Phytochemicals, Plant extracts, Alkylphenols to Tyrosols.

School Science Lessons
2024-06-20

Phytochemicals
(topic16e)
Phytochemicals are carotenoids and polyphenols, and include phenolic acids, flavonoids, stilbenes or lignans
Flavonoids include flavanones, flavanols, flavonols, flavones, anthocyanidins and isoflavones.
Flavanols include catechins, epicatechins, and proanthocyanidins. Phytochemicals include essential nutrients, but also non-digestible dietary fibers and phytotoxins Contents
Aminoglycosides
Anthocyanidins
Anthoxanthins
Anthraqinone glycosides
Betalains, betains
Coumarin glycosides
Dihydrochalcones
Estradiol
Flavonoids
Glucosides
Glucosinolates
Hydroxybenzaldehydes
Hydroxybenzoic acids
Hydroxybenzoketones
Hydroxycinnamic acids
Hydroxyphenylacetic acids
Hydroxyphenylpropenes
Irilone
Isoflavonoids, isoflavones, phytoestrogens
Legheamoglobin
Lignans
Myrosinase
Neoflavonoids, polyphenols
Organosulfur compounds
Phenolic acids
Phenolic ketones
Phenolics
Phenolic terpenes
Phycobilins
Phycobiliproteins
Phytochromes
Plant extracts
Polyphenol flavonoids
Polyphenols
Polyvinyl pyrrolidene, povidone, PVP
Porphyrins
Saponins
Steroids
Sterolins
Sterols
Stilbenes and Stilbenoids
Tetrapyrroles
Tyrosols

Acetylenes, (Carbohydrates and Lipids)
Acetylenes (polyacetylenes) have acetylenic group in their structures and are toxins.
Capillin, Cicutoxin, Falcarinol, Mycosinol, Safynol, Stearolic acid, Wyerone acid

Miscellaneous Aliphatics, (other Carbohydrates and Lipids)
Lactones: Ranunculin, Tuleposide A, Nonalactone (coconuts), Undecalactone (peaches), Chelidonic acid, Cucurbic acid, Jasmonic acid, Ethyl acetate, Jasmone, Leaf Aldehyde

Amino acids, (Nitrogen-containing compounds)
Amino acids | 16.1.0 Amino acids functional groups
Alamine, Alliin, Arginine, Asparagine, Aspartic acid, Citrulline, Cysteine, Cystine, Dopa, Glutamic acid, Glycine, Histidine, Leucine, Lysine, Methionine

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 derived from Streptomyces bacteria, have the suffix "mycin", e.g. Neomycins, B and C, Neomycin E and Streptomycin.
Aminoglycosides derived from Micromonospora bacteria, have the suffix "micin", e.g. Kanamycin A, Amikacin, Tobra mycin, Dibehacin, Gentamucin, Amikacin hydrate, C22H43N5O13.xH2O, broad spectrum antibiotic

Anthocyanidins
Anthocyanidins are natural dyes, coloured pigments, antioxidative, antimicrobial activities, improve visual and neurological health
, Anthocyanidins are anthocyanin aglycones
Anthocyanidin, Aurantinidin, Capensinidin, Cyanidin, Delphinidin, Europinidin, Hirsutidin, Malvidin, Pelargonidin, Peonidin, Petunidin, Pulchellidin, Rosinidin

Anthocyanins
Anthocyanins are glycosides of anthocyanidins, e.g. Cyanin is Cyanidin3,5-di-O-glucoside.
Butein, Cyanin, Delphindin, Gentiodelphin, Isobutrin, Luteolinidin, Malvin, Pelargonin
Anthocyanins, glycosides, C15H11O + (glycosides of anthocyanidins), red, blue and purple flavonoids
They occurs in cell sap, natural antioxidants (blueberry, boysenberry, black raspberry, black currant pigments) (cyanidin chloride), C15H11ClO6, e.g. the anthocyinidin cyanidin (cyanidine) C15H11O6, malvidin C17H15O7, rosinidin.
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, pecans, pistachios, potatoes, red wine.

Anthoxanthins
Anthoxanthins, (flavones and flavonols) are water-soluble white to yellow flavonoid pigments, antioxidant
They occur in potatoes, cauliflower, onions, parsnips, bananas.
Anthoxanthins cause bright white colour of food in acid medium, yellow in alkaline medium.
Colour in flower petals depends on the soil minerals.
Anthoxanthins, e.g. quercetin, are used for vegetables in a good diet and as food additives
Canthaxanthin

Anthraqinone glycosides
Anthraqinone glycosides occur in alizarin, hypericin, physcion, rhubarb, Cascara, Senna, Aloe

Aviculin, C26H34O10, in Knotgrass
1-Acetoxypinoresinol, C22H24O8
Honokiol, C18H18O2, neilignan biphenol, spicy odour, in traditional Asian herbal medicine, analgesic, used to treat anxiety.
Magnolol, C18H18O2, in traditional herbal medicine, antifungal, in bark of Magnolia grandiflora, M officinalis.
4-O-methylhonokiol, C19H20O2, occurs in bark of Magnolia grandiflora

Benzofurans, Benzofuranoids, Benzopyranoids, (Phenolics, Polyphenols)
16.2.14 Benzofuranoids

Betalains, betains (Glycosides)
Betalains, betains, in beets, Beta vulgaris (beetroot extract), in Swiss chard Carpobrotus, in all Azoiaceae, in cactus Opuntia species, in Amaranthus spinosus leaves, in Bougainvillea glabra floral bracts, in Phytolacca, in Portulaca
Water soluble glycoside plant pigment in vacuoles, function in plants not known, never occurs in plants with anthocyanins.
Aromatic indole derivative
1. Betacyanins red-violet
2. Betaxanthins yellow-orange, Indicaxanthin | Red dragonfruit |
Betalains, beetroot 3. Indicaxanthin beets, sicilian prickly pear. 4. Vulgaxanthin beets.

Betavulgarin, antifungal isoflavonoid, C17H12O6
Betavulgarin, (2'-Hydroxy-5-methoxy-6, 7-methylenedioxyisoflavone), an hydroxyisoflavone, hydroxyisoflavone, methoxyisoflavone)
It occurs in Beta vulgaris.
Daidzein, C15H10O4, Dihydroxyisoflavone, in soybean, in tofu, anti-inflammatory, anti-microbial, antioxidant, phytoestrogenic, estrogenic metabolite Equol is the main active product of daidzein metabolism produced by microflora in the gut, biomarker for the consumption of soy beans and other soy products, antineoplastic, phytoestrogen.
Daidzin, C21H20O9, isoflavone, anti-oxidant, daidzoside, anti-carcinogenic, anti-antheroscerotic, in TCM Chinese medicine, treat alcohol
abuse, in Pueraria lobata, kudzu
Formononetin, C16H12O4

Cardiac glycosides (steroidal glycosides, digitalis glycosides, cardiovascular glycosides) (aglycone steroidal nucleus) cymarin, (steroidal cardenolide aglycone), in plants, heart stimulants, in Digitalis, Convallaria
Digitalis glycosides, e.g. Digitoxin, C41H64O13, Digoxin, C41H64O14, Digitalis lanata
Scilla glycosides, e.g. proscillardin, C30H42O8, Scilla, Drimia maratima
Strophanthus glycosides, e.g. Ouabain (G-strophanthin), C29H44O12, arrow poison, Strophanthus gratus, Acokanthera schimperi

Cardenolide
Cardenolide, C23H34O2 is a steroid molecule, but "cardenolides" are usually cardenolide glycosides, e.g.Cymarine | Digitoxin | Digoxin | Ouabain
| Strophanthin |
Cardenolides are cardiac-active steroids, with five- or six- lactone ring and a sugar moiety and occur mainly in toxic latex of Asclepidaceae.
Apocynaceae, Moraceae, e.g. ouabain C29H44O12.8H2O, in Acokanthera ouabaio (Apocynaceae)
See diagram: Cardenolide

Carotenes
Carotenes are terpenoids, isoprenoids
Carotene is a carotenoid
Carotene (Latin carotin, carrot, C40Hx, in many plants, photosynthetic pigments.
Carotenes are orange pigments, which cause the colour of carrots.
α-Carotene occurs in vitamin A, carrots, pumpkins, maize, tangerine, orange.
β-Carotene, C40H56, beta-carotene, cyclic carotene, strongly-coloured red-orange pigment, is a precursor of the vitamin A.
It occurs in dark leafy greens, red, orange and yellow fruits and vegetables.
γ-Carotene occurs in vitamin A.
δ-Carotene
ε-carotene
Lycopene occurs in Vietnam Gac, tomatoes, grapefruit, watermelon, guava, apricots, carrots, autumn olive.
Phytofluene occurs in star fruit, sweet potato, orange.
Phytoene occurs in sweet potato, orange.

Carotenoids, (C₄₀ tetraterpenoids), (Terpenes and Terpenoids)
Carotenoids are classified depending on the presence or absence of oxygen: Carotenes and Xanthophylls
Carotenes, C40H56, are simple orange or red unsaturated hydrocarbons, many isomers, in carrots, precursor of vitamin A
Xanthophylls are yellow or brown oxygenated carotenoids, carotene derivatives, (C40H56)n
Xanthophylls are hydrocarbons + oxygen, and are usually yellow pigments.
Xanthophylls, contain oxygen, usually yellow pigments, in the leaves of most plants.
Xanthophylls are oxygenated carotenes, the yellow leaf pigments of leaves, synthesized within plastids without need for light for synthesis.
However, theyt do absorb some wavelengths not absorbed by chlorophyll, so appear in etiolated leaves and plants with chlorosis nutrient deficiency.
In the leaves of deciduous plants, green chlorophyll covers up the yellow from the carotenoid pigments, except during autumn.

Catechins, green tea, grapes
Catechins are polyphenolic antioxidants with phytotonic properties, used for treating obesity.
Catechins are water soluble polyphenols and antioxidants that are easily oxidized, flavon structure and are called flavonoids.
Catechin, Catechinic acid, Catechol, Cianidanol, C15H14O6, flavonoid, flavan-3-ol, colourless, (isomer epicatechin), bioflavonoid, tannin, antioxidant, anti-viral, anti-bacterial,
Catechin occurs as both (+)-catechin and (-)-epicatechin (cis) forms, (+)-catechin is a polyphenolic antioxidant, an antioxidant flavonoid, is found in woody plants.
Also it occurs in woody plants, in willow catkin, Salix haemostatic, Potentilla fragarioides, and in Salix capra (willow catkin).
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.
Catechins are polyphenolic antioxidants with phytotonic properties, used for treating obesity.
Catechins occur in many plant species of white tea, green tea, black tea, grapes, apple, cocoa, lentils, black-eyed peas.
Catechin is a major constituent of 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.
Catechin is used to treat liver diseases, e.g. hepatitis, possible radical scavenger, but excess treatment causes haemolysis and renal failure, skin rashes.
Catechin hydrate, C15H16O7, C15H14O6.xH2O, polyphenolic antioxidant, Chinese medicine, antioxidant, free radical scavenger, suppresses DNA strand breaks
The black tea oxidation process reduces catechin in black tea.
(+)-catechin, Cianidanol, C15H14O6, antioxidant flavonoid, in woody plants.
Dark chocolate and red table wine contain high concentrations of catechins and their compounds.
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.
The most common catechin isomers are (+)-catechin, called catechin, and (-)-catechin, called epicatechin (entcatechin).

Charantin
Charantin, C36H60O6, β-sitosteryl glucoside, white crystals, neutral, tasteless, hypoglycaemic, because causes low blood sugar levels.
It occurs in Asian bitter melon (Momordica charantia)
Digitonin
Foxglove
Diosgenin diosgenin contains disoscin glycoside.
It occurs in bark of wild yam, Discorea villosa.
Eleutheroside A, daucosterol, C35H60O6, in Siberian ginseng
Esculeoside A, C56H95NO29, Solanum lycopersicon var.cerasiforme
Osladin
Protodioscin, C51H84O22, Puncture vine, Solanine, Hedera, Ruscus, Smilax sarsasspiralla, Withania, Yucca schidigera
Agavaceae, steroidal saponins
Allium, Beth root, Trillium erectum
Climbing oleander, rose oleander, Stropanthus gratus, steroid saponins, cardiac tonic
Foxglove, Digitalis purpurea, steroid saponins, cardiac tonic
Indian squill, Drimia indica, steroid saponins, cardiac tonic, congestive cardiac failure
Oleander, Nerium oleander, Oleandrin, C32H48O9, steroid saponin, from toxic sap, for suicide, formerly had therapeutic uses.
Alfalfa Lucerne, Medicago sativa, hederagenin, C30H48O4, soyasaponin 1
ChickpeasCicer arietinum
Horse chestnut, Aesculus hippocastanum, saponins that foam in water.
Maesa balansae in Vietnam is used to treat leishmaniasis.
Oleanolic acid, C30H48O3
Sarsaparilla, sarsapogenin, smilognin
Soapnut, Sapindus mukorossi
Soapwort, Saponaria officinalis, saponarin, C27H30O15, white-yellow, flavonoid, diglycoside
Soap bark tree, Quillaja saponaria (bark has sapogenin content 10 %, harmful, irritant)
Soya beans
Wavy-leafed soap plant, Chlorogalum pomeridianum

Coumarins, (Phenolics, Polyphenols)
Coumarin
Angelicin, Cichorin, Coumarin, Decursinol, Esculetin, Psoralen, Scopoletin, Umbelliferone

Chromones, Chromone glycosides, Chromenes, (Phenolics, Polyphenols)
Chromone | 16.3.4.1a Benzofuranoids

Coumarin glycosides (Glycoside)
Coumarin glycosides (coumarin aglycone), apterin, corylifolin, psoralin (psoralen Psoralea corylifolia)

Cucurbitacins
Cucurbitacin A, Bryonia alba, bryony, white bryony, poisonous, cucurbitacins saponins, English mandrake, kua-lou, ladies' seal, tamus, tetter berry, wild bryony wild hops, wild vine, noxious weed, Cucurbitaceae.
It functions as a protective plant taste repellent.
Eleutheroside B, syringin, C17H24O9, occurs in Siberian ginseng, Syringa vulgaris, lilac bark.
Ginsenoside-Rg1, Sanchinoside C1, Panaxoside A, Panaxoside Rg1, Sanchinoside Rg1, (C42H72O14), root triterpenoid saponin, cardioprotective agent.
It occurs most abundantly in Ginseng, (Panax ginseng), (Korean ginseng), and Panax japonicus var. major, Araliaceae.
It is used to improve spatial learning, and has estrogen-like activity.
Ginsenosides are a class of steroid glycosides, and triterpene saponins, found only in Panax (ginseng), which appear to affect multiple physiological pathways.
See diagram: Ginsenoside compound.
Glycyrrhizin, C42H62O16, liquorice plant, triterpenoid aglycone occurs in Glycyrrhiza glabra.
Glycyrrhizic acid ammonium salt is from glycyrrhiza root, (licorice).

Cyanogenic glycosides
Chemicals cause protective cyanogenesis, produce HCN, when plant is attacked.
Amygdalin, Cardiospermin, Dhurrin, Linamarin, Lotaustralin, Prunasin, Sarmentosin.
Cyanogenic glycosides (cyanophore glycosides), (aglycone contains CN group), amygdalin
Betanin, dhurrin
Hydrocyanic acid
21.0 Linamarin, lotaus, prunisin, rose family, bamboo, cassava, sorghum
Naringin
Betanin, 5-O-beta-glucoside, a red-violet betacyanin, purple pigment, glucopyranosylbetanidin, a phytolaccanin, E162 Beetroot Red, from beet, Food additive
The colorant in cosmetics and pharmaceuticals.
Betanin, C24H26N2O13, Red beef extract diluted with dextrin, Food dye, cosmetic and pharmaceutical colorant.
Betanin may not broken down in the body so can cause temporary red urine (beeturia and red faeces).
It may cause distress in people who think they are suffering haematuria, (blood in the urine)!

Cymarin
Cymarin, C30H44O9, cymarine, stropheantin K, a cardenolide glycoside
It occurs in Apocynum cannabium, dogbane, Strophanthus hispidus, and Adonis amurensis.

Dihydrochalcones
Phloretin, C15H14O5, a dihydrochalcone, Phloretin 2'-O-xylosyl-glucoside, C26H32O14, Phloridzin, C21H24O10
3-Hydroxyphloretin 2'-O-glucoside, C21H24O11, (3-Hydroxyphloretin), ( 2'-O-xylosyl-glucoside), C26H32O15

Diterpenes
Abietic acid, Casbene, Gibberellin, Grayanotoxic I, Phytol, Pimaric acid, Stevioside

Fatty acids
A fatty acid is carboxylic acid, which has an hydrocarbon chain and a terminal carboxyl group, e.g. oleic acid, CH3(CH2)7CH=CH(CH2)7COOH
It occurs in esters, fats and oils.
16.3.8.1 Fatty acids
Fatty acids, List of fatty acids
16.3.3.0 Lipids

Flavonoids
1. 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.
See diagram: 16.3.4.2: Flavonoids (apigenin-7-monoglucoside), flavones, riboflavin, anthicyanin.
Flavonoids contain a common chemical structure, C6-C3-C6, modified to give flavanones, flavanols, flavonols, flavones, anthocyanidins and isoflavones.
See diagram: Flavonoid basic structure, 6-3-6
Plant pigments, based on flavone or similar to flavone, C15H10O2, including anthocyanins.
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.
Aglycone (flavonoid - sugar = aglycone), cardiac glycoside -->; steroid molecule is the aglycone.
Flavonoids are polyphenolic compounds, secondary metabolites, blue-pigments.
Flavonoids antioxidants, prevent the bad LDL cholesterol from forming oxidized LDL, which forms plaques in arteries, prevent heart attacks, antiviral, anti-allergic, antiplatelet, anti-inflammatory, and antitumor and antioxidant activities.
Almost all fruits, vegetables, herbs and spices contain flavonoids.
Favanone glycosides, occurs in citrus fruits, e.g. kumquat, lemon, lime, grapefruit, orange, tangerine, artichoke, red and white wine.
Neoflavonoids
Neoflavones, Alexandrian laurel
Neoflavenes, Dalbergia sissoo | Dalbergin | Nivetin | in Echinops niveus
Isoflavonoids
Daidzein (formononetin) occurs in soy, alfalfa sprouts, red clover, chickpeas, peanuts, kudzu, other legumes.
Genistein (biochanin A) occurs in soy, alfalfa sprouts, red clover, chickpeas, peanuts, other legumes.
2. Flavonols
Quercetin occurs in red and yellow onions, tea, wine, apples, cranberries, buckwheat, beans, lovage.
Kaempferol occurs in tea, strawberries, gooseberries, cranberries, grapefruit, apples, peas, brassicates (broccoli, kale, brussels sprouts, cabbage), chives, spinach, endive, leek, tomatoes.
Myricetin occurs in grapes, red wine, berries, walnuts.
Fisetin occurs in strawberries, cucumbers.
Rutin occurs in citrus fruits, oranges, lemons, limes, grapefruit, berries, peaches, apples, pagoda tree fruits, asparagus, buckwheat, parsley, tomatoes, apricots, rhubarb, tea.
Isorhamnetin occurs in red turnip, goldenrod, mustard leaf, ginkgo biloba, onion.
3. Flavan-3-ols (flavanols)
Catechins white tea, green tea, black tea, grapes, wine, apple juice, cocoa, lentils, black-eyed peas
(+)-Catechin | (+)-Gallocatechin | (−)-Epicatechin | (−)-Epigallocatechin | (−)-Epigallocatechin gallate (EGCG)
It occurs in green tea | (−)-Epicatechin 3-gallate
Theaflavin | Theaflavin-3-gallate | Thearubigins | occur in black tea.
4. Flavanones
Hesperidin occurs in citrus fruits.
Naringenin occurs in citrus fruits.
Silybin occurs in thistle.
Eriodictyol occurs in citrus fruits.
5. Flavanonols
Anthocyanidins (flavonals) and Anthocyanins occur in red wine, many red, purple or blue fruits and vegetables.
Pelargonidin occurs in bilberry, raspberry, strawberry.
Peonidin occurs in bilberry, blueberry, cherry, cranberry, peach.
Cyanidin occurs in red apple & pear, bilberry, blackberry, blueberry, cherry, cranberry, peach, plum, hawthorn, loganberry, cocoa.
Delphinidin occurs in bilberry, blueberry, eggplant.
Malvidin occurs in bilberry, blueberry.
Petunidin, C31H29O14+, a coumaroyl-glucoside), a flavonoid and glycoside, occurs in grapes ans some flower petals.
6. Flavones
Acacetin Robinia pseudoacacia, Turnera diffusa
Apigenin chamomile, celery, parsley
Chrysin Passiflora caerulea, Pleurotus ostreatus, Oroxylum indicum
Tangeritin tangerine and other citrus peels
Luteolin beets, artichokes, celery, carrots, celeriac, rutabaga, parsley, mint, chamomile, lemongrass, chrysanthemum

Glucosides
1. A glucoside is a glycoside with a glucose sugar component, a glycoside that yield glucose upon hydrolysis, 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
2. List of glucosides
Aesculin, Esculin, C15H16O9
Aloenin, Aloearbonaside, C19H22O10, bitter glucoside, in Candelabra aloe
It occurs in skin care cosmetics, possibly anti-cancer.
Apterin, Coumarin, C20H24O10
Arctiin, anti-tumour, antiviral, glucoside of Arctigenin, C21H24O3, Arctium lappa, burdock, C27H34O11
Arjunglucoside I, sericoside, C36H58O11
Benzyl-Beta-D-glucoside, benzyl Beta-d-glucopyranoside, (derived from a benzyl alcohol, C13H18O6)
Betanin, C24H26N2O13
Cycasin glucoside, C8H16N2O7
Cornuside, secoiridoid glucoside, anti-inflammatory, C24H30O14
Decyl glucoside, non-ionic surfactant, C16H32O6
Fraxin, C16H18O10
Icariin, C33H40O15
Lauryl glucoside, C18H36O6, surfactant
21.0 Linamarin, C10H17NO6
Octyl glucoside, C14H28O6, non-ionic surfactant
Piceid, C20H22O8
Piceatannol
Picrocrocin, C16H26O7
Populin, in poplar, C20H22O8
Prunin, (naringenin-7-0-glucoside), C21H22O10
Quercitrin, C21H20O11
Ranunculin, in Ranunculaceae, C11H16O8
Rhamnazin, C17H14O7.
Rhamnetin, C16H12O7
Rhaponticin, C21H24O9
Salicin, C13H18O7
Sakakin, C13H18O7, orcinol glucoside
Salidroside, rhodioloside, 8-o- β-D glucoside of tyrosol, neuroprotective, antidepressant, anxiolytic,. C14H20O7

Glucosinolates
Glucosinolates, mustard oil glycosides, (derived from sugar + amino acid), contain S and N.
Glucosinolates + enzyme hydrolysis by thioglucosidases --> mustard oil glycosides, when plant cells are damaged or chewed.
List of glucosinolates:
Epiprogoitrin, C11H19NO10S2, in Crambe abyssinica oil, Brassicaceae
Glucoalyssin
Glucoaubrietin
Glucobarbarin
Glucoberteroin
Glucobrassicanapin
Glucobrassicin
Glucocapparin
Glucocheirolin
Glucoconringiin
Glucocleomin
Glucoerucin
Glucoiberverin
Gluconapoleiferin
Glucoiberin
Glucolepidiin
Glucolimnanthin
Gluconapin
Gluconasturtiin
Glucoputranjivin
Glucoraphanin
Glucoraphenin
Glucosibarin
Glucosisymbrin
Glucotropaeolin
Hydroxyglucobrassicin
Methoxyglucobrassicin
Neoglucobrassicin
Progoitrin
Sinalbin
Sinigrin

Glycosides
1. A glycoside is a compound that contains a constituent sugar, the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other 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.
A glucoside is a glycoside derived from glucose. 2. Some types of glycosides:
Alcoholic glycoside, e.g. salicin, C13H18O7
Anthraquinone glycoside, e.g. aloin, C21H22O9
Cardiac glycoside, (Cardenolide glycoside), e.g. digoxin, C41H64O14
Coumarin glycoside, e.g. apterin, C20H24O10
Cyanogenic glycoside, e.g. amygdalin, C20H27NO11
Flavonoid glycoside, e.g. quercetin, C15H10O7
Phenolic glycoside, e.g. arbutin, C12H16O7
Saponin glycoside, e.g. glycyrrhizin, C42H62O16
Steviol glycoside, e.g. stevioside, C38H60O18
Steroid glycosides, Triterpene glycosides
Digitonin, C56H92O29, Steroidal saponin, toxic, solubilizes lipids.
It occurs in Digitalis purpurea, foxglove seeds.
Diosgenin, C27H42O3, Steroidal sapogin
It occurs in Costus speciosis, bark of Wild yam, Discorea villosa, disoscin glycoside.

Glycone and aglycone
glycoside (hydrolysis) --> glycone (sugar group) + aglycone (non-sugar group)
The sugar group is called a "glycone" and the non-sugar group is called an "aglycone" or genin part of the glycoside.
Upon hydrolysis, a sugar and non-sugar component (aglycone) are formed.
Cadenolide glycosides are steroids derived from sugars.
They are usually potentially heart toxic, but Digitalis species are used medically.
The glycone can consist of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide).
Aglycone, is the non-sugar component formed when a glycoside is hydrolysed, the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom.
See diagram: Fructose, Glycosyl group.
For example: Hesperetin, C16H14O6, occurs in lemon, orange.

Genistein
Genistein, Prunetol, (4',5,7-Trihydroxyisoflavone), Genisteol, C15H10O5, phytoestrogen, isoflavone, phytoestrogenic isoflavone, antineoplastic, derived from soy product, induces apoptosis, antioxidant, antiangiogenic, immunosuppressive, anti-inflammatory, anti-atherosclerosis, biomarker for soy consumption, antitumor
It may lessens risk of cardiovascular diseases.
It occurs in Pueraria mirifica.
Kwao, Krua, Pueraria lobata, kudzu, Glycine max, tofu, fava beans, soybeans, lupin in dyer's broom, (Genista tinctoria), in Felmingia vestita anti-cestode medicine
Genistin, C21H20O10, genistine, isoflavone, in soya, in kudzu
Glycitein, C16H12O5, isoflavone, O-methylated isoflavone, weak oestrogen activity, in soybean, Centrosema haiense, C. Pubescens, in Glycine max
Glycitin, C22H22O10
Onion in C22H22O9, isoflavone glucoside, in Radix astragali, Chinese medicine
Puerarin, C21H20O9, isoflavone, in kudzu, reduces alcohol withdrawal anxiety

Gypenoside
Gypenosides, (Gyp), anti-cancer
Gypenoside XXV, Gypenoside L, C47H78O18, (Gynostemma pentaphyllum), jiaogulan (82 saponins), Cucurbitaceae
Gypenoside XLIX, C52H86O21, Gypenoside, XVII, C48H8O18, Gypenoside LXXV, C42H72O13, Gypenoside VIII, C48H82O18

Hydrocarbons
Short chain hydrocarbons are in flower scents and fruits and also bad smelling molecules, e.g diallyls and mercaptans.
Long chain hydrocarbons, especially alkanes, are in cuticle waxes.
Allicin, Diallyl sulfide, Diallyl disulfide, Dodecane, Hentriacontane, Methyl mercaptan, Naphthalene, Octan-1-ol, Pentadecane, Ranunculin

Hydroxybenzaldehydes
4-Hydroxybenzaldehyde, C7H6O2, Gallic aldehyde, C7H6O4, Anisaldehyde
Protocatechuic aldehyde, C7H6O3, Syringaldehyde, C9H10O4, Vanillin

Hydroxybenzoic acids
Note: "hydroxybenzoic acid" may refer to different compounds:
Gallic acid 4-O-glucoside, C13H16O10, Gentisic acid, C7H6O4, Lambertianin C, C123H80O78, Protocatechuic acid, C7H6O4
Punicalagin, C48H28O30, Sanguiin H-6, C82H54O52, Syringic acid, C9H10O5
Valoneic acid dilactone, C21H10O13, Vanillic acid, C8H8O4
Salicyclic acid, C7H6O3 2-hydroxybenzoic acid
3-hydroxybenzoic acid, C7H6O3, in gut microfauna
4-hydroxybenzoic acid, C7H6O3 --> esters --> parabens
trihydroxybenzoic acid Gallic acid, C7H6O5, hydrolysable tannin, pseudotannin
Benzoic acid, C6H5COOH, C7H6O2
Ellagic acid, C14H6O8
Hydroxybenzoic acids
Hydroxycinnamic acids
Hydroxyphenylacetic acids

Hydroxybenzoic acids
Gallic acid 4-O-glucoside, C13H16O10, Gentisic acid, C7H6O4, Lambertianin C, C123H80O78, Protocatechuic acid, C7H6O4
Punicalagin, C48H28O30, Sanguiin H-6, C82H54O52, Syringic acid, C9H10O5
Valoneic acid dilactone, C21H10O13, Vanillic acid, C8H8O4

Hydroxybenzoketones
2,3-Dihydroxy-1-guaiacylpropanone, C10H12O5 | (3-Methoxyacetophenone), C9H10O2

Hydroxycinnamic acids
Caffeic acid occurs in burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple, olive oil.
Chlorogenic acid occurs in echinacea, strawberries, pineapple, coffee, sunflower, blueberries.
Cinnamic acid occurs in cinnamon, aloe.
Ferulic acid occurs in oats, rice, artichoke, orange, pineapple, apple, peanut, açaí oil.
| Caffeic acid | Chlorogenic acid
| Cichoric acid
| Cinnamic Acid
| Coumaric acid
| Ferulic acid
| Phaseolic acid
| Rosmarinic Acid
| Sinapinic acid

Hydroxycinnamaldehydes
Ferulaldehyde, C10H10O3, Sinapaldehyde, C11H12O4

Hydroxycoumarins
| Coumarin | Eculetin | Esculin

Hydroxyphenylacetic acids, Polyphenols
3,4-Dihydroxyphenylacetic acid, C8H8O4 | 4-Hydroxyphenylacetic acid, C8H8O3 | Homovanillic acid, C9H10O4
Homoveratric acid, C10H12O4 | Methoxyphenylacetic acid, C9H10O3

Hydroxyphenylpropenes
Acetyl eugenol, C12H14O3
Anethole, C10H12O, monoterpene
Estragole, C10H12O, methyl chavicol
Eugenol, C10H12O2
Gingerol, C17H32O4

Indoles
Indole-3-carbinol occurs in cabbage, kale, brussels sprouts, rutabaga, mustard greens, broccoli.
3,3'-Diindolylmethane or DIM occurs in broccoli family, brussels sprouts, cabbage, kale.
Indole-3-acetic acid is a commonly occurring plant hormone, a part of the auxin family.

Isoflavonoids
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 (subclasses):
Isoflavones: Betavulgarin, Biochanin A, Daidzein, Formononetin Genistein, Genistin, Irilone, Luteone. Pomiferin
Isoflavanones: Ferreirin
Pterocarpans: Acanthocarpan, Glycinol, Medicarpin
Isoflavans: Glabridin, Sativan, Vestitol
Rotenoids: Deguelin, Rotenone, Sumatrol
Neoflavonoids occur mainly in Fabaceae: Dalbergin, Melannin, Methoxydalbergione
Coumestans: Coumestrol, Psoralidin. Sojagol

Legheamoglobin
Legheamoglobin is a phytoglobin, a globular plant protein.
Legheamoglobin, leghemoglobin, legoglobin, 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.
The poprotein is produced by the plant and the haeme (an iron atom bound in a porphyrin ring) is also produced by the plant.
It stores enough oxygen to support nodule respiration for a few seconds.
Its function is to help transport oxygen to the respiring symbiotic bacterial cells, analogous to haemoglobin transporting oxygen to respiring tissues occurs in animals.
Phycobilins, phycocyanin, phycoerythrin, Cyanobacteria, Rhodophyta
Phycobiliproteins, nitrogen-fixing cyanobacteria, Anabaena azollae
Polyvinyl pyrrolidene, povidone
Porphyrins, porphine

Lignans
Lignans are plant polyphenolic compounds that occurs 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.
See diagram Lignan

Menthol, C10H19OH
1. Menthol, dl-Menthol, (2-Isopropyl-5-methylcyclohexanol), white crystalline solid with a peppermint odour and taste, C10H20O, C10H19OH
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 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 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).
Garden mint, (Mentha sachalinensis), Lamiaceae
In peppermint leaves, the concentration of menthol increase with age, and menthol breaks down with heating, so peppermint leaf is not usually cooked.
Methoxyphenols
Guaiacol
Monophenols
Monophenols, containing one phenolic hydroxyl group
Apiole, parsley, celery leaf, Carnosol
Carvacrol, oregano, thyme, pepperwort, wild bergamot, Dillapiole, dill weed, fennel root

Methoxyphenols
Guaiacol

Monophenols
Monophenols, containing one phenolic hydroxyl group
Apiole, parsley, celery leaf, Carnosol
Carvacrol, oregano, thyme, pepperwort, wild bergamot.
Dillapiole, dill weed, fennel root

Monoterpenoids, (Monoterpene), (Terpenes and Terpenoids)
Borneol, Camphor, Carvone, Citronellal, Geraniol, Limonene, Linalool, Menthol, Menthone, Nerol, Pinene, Thujone, Thymol

Monosaccharides, (Carbohydrates and Lipids)
16.3.1.3 Monosaccharides | 16.3.1.0 Aliphatic compounds
Arabinose, Deoxyribose, Digitalose, Fructose, Galactose, Glucose, Glucuonic acid, Mannose, Rhamnose, Ribose, Ribulose, Sorbose, Xylose

Myrosinase
Myrosinase enzyme, also called: glucosinolase, thioglucosidase, thioglucoside glucohydrolase
Myrosinase enzyme is a singrinase and a sinigrase.
glucosinolate + myrosinase --> toxic compounds to deter grazing
glucosinolate + myrosinase --> glucose + isothionate
glucosinate + myrosinase --> thiocynates (SCN-), and nitriles (R-C triple bond N)

Napththoquinones
1,2-Naphthoquinone, C10H6O2, occurs in diesel exhaust, strong odour, red-brown alkaline solution, cytotoxic derivatives occur in vitamin K.
Naphthoquinones C6-C4 skeleton, 1,2-Naphthoquinone C10H6O2 in diesel exhaust, 1,4-Naphthoquinone, (C10H6O2, strong odour, red-brown alkaline solution, cytotoxic derivatives in vitamin K
Triphophyllum peltatum
Napthoquinone derivatives
Drosera species, Droserone C11H8O4,
Plumbagin, C11H8O3
Juglone, C10H6O3

Neoflavonoids, polyphenols
1. Neoflavones, Alexandrian laurel
2. Neoflavenes, Dalbergia sissoo | Dalbergin | Nivetin | in Echinops niveus

Other polyphenols
3,4-Dihydroxyphenylglycol C8H10O4, Arbutin
Catechol, Coumestrol, C15H8O5
Pyrogallol

Miscellaneous Nitrogen compounds
Chlorophyll a, Chlorophyll b, Nicotinic acid, Phytochrome
Toxins: Aristolochic acid, Miserotoxin
Phytoalexins: Avenalumin, Dianthalexin, Methoxybrassinin
Vitamins containing nitrogen: Biotin, Cyanocobalamin, Folic acid, Nicotinamide, Pantothenic acid, Pyridoxine, Riboflavin, Thiamine

Nortriterpenoids, (Terpenes and Terpenoids)
Azadirachtin A, Glaucarubin, Limonin, Nomilin, Obacunone, Quassin

Oligosaccharides, (Carbohydrates and Lipids)
Cellobiose, gentiobiose, Lactose, Maltose, Raffinose, Stachyose, Sucrose, Trehalose, Verbascose

Organosulfur compounds
Allicin, C6H10OS2, in Garlic | 16.2.8.9 Sulfoxide, Alliin
Allyl isothiocyanate, C4H5NS, in (Armoracia rusticana), Horseradish
Propanethial S-oxide, C3H6OS, occurs in cut onions: 16.2.8.9.

Pallidol
Pallidol, C28H22O6, tetracyclic stilbenoid, (derived from resveratrol), antioxidant, antifungal, polyphenol
It occurs in red wine, Cissus, and Parthenocissus.

Phenol, C6H5OH, C6H6O
Phenol, benzenol, carbolic acid, monohydroxybenzene, hydroxybenzene, phenic acid, C6H6O or C6H5OH, aromatic organic compound, corrosive, acute toxic, phenyl group (−C6H5) + hydroxy group (−OH), volatile white crystalline solid, mildly acidic, cause chemical burns or numbs, throat spray, oral analgesic, antiseptic, disinfectant, kill bacteria and fungi in slimes, colourless to white solid when pure, liquid commercial product, distinct sweet odour, does not react with water, 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.
See diagram 16.3.5.4: Phenol
Phenol, Carbolic acid, Hydroxybenzene, Phenic acid, C6H6O or C6H5OH, is highly toxic, corrosive to skin, organic hydroxy compound, (benzene + a hydroxy substituent), parent of the class of phenols, germicidal agent, disinfectant, antiseptic, (TCP, Dettol).
Phenol solution, white crystalline mass dissolved in a colourless to slightly pink aqueous solution, with a distinctive phenol odour, sharp burning taste, toxic by ingestion, inhalation>and skin absorption, irritant.
1. Carbolic acid, C6H5OH, "phenol" from coal tar fraction 170^oC to 230^oC, colourless hygroscopic crystals
Phenol is acidic so ionizes in water:
C6H5OH --> H⁺ + C6H5O^-
Do not wash off phenol with alcohol because carcinogenic products or explosive materials may form.
2. "Phenol", carbolic acid C6H5OH, pale pink crystalline solid, (is solid because of the hydrogen bonds between the phenol molecules).
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^-.
C6H5OH --> C6H5O^- + (H+)
phenol --> phenoxide ion + a proton, H+ ion
5. Phenol reacts with alkalis.
NaOH (aq) <=> C6H5NaO + H2O
phenol + sodium hydroxide <=> sodium phenoxide + water
Sodium phenolate formula: NaOC6H5
6. Halogenation of phenol
phenol + bromine --> 2.4.6-tribromophenol, (TBP), C6H3Br3O
phenol + chlorine --> 2-chlorophenol, C6H5OHCl
7. Chlorophenol red, C19H12Cl2O5S, is an acid-base indicator: 9.0
8. Carvacrol, C10H14O
Carvacrol, cymophenol, a monoterpenoid phenol, (5-Isopropyl-2-methylphenol), Karvakrol, Isopropyl-o-cresol, a p-menthane monoterpenoid derivative of cymene, inhibits bacterial growth, food additive, volatile oil component, flavouring agent, antimicrobial agent, agrochemical (botanical anti-fungal agent), n black walnut.
It oin many essential oils, e.g. Thyme oil and Origanum oil, smells like oregano.
Carvacrol, C10H14O
9. TCP, antiseptic for sore throats, was originally (2,4,6-trichlorophenol), trichlorophenylmethyliodosalicyl, but nowadays commercial TCP contains mixture of phenol and halogenated phenols.
TCP has a distinctive "medicine" smell.
TCP (antiseptic) now C13H12Cl2I2O4
10. "Dettol", chloroxylenol (4-chloro-3,5-dimethylphenol), (4-Chloro-3,5-xylenol), C8H9ClO, (para-chloro-meta-xylenol, PCMX), an halophenol, monochlorobenzene, antiseptic, disinfectant agent in antibacterial soaps, in household antiseptics, bactericidal against most Gram-positive bacteria, but less effective against Staphylococci and Gram-negative bacteria, inactive against Pseudomonas species and bacterial spores.

Phenols
Phenols | 16.1.0
Benzoic acid, Catechol, p-Cresol, Ellagic Acid, Gallic acid, Gentisic acid, Hydroquinone, Orcinol, Phenol, Phloroglucinol, Pyrogallol, Resorcinol, Salicin, Salicyclic acid, Sesamol, Syringic acid, Tannic acid (polyphenol), Tetrahydrocannabinol, Urushiol III, Vanillic acid, Vanillin
Isoflavonoids, (phytoestrogens)
Phenol, phenolic, is a derivative of an aromatic hydrocarbon where a hydroxyl group is attached to a benzene ring.

Phenols
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 crystals, C6H5OH, Highly toxic by all routes, lung irritant, corrosive to skin
Phenol solution < 1%, Not hazardous
Phenol-indo-2, 6-dichloro phenol
Phenol fuchsin, carbol fuchsin
Phenols, group: (OH-C)
Phenol red, C19H14O5S: 28 (indicator)
Phenolic acids: Phenolic acids
Phenolic ketones, phenylacetone
Phenols by number of Carbon atoms:
C6 Simple phenols: Benzoquinone, C6H4O2, (1,4-benzoquinone)
C7 Phenolic acids: Phenolic acids
C8 Tyrosol
C9 Hydroxycinnamic acids: Hydroxycinnamic acids
C10 Napththoquinones: Napththoquinones
C15 Emodin
C16 Quercetin
C18 Lignans, C18H18O2
C20 Sesamin, C20H18O6

Phenolic ketones
Apocynin, Danielone, Humulone, Lupulone, Picein
1. Acetophenones: Ameliaroside, Picein, Salicinerein, Salinigrin, p-Hydroxyacetophenone glucoside, C14H18PO7, phenolic compound, glucoside of piceol, glycoside, in roots of>Norway spruce (Picea abies), in Salix, in Homogyne.
2. Phloroglucinol derivatives
Lupulone
Humulane
Aspidin, Polystichin, C25H32O8, occurs in Aspidium, in Dryopteris, antihelminthic Filixic acid, Filixic acid BBB, Filicin, Filicic acid, C36H44O12 in Aspidium roots, in Dryopteris, antihelminthic.
Rottlerin, Mallotoxin, C30H28O8, pink-brown pigment, in Rottleria, in Mallotus, toxic, antihelminthic used to treat tumours in India, used as silk dye.
ApocyninApocynin in Iris
Apocynin occurs in Iris.

Phenylpropanoids
Anethole, Apiole, Caffeic acid, Chicoric acid, Chlorogenic acid, p-Coumaric acid, Estragole, Ferulic acid, Eugenol, Gingerol, Myristicin, Rosmarinic acid, Safrole
Quinones, Alizarin, Alkannin, Barbaloin, Juglone. Stilbenoids, resveratrol
Sugars
Tannins
Xanthones, Gentisin
Deoxykaempferol
16.5.6.0
Anethole
Apiole
Caffeic acid
Chlorogenic acid
Cichoric acid
Coumaric acid
Curcumin
Estragole
Eugenol
Ferulic acid
Myristicin
Rosmarinic Acid
Safrole
Sinapic Acid

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 (dye, acid-base indicator, occurs in Brazil wood).
16.3.4.1.1 Benzofurans
Chromones and Chromenes
Coumarins
Coumarone, 16.3.4.1a
16.2.2.0 Isoflavonoids and Neoflavonoids
Lignans
Neoflavonoids, polyphenols
Phenolic acids
Phenols
Phenolic ketones
Phenylpropanoids
Quinones
Stilbenes and Stilbenoids
Tannins
Xanthones
Phenolic acids
Salicylic acid occurs in peppermint, licorice, peanut, wheat.
Vanillin and Vanillic acid açaí oil, occurs in vanilla beans, cloves.
Gallic acid occurs in tea, mango, strawberries, rhubarb, soy.
Ellagic acid occurs in walnuts, strawberries, cranberries, blackberries, guava, grapes.
Tannic acid occurs in nettles, tea, berries.

Phycobilins, red algae, Cyanobacteria
Phycobilins, phycocyanin, phycoerythrin, Cyanobacteria, Rhodophyta
Phycobilins include the blue-green pigment phycocyanin and the red pigment phycoerythrin to enable red algae to be photosynthetically.
They are occur in deep water where blue light predominates.
Phycobilin pigments are water-soluble and occur in the cytoplasm and stroma of chloroplasts.
They occur only in Cyanobacteria and Rhodophyta.
The blue green pigment phycocyanin occurs in the Cyanobacteria.
The red brown pigment phycoerythrin occurs in the red algae.
Phycobilin pigments absorb light energy that is passed on to other processes.
Pycocyanin and phycoerythrin are fluorescent.
Phytochromes
Red light sensitive Phytochromes are phycobilin-protein pigments involved in floral induction, and are activated by the length of day, hours of darkness, red light, with peak response 660 nm.

Phycobiliproteins
Phycobiliproteins, nitrogen-fixing cyanobacteria, occurs in cyanobacteria and red algae are composed of water-soluble phycobilin pigments and protein.
Nitrogen-fixing cyanobacteria, e.g. Anabaena azollae, live symbiotically within leaf cavities of the water fern Azolla.
The genus Azolla is an important source of nitrogen fertilizer for the rice industry in Vietnam, China and the Philippines.
Nitrogen-fixing cyanobacteria, e.g. Anabaena azollae, lives symbiotically within leaf cavities of the water fern Azolla.
Azolla, floating fern

Phytochromes
Red light sensitive Phytochromes are phycobilin-protein pigments involved in floral induction, and are activated by the length of day, hours of darkness, red light, with peak response 660 nm.

Plant extracts
1. Butylphthalide, C12H14O2, celery seed, Chinese medicine, antioxidant
2. Creosote, from beechwood tar
3. Lycopodium, clubmoss, fine yellow powder, highly flammable
4. Mangiferin (MGF), C19H18O11, xanthoid, antimicrobial, anti-inflammatory, antioxidant, occurs in Mangifera indica.
5. Protopanaxadiol, C30H52O3, sapogenin
6. Pollen from Sorghum halepense, Betula fontinalis occidentalis, water birch, Juglans nigra, black walnut, Populus deltoides, eastern cottonwood

Polyhydric alcohols, (Sugar alcohols and Cyclitols), (Carbohydrates and Lipids)
19.1.0.4 Polyhydric alcohols
Dulcitol, Galactinol, Glycerol, myo-Inositol, d-Mannitol, Pinitol (monomethyl ether), Quebrachitol, Quercitol, d-Sorbitol

Polyphenols
Phenolic acids
Hydroxybenzoic acids
Hydroxycinnamic acids
Hydroxyphenylacetic acids
Stilbenes and Stilbenoids
Lignans
Phenylpropanoids
Polyphenols are often repeated connected units of:
Catechol
Resorcinol, C6H4(OH)2
Pyrogallol, 1,2,3-trihydroxybenzene
Phloroglucinol, C6H3(OH)3, a phlorotannin
Other polyphenols
3,4-Dihydroxyphenylglycol C8H10O4, Arbutin
Catechol, Coumestrol, C15H8O5
Pyrogallol

Polysaccharides, (Carbohydrates and Lipids)
Polysaccharides
Starch comprises components Amylose + Amylopectin.
Gums are almost pure polysaccharides
Agar, Alginic acid, Carrageenan, Cellulose, Gum arabic, Gum Tragacanth, Inulin, Laminarin, Pectin, Phytoglycogen, Porphyran, Starch

Polyvinyl pyrrolidene, povidone, PVP
See diagram 16.3.5.4: Povidone, PVP
E1201 Polyvinyl pyrrolidene, povidone, PVP, is a water-soluble polymer, used as a coating or binder in medical tablets.
The povidone-iodine complex (PVD-iodine) in the antiseptic "Betadine", which has replaced tincture of iodine solution used in medicine.

Porphyrins, haemoglobin
Porphyrins are natural pigments containing a fundamental skeleton of four pyrrole nuclei united through the α-positions by four methine groups to form a macrocyclic structure.
(IUPAC): 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.
The most common type is Haeme B, C34H32O4N4Fe,
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 16.3.5.4: Porphine
See diagram 16.3.5.01: Porphyrin, Porcine
For oxidative phosphorylation, electron transport system, and ATP production.
See diagram 16.3.5.2.1, Haeme
See diagram 16.3.5.4, Porphine
See diagram 16.3.5.01, Porphyrin, Porcine

Proanthocyanidin
Proanthocyanidin, rotenone, pisatin, isoflavan, pisatin, proanthocyanidins, orcein, vulpinic acid, taxol, urushiol (pentadecyl-catechol), (phytoalexins: resveratrol, psoralen), (flavone alkaloids: ficine, vochysine)
Vestitol
Flavonoids
Fisetin
Galangin
Isorhamnetin
Myricetin

Proteins and peptides
Proteins
Actinidin, Bromelain, Capsaicin (neuropeptide), Ficin, Glutathione, Gluten, Leghaemoglobin, Papaine, Peanut lectin, Ricin, Soybean lectin, Wheat germ agglutinin

Purines and Pyrimidine derivatives
Bases of nucleic acids: Adenine, Guanine, Cytosine, Uracil, Adenosine triphosphate, Thymine, (RNA, DNA)
Related to nucleic acid bases: (Pyrimidine glycosides: Convicine, Vicine), (in wheat germ DNA: 5-Methylcytosine)
Methylated purines: Caffeine, Theobromine Theophylline
Cytokinins purines: Kinetin (Hyalurinidase), Zeatin

Phytoestrogens
Phytoestrogens occur in seeds (flax, sesame, pumpkin, sunflower, poppy), whole grains (rye, oats, barley), bran (wheat, oat, rye), fruits (particularly berries) and vegetables.
[3] Matairesinol occurs in flax seed, sesame seed, rye bran and meal, oat bran, poppy seed, strawberries, blackcurrants, broccoli.
Secoisolariciresinol occurs in flax seeds, sunflower seeds, sesame seeds, pumpkin, strawberries, blueberries, cranberries, zucchini, blackcurrant, carrots.
Pinoresinol and lariciresinol occur in sesame seed, Brassica vegetables.

Quinones, (Phenolics, Polyphenols)
Benzoquinones, Naphthoquinones, Anthraquinones 16.3.10.0 Quinones
Aloe-emodin, Alkannin, Chrysophanol, Emodin, Juglone, Physcion, Primin, Plastoquinine-9, Ubiquinone-10

Saponins, horse chestnut
Saponin glycosides, triterpene glycoside, plant glycosides, soluble in water and alcohol, but is insoluble in non-polar organic solvents, e.g. benzene.
Saponin hydrolysis --> sugars + aglycones
Saponins are terpenoid and steroid toxic glycosides, forming frothy colloidal soapy solutions when agitated in water, emulsifiers, detergents, often toxic to fish.
Escin or aescin, C55H86O24: 16.3.5.1a, occur in horse chestnut, Aesculus hippocastanum, Sapindaceae.
1. Triterpenoid glycosides, triterpenoid saponins, triterpenene glycosides, triterpene saponins, pentacyclic triterpenoid saponins
Alpha-Hederin, Helixin, Hederoside C, Tauroside E, Kalopanaxsaponin A, C41H66O12, pentacyclic triterpenoid saponin, irritant, anti-inflammatory, antifungal, strong haemolytiic activity, cancerostatic
It occurs in Kalopanax pictus stem bark, and in Nigella sativa Nigella
Beta-Hederin, Eleutheroside K, C41H66O11, a triterpenoid saponin, antifungal, strong haemolytic activity
It occurs in ivy Hedera helix leaves.
Araloside, C47H74O18, occurs in Japanese angelica tree, Aralia alata, Araliaceae, possible anti-ulcer.
Astragaloside, Astragalosides (I, II, III), Astragaloside I, C44H72O16, occurs in Mongolian milkvetch, Huang qi Astragalus propinquus, may increase gastric pH.
Astragaloside II, C43H70O15, in Mongolian milkvetch, Huang qi (Astragalus propinquus, A. membranaceus), stimulates bone formation.
Astragaloside IV, C41H68O14, occurs in Astragali radix, anti-inflammatory.
BacosideBacoside A3, C47H76O18
Betulinic acid, occurs in Water hyssop Bacopa monieri, Plantaginaceae.

Sesamin
Sesamin, C20H18O6, a lignan, occurs in sesame oil, sesame, (Sesamum indicum), in bark of Fagara cujabensis, Otanthus maritimus, and Cinnamomum camphora,.
Sesamol, C7H6O3, antioxidant, occurs in sesame seeds and sesame oil.
Sesamin in sesame oil.
Sesame, (Sesamum indicum), and in bark of Fagara cujabensis
Sesame oil, Composition of edible oils: 19.2.11 (Table)
Sesamol, C7H6O3, antioxidant, in sesame seeds and sesame oil
Matairesinol, C20H22O6
Pinoresinol, C20H22O6
Podophyllotoxin, C22H22O8, lignan
Todolactol A, C20H24O7
Rachelogenin, C21H24O7

Sesquiterpene lactones, (Terpenes and Terpenoids)
Absinthin, Cnicin, Geigerin, Lactucin, Lactupicrin, Parthenin, Vulgarin

Sesquiterpenoids, (Terpenes and Terpenoids)
Abscissic acid, Bisabolol, Beta-cadinene, Carotol, Caryophelline, Dehydromyodesmone, Farnesol, Beta-Farnesene, Gossypol, Rishitin, Sclerosporin, Beta-Selinene

Stilbenes, Resveratrol
Stilbene, trans-stilbene, C6H5CH=CHC6H5 is a diarylethene polyphenol
Stilbenoids are derivatives of stilbene and the products of heartwood formation in trees.
Glepidotin
Pallidol tetracyclic stilbenoid
Phyllodulcin, C16H14O5, a hydroxybenzoic acid
Piceid stilbenoid glucoside
Piceatannol a stilbenol, occurs in grapes.
Resveratrol occurs in grape (skins and seeds, grape wine), nuts, peanuts, Japanese Knotweed root.
Rhaponticin, C21H24O9, stilbenoid glucoside, phytoestrogen, occurs in rhubarb rhizomes.

Steroids
Steroids, sterols, steroid alcohols, natural steroids, have a nucleus of three six-member carbon rings and one five-member ring.
Steroids are naturally occurring compounds and synthetic analogues, based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated, and usually with methyl groups at C-10 and C-13, and an alkyl group at C-17.
Natural steroids are derived biogenetically 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), oestrogen, cardiac glucosides, diosgenin, androstane, 19-norpregnane, 7-dehydrocholesterol, previtamin D3, ergocalciferol (vitamin D2), cholecalciferol (vitamin D3).
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 sterolin.
Estradiol, (oestradiol), C18H24O2, steroid, an estrogen (oestrogen), female growth hormone for reproductive organs.
See diagram 16.3.5.3: Cholesterol, cholic acid, bile salt, estradiol, progesterone, northindrone
See diagram: Testosterone
Steroid structure
Steroids are naturally occurring compounds and synthetic analogues, based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated, and usually with methyl groups at C-10 and C-13, and an alkyl group at C-17.
Natural steroids are derived biogenetically 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), oestrogen, cardiac glucosides, diosgenin, androstane, 19-norpregnane, 7-dehydrocholesterol, previtamin D3, ergocalciferol (vitamin D2), cholecalciferol (vitamin D3).
Steroid glycosides, sterol glycoside, steroidal saponins, phytosteroid saponins, tetracyclic triterpenoid saponins
Horse chestnutAesculus hippocastanum, Saponins that foam in water.
Steroid saponins, Digitogenin, Digitonin, Diosgenin, Sarsaparilloside

Sterols, Cholesterol
Sterols are solid, waxy, unsaturated steroid alcohols, anti-inflammatory, analgesic agents.
Sterols (steroids) occurs in animal sex hormones, squalene (in shark liver oil), cephalosporin, gonane, hopane, diplotene, lupeol.
See diagram: Gonane
Plant sterols are called phytosterols, some existing naturally free and some exist in combination as esters or glycosides.
β-sitosterol, C29H50O, oestrogenic activity, in human leukemia cells, in vegetable oils, in nuts, in avocado
Naturally occurring non-delta-5 plant sterols: | Cycloartenol | 24-methylene cycloartenol | cycloeucalenol | obtusifoliol|
List of sterols:
Avenacoside
Beta-Sitosterol, C29H50O
Campesterol
Cholesterol C27H46O
Cycloastragenol C30H50O5
Ecdysone C27H44O6
Ergosterol C28H44O
Fucosterol C29H48O
Lupeol C30H50O
Sitosterol C29H50O
Stigmasterol C29H48O

Stilbenoids, (Phenolics, Polyphenols)
Stilbenes: Piceid, e-Viniferin
Phenanthrenes: Batatasin I
Lunularic acid, Pterostilbene, Rhaponticin

Tannins, (Phenolics, Polyphenols) 16.2.7.0
Condensed tannins (favolans, proanthocyinadins): Procyanidin B4
Hydrolysable tannins, (ellagitannins): Agrimoniin
Hydrolyzable tannins, pyrogallol-type tannins, occur in Castanea, Quercus, Caesalpinia species.
Hydrolyzable tannins include gallotannins (GTs), and ellagitannins (ETs).
Condensed tannins
Condensed tannins occur in grape seeds.
Condensed tannins (CT), may be used for sustainable food packaging.
Phlorotannins occur in algae, kelp, rockweeds, brown alga species (Ecklonia cava, Sargassum mcclurei), sea oak (Eisenia bicyclis, Fucus vesiculosus).
Flavono-ellagitannin is extracted from Mongolian Oak (Quercus mongolica).

Tetrapyrroles, Haeme
Tetrapyrroles are natural pigments containing four pyrrole rings joined by one-carbon units linking a pyrrole ring to the next pyrrole ring.
Tetrapyrroles have the following related compounds: haemin, haematin, haemoglobin, myoglobin, cytochromes, chlorophylls a and b, bile pigments biliverdin and bilirubin, vitamin B12, bilin, in congenital disease polyphyria, tetrapyrrole derivative DPEP in geological deposits possibly from chlorophyll, chlorin (2,3-dihydroporphyrin).
Haeme
Haeme (heme), occurs in haemoglobin, a globular protein in animals, which is an oxygen carrier.
Haeme A, C49H56O6N4Fe, is a cytochrome oxidase ligand complex.
(Greek haîma blood + Latin globus ball, sphere)
Haeme
See diagram 16.3.5.4: Bilin, a linear tetrapyrrole
See diagram 16.3.5.2.1: Haeme (heme)
See diagram 16.3.5.2.2 Tetrapyrroles
See diagram: Biliverdin, a bile pigment

Triterpenoids
Terpene (C5H8)n for n ≥ 2, unsaturated hydrocarbon, e.g. polyisoprene, natural rubber
Triterpene, e.g. cholesterol
Saponins occur in soybeans, beans, other legumes, maize, alfalfa.
Oleanolic acid occurs in American pokeweed, honey mesquite, garlic, java apple, cloves, and many other Syzygium species.
Ursolic acid occurs in apples, basil, bilberries, cranberries, elder flower, peppermint, lavender, oregano, thyme, hawthorn, prunes.
Betulinic acid occurs in Ber tree, white birch, winged beans, tropical carnivorous plants Triphyophyllum peltatum, Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), chaga (Inonotus obliquus), and many other Syzygium species.
Moronic acid occurs in Rhus javanica (a sumac), mistletoe.
Triterpenoid saponins (Triterpenoids), (Terpenes and Terpenoids)
Aescin, Avenacin A1, Ginsenosides, Gymnemic acid, Ursolic acid

Tyrosols
Oleuropein | Tyrosol

Xanthones, (Phenolics, Polyphenols)
Xanthone, Xanthenone, 9H-Xanthen-9-one, C13H8O2, prepared from phenyl salicylate, insecticide, ovicide, used to prepare xanthydrol to determine urea levels in blood, photocatalyst, parent compound of xanthone derivatives called xanthones or xanthonoids, phenylpropanoid precurser, fluorescent, occur mainly in Gentianaceae and Gutterferae roots and leaves.
List of xanthones
Athyriol C14H10O6, in Athyrium mesosorum fern
Bellidifolin C14H10O6, anti-heptotoxic, mutagenic, in (Gentiana lutea), in Swertia chirata
Gambogic acid C33H44O3, in gamboge the gum resin of Garcinia hamburgyi
Gentisein, C13H8O5, in (Gentiana lutea)
Gentisin C14H10O5, in (Gentiana lutea)
Gartanin C24H27O10, antifungal, antibacterial, in Garcinia mangastana
Mangiferin C19H18O11, Aphloid, Chimonin, Euxanthogen, widespread occurrence with Isomangiferin, in (Mangifera indica)
Mangostin C24H26O6, mainly in Bonnetiaceae, Clusiaceae, Podostemaceae, in Iris, in Mesua thwaitesii bark and timber, in Garcinia mangostana
Morellin C33H36O7, antibiotic, in Garcinia morella
Norathyriol C13H8O6, tuberculostatic, in Garcinia mangastana
Swertianin C14H10O6

Xanthophylls, Zeaxanthin
Xanthophylls are yellow pigments.
Astaxanthin occurs in microalgae, yeast, krill, shrimp, salmon, lobsters, and some crabs.
Canthaxanthin occurs in paprika, mushrooms, crustaceans, fish and eggs.
β-Cryptoxanthin occurs in vitamin A mango, tangerine, orange, papaya, peaches, avocado, pea, grapefruit, kiwi.
Lutein occurs in spinach, turnip greens, romaine lettuce, eggs, red pepper, pumpkin, mango, papaya, oranges, kiwi, peaches, squash, brassicas, prunes, sweet potatoes, honeydew melon, rhubarb, plum, avocado, pear, cilantro.
Rubixanthin occurs in rose hip.
Zeaxanthin occurs in wolfberry, spinach, kale, turnip greens, maize, eggs, red pepper, pumpkin, orange.
Zeaxanthin, C40H56O2, yellow xanthophyll carotenoid pigment, the most common xanthophyll pigment, (ester of an alcohol) furanoxide, gives colour to peppers, paprika, saffron, wolfberry (beta, Beta-carotene-3-3'-diol), yellow colour of maize (corn flakes) Zea mays, in dark green leafy vegetables, (in broccoli, spinach, collard greens, kale, mustard greens, turnip greens, kale).
Zeaxanthin accumulates within the eye retina, may decrease the incidence of macular degeneration.
Zeaxanthin and lutein, C40H56O2, are the two carotenoid pigments contained within the retina of the eye, in the macula lutea.
They are both powerful antioxidants, absorb blue light and may protect the retina, prevent macular degeneration and cataracts.
Chicken egg yolks contain about 290 micrograms of lutein per yolk, and 210 micrograms of zeaxanthin per yolk.
Name is from Zea Mays, maize (corn flakes).
Zeaxanthin breaks down to form | Picrocrocin | and Safranal |.
See diagram: Zeaxanthin

Gymnemic acid
Gymnemic acid I, C43H66O14, triterpenoid saponin, flavour modifier, makes food tasteless, occurs in Gymnema sylvestre leaves.

Withanolides, in Withania
Ziziphin, C51H80O18

Nightshade glycosides, (solanine glycoside in Solanum nigrum) (glycoalkaloid, α-Solanine from potato sprouts, C45H73NO15 in potato, tomato, eggplant
Tangshenoside, Tangshenoside
Tangshenoside I, C29H42O18, occurs in Dangshen, (Codonopsis pilosula), bell flower, "Poor man's ginseng", climbing perennial, twining stems, bell-shaped flowers, roots for | Tangshenoside saponin | traditional Chinese medicine, tonic to improve well-being, Campanulaceae
Dried herb is sold as root pieces.
Codonopsis pilosula and Codonopsis tangshen are plants widely used in traditional Chinese medicine.
Irilone
Irilone, C16H10O6, isoflavone, inhibits growth of malignant cells, occurs in Trifolium pratense (red clover), and Iris species
Eleutheroside A, daucosterol, C35H60O6, occurs in Siberian ginseng.
Esculeoside A, C56H95NO29, Solanum lycopersicon var.cerasiforme
Protodioscin, C51H84O22, Puncture vine, Solanine, Hedera, Ruscus, Smilax sarsasspiralla, Withania, Yucca schidigera

Diterpenes
Cafestol occurs in Coffea arabica occurs in unfiltered form such as French press coffee or Turkish coffee/Greek coffee.
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Monoterpenes
Limonene occurs in oils of citrus, cherries, spearmint, dill, garlic, celery, maize, rosemary, ginger, basil.
Perillyl alcohol occurs in citrus oils, hops, caraway, mints.

Natural monophenols
Apiole occurs in parsley, celery leaf.
Carnosol occurs in rosemary, sage.
Carvacrol occurs in oregano, thyme, pepperwort, wild bergamot.
Dillapiole occurs in dill, fennel root.
Rosemarinol occurs in rosemary.
Phenolic acids
The term “phenolic acids” is used for 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:
1. Hydroxybenzoic acids, (derived from benzoic acid), 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.
2. Hydroxycinnamic acids, (derived from cinnamic acid), occur as simple esters with quinic acid or glucose.
The most common hydroxycinnamic acids are ferulic acid, caffeic acid, p-coumaric acid and sinapic acid.