenolic resins, plastics and adhesives, corrosive to lead, aluminum and its alloys, plastics, and rubber.

Phenol is the parent of the class of phenols, group of 6 in an aromatic ring + OH.

Phenol is the parent of the class of phenols, germicidal agent, disinfectant, and antiseptics.

Phenol solution, white crystalline mass dissolved in a colourless to slightly pink aqueous solution, distinctive phenol odour, sharp burning taste, toxic by ingestion.

1. Carbolic acid, C₆H₅OH, "phenol" from coal tar fraction 170 oC to 230 oC, colourless hygroscopic crystals source

Phenol is acidic so ionizes in water.

C₆H₅OH → H+ + C₆H₅O^- source

Do not wash off phenol with alcohol, because carcinogenic products or explosive materials may form.

2. "Phenol", carbolic acid C₆H₅OH, pale pink crystalline solid, because of the hydrogen bonds between the phenol molecules). source

Pure phenol blisters the skin, but it is still used in carbolic soaps as an antiseptic.

3. Formerly, carbolic acid was used as an antiseptic spray in early medical operations.

4. Phenol as a weak acid

Phenol loses a proton, H+ ion, to form a phenoxide ion, C₆H₅O^-. source

C₆H₅OH → C₆H₅O^- + (H+) source

phenol → phenoxide ion + a proton, H+ ion source

5. Phenol reacts with alkalis.

NaOH (aq) ⇌ C₆H₅NaO + H₂O source

phenol + sodium hydroxide ⇌ sodium phenoxide + water source

Sodium phenolate formula. NaOC₆H₅ source

6. Halogenation of phenol

phenol + bromine → 2.4.6-tribromophenol, (TBP), C₆H₃Br₃O source

phenol + chlorine → 2-chlorophenol, C₆H₅OHCl source

Carvacrol

Chloroxylenol

TCP

Carvacrol¶

Carvacrol, C₁₀H₁₄O, [C₆H₃(CH₃)(OH)C₃H₇], cymophenol, is a monoterpenoid phenol, isopropyl-o-cresol, antioxidant, aromatic. source

It inhibits bacterial growth, food additive, volatile oil component, flavouring agent, antimicrobial agent, agrochemical, (anti-fungal agent).

It is a flavouring agent, which gives "penetrating" flavour to some varieties of oregano, food additive.

It occurs in black walnut, and many essential oils, e.g. Thyme oil and Origanum oil, and it smells like oregano.

Chloroxylenol

Chloroxylenol, C₈H₉ClO, (4-chloro-3,5-dimethylphenol), is an halophenol, monochlorobenzene, antiseptic, disinfectant agent in antibacterial soaps. source

It is a widely-used antiseptic, "Dettol", "PCMX", and is a bactericidal against most Gram-positive bacteria, for skin disinfection and surgical instruments.

However, it is is less effective against Staphylococci and Gram-negative bacteria, and is inactive against Pseudomonas, and bacterial spores.

TCP

TCP, antiseptic for sore throats, was originally (2,4,6-trichlorophenol), trichlorophenylmethyliodosalicyl.

Nowadays, commercial TCP contains a mixture of phenol and halogenated phenols.

TCP has a distinctive "medicine" smell.

TCP (antiseptic) now C₁₃H₁₂Cl₂I₂O₄. source

Phenolic acids

Phenolic acids are phenolic compounds having one carboxylic acid group.

Phenolic acids, phenolcarboxylic acids, are aromatic acid compounds with a phenolic ring and a C6-C1 skeleton, and are weak acids.

Phenolic acids occur in many plant species, especially in dried fruits, basidiomycetes mushrooms, soil humus, and human urine.

Phenolic acids are natural antioxidants, a vital human dietary component, a variety of functions in plants, and are in the therapeutic, cosmetics, and food industries.

These dietary antioxidant property through radical scavenging mechanism, shields against pathological conditions arise from oxidative stress.

Oxidative stress is imbalance between reactive oxygen species and the system's ability to detoxify the reactive intermediates or to repair the resulting damage.

Disturbances in the normal redox state of tissues can cause toxic effects through the production of peroxides and free radicals that damage all components of the cell.

Oxidative stress is involved in atherosclerosis, Parkinson's disease, heart failure, myocardial infarction, Alzheimer's disease, and chronic fatigue syndrome.

The two sub-groups of phenolic acids.

Sub-group 1: Hydroxybenzoic acids, occur conjugated with sugars or organic acids and bound with cell wall lignin.

They occur in red fruits, onions and black radish.

The four commonly found hydroxybenzoic acids are p-hydroxybenzoic, protocatechuic, vanillic, and syringic acids.

Gallic acid, C₇H₆O₅ source

Salicyclic acid, C₇H₆O₃ source

Sub-group 2: Hydroxycinnamic acids, occur as simple esters with quinic acid or glucose.

Ferulic acid, C₁₀H₁₀O₄ source

Caffeic acid, C₉H₈O₄ source

Phenolic ketones¶

Phenolic ketones are used as organic synthesis raw materials and solvents, dewaxing agents, organic synthesis, materials for synthetic fragrances and medicine.

1. Acetophenones

2. Phloroglucinol derivatives

Phloroglucinol, C₆H₆O₃, Benzene-1,3,5-triol source

Apocynin A, C₂₄H₂₀O₁₀ source

Aspidin, C₂₅H₃₂O₈ source

Humulone, C₂₁H₃₀O₅ source

Lupulone, C₂₆H₃₈O₄ source

Picein, C₁₄H₁₈O₇ source

Rottlerin, C₃₀H₂₈O₈ source

Phenolics

Water-soluble phenolics are in central vacuoles of plant cells.

Lipophilic phenolics are in cell cytoplasm and in surfaces as waxes or bud exudates.

Brazilin, C₁₆H₁₄O₅ source

16.3.4.1.1 Benzofurans

Chromones and Chromenes

Coumarone, 16.3.4.1a

Polyphenols¶

Polyphenols have aromatic phenyl ring + -OH group

Phenolics are classified into two main groups:

1. Flavonoid phenolics

Subclass: Flavonoids

2. Non-flavonoids phenolics

Subclass: Lignans

Subclass: Phenolic acids

Subclass: Stilbenes and Stilbenoids

Polyphenols:

Catechins

Tyrosol, a phenylethanoid, C₈H₁₀O₂ source

Guaiacol, a methoxyphenol, C₇H₈O₂ source

Gentisin, a polyphenol, a xanthone, C₁₄H₁₀O₅ source

Juglone, an hydroxy-naphthoquinone, C₁₀H₆O₃ source

Plumbagin, an hydroxy-methyl-naphthoquinonegin, C₁₁H₈O₃ source

Hydroxybenzaldehydes

Hydroxybenzoic acids

Hydroxycinnamic acids

Polyphenols are often repeated connected units of:

Catechol, C₆H₆O₂ source

Resorcinol, C₆H₄(OH)₂ source

Phloroglucinol, C₆H₃(OH)₃ source

Arbutin, C₁₂H₁₆O₇ source

Pyrogallol, C₆H₆O₃ source

Monophenols

Apiole, Apiole, C₁₂H₁₄O₄ source

Carnosol, C₂₀H₂₆O₄ source

Dillapiole, C₁₂H₁₄O₄ source

Glycosides

A substance containing a glycosidic bond is a glycoside.

Glycosides are a sugar group, called the glycone, with a covalent glycosidic bond to a non-sugar group, called the aglycone.

The sugar group can be a monosaccharide or an oligosaccharide, but not polysaccharides.

There are many different types of glycosides, e.g a glucoside has a glucose glycone group, and a fructoside has a fructose glycone group.

are soap-like steroid glycosides.

1. A glycoside contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other organic group.

Glycosides are named from the constituent sugar, e.g. glucoside (glucose), pentoside (pentose), fructoside (fructose).

Glycosides, unlike polysaccharides, are sugars bonded to a non-sugar, so they contain a carbohydrate and a non-carbohydrate residue occurs in the same molecule.

2. Anthoxanthins, glycosides, are similar to and associated with anthocyanin.

They are water-soluble white to yellow flavonoid pigments, antioxidants, occur occurs in potatoes, cauliflower, onions, parsnips, bananas.

Anthoxanthins cause bright white colour of food occurs in acid medium, yellow occurs in alkaline medium.

Canthaxanthin

3. Anthraqinone glycosides, (aglycone from anthraquinone), alizarin, hypericin, physcion, rhubarb, Cascara, Senna, Aloe

4. Cardiac glycosides, (steroidal glycosides, digitalis glycosides, cardiovascular glycosides), heart stimulants, occurs in Digitalis, Convallaria.

Cardenolide, C₂₃H₃₄O₂, is a steroid molecule, but "cardenolides" are usually cardenolide glycosides source

Types of glycosides

Cyanogenic glycosides

Glucosideskk

Saponinskk

Aminoglycosides¶

Aminoglycosides have a broad spectrum of activity covering aerobic organisms, including gram-negative bacteria and mycobacteria.

Aminoglycoside drugs. Gentamycin, tobramycin, amikacin, streptomycin, neomycin, paromomycin, and streptomycin

Aminoglycosides from Streptomyces bacteria, have the suffix "mycin", e.g. Neomycins, B and C, Neomycin E and Streptomycin.

Aminoglycosides from Micromonospora bacteria, have the suffix "micin", e.g. Kanamycin A, Amikacin, Tobra mycin, Dibehacin, Gentamucin.

Amikacin, C₂₂H₄₃N₅O₁₃, amicacin, an aminoglycoside, is antimicrobial, antibacterial, a semi-synthetic aminoglycoside antibiotic It is active against more resistant gram-negative bacilli, e.g. Acinetobacter baumanii and most aerobic gram-negative bacilli source

It occurs in water and soil.

Betalains¶

Betalains, C₂₄H₂₆N₂O₁₃, Betalain, compounds derived from the non-essential amino acid Tyrosine,C₉H₁₁NO₃, and include the Betaxanthins and Betacyanins. source

They are water-soluble glycoside plant pigments in vacuoles, but their function in plants is not known, and they never occur in plants with anthocyanins.

Betalains, occur in beets (Beta vulgaris subsp. vulgaris), Opunti, leaves of (Amaranthus spinosus), floral bracts of (Bougainvillea glabra), and in Portulaca.

They also occur in Gomphrena globosa, and in some Basidiomycota fungi.

Cardiac glycosides¶

Cardenolides - the aglycone constituents of cardiac glycosides

* Cardiac glycosides, (steroidal glycosides, digitalis glycosides, cardiovascular glycosides), heart stimulants, occur in Digitalis, and in Convallaria.

Cymarine, C30H44O9br> * Digitalis glycosides Digitoxin, C₄₁H₆₄O₁₃ source

Digoxin, C₄₁H₆₄O₁₄ source

Scilla glycosides Proscillardin, C30H42O8
Strophanthus glycosides Ouabain, C29H44O12

Strophanthin, C₃₆H₅₄O₁₄ source

* Cardenolides Cardenolides

Cyanogenic glycosides¶

Cyanogenic glycosides are chemicals that cause protective cyanogenesis, i.e. they produce HCN, when plant is attacked.

Cyanogenic glycosides (cyanophore glycosides), (aglycone contains CN group)

Amygdalin, C₂₀H₂₇NO₁₁ source

Betanin, C₂₄H₂₆N₂O₁₃ source

Dhurrin, C₁₄H₁₇NO₇ source

Linamarin, C₁₀H₁₇NO₆ source

Prunasin, C₁₄H₁₇NO₆ source

Cardenolides¶

Cardenolide, C₂₃H₃₄O₂, is a steroid lactone, and the parent of the cardenolides. source

Cardenolide is a steroid molecule, but "Cardenolides" are usually cardiac glycosides

Cardenolides inhibit the ion-transporting enzyme Na+/K+-ATPase, which controls many physiological processes, cell resting potential, ion transport, cellular volume.

Cardenolides are cardiac glycosides and occur mainly in the toxic latex of Asclepidaceae, and in the foxglove plant, Digitalis purpurea.

Cadenolide glycosides are usually potentially heart toxic, but Digitalis is used medically.

Cardenolides:

Glucosides¶

A glucoside is a glycoside from glucose, a glycoside with a glucose sugar component, a glycoside that yield glucose upon hydrolysis.

A glucoside is a glycoside in which the sugar is glucose.

Glucosides are natural compounds linked to glucose.

Glucoside. sugar + non-carbohydrate R, e.g. glucose + terpene or glucose + phenolic compound

Bracteatin 6-glucoside, C₂₁H₂₀O₁₂, yellow colour of Antirrhinum majus (snapdragon) Glucosides source

Aesculin, Esculin, C₁₅H₁₆O₉ source

Aloin

Aloenin

Arctigenin, C₂₁H₂₄O₃ source

Betanin, C₂₄H₂₆N₂O₁₃ source

Cycasin, C₈H₁₆N₂O₇ source

Fraxin, C₁₆H₁₈O₁₀ source

Icariin, C₃₃H₄₀O₁₅ source

Linamarin, C₁₀H₁₇NO₆ source

Piceatannol, C₁₄H₁₂O₄ source

Picrocrocin, C₁₆H₂₆O₇ source

Quercitrin, C₂₁H₂₀O₁₁ source

Rhamnazin, C₁₇H₁₄O₇ source

Rhamnetin, C₁₆H₁₂O₇ source

Rhaponticin, C₂₁H₂₄O₉ source

Salicin, C₁₃H₁₈O₇ source

Gluco-chemicals

Glucose, C₆H₁₂O₆ source

Fructose, C₆H₁₂O₆ source

Pentose, C₅H₁₀O₅₅ source

Salidroside, rhodioloside, glucoside of tyrosol, neuroprotective, antidepressant, anxiolytic, C₁₄H₂₀O₇ source

Napththoquinones¶

1,2-Naphthoquinone, C₁₀H₆O₂, occurs in diesel exhaust, strong odour, red-brown alkaline solution, cytotoxic derivatives occur in vitamin K. source

1,4-Naphthoquinone, (C₁₀H₆O₂), strong odour, red-brown alkaline solution source

Triphophyllum peltatum

Naphthoquinones C6-C4 skeleton, 1,2-Naphthoquinone C₁₀H₆O₂ occurs in diesel exhaust, 1,4-Naphthoquinone, (C₁₀H₆O₂) source

It has a strong odour, red-brown alkaline solution, cytotoxic derivatives occurs in vitamin K.

Triphophyllum peltatum

Napthoquinone derivatives

Drosera, Droserone, C₁₁H₈O₄ source

Plumbagin, C₁₁H₈O₃ source

Juglone, C₁₀H₆O₃ source

Saponins¶

A saponin consists of a steroid or a triterpene sapogenin and a sugar, which may be glucose, galactose, a pentose, or a methylpentose.

Saponins are 1. Triterpene glycosides and 2. Steroid glycosides.

1. Triterpene glycosides are natural glycosides present in various plants, herbs and sea cucumbers. and are used for traditional medicine.

Triterpenoid saponins are triterpenes which belong to the saponin group of compounds, so are triterpenoid glycosides.

Senegin II, C₇₀H₁₀₄O₃₂, triterpenoid saponin source

Glycyrrhizin, C₄₂H₆₂O₁₆, glycyrrhizinic acid, triterpenoid saponin source

2. Steroid glycosides are saponins with 27-C atoms, modified triterpenoids, with cytotoxic, neurotrophic and antibacterial properties.

Steroid saponins are similar to triterpenoid saponins and are used as non-toxic to humans detergents, fish poisons, fire extinguisher foaming agents.

Steroid glycosides form frothy colloidal soapy solutions when agitated in water, emulsifiers, detergents, often toxic to fish.

See: Quillaja saponaria, the soap bark tree, the source of quillaia, which contains saponins.

Tests for saponins:

Add ground plant material to test-tube of water, heat to boiling, add stopper, shake the test-tube and note presence of stable froth.

#SteroidsaponinsH">Steroid saponins

Steroid saponins

Triterpenoid saponins

Carotenoids

A terpene is an unsaturated hydrocarbon molecule with the chemical formula, C₁₀H₁₆. source

A tetraterpene, (tetra terpene), = 4 terpenes, 4 X C₁₀H₁₆ = C₄₀H₆₄. source

Carotenoids have the chemical formula C₄₀H₆₄, so carotenoids are tetraterpenes. C₅H₈ in a molecule is called an isoprene unit, so 8 isoprene units = 8 X C₅H₈ = C₄₀H₆₄. source

Carotenoids are hydrocarbons, which have a similar base structure consisting of 8 isoprene units.

Carotenoids are a type of accessory pigment, created by plants to help them absorb light energy and convert it to chemical energy. The two types of carotenoids are the Carotenes (hydrocarbons, contain no oxygen), and the Xanthophylls, (hydrocarbons + oxygen).

See: Carotenes

See: href="#XanthophyllsH">Xanthophylls

1. Carotenoid pigments are tetraterpenoids from the acyclic parent carotene, and are produced from 8 isoprene molecules.

They have 40 C atoms, in two six-carbon rings connected by a chain of carbon atoms.

2. Carotenoids are red, orange and yellow, fat-soluble, insoluble in water, plant and animal organic pigments in plants, algae, fungi and bacteria.

3. Presence of carotenoids is shown by the bright red, orange and yellow pigments.

Carotenoids occur in beet greens, broccoli, cantaloupe, carrots, collard greens, green peas, kale, leafy green vegetables, mango, okra, oranges, papaya, parsley, pink grapefruit, pumpkin, red peppers spinach, sweet potatoes, Swiss chard, tangerines, tomatoes, watermelon, winter squash, and fish liver oil.

4. Carotenoids should be ingested with fats in the diet and are stored in fatty tissue, and may be antioxidants.

A high carotenoid diet may help reduce the risk of lung cancer in non-smokers and breast cancer.

Most carotenoids are not damaged by cooking.

5. Carotenoids absorb blue and green wavelengths of light causing yellow and orange colours.

Carotenoids occur in chromoplasts, which show when fruit is ripe, and in chloroplast membranes to absorb light energy for photosynthesis.

They are accessory pigments and protect chlorophyll from damaging wavelengths.

The most common carotenoids in food are alpha-carotene, beta-carotene, beta-cryptoxanthin, lutein, zeaxanthin, and lycopene.

6. Provitamin A carotenoids, alpha-carotene, beta-carotene, and beta-cryptoxanthin, can be converted to retinol (vitamin A).

Lutein and zeaxanthin, in the macula of the eye, absorb most incident blue light, and may prevent age-related macular degeneration.

Carotenes¶

Carotene, C40Hx, (Latin carotin, 'carrot')

Carotenes, C40Hx, contain no oxygen,and are orange or red photosynthetic pigments

Carotenes are hydrocarbon carotenoids, a subclass of tetraterpenes and C5n polyterpenes, C40Hx

Plants rich in carotenes include sweet potato (red variety), kale, (carrot, mustard greens, spinach driedbasil, butternut squash, lettuce (red leaf variety).

Carotenes occur in many plants, and are pigments.

Carotenes that are are orange pigments cause the colour of carrots.

Carotenes, C₄₀H₅₆, are simple orange or red unsaturated hydrocarbons. source

Test the cooking water of boiled vegetables: 19.2.12, (See 1. and 6.)

Chromatography of chlorophyll pigments: 10.2.1 (See: 3.)

Vitamin A: 9.6.1 (See: Carotenes)

Alpha-carotene

Alpha-carotene, C₄₀H₅₆, α-Carotene, a carotene isomer, carotenoid pigment, occurs in vitamin A, carrots, pumpkins, maize, tangerine, orange, Alhagi, and Corbicula. source

Alpha-carotene is used as a yellow food colouring, and it occurs in green leaves of many plants.

Alpha-carotene occurs in in carrot roots, maize seed, oil palm and in tomato.

α-Carotene, less than half the vitamin A activity of beta-carotene, in carrots, pumpkin, maize seeds, orange, tangerine, tomato.

Vitamin A precursor is used as yellow food colouring.

Beta-carotene, C₄₀H₅₆, β-Carotene, carotenoid pigment, cyclic carotene, strongly-coloured red-orange pigment, antioxidant, occurs in dark leafy greens, red, orange and yellow fruits and vegetables. source

Beta-carotene occurs widelyin most green leaves and coloured fruits and vegetables

Beta-carotene is used as yellow food colouring of fats, e.g. margarine, used as sunscreen, red-purple oil, not soluble in water, in dark orange varieties of sweet potato.

β-Carotene, Type I, synthetic, 93% (UV), powder, β, β-Carotene, Provitamin A, C₄₀H₅₆, commercial product source

β-Carotene, Type II, synthetic, 95% (HPLC), crystalline, β, β-Carotene, Provitamin A, C₄₀H₅₆, commercial product source

E160e, Beta-apo-8' carotenal

E160f, Ethyl ester of beta-apo-8

Both α-carotene and β-carotene are precursors of vitamin A, C₂₀H₃₀O, retinol. source

Gamma-carotene, C₄₀H₅₆, (γ-carotene), carotenoid pigment, Vitamin A precursor source

Delta-Carotene. C₄₀H₅₆, δ-Carotene source

Epsilon-carotene, C₄₀H₅₆, ε-carotene source

Carotene epoxide, zeta-Carotene epoxide, (1,2-Epoxy-1,2-dihydro-z-carotene), C₄₀H₆₀O source

It occurs in garden tomato and in cherry tomato, (Solanum lycopersicum var. cerasiforme).

Xanthophylls

Xanthophylls, contain oxygen, and are yellow or brown oxygenated carotenoids, carotene derivatives

Xanthophylls, (C₄₀H₅₆)n, are hydrocarbons + oxygen, and are usually yellow pigments in the leaves of most plants. source

Xanthophylls are oxygenated carotenes, synthesised within plastids without need for light for synthesis.

They do absorb some wavelengths not absorbed by chlorophyll, so in etiolated leaves with chlorosis nutrient deficiency.

In the leaves of deciduous plants, green chlorophyll covers up the yellow from the carotenoid pigments, except during autumn.

Xanthophylls are yellow or brown carotenoid pigments in green plants and cause the colours of leaves in the autumn, the fall.

The carotenoids, carotenes are hydrocarbons, and the xanthophylls are hydrocarbons + oxygen.

Xanthophylls, are yellow or brown oxygenated carotenoids, carotene derivatives.

However, they do absorb some wavelengths not absorbed by chlorophyll, so they appear in etiolated leaves and plants with chlorosis.

In the leaves of deciduous plants, green chlorophyll covers up the yellow from the carotenoid pigments, except during autumn.

Xanthophylls act to modulate light energy and deal with triplet chlorophyll, (an excited form of chlorophyll).

(an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis.

Astaxanthin

Antheraxanthin, an epoxycarotenol, C₄₀H₅₆O₃ source

Cryptoxanthin, a carotenol, C₄₀H₅₆O source

Fucoxanthin, an epoxycarotenol, C₄₂H₅₈O₆ source

Astaxanthin C₄₀H₅₂O₄ source

Astaxanthin, a terpene, keto-carotenoid pigment, β-carotene derivative, as a free red pigment, or ester, or brown to green chromoprotein, an anticoagulant, an antioxidant, widely used additive for colouring of fish food

Steroids¶

Steroids are compounds containing a 17-carbon 4-ring system, e.g. Cholesterol, C₂₇H₄₆O source

3.9.1 Cholesterol

Steroids, sterols, steroid alcohols, natural steroids, have a nucleus of three six-member carbon rings and one five-member ring.

Natural steroids are from triterpenoids and have a saturated 4 ring steroid structure.

Steroids include sex hormones, coricosteroid hormones, cardiac glycosides, bile acids, cholesterol lanosterol (animal sterols), β-sitosteron (plant sterol), ergosterol (fungus sterol), cardiac glucosides, diosgenin, androstane, 19-norpregnane, 7-dehydrocholesterol, previtamin D3, ergocalciferol (vitamin D2), cholecalciferol (vitamin D3).

Sterolins

Sterols

Estradiol, an estrogen steroid hormone, C₁₈H₂₄O₂ source

Esculeoside, a steroidal alkaloid glycoside, a steroid saponin C₅₈H₉₅NO₂₉ source

Sterols¶

Sterols are solid, waxy, unsaturated steroid alcohols, anti-inflammatory, analgesic agents and occur in animal sex hormones.

Plant sterols are called phytosterols, some existing naturally free and some exist in combination as esters or glycosides.

Phytosterols are the plant sterols, and they differ from animal sterols, because they have extra ethyl or methy substituent occurs in the chemical side chain.

They are obtained from vegetable oils or from industrial wastes, are used occurs in pharmaceuticals, food additives and cosmetics.

Phytosterols occur occurs in almonds, cashews, peanuts, sesame seeds, sunflower seeds, whole wheat, maize, soybeans, and many vegetable oils.

Sterols (steroids) occurs in animal sex hormones, squalene (in shark liver oil), cephalosporin, gonane, hopane, diplotene, lupeol.

β-sitosterol, C₂₉H₅₀O, oestrogenic activity, occurs in human leukemia cells, occurs in vegetable oils, nuts, and in avocado. source

The most commonly occurring phytosterols are Campesterol, Beta-sitosterol, and Stigmasterol.

Sterols

Sterolins

Sterolins¶

Sterolins are glucosides, which are molecular structures joined to the sterol.

Sterolin is easily destroyed, and without it, the sterol does not have the same immune-enhancing benefits.

In nature, plants never contain sterols only, because the sterols are always associated with their glucoside sterolins.

Carotenes¶

Carotenes, C40Hx

Alpha-carotene (α-carotene), C40H56, is a carotenoid pigment, Vitamin A precursor, and is used as yellow food colouring, occur in green leaves of many plants, including carrot roots, maize seed, oil palm and in tomato.
Beta-carotene (β-carotene), C40H56, strongly-coloured red-orange cyclic carotenoid pigment, an antioxidant, an important provitamin A carotenoid precursor, wide occurrence most green leaves and coloured fruits and vegetables, used as yellow food colouring of fats, e.g. margarine, used as sunscreen, red-purple oil, not soluble in water, and occurs in dark orange sweet potato.

β-Carotene, Type II, synthetic, 95% (HPLC), crystalline, β, β-Carotene, Provitamin A, C 40 H 56, commercial

* Gamma carotene (γ-carotene), C₄₀H₅₆, carotenoid pigment, Vitamin A precursor source

β-Carotene, Type I, synthetic, 93% (UV), powder, β, β-Carotene, Provitamin A, C₄₀H₅₆ source

β-Carotene, Type II, synthetic, 95% (HPLC), crystalline, β, β-Carotene, Provitamin A, C₄₀H₅₆ source

Carotene epoxide, zeta-Carotene epoxide, (1,2-Epoxy-1,2-dihydro-z-carotene), C₄₀H₆₀O, occurs in garden tomato, and cherry tomato, (Solanum lycopersicum var. cerasiforme). source

Sesquiterpenoids¶

Sesquiterpenoids C₁₅H₂₄, Natural sesquiterpenoids. source

Cuparene, C₁₅H₂₂, occurs in (Perilla frutescens). source

Allo-aromadendrane, C₁₅H₂₄, woody odour, occurs in allspice, Tasmanian gum, (Eucalyptus globulus). source

Alpha-bisabolene, C₁₅H₂₄, Caryophyllane, (Cedrene in essential oil of cedar). source

Beta-bisabolene, C₁₅H₂₄, balsamic odour, food additive. source

Cadinane, C₁₅H₂₈, cadinene, from cade oil in (Juniperus oxycedrus), occurs in prickly juniper, sharp cedar. source

Debneyol, C₁₅H₂₆O₂, a sesquiterpenoid propane-1,2-diol, occurs in (Nicotiana fragrans), and (Nicotiana debneyi), and in cigarette tobacco source

.

Steroid saponins¶

Agavoside A, C₃₃H₅₂O₉, a steroid saponin, anti-leukaemic, occurs in green vegetables, occurs in (Agave americana). source

Asparagoside B, C₃₃H₅₆O₉, a steroid saponin, occurs in (Aspagus officinalis). source

Avenacoside A, C₅₃H₈₂O₂₃, a steroid saponin, occurs in cereals, (Avena sativa). source

Digitogenin, C₂₇H₄₄O₅, a sapogenin, occurs in (Digitalispurpura). source

"Digitonin, Digitin, C₅₆H₉₂O₂₉, a steroid saponin, toxic, solubilizes lipids, occurs in (Digitalis purpurea). source

Diosgenin, C₂₇H₄₂O₃, a steroid sapogenin, nitogenin, a hexacyclic triterpenoid, occurs in bark of wild yam, (Discorea villosa). source

It is used to synthesise steroids, e.g. cortisone, pregnenolone and progesterone, apoptosis inducer, antiviral, antineoplastic.

Gitoxygenin, C₂₃H₃₄O₅, an hydroxy steroid, acute toxic, occurs in (Strophanthus divaricatus).br> Nuatigenin, C₂₇H₄₂O₄, an hydroxy-steroid, occurs in oats (Avena sativa) source

Osladin, C₄₅H₇₄O₁₇, a steroid saponin, very sweet taste, in fern rhizome (Polypodium vulgare) source

Ruscogenin, C₂₇H₄₂O₄, a triterpenoid, irritant, used to treat haemorrhoids, anti-hypertensive, occurs in (Ruscus aculeatus). source

Ruscoside, C₅₀H₈₀O₂₃, a steroid saponin, anti-inflammatory, occurs in (Ruscus aculeatus). source

Sarsaparilloside, C₅₇H₉₆O₂₈, a steroid saponin, used to flavour confectionary, occurs in sarsaparilla roots and Smilax rhizomes. source

Sarsasapogenin, C₂₇H₄₄O₃, a sapogenin, occurs in Spanish sarsasparilla (Smilax aspera), asparagus, and in Sarsaparilla root (Radix sarsaparilla) source

Paclitaxel, (C₄₅H₅₁NO₁₄), Taxol A, Yewtaxan, "taxol", a tetracyclic diterpenoid, appears as needles or fine white powder, inhibits mitosis, stabilizes microtubules leading to cell death, so it is an antileukaemia and antitumour medicine, can cause female reproductive toxicity and male reproductive toxicity, occurs in the bark of the Pacific yew tree, (Taxus brevifolia). source

The name "Taxol" is now a registered trade mark.

Triterpenoid saponins¶

Deltonin, C₄₅H₇₂O₁₇, a triterpenoid, used in synthesis of steroid hormones, occurs in (Dioscorea deltoidea). Dioscin, C₄₅H₇₂O₁₆, a triterpenoid, treat liver injury, potential anticancer, antifungal, occurs in (Dioscorea nipponica), Costus, and Trigonella. Gitogenin, C₂₇H₄₄O₄, a triterpenoid, in (Digitalis purpurea), foxglove Gitonin, C₅₀H₈₂O₂₃, a triterpenoid, steroidal saponin, in (Digitalis purpurea), foxglove leaves Hocogenin, C₂₇H₄₂O₄, a triterpenoid, sapogenin of Agavoside A, irritant, is used to prepare steroid hormones, occurs in Agave. Parillin, Sarsasaponin, Smilacin, C₅₁H₈₄O₂₂, a triterpenoid, haemolytic, antibiotic, cancerostatic, occurs in roots of Sarsaparilla (Smilax ornata). Tigogenin, C₂₇H₄₄O₃, a triterpenoid, steroidal saponin, occurs in Fenugreek (Trigonella foenum-graecum), in (Digitalis lanata), and in Sisal (Agave sisalana). Tigonin, C₅₆H₉₂O₂₇, a triterpenoid, occurs in Digitalis, and in Chlorogalum Yamogenin, C₂₇H₄₂O₃, a triterpenoid sapogenin, occurs in (Trigonella foenum-graecum), fenugreek, in asparagus, and in Smilax. source

Diterpenoids¶

Ajugarin I C₂₄H₃₄O₇, a diterpenoid, insect antifeedant, has anti-neuropathic pain activity, and occurs in leaves of (Ajuga remota). source

Andrographolide C₂₀H₃₀O₅, a diterpenoid, bitter taste, anti-inflammatory, antioxidant, anti-cancer, used in many traditional medicines to treat infectious diseases and cardiovascular poblems, occurs in (Andrographis paniculata). source

Candletoxin A C₃₅H₄₄O₉, a diterpenoid, toxic, in (Euphorbia poisonii) latex. source

Caryoptin C₂₆H₃₆O₉, a diterpenoid, bitter, insect antifeedant, in Caryopteris. source

Geranylgeraniol C₂₀H₃₄O, a diterpenoid, geranylgeraniol, occurs in linseed oil (Linum usitatissum), in wood oil Australian red cedar (Toona ciliata). source

Gibberellin C₁₉H₂₂O₆, a pentacyclic diterpenoid, (Gibberellin A3, GA, GA3, Gibberellic acid), gibreskol,, irritant, a C19-gibberellin, monocarboxylic acid, white powder, potent plant hormone that regulates growth and cell elongation, stimulates cells of germinating seeds. source

Ginkgolide C₂₀H₂₄O₉, a diterpenoid, irritant, bitter, Platelet Activating Factor antagonist, bronchdilator, anti-asthmatic, and occurs in (Ginkgo biloba) root bark and leaves. source

Gnidicin C₃₆H₃₆O₁₀, a diterpenoid, thymeleatoxin A, anti-tumour, and occurs in in Gnidia. source

Grayanotoxin Grayanotoxin I, (GI), Rhodotoxin, Asebotoxin, Acetylandromedol, C₂₂H₃₆O₇, tetracyclic diterpenoid, acetate ester, phytotoxin, antihypertensive, occurs in Rhododendron and its honey. source

Labdane C₂₀H₃₂O₂, a diterpenoid, antifungal and occurs in (Nicotiana glutinosa) epicuticle leaf wax. source

Mascaroside C₂₀H₃₆O₁₁, a diterpenoid, naphthofuran, very bitter, in (Coffea viyanneya) beans. source

Neocembrene C₂₀H₃₂, a diterpenoid, cembrene A, a macrocycle, and occurs in (Picea obovata). source

Palmarin C₂₀H₂₂O₇, a diterpenoid, tinosporide, arcangelisin, isochasmanthin, organo-oxygen compound, organic heterotricyclic compound, bitter, was used in (Radix columba) tonic, occurs in Jateorhiza roots. source

PhorbolPhorbol, C₂₀H₂₈O₆, a tetracyclic diterpenoid, acute toxic, cyclic ketone, a tertiary alcohol, an acyclic diterpene alcohol, white solid, irritant phorbol, Phorbol diesters may be anti-leukaemic and carcinogenic, occurs in (Croton tiglium) seed oil. source

Phytol, trans-Phytol, (20H₄₀O), a diterpenoid, acyclic diterpene alcohol, irritant, environmental hazard, used to prepare vitamin E and vitamin K1, modulates transcription in cells, long-chain primary fatty alcohol, oily liquid, modulates transcription in cells, a decomposition product of chlorophyll. source

List of Phytochemicals, Araloside toTangshenoside Phytochemicals

Contents

16.0.0¶

Araloside¶

Araloside, C₄₇H₇₄O₁₈, Chikusetsusaponin IV, a triterpenoid saponin, occurs in Japanese angelica tree, (Aralia alata), (Caragana sinica), and in (Panax pseudoginseng). source

Aspidin¶

Aspidin, C₂₅H₃₂O₈, polystichin, antihelminthic source

It occurs in Aspidium roots, in Dryopteris, antihelminthic.

Astragalosides¶

Astragalosides are chemicals from Astragalus, for example:

Astragaloside IV, C₄₁H₆₈O₁₄, is a pentacyclic triterpenoid, anti-inflammatory, neuroprotective, antioxidant. source

It assists new blood vessels formation, and it inhibits formation of abnormal fibrous tissues.

"Astragaloside IV Astragalus Root Extract Powder" is sold as a health food.

Betavulgarin¶

Betavulgarin, C₁₇H₁₂O₆, antifungal isoflavonoid, is an hydroxyisoflavone. source

It occurs in (Beta vulgaris), (Beta lomatogona), and in (Iris tingitana).

"Brassicasterol¶

Brassicasterol, C₂₈H₄₆O, a phytosterol, a component of plant cell membranes, occurs in seed oil of (Brassica rapis). source

It is used as a biomarker for the presence of marine algae

Brazilin¶

Brazilin, C₁₆H₁₄O₅, is an organic heterotetracyclic compound, is a red pigment. source

It occurs as a red pigment, Natural Red 24, in Brazil-wood (Caesalpinia echinata), and in sappan-wood (Caesalpinia sappan).

"Brazil wood" was originally called "bresel wood".

Charantin¶

Charantin, glucoside, (C₃₅H₆₀O₆) + (C₃₅H₅₈O₆), hypoglycaemic so may cause low blood sugar. source

It occurs, in Asian bitter melon (Momordica charantia).

Daidzin,¶

Daidzin,

Daidzin, C₂₁H₂₀O₉, isoflavone, anti-oxidant, daidzoside, anti-carcinogenic, anti-antheroscerotic source

It occurs in TCM Chinese medicine and it is used to treat alcohol abuse.

It occurs in kudzu (Pueraria lobata).

Daidzein¶

Daidzein, C₁₅H₁₀O₄, dihydroxyisoflavone, a phytoestrogen, is anti-inflammatory, anti-microbial, antioxidant, phytoestrogenic, antineoplastic. source

It occurs in soybean, tofu, alfalfa sprouts, red clover, chickpeas, peanuts, kudzu, (Streptomyces padanus), and in (Glycine soja).

Equol, C₁₅H₁₄O₃, (S)-Equol, a hydroxyisoflavan, is the main active product of daidzein metabolism produced by microflora in the gut. source

It is a biomarker for the consumption of soy beans and other soy products.

It occurs in (Punica granatum).

Daidzin, C₂₁H₂₀O₉, a glycosyloxyisoflavone, anti-oxidant, anti-carcinogenic, anti-antheroscerotic, in TCM Chinese medicine, is used to treat alcohol abuse. source

It occurs in (Pueraria lobata), (Salvia hispanica), and (Begonia nantoensis).

Eleutheroside¶

Eleutheroside B, C₁₇H₂₄O₉, syringin, phenyl propanoid glycoside occurs in Siberian ginseng, (Syringa vulgaris). source

Eleutheroside A, C₃₅H₆₀O₆, daucosterol, saponin and sterol glycoside, occurs in Siberian ginseng source

Eriodictiol¶

Eriodictiol, C₁₅H₁₂O₆, eriodictyol, a tetrahydroxyflavanone, flavanone glycoside source

It occurs in (Camellia sinensis), (Prunus serrulata), and in citrus fruits.

Esculeoside¶

Esculeoside A, C₅₆H₉₅NO₂₉, a steroid alkaloid, glycoside, a steroid saponin, occurs in cherry tomato (Solanum lycopersicum). source

Estradiol¶

Estradiol, C₁₈H₂₄O₂, oestradiol, female sex hormone, an estrogen (oestrogen), an hydroxy steroid, female growth hormone for reproductive organs. source

It is used in contraceptives (OCPs), but the synthetic steroid ethinyl estradiol, C₂₀H₂₄O₂, is more suitable for oral contraception. source

It is commercially available in hormone therapy products for treating menopause problems, such as hot flashes.

It is used in oral tablets, vaginal rings, transdermal patches, sprays, gels, and creams.

See diagram 16.3.5.3. Cholesterol, cholic acid, bile salt, estradiol, progesterone, northindrone

Formononetin¶

Formononetin, C₁₆H₁₂O₄, biochanin B, formononetol, is a methoxyisoflavone, and a phytoestrogen. source

It occurs in (Dalbergia nigrescens), and in (Glycyrrhiza pallidiflora).

It caused reproductive malfunction, "clover disease”, in Australian sheep grazing on subterranean clover (Trifolium subterraneum)

Genistein¶

Genistein, C₁₅H₁₀O₅, an isoflavone, phytoestrogen, antineoplastic, from soy products, induces apoptosis, antioxidant, anti-inflammatory, anti-atherosclerosis source

It is used as an antineoplastic and antitumor agent.

Genistein has antihelmintic activity, and it is the active ingredient in (Felmingia vestita), a plant traditionally used against worms infections of humans

It has shown to be effective in the treatment of common liver fluke, pork trematode and poultry cestode.

It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women.

Natural sources of genistein include tofu, fava beans, soybeans, kudzu, (Salvia hispanica), and (Glycine soja).

It has antihelmintic activity, and it is the active ingredient in (Felmingia vestita), traditionally used against worms, liver fluke, pork trematode and poultry cestode

It may be an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women.

Glycone and aglycone¶

glycoside (hydrolysis) → glycone (sugar group) + aglycone (non-sugar group) source

The sugar group is called a "glycone" and the non-sugar group is called an "aglycone".

The glycone can consist of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide).

Upon hydrolysis, a sugar and non-sugar component (aglycone) are formed.

An aglycone, is the non-sugar component formed when a glycoside is hydrolysed.

It is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom.

For example

Vanilla species → pods → Glucovanillin, (a glucoside) + β-glucosidase enzyme → vanillin source

Glucovanillin (hydrolysis) → glycone glucose + aglycone vanillin source

C₁₄H₁₈O₈ + (glucosidase) → C₆H₁₂O₆ + C₈H₈O₃ source

Gymnemic acid¶

Gymnemic acid I, C₄₃H₆₆O₁₄, triterpenoid glycoside, triterpenoid saponin, flavour modifier, makes food tasteless, occurs in leaves of (Gymnema sylvestre). source

Haeme¶

Haeme C₄₉H₅₆O₆N₄Fe, (heme), occurs in haemoglobin, a globular protein in animals source

Haeme A, is a cytochrome oxidase ligand complex, (Greek haîma 'blood' + Latin globus 'ball, sphere')

Haemoglobin is the protein that carries oxygen in the blood.

The haem group causes the red colour of blood.

The different kinds of haem are Haeme A, B, C and O.

Haeme A is a cytochrome oxidase ligand complex, C₄₉H₅₆O₆N₄Fe, a tetradentate ligand. source

The most common type is Haeme B, C₃₄H₃₂O₄N₄Fe. source

The "quaternary proteins" have four joined tertiary proteins, e.g. haemoglobin.

The "transition metals" form complex ions and often have catalytic activity, e.g. Fe in haemoglobin molecule.

Porphyrin chelates include haeme, in haemoglobin, bonded to iron (II) ion, and chlorophyll bonded to Mg (II) ion.

Glycosylated haemoglobin

Glycosylated hemoglobins are minor components of human red cell hemoglobin.

They are formed by condensation of glucose with hemoglobin A.

Glycosylated hemoglobins are increased X 2 - X 3 in the red blood cells of diabetic patients, so are an indicator for assessing the control of diabetes mellitus.

HbA1c is a blood test to diagnose type 2 diabetes and monitor blood sugar levels in people with diabetes.

It measures the average blood sugar level from the past 8 to 12 weeks.

. HbA1c is glycated haemoglobin, which measures how much haemoglobin in the blood has glucose (sugar) attached to it..

(Hb), haemoglobin is a protein in red blood cells that carries oxygen throughout the body.

(A1c) is the glucose attached to the haemoglobin.

See: Tests for haemoglobin, Hematrace test

See diagram 16.3.5.4. Bilin, C19H14N4, a linear tetrapyrrole

See diagram 16.3.5.2.1. Haeme (heme), C49H56O6N4Fe

See diagram, Biliverdin, a bile pigment, C33H32N4O6-2

Hederin¶

Alpha-Hederin, C₄₁H₆₆O₁₂, koronaroside A, a pentacyclic triterpenoid saponin, anti-inflammatory, antifungal, strong haemolytiic activity source

It occurs in stem bark of (Kalopanax pictus), (Nigella sativa), (Lonicera macrantha), and in (Anemone taipaiensis).

Beta-Hederin, C₄₁H₆₆O₁₁, eleutheroside K, a triterpenoid saponin, antifungal, strong haemolytic activity source

Beta-Hederin occurs in leaves of ivy (Hedera helix), (Akebia quinata), and Anemoclema.

Hesperetin¶

Hesperetin, C₁₆H₁₄O₆, a trihydroxyflavanone, antioxidant, antineoplastic agent, is the predominant flavonoid in lemons and oranges. source

It occurs in (Camellia sinensis).

Irilone¶

Irilone, C₁₆H₁₀O₆, a methylenedioxyisoflavone, an hydroxyisoflavone, immunomodulator, antineoplastic agent, inhibits growth of malignant cells. source

It occurs in red clover (Trifolium pratense), and in Iris.

Magnolol¶

Magnolol, C₁₈H₁₈O₂, a biphenyldiol, in traditional herbal medicine, antifungal, occurs in bark of (Magnolia grandiflora), and in (Magnolia officinalis). source

Matairesinol¶

Matairesinol, C₂₀H₂₂O₆, a phenylpropanoid, lignan, gamma-butyrolactone, is a phytoestrogen. source

It occurs in flax seed, sesame seed, rye bran and meal, oat bran, poppy seed, strawberries, blackcurrants, and broccoli.

Menthol¶

1. Menthol, C₁₀H₂₀O, C₁₀H₁₉OH, dl-Menthol, (2-Isopropyl-5-methylcyclohexanol), is a white crystalline solid with a peppermint odour and taste. source

Menthol is an organic compound made synthetically or obtained from peppermint or mint oils with flavoring and local anesthetic properties.

Menthol, hexahydrothymol, a monoterpene, peppermint camphor (a methyl cyclohexanol) (mint flavour, peppermint flavour), eight sterioisomers

Menthol, mint camphorrubifacient, white crystalline organic compound resembling camphor, extracted from oil of peppermint.

This compound is solid at room temperature and melts at about 37 oC.

2. Menthol is used occurs in perfumes, menthol cigarettes, mild topical anaesthetic, and as a mint flavouring.

Menthol binds to receptors on temperature-sensin nerve cells to give cooling sensation.

Menthol is antipruritic, reduces itching, so is used for relief of minor sore throat and mouth irritation.

When added to pharmaceuticals and foods, menthol functions as a fortifier for peppermint flavours.

It has a counterirritant effect on skin and mucous membranes, thereby producing a local analgesic or anesthetic effect.

The pure solution may damage eyes and sensitize skin, but < 10 mg occurs in throat medicine lozenges is harmless.

3. Menthol occurs in the peppermint plant, a hybrid mint (Mentha X piperita) and in wild mint (Mentha arvensis).

Spearmint, "mint", garden mint, (Mentha spicata), Lamiaceae

It occurs in peppermint leaves, where the concentration of menthol increase with age.

Menthol breaks down with heating, so peppermint leaf is not usually cooked.

Myrosinase¶

Myrosinase enzyme, is also called glucosinolase, thioglucosidase, thioglucoside glucohydrolase.

Myrosinase enzyme is a singrinase and a sinigrase.

It can catalyze the hydrolysis of glucosinolates. glucosinolate + myrosinase → toxic compounds to deter grazing. source

glucosinolate + myrosinase → glucose + isothionate source

glucosinate + myrosinase → thiocynates (SCN-), and nitriles (R-C triple bond N) source

Ononin¶

Ononin, C₂₂H₂₂O₉, isoflavone glucoside, formononetin-7-O-glucoside, Chinese medicine. source

It occurs in (Radix astragali), (Daphnia pulex), and in (Astragalus hoantchy).

idth="100%" size="2">Pallidol

Pallidol, C₂₈H₂₂O₆, a tetracyclic stilbenoid, antioxidant, antifungal, polyphenol source

It occurs in red wine, Cissus, and in Parthenocissus.

Phenanthracene¶

Phenanthracene, C₁₄H₁₀, phenanthrin, colourless monoclinic crystals, has a faint aromatic smell, is a polycyclic aromatic hydrocarbon. source

It consists of three fused benzene rings.

It occurs in (Nicotiana tabacum), and in (Buddleja lindleyana).

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C₁₄H₁₀. source

Picein¶

Picein, C₁₄H₁₈O₇, glycoside, has antioxidant and anti-inflammatory properties in cellular and plant studies. source

It occurs in (Rhodiola crenulata), and (Salvia officinalis).

Protodioscin¶

Protodioscin, C₅₁H₈₄O₂₂, glycoside, steroid saponin, beta-D-glucoside, is a pentacyclic triterpenoid. source

It occurs in aphrodisiac puncture vine, (Tribulus terrestris), yams, asparagus, fenugreek, and in Dioscorea.

Pterocarpan¶

Pterocarpan, C₁₅H₁₂O₂, is the simplest member of the class of pterocarpans, which occur only occurs in Fabaceae, e.g. Phaseolin, C₂₀H₁₀O₄, phytoalexin, It occurs in French bean, (Phaseolus vulgaris), and in the stems of (Erythrina subumbrans). source

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Rottlerin¶

Rottlerin, C₃₀H₂₈O₈, mallotoxin, pink-brown pigment, toxic, antihelminthic, is used to treat tumours in India, and is used as silk dye. source

It occurs in Rottleria, and in Mallotus.

Silybin¶

Silybin, C₂₅H₂₂O₁₀, silibinin, a flavonolignan, polyphenol, antioxidant, antineoplastic, anticancer, protect liver cells against toxins. source

It occurs in milk thistle, (Silybum marianum), (Silybum eburneum), and in (Aspergillus iizukae).

Tangshenoside¶

Tangshenoside I, C₂₉H₄₂O₁₈, a pentanoic acid, occurs in (Codonopsis pilosula). source

Dang shen, and Codonopsis tangshen are plants widely and used in traditional Chinese medicine.

Leghemoglobin¶

Leghemoglobin, a protein that carries heme is a phytoglobin, a globular plant protein, which occurs in nitrogen-fixing bacteria, and in the root nodules of legumes.

It is an oxygen carrier and a hemoprotein, produced by legumes occurs in response to the roots being infected by nitrogen-fixing bacteria, Rhizobium.

Like haemoglobin, it is red in colour and is an essential component for nitrogen fixation by legumes.

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