Phytochemicals, Plant extracts, Alkylphenols to Tyrosols.

Phytochemicals, Plant extracts, Alkylphenols to Tyrosols. School Science Lessons
(topic16e)
2025-04-23

Phytochemicals, (after Wikipedia)
Contents
Terpenes
Carotenoids
Flavonoids
Glycosides
Hemicelluloses
Phenols, phenolics
Phytosterols
Polysaccharides
Saponins
Steroids
Terpenoids, (isoprenoids)
Xanthophylls

Terpenoids (Isoprenoids)
Terpenes, polymers of isoprene, (C5H8)n
Hemiterpene, 1 isoprene unit, C5H8
Monoterpenes, 2 isoprene units, C10H16
Sesquiterpenes, 3 isoprene units, C15H24
Diterpenes, 4 isoprene units, C20H32.
Sesterterpenes, 5 isoprene units, C25H40
Triterpenes, 6 isoprene units, C30H48
Sesquiterpenes, 7 isoprene units, C15H24
Tetraterpenes, 8 isoprene units, Carotenoids, C40H64
Polyterpenes, many isoprene units, (C5H8)n

Hemiterpenes
Isoprene, C5H8, CH2=C(CH3)CH=CH2
Isoprenol, C5H8O2
Isovaleric acid, C5H10O2
Prenol, C5H10O

Monoterpenes
Monoterpenes and monoterpenoids, two isoprene units, C10H16
Anethole, C10H12O
Bornyl acetate, C12H20O2
Camphor, C10H16O
Carvacrol, C10H14O
Carvone, C10H14O
Citral C10H16O
Geraniol, C10H18O
Hinokitiol, C10H12O2
Limonene, C10H16
Linalool, C10H18O
Menthol, C10H20O
Myrcene, C10H16
Perillyl alcohol, C10H16O
Pinene, alpha-pinene, C10H16
Thujone, alpha-thujone, C10H16O
Thymol, Thymol, C10H14O
Eucalyptol, Cineole, 1,4-Cineole, C10H18O

Sesquiterpenes
Sesquiterpenes and sesquiterpenoids, three isoprene units, C15H24
Humulene, C15H24
Geosmin, C12H22O
Farnesol, C15H26O

Diterpenes
Diterpenes and diterpenoids, four isoprene units, C20H32
Abietic acid, C20H30O2
Cafestol, C20H28O3
Carnosol, C20H26O4
Steviol, C20H30O3
Retinol, C20H30O

Sesterterpenes
Sesterterpenes, five isoprene units, C25H40
Andrastin, C28

Triterpenes
Triterpenes and Triterpenoids
Triterpene, Triterpenoid, a carboxylic acid, C30H48O7S
Triterpenes are a class of terpenes (C30H48) formed by the condensation of six isoprene units.
Saponins

Polyterpenes, (C5H8)n
Gutta-percha, a polyisoprene, natural rubber, (C5H8)n

Fibres
Pectin, (β-D-Galactopyranuronic acid)n, (C6H10O7)n
Lignin, C18H13N3Na2O8S2

Hemicelluloses
Gymnemic acid, C43H66O14
Ginsenosides triterpenid saponin
Hederin, alpha-Hederin, C41H66O12
Araloside, C47H74O18
Escin, Aescin, C55H86O24
Hydroxymethyl terpenes
Anethole, C10H12O
Estragole, C10H12O
Eugenol, C10H12O2
Gingerol, C17H32O4

Steroids
Steroids are compounds containing a 17-carbon 4-ring system, e.g. Cholesterol, C27H46O
See diagram 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), oestrogen, cardiac glucosides, diosgenin, androstane, 19-norpregnane, 7-dehydrocholesterol, previtamin D3,
ergocalciferol (vitamin D2), cholecalciferol (vitamin D3).
Brassicasterol, C28H46O
Estradiol, C18H24O2
Phytosterols
Sterolins
Sterols

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 sterolin.

Sterols
Sterols are solid, waxy, unsaturated steroid alcohols, anti-inflammatory, analgesic agents and occur in animal sex hormones.
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, C53H82O23
Beta-Sitosterol, C29H50O
Campesterol, C28H48O
Cholesterol C27H46O
Cycloastragenol C30H50O5
Ecdysone C27H44O6
Ergosterol C28H44O
Fucosterol C29H48O
Lupeol C30H50O
Sitosterol C29H50O
Stigmasterol C29H48O

Phytosterols
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, many vegetable oils.

List of phytosterols
Campesterol C28H48O
Cholesterol C27H46O
Ecdysone C27H44O6
Ergosterol C28H44O
Fucosterol C29H48O
Spinasterol C29H48O
Sitosterol C29H50O
Stigmasterol C29H48O
Stilbenes
Pallidol, C28H22O6
Proanthocyanidins
Quercetin, a pentahydroxyflavone, C15H10O7
Hesperetin, C16H14O6

Neoflavonoids
16.2.2.0 Isoflavonoids and Neoflavonoids
UNBiolN3C.html#CalophyllumspH">Alexandrian laurel
Dalbergin, neoflavonoid, occurs in Dalbergia species, C16H12O4
Nivetin a neoflavonoid, occurs in Echinops niveus

Flavones
Acacetin
Apigenin
Baicalein
Chrysin
Diosmetin
Herbacetin
Luteolin
Tangeritin
Sinensetin
Chromone

Flavanones
Flavanones
Hesperidin, C28H34O15
NaringeninC15H12O5
SilybinC25H22O10
EriodictiolC15H12O6

Flavonols
Flavonols

Flavan-3-ols, (Flavanols)
Catechins
Catechins
(+)-Catechin | (+)-Gallocatechin | (−)-Epicatechin | (−)-Epigallocatechin | (−)-Epigallocatechin gallate (EGCG) | (−)-Epicatechin 3-gallate, in green tea
Theaflavin, Theaflavin-3-gallate
Thearubigins, in black tea.
br> Proanthocyanidins

Flavanonols
Anthocyanidins and Anthocyanins
Polyphenol amides
Anthocyanins
, C15H11ClO7
Malvidin
Pelargonidin
Peonidin

Isoflavones Isoflavones
Isoflavonoids
Isoflavonoids

Isoflavanes
Isoflavandiols
Isoflavenes
Pterocarpans or Coumestans (phytoestrogens)
Coumestrol
Phytoestrogens:
Matairesinol
Secoisolariciresinol
Pinoresinol
Lariciresinol
Phenolic acids include caffeic acid
Phytoestrogens occur in flax seed and sesame seed.
Stilbenoids
Resveratrol
Pterostilbene
Pinosylvin
Curcuminoids
Curcumin

Tannins
1. Hydrolyzable tannins: Ellagitannins: Punicalagins, Castalagins, Vescalagins, Castalins, Casuarictins, Grandinins, Punicalins, Roburin, Tellimagrandin, Terflavin
Gallotannins: Digalloyl glucose, 1,3,6-Trigalloyl glucose
2. Condensed tannins: Proanthocyanidins, Polyflavonoid tannins, Catechol-type tannins, Pyrocatecollic type tannins, Flavolans
3. Phlorotannins from brown alga
4. Flavono-ellagitannins from Mongolian Oak (Quercus mongolica)

Aromatic acids
Phenolic acids
Salicylic acid
Gallic acid Ellagic acid, C14H6O8
Hydroxycinnamic acid
Caffeic acid
Chlorogenic acid
Cinnamic acid
Ferulic acid
Coumarin
Hydroxybenzoic acids

Saturated cyclic acids
Glycyrrhizin
Eculetin
Esculin

Phenylethanoids
Tyrosol
Hydroxytyrosol
Oleocanthal
Oleuropein
Capsaicin
Gingerol
Alkylresorcinols
Piperine

Glucosinolates
Glucosinolates
The precursors to isothiocyanates:
Sinigrin
Glucotropaeolin
Gluconasturtiin
Glucoraphanin

Aglycone derivatives:
Dithiolthiones (isothiocyanates)
Sulforaphane
Allyl isothiocyanate
Phenethyl Isothiocyanate
Benzyl Isothiocyanate
Oxazolidine-2-thiones
Nitriles
Thiocyanates

Myrosinase

Aglycone derivatives
Glycone and aglycone
Dithiolthiones (isothiocyanates), Sulforaphane brassicas, Allyl isothiocyanate, Phenethyl Isothiocyanate, Benzyl Isothiocyanate
Oxazolidine-2-thiones, Nitriles, Thiocyanates

Organosulfides, Organosulfur compounds
Organosulfur compounds
Sulfur organic compounds

Organic acids
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Indoles
Indole-3-carbinol
3,3'-Diindolylmethane, DIM
Indole-3-acetic acid
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Betalains
Betalains
Betacyanins
Betanin
Isobetanin
Probetanin
Neobetanin
Betaxanthin
Indicaxanthin
Vulgaxanthin

Indicaxanthin

Chlorophylls
Chlorophyllin

Other organic acids
Saturated cyclic acids
Phytic acid
Quinic acid
Oxalic acid
Tartaric acid
Anacardic acid
Malic acid
Caftaric acid
Coutaric acid

Carbohydrates
Monosaccharides
Hexose
Pentose
Polysaccharides
Amylose Amylopectin Resistant starch Arabinoxylan Beta-glucan

Chitin: fungi includes other edible mushrooms
Lentinan: fruit body of shiitake (Lentinula edodes mycelium (LEM)) and other edible mushrooms
Fructan
Inulin

Protease inhibitors:
By protease: Aspartic, Cysteine, Metalloprotease, Serine, Threonine, Trypsin, Kunitz protease inhibitors
By mechanism: Suicide, Transition, Protein protease inhibitors and Chelating agents

Glycosides Aminoglycosides
Cardiac glycosides
Piceid, cis-Piceid, C20H22O8
Strophanthin, C36H54O14
Protodioscin, C51H84O22
Cyanogenic glycosides
Eleutheroside, C34H46O18
Cymarine, C30H44O9
Charantin, C35H60O6 + C35H58O6
Digitoxin, C41H64O13
Digoxin, C41H64O14
Fatty acids
Glucosides
Linamarin, C10H17NO6
Ouabain, C29H44O12
Polyhydric alcohols

Proteins
Phycobilins
Phycobiliproteins
Plant extracts
Phytochromes
Haeme, heme b, C34H30FeN4O4-4
Porphyrins
Legheamoglobin

Protease inhibitors
Tangshenoside, Tangshenoside I, C29H42O18
Astragaloside, C28H32O17
Benzofuranoids
Polyvinyl pyrrolidene, 1-Vinyl-2-pyrrolidone, C6H9NO

Alkaloids
Estradiol, C18H24O2
Esculeoside, C58H95NO29

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

Brassicasterol
Brassicasterol, C28H46O,a phytosterol, in marine algae, fish, and rapeseed oil, in Tuber indicum, and Cyttaria johowii
It is used as a biomarker for the presence of marine algae

Flavonoids
Flavonoids, (benzene ring.3-carbon link.benzene ring), C6-C3-C6 compounds
See diagram 16.3.4.2. Flavonoids (apigenin-7-monoglucoside), flavones, riboflavin, anthicyanin.
Aglycone (flavonoid - sugar = aglycone), cardiac glycoside -->; steroid molecule is the aglycone.
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, are 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.
Tannic acid, C76H52O46
Almost all fruits, vegetables, herbs and spices contain flavonoids.
Flavonols
Flavanones
Flavan-3-ols, (Flavanols)
Flavanonols
Flavones
Isoflavones

Flavonols
3-Hydroxyflavone, C15H10O3, flavonol, Flavon-3-ol
Azaleatin, C16H12O7, a monomethoxyflavone
Fisetin
Fisetin, C15H10O6, a tetrahydroxyflavone
Galangin
Gossypetin, C15H10O8, a hexahydroxyflavone
Kaempferide, C16H12O6, a monomethoxyflavone
Kaempferol
Isorhamnetin
Morin
Myricetin
Quercetin
Rutin
Natsudaidain
Pachypodol, C18H16O7, a trimethoxyflavone
Quercetin, C15H10O7, a pentahydroxyflavone
Rhamnazin
Rhamnetin

Rutin
Rutin, C27H30O16, a tetrahydroxyflavone, flavonol glycosides, occurs in citrus fruits, oranges, lemons, limes, grapefruit, berries, peaches, apples, pagoda tree fruits, asparagus, buckwheat, parsley, tomatoes, rhubarb, tea, tobacco

Hesperidin
Hesperidin, C28H34O15, Hesperidoside, a disaccharide derivative, a flavanone glycoside, (flavanones are ketones derived from flavone)
It occurs in citrus fruits, Humulus lupulus, Ficus erecta
Hesperetin
Naringin, flavonoid glycoside

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 hydrate, C22H43N5O13.xH2O, broad spectrum antibiotic

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

Anthocyanins
Anthocyanins [Greek (ánthos) 'flower' (kuáneos) 'dark blue'], anthocyans, flavonoids, vacuolar pigments red to black, blueberry, raspberry, (after Wikipedia)
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), and in cyanidin chloride, C15H11ClO6.
For example, in 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, pistachios.

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.
For example. Quercetin, C15H10O7, flavonoid, yellow powder, antioxidant in many plants, a phytoestrogen, are used for vegetables in a good diet and food additive.

Astragaloside
Astragalosides are chemicals from Astragalus membranaceus, e.g. Astragaloside IV, C41H68O14.
"Astragaloside IV Astragalus Root Extract Powder" is sold as a health food.

Betalains
Betalains, C24H26N2O13, Betalain, compounds derived from the non-essential amino acid Tyrosine,C9H11NO3, and include the Betaxanthins and Betacyanins.
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), Opuntia sp., Amaranthus spinosus leaves, Bougainvillea glabra floral bracts, in Portulaca sp.
They also occur in Gomphrena globosa, and in some Basidiomycota fungi.
width="100%" size="2"> Cardiac glycosides
Cardiac glycosides, (steroidal glycosides, digitalis glycosides, cardiovascular glycosides), cymarin, heart stimulants, occur in Digitalis sp. and in Convallaria sp.
Digitalis glycosides, e.g. Digitoxin, C41H64O13, Digoxin, C41H64O14
Scilla glycosides, e.g. proscillardin, C30H42O8, occur in Scilla, and Drimia maratima
Strophanthus glycosides, e.g. Ouabain, C29H44O12, C29H44O12.8H2O, arrow poison, occurs in Acokanthera ouabaio.

Cardenolides.
Cardenolides are cardiac glycosides and they occur mainly in the toxic latex of Asclepidaceae.
Cardenolide, C23H34O2, occurs in Digitalis purpurea. is a steroid molecule, but "cardenolides" are usually cardiac glycosides.
Cardenolides.
See diagram. Cardenolide
Cymarine
Digitoxin
Digoxin
Ouabain
Strophanthin

Carotenes
Carotenoids are classified depending on the presence or absence of oxygen. Carotenes, (C40H56), and Xanthophylls.(C40H56)n.
Carotenes are terpenoids, isoprenoids, a carotenoid, Carotene (Latin carotin, carrot, C40Hx, occurs in many plants, photosynthetic pigments.
Carotenes are orange pigments, which cause the colour of carrots.
Carotenes, C40H56, are simple orange or red unsaturated hydrocarbons, many isomers, precursor of vitamin A.
α-Carotene occurs in vitamin A, carrots, pumpkins, maize, tangerine, orange.
β-Carotene, C40H56, beta-carotene, cyclic carotene, strongly-coloured red-orange pigment.
It occurs in dark leafy greens, red, orange and yellow fruits and vegetables.
γ-Carotene occurs in vitamin A, δ-Carotene, ε-carotene.
Phytofluene, C40H62, occurs in sweet potato, and in oranges.
Squalene, C30H50
Cucurbitacins, C32
Oleanolic acid C30H48O3
Ursolic acid C30H48O3
Betulinic acid C30H48O3

Carotenoids Tetraterpenes, C40H64
Carotenoids
The carotenoids are hydrocarbons, -CH
Carotenes: α-Carotene, β-Carotene, γ-Carotene, δ-Carotene, ε-carotene - all C40H56
Lycopene C40H56
Phytoene, C40H64

Catechins
Catechins are polyphenolic antioxidants with phytotonic properties, are used for treating obesity.
Catechins are water soluble polyphenols and antioxidants that are easily oxidized, flavon structure and are called flavonoids.
Catechin, C15H14O6, catechinic acid, a flavan-3-ol, colourless, bioflavonoid, tannin, antioxidant, anti-viral, anti-bacterial,
Catechin occurs as both (+)-catechin and (-)-epicatechin (cis) forms, (+)-catechin is a polyphenolic antioxidant, an antioxidant flavonoid, occurs in woody plants.
Catechin occurs in woody plants, willow catkin, Salix haemostatic, Potentilla fragarioides, Salix capra (willow catkin) Cinnamomum kotoense, Begonia nantoensis.
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 sp. of white tea, green tea, black tea, grapes, apple, cocoa, lentils, black-eyed peas.
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.
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, occurs 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).
Dark chocolate and red table wine contain high concentrations of catechins and their compounds.
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).
Catechins
Catechin gallate
Catechin hydrate
Epicatechin, (EC), Flavonoid
ECG Epicatechin gallate (ECG), Flavonoid
EGC Epigallocatechin, Bioflavonoid.

Charantin
Charantin, glucoside, (C35H60O6) + (C35H58O6), hypoglycaemic so may cause low blood sugar, in Asian bitter melon (Momordica charantia)

Cyanogenic glycosides
Chemicals cause protective cyanogenesis, produce HCN, when plant is attacked.
Cyanogenic glycosides include. Amygdalin, Cardiospermin, Dhurrin, Linamarin, Lotaustralin, Prunasin, Sarmentosin.
Cyanogenic glycosides (cyanophore glycosides), (aglycone contains CN group), amygdalin
Betanin, dhurrin
Naringin, flavonoid glycoside
Betanine, C24H26N2O13, Phytolaccanin, in Portulaca jacobseniana, AND Hylocereus polyrhizus.
, 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 be 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)!
Amygdalin , C20H27NO11, a cyanogenic glucoside isolated from almonds, occurs in Malus sp. and Prunus salicina, family Rosaceae.
Cardiospermin, C11H17NO7.
Dhurrin, C14H17NO7, a beta-D-glucoside, a nitrile, a cyanogenic glycoside, occurs in Sorghum arundinaceum, and Ostrya virginiana.
21.0 Linamarin, lotaus, prunisin, rose family, bamboo, cassava, sorghum
Lotaustralin, C11H19NO6, a cyanogenic glycoside, occurs in Rhodiola sachalinensis, aand Phaseolus lunatus.
Prunasin, C14H17NO6, in kernels of Prunus sp., immature fruits of Passiflora sp., leaves of perilla (Perilla frutescens), Camellia sinensis,Vasconcellea quercifolia
Sarmentosin, C11H17NO7, a glycoside, in Rhodiola sacra, and Rhodiola crenulata.

Eleutheroside
Eleutheroside B, C17H24O9, syringin, phenyl propanoid glycoside occurs in Siberian ginseng, Syringa vulgaris, lilac bark
Eleutheroside A, C35H60O6, daucosterol, saponin and sterol glycoside, in Siberian ginseng

Escin
Escin or aescin, C55H86O24. 16.3.5.1a, occur in horse chestnut, Aesculus hippocastanum, Sapindaceae.

Eriodictiol
Eriodictiol, C15H12O6, a tetrahydroxyflavanone, and occurs in Camellia sinensis, Prunus serrulata, and citrus fruits.

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

Estradiol
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

Flavanonols
Anthocyanidins (flavonals) and Anthocyanins occur occurs 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 and some flower petals.

Flavones
Flavone, (2-Phenylchromone), C15H10O2, colourless crystalline aromatic ketone, simplest flavone, flavonoid that forms the "backbone" for flavonoids, nematicide.
It occurs in leaves, stems, and seed capsules of primroses, (in citrus flavonoids. rutin, hesperidin, naringin, tangeritin), the most active flavonoid.
A flavonoid has structure based on, or similar to, the structure of a flavone.
Flavone ketone derivatives, yellow glycoside plant pigments, used as dyestuffs.
List of flavones: Acacetin, Apigenin, Baicalein, Chrysin, Diosmetin, Herbacetin, Luteolin

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
Aloin
Aloenin
Arctigenin, C21H24O3
Betanin, C24H26N2O13
Cycasin, C8H16N2O7
Fraxin, C16H18O10
Icariin, C33H40O15
Linamarin, C10H17NO6
Piceid, C20H22O8
Piceatannol, C14H12O4, 3-Hydroxyresveratol
Picrocrocin, C16H26O7
Quercitrin, C21H20O11
Rhamnazin, C17H14O7
Rhamnetin, C16H12O7
Rhaponticin, C21H24O9
Salicin, C13H18O7
Salidroside, rhodioloside, 8-o- β-D glucoside of tyrosol, neuroprotective, antidepressant, anxiolytic,. C14H20O7
21.0 Linamarin, C10H17NO6
Piceid, C20H22O8
Piceatannol

Glucosinolates
(Nitrogen-containing compounds)
Glucosinolates, mustard oil glycosides, are from sugar + amino acid, contain S and N.
Glucosinolates + enzyme hydrolysis by thioglucosidases --> mustard oil glycosides, when plant cells are damaged or chewed.
Glucosinolates are the precursors to isothiocyanates.
List of glucosinolates.
Epiprogoitrin, C11H19NO10S2, in Crambe abyssinica oil, Brassicaceae
Hydroxyglucobrassicin
Methoxyglucobrassicin
Neoglucobrassicin
Progoitrin
Sinalbin
Glucoalyssin
Sinigrin (the precursor to allyl isothiocyanate)

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 from sugars.
They are usually potentially heart toxic, but Digitalis sp. 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.
It is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom.
See diagram. Fructose, Glycosyl group.

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 from glucose. Saponins
Saponins are Triterpene glycosides and Steroid glycosides Triterpene glycosides are natural glycosides present in various plants, herbs and sea cucumbers. used for traditional medicine.
Steroid toxic glycosides, forming frothy colloidal soapy solutions when agitated in water, emulsifiers, detergents, often toxic to fish.
Quillaja saponaria, the soap bark tree or soapbark, Quillajaceae, powdered inner bark used as soap, contains glycoside saponin, Chilean medicinal plant.
The bark is the source of quillaia, which contains saponins.
Saponin
Saponin, C58H94O27, sapogenin glycoside, occurs in many plants, occurs in Saponaria officinalis and Trigonella foenum-graecum.
Glycyrrhizin
Glycyrrhizin, C42H62O16, glycyrrhizic acid, triterpenoid saponin,a tricarboxylic acid,is extracted from the root of the licorice plant; Glycyrrhiza glabra. It is used as a hepatoprotective drug to treat hepatitiss.
2. Steroid glycosides, saponins with 27-C atoms
Steroid glycosides are modified triterpenoids, cytotoxic, neurotrophic and antibacterial properties.
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.

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

Haeme
Haeme (heme), occurs in haemoglobin, a globular protein in animals, 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, C19H14N4, a linear tetrapyrrole
See diagram 16.3.5.2.1. Haeme (heme), C49H56O6N4Fe
See diagram 16.3.5.2.2 Tetrapyrroles
See diagram, Biliverdin, a bile pigment, C33H32N4O6-2

Hederin
Alpha-Hederin, C41H66O12, helixin, a pentacyclic triterpenoid saponin, anti-inflammatory, antifungal, strong haemolytiic activity
It occurs in stem bark of Kalopanax pictus, Nigella sativa, Lonicera macrantha, and in Anemone taipaiensis.
l Beta-Hederin, C41H66O11, eleutheroside K, a triterpenoid saponin, antifungal, strong haemolytic activity
Beta-Hederin occurs in ivy Hedera helix leaves, Akebia quinata, and Anemoclema sp.

Hesperetin
Hesperetin, C16H14O6, a trihydroxyflavanone, antioxidant, antineoplastic agent, the predominant flavonoid in lemons and oranges, occurs in Camellia sinensis.

Hydroxybenzaldehydes
Hydroxybenzaldehydes are phenolic aldehydes, e.g. 4-Hydroxybenzaldehyde, C6H4OH(CHO), a benzaldehyde, C6H5CHO, with a hydroxy group at position C-4.
| 4-Hydroxybenzaldehyde, C7H6O2 | Gallic aldehyde, C7H6O4 | AnisaldehydeC8H8O2 |
| Protocatechuic aldehyde, C7H6O3 | Syringaldehyde, C9H10O4 | VanillinC8H8O3 |

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 |
3-hydroxybenzoic acid, C7H6O3, in gut microfauna
4-hydroxybenzoic acid, C7H6O3 --> esters --> parabens, (esters of para-hydroxybenzoic acid)
trihydroxybenzoic acid Gallic acid, C7H6O5, hydrolysable tannin, pseudotannin
Benzoic acid, C6H5COOH, C7H6O2
Ellagic acid, C14H6O8
Hydroxybenzoic acids
Hydroxycinnamic acids

Indoles
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.
IAA, Indole-3-acetic acid, C10H9NO2, (See: 1.)

Iridoids
Iridoids, (monoterpenoid lactones), (Terpenes and Terpenoids)
Allamandin Asperuloside |
Aucubin Catalposide |
Fulvoplumierin, C14H12O4 Harpagoside Loganin|
Nepetalactone Plumericin, C15H14O6 Secologanin |

Isoflavones
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.
Red clover, Trifolium pratense, contains the most isoflavones of any plant.
Isoflavones are similar to estradiol, beta-estradiol, 17beta-estradiol, C18H24O2, in chemical structure.
Isoflavones are found exclusively in the family Fabaceae.
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).
Isoflavones BetavulgarinC17H12O6
Daidzein, C15H10O4
Formononetin, C16H12O4
Genistein, C15H10O5
Glycitein, C16H12O5
Prunetin, C16H12O5
Puerarin, C21H20O9

Betavulgarin
Betavulgarin, C17H12O6, antifungal isoflavonoid, an hydroxyisoflavone, occurs in Beta vulgaris, B, lomatogona, and in Iris tingitana

Daidzein
Daidzein, C15H10O4, dihydroxyisoflavone, is anti-inflammatory, anti-microbial, antioxidant, phytoestrogenic, antineoplastic.
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.
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.
It occurs in Pueraria lobata, Salvia hispanica, and Begonia nantoensis.

Formononetin
Formononetin, C16H12O4, Biochanin B. Formononetol, a methoxyisoflavone, a phytoestrogen, occurs in n Dalbergia nigrescens, and in Glycyrrhiza pallidiflora.

Genistein
Genistein, C15H10O5, (4',5,7-Trihydroxyisoflavone), Genisteol, phytoestrogenic isoflavone, antineoplastic, from soy products, induces apoptosis, antioxidant
It is antiangiogenic, immunosuppressive, anti-inflammatory, anti-atherosclerosis, a biomarker for soy consumption, and an antitumour
It may lessens risk of cardiovascular diseases.
It occurs in Pueraria mirifica.
It is an isoflavonoid derived from soy products. 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, 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
Genistein, C15H10O5, is a 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4', with antioxidant properties.
It is an antineoplastic agent, a phytoestrogen, and an isoflavonoid derived from soy products.
It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent.
Additionally, genistein has antihelmintic activity, and it is the active ingredient in Felmingia vestita, is 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, and lupin.
Genistein occurs in Salvia hispanica, and Glycine soja.

Glycitein
Glycitein, C16H12O5, a methoxyisoflavon, a phytoestrogen, occurs in mycelia of the fungus Cordyceps sinensis, Salvia hispanica, and in Glycine max.

Isoflavone
Isoflavone, C15H10O2, the simplest isoflavone, it lessens coronary heart disease, atherosclerosis, type II diabetes mellitus, breast / prostate cancer.
Soybean is rich in dietary isoflavones, soy phytoestrogen, 1-2 mg/gram. Isoflavone is used in oral over-the-counter dietary supplements It occurs in Iris domestica, and in Pueraria montana, kudzu.

Prunetin
Prunetin, C16H12O5, a hydroxyisoflavone, anti-inflammatory, occurs in Iris milesii, and in Ficus nervosa.

Puerarin
Puerarin, C21H20O9, kakonein, a hydroxyisoflavone, cardioprotective, antioxidant, anti-inflammatory, occurs in Bupleurum chinense, and Pueraria calycina.

Isoflavonoids phytoestrogens
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, Isoflavanones
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.
Favanone glycosides, occurs in citrus fruits, e.g. kumquat, lemon, lime, grapefruit, orange, tangerine, artichoke, red and white wine.

Isorhamnetin
Isorhamnetin, C16H12O7, 3-Methylquercetin, monomethoxyflavone, anticoagulant, hydroxyflavonol, flavone, occurs in Caragana frutex, and in Camellia sinensis

Legheamoglobin
Legheamoglobin 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.
Phycobilins
Phycobiliproteins
Polyvinyl pyrrolidene
Porphyrins

Lignans
Lignans C25H30O8, an ethyl carboxylate
Lignans are plant polyphenols derived from phenylalanine, 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
See diagram Lignan

Limonene
Limonene, C10H16, a monoterpene, colourless liquid, odour of lemons. insoluble in water, used as a solvent, in floor polishes, in oils of citrus, cherries, spearmint

Magnolol
Magnolol, C18H18O2, a biphenyldiol, in traditional herbal medicine, antifungal, in bark of Magnolia grandiflora, and in M officinalis.

Menthol
1. Menthol, C10H20O, C10H19OH, dl-Menthol, (2-Isopropyl-5-methylcyclohexanol), is a white crystalline solid with a peppermint odour and taste.
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.
Apiole, parsley, celery leaf
Carnosol
Carvacrol, oregano, thyme, pepperwort, wild bergamot
Dillapiole, dill weed, fennel root

Myrosinase
Myrosinase enzyme, 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.
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.
1,4-Naphthoquinone, (C10H6O2), strong odour, red-brown alkaline solution
Triphophyllum peltatum

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

Syn-propanethial-S-oxide cut onions., C6H10OS2, occurs in Garlic 16.2.8.9 Sulfoxide, Alliin
Allyl isothiocyanate, C4H5NS, occurs in (Armoracia rusticana), Horseradish
Propanethial S-oxide, C3H6OS, occurs in cut onions. 16.2.8.9
Allyl methyl trisulfide occurs in garlic, onions, leeks, chives, shallots
Diallyl disulfide occurs in garlic, onions, leeks, chives, shallots.
Allicin occurs in garlic.
Allyl isothiocyanate occurs in horseradish, mustard, wasabi.

Pallidol
Pallidol, C28H22O6, a tetracyclic stilbenoid, antioxidant, antifungal, polyphenol
It occurs in red wine, Cissus, and Parthenocissus.

Perillyl alcohol
Perilla alcohol, C10H16O, a limonene monoterpenoid, in essential oils, lavender Tetradenia riparia, Magnolia officinalis, citrus oils, hops, caraway, mints.

Phenol
Phenol, C6H5OH, carbolic acid, the simplst of the phenols, aromatic organic compound, corrosive, acute toxic
Phenyl group (−C6H5) + hydroxy group (−OH), volatile white crystalline solid, mildly acidic, cause chemical burns or numbs
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)
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.
See diagram 16.3.5.4. Phenol
Phenol is the 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, 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
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, 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, cymophenol, a monoterpenoid phenol, (5-Isopropyl-2-methylphenol), Karvakrol, Isopropyl-o-cresol, p-menthane monoterpenoid
It inhibits bacterial growth, food additive, volatile oil component, flavouring agent, antimicrobial agent, agrochemical, (anti-fungal agent), in black walnut.
It occurs in many essential oils, e.g. Thyme oil and Origanum oil, and 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. Chloroxylenol, C8H9ClO, (4-chloro-3,5-dimethylphenol), an halophenol, monochlorobenzene, antiseptic, disinfectant agent in antibacterial soaps
It is a widely-used antiseptic, "Dettol", "PCMX"), bactericidal against most Gram-positive bacteria, for skin disinfection and surgical instruments
But is is less effective against Staphylococci and Gram-negative bacteria, inactive against Pseudomonas sp. and bacterial spores.

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 sp. 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, 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.
Salicylic acid, C7H6O3, HOC6H4COOH, 2-Hydroxybenzoic acid, a monohydroxybenzoic acid
Vanillic acid, C8H8O4, a monohydroxybenzoic acid
Gallic acid, C7H6O5, a trihydroxybenzoic acid
2. Hydroxycinnamic acids, occur as simple esters with quinic acid or glucose.
Ferulic acid, C10H10O4, 4-Hydroxy-3-methoxycinnamic acid
Caffeic acid, C9H8O4, 3,4-Dihydroxycinnamic acid

Phenolic ketones
Phenolic ketones are used as organic synthesis raw materials and solvents, dewaxing agents, organic synthesis, raw material for synthetic fragrances and medicine.
Apocynin, Danielone, Humulone, Lupulone, Picein
1. Acetophenones. Ameliaroside, Picein, Salicinerein, Salinigrin, p-Hydroxyacetophenone glucoside, phenolic compound, glucoside of piceol, glycoside, Phenanthrene, C14H18PO7, occcurs in roots of>Norway spruce (Picea abies), Salix, and in Homogyne.
2. Phloroglucinol derivatives
Phloroglucinol, C6H6O3, Benzene-1,3,5-triol
ApocyninApocynin in Iris
Humulone
Lupulone, in Humulus lupulus
Picein, C14H18O7, glycoside occurs in Rhodiola crenulata, and Salvia officinalis.
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, and in Mallotus, toxic, antihelminthic used to treat tumours in India, used as silk dye.

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, an organic heterotetracyclic compound, is a red pigment in Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood) 16.3.4.1.1 Benzofurans
Chromones and Chromenes
Coumarins
Coumarone, 16.3.4.1a
16.2.2.0 Isoflavonoids and Neoflavonoids
Lignans
16.2.2.0 Isoflavonoids and Neoflavonoids
Phenolic acids
Phenols
Phenolic ketones
Phenylpropanoids
Quinones
Stilbenes and Stilbenoids
Tannins
Xanthones

Phenols, phenolics
Phenols are compounds having one or more hydroxy groups attached to a benzene ring, C6H6, or other aromatic hydrocarbon, e.g. 2-naphthol, C10H8O
Isoflavonoids, (phytoestrogens)
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)
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 acids. Phenolic acids
Phenolic ketones. Phenolic ketones
Phenols, phenolics
Phenol, carbolic acid, the simplest phenol, C6H5OH
Phenolic acids
Phenolic ketones
Polyphenols
Tyrosol, C8H10O2
.. Guaiacol,2-Methoxyphenol, C7H8O2
Juglone, C10H6O3
Plumbagin, C11H8O3
Hydroxybenzaldehydes
Magnolol, C18H18O2
Phenolic acids
Hydroxybenzoic acids
Hydroxycinnamic acids
Stilbenes and Stilbenoids
Lignans
Phenylpropanoids
Polyphenols are often repeated connected units of.
Catechol, pyrocatechol, C6H6O2
Resorcinol, C6H4(OH)2
Phloroglucinol, a phlorotannin, C6H3(OH)3
Arbutin, C12H16O7
Catechol, Coumestrol, C15H8O5
Pyrogallol, C6H6O3

Monophenols
Apiole, Apiole (parsley), C12H14O4
Carnosol, C20H26O4
Carvacrol, C10H14O
Dillapiole, C12H14O4

Polyphenols
Anthocyanins
Tannins
Phenolic acids

Phenylpropanoids
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

Phycobilins
Phycobilins, include the blue-green pigment phycocyanin and the red pigment phycoerythrin to enable red algae to live photosynthetically.
Phycobilin pigments occur in the cytoplasm and stroma of chloroplasts, where they absorb light energy that is passed on to other processes.
Phycobilin, C33H38N4O6, phycocyanobilin.
The metal-free blue phycobilin pigment in a conjugated chromoprotein of blue-green algae, which functions as light-absorbing substance together with chlorophylls.
Pycocyanin and phycoerythrin are fluorescent.
1. Phycocyanin is a blue-green pigment in Phylum Cyanobacteria, pigment-protein complex, an accessory pigment to chlorophyll.
2. Phycoerythrin (PE) is a red protein-pigment complex, in red algae, Division Rhodophytan, an accessory pigment to chlorophyll.
It is red pigment, because of the prosthetic group, phycoerythrobilin, C33H38N4O6.
Red algae occur in deep water where blue light predominates.

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

Phytoestrogens
Phytoestrogens occur in seeds (flax, sesame, pumpkin, sunflower, poppy), whole grains (rye, oats, barley), bran (wheat, oat, rye), fruits and vegetables.
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.

Plant extracts
1. Butylphthalide, C12H14O2, celery seed, Chinese medicine, antioxidant
2. Creosote, from beechwood tar
3. Lycopodium, clubmoss, Family Lycopodiaceae, 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

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

Polyvinyl pyrrolidene
Polyvinyl pyrrolidene, C6H9NO, n-vinyl-2-pyrrolidone, "Povidone", PVP, is a water-soluble polymer, used as a coating or binder in medical tablets.
The povidone-iodine complex (PVD-iodine) is in the antiseptic "Betadine"
It has replaced tincture of iodine solution for the topical application of iodine as an antiseptic.
See diagram 16.3.5.4. Povidone, PVP
E1201

Porphyrins
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

Protodioscin
Protodioscin, C51H84O22, glycoside, steroidal saponin in aphrodisiac Puncture vine, (Tribulus terrestris)

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

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

Sesamin
Sesamin, C20H18O6, occurs in sesame oil.
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.
Sesame, (Sesamum indicum), and in bark of Fagara cujabensis
Sesame oil, Composition of edible oils. 3.9.3 (Table)
Sesamol, C7H6O3, antioxidant, in sesame seeds and sesame oil
Podophyllotoxin, C22H22O8, lignan

Silybin
Silybin, C25H22O10, silibinin, a flavonolignan, polyphenol, antioxidant, antineoplastic, anticancer, protect liver cells against toxins.
It occurs in milk thistle, Silybum marianum, Silybum eburneum, and in Aspergillus iizukae.

Stilbenes
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
Resveratrol occurs in grape (skins and seeds, grape wine), nuts, peanuts, Japanese Knotweed root.
Rhaponticin, C21H24O9, stilbenoid glucoside, phytoestrogen, occurs in rhubarb rhizomes.

Tangshenoside
Tangshenoside I, C29H42O18, a pentanoic acid, occurs in Codonopsis pilosula, Dang shen, and Codonopsis tangshen are plants widely and used in traditional Chinese medicine.

Xanthones
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, occurs in Athyrium mesosorum, fern.
Bellidifolin C14H10O6, anti-heptotoxic, mutagenic, occurs in Gentiana lutea.
Gambogic acid C33H44O3, occurs in gamboge the gum resin of Garcinia hamburgyi.
Gentisein, C13H8O5, occurs in Garciniama sp.
Gentisin C14H10O5, occurs in Garcinia lutea.
Gartanin C24H27O10, antifungal, antibacterial, occurs in Garciniama sp.
Mangiferin C19H18O11, Aphloid, Chimonin, Euxanthogen, widespread occurrence with Isomangiferin, occurs in Mangifera indica.
Mangostin C24H26O6, mainly occurs in Garciniama sp.
Morellin C33H36O7, antibiotic, occurs in Garcinia morella.
Norathyriol C13H8O6, tuberculostatic, occurs in Garciniama sp.
Swertianin C14H10O6

Xanthophylls
Xanthophylls, (C40H56)n, are hydrocarbons + oxygen, and are usually yellow pigments in the leaves of most plants.
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 oxygenated carotenoids, carotene derivatives.
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.
Antheraxanthin
Cryptoxanthin
Fucoxanthin
Violaxanthin
Zeanthin

Aviculin, C26H34O10, occurs in >Knotgrass.
Honokiol, C18H18O2, neilignan biphenol, spicy odour, occurs in traditional Asian herbal medicine, analgesic, used to treat anxiety.