School Science Lessons
Topic16e
2019-03-21
Please send comments to: J.Elfick@uq.edu.au

Phytochemicals
Table of contents
See: OrganicChemistry, Biochemistry (Commercial)
16.3.1.0 Phytochemicals
1.0 Carbohydrates and Lipids
2.0 Compounds containing Nitrogen
3.0 16.3.0.0 Alkaloids
4.0 Phenolics
5.0 16.3.5.0 Terpenes and Terpenoids (Isoprenoids)

Alphabetic index
Allantoin
16.4.3.0 Amines
16.3.4.2.5 Anthocyanidins, anthocyanins
16.3.4.0 Aromatic compounds
Benzfuran, coumarone, C8H6O 16.3.5.3.0 Betalains, betains
Brazilin
Cardenolides
16.3.5.1.8a Carotenoids, Tetraterpenoids
Chromones, Chromone glycosides
CPY3A4
Coumarin
16.3.3.0 Furanocoumarin, furocoumarin
16.3.4.2.0 Flavonoids (Bioflavonoids), Flavonols, Flavanols
Haematoxylin
Glycerine
Glycolic acid, hydroxyacetic acid, HOCH2COOH, α-hydroxy acid
16.3.2.6.0 Glycosides
16.2.2.0 Isoflavonoids, isoflavones, phytoestrogens
16.3.4.2.18 Lignans
16.6.0 Oils, essential oils, fixed oils, vegetable oils, and resin-derived
6.3.4.2.14.0H Phenolic acids, Polyphenols
16.4.7.0 Phenols, phenol derivatives, phenolics
Phenolic ketones
16.3.4.2.24 Hydroxybenzoketones
16.4.8.0 Plant extracts (10)
16.3.10.0 Quinones
16.3.4.2.28 Naphtoquinones
16.4.6.0 Organosulfur compounds, organosulfides
Proanthocyanidin rotenone
16.3.5.2.0 Tetrapyrroles, porphyrins (haem)
16.3.7.0 Saponins
16.3.8.0 Steroids, sterols, steroid alcohols, natural steroids
16.3.4.2.18a Stilbenes, stilbenoids
16.2.7.0 Tannins, plant polyphenols
16.3.5.0 Terpenes and Terpenoids (Isoprenoids)
Xanthones
Miscellaneous pohenolics

16.3.4.2.0 Flavonoids
16.3.4.2.5 Anthocyanidins, anthocyanins
16.3.4.2.1 Anthoxanthins
16.3.4.2.8 Chalcones, dihydroxychalcones
16.3.4.2.9 Dihydrochalcones
16.3.4.2.10 Dihydroflavonols
16.3.4.2.1b Flavanols, flavan-3-ols
16.3.4.2.2 Flavanones, dihydroflavones
16.3.4.2.3 Flavanonols, dihydroflavonols
16.3.4.2.4 Flavans
16.3.4.2.1a Flavones, condensed tannins
16.3.4.2.1b Flavonols, flavan-3-ols, catechins
ECG Epicatechin gallate
EGC Epigallocatechin
EGCG Epigallocatechin gallate
Gallocatechin
16.3.4.2.6 Isoflavonoids, isoflavones, phytoestrogens
16.3.4.2.7 Neoflavonoids, polyphenols
Betagarin, anti-fungal flavonoid, C18H16O6

16.3.4.2.14.0H Phenolic acids, Polyphenols
Phenolic acids
16.3.4.2.14 Hydroxybenzoic acids
16.3.4.2.15 Hydroxycinnamic acids
16.3.4.2.16 Hydroxyphenylacetic acids
16.3.4.2.17 Hydroxyphenylpropanoic acids

Polyphenols
16.3.4.2.19 Alkylmethoxyphenols
16.3.4.2.20 Alkylphenols
16.3.4.2.21 Curcuminoids
16.3.4.2.22 Furanocoumarins
16.3.4.2.23 Hydroxybenzaldehydes
16.3.4.2.24 Hydroxybenzoketones
16.3.4.2.25 Hydroxycinnamaldehydes
16.3.4.2.25a Hydroxycoumarins
16.3.4.2.26 Hydroxyphenylpropenes
16.3.4.2.18 Lignans
16.3.4.2.27 Methyoxyphenols
16.3.4.2.28 Naphtoquinones
16.3.4.2.29 Phenolic terpenes
16.3.4.2.18a Stilbenes, stilbenoids
16.3.4.2.30 Tyrosols
16.3.4.2.31 Other polyphenols

16.3.5.2.0 Tetrapyrroles, porphyrins (haem)
16.3.5.2.1 Tetrapyrroles, bilin, bilirubin, biliverdin, haeme
16.3.5.2.4 Legheamoglobin, nitrogen-fixing bacteria, legumes
16.3.5.2.3 Photosynthetic pigments, chlorophyll a and chlorophyll b
16.3.5.2.6 Phycobilin, phycocyanin, phycoerythrin, Cyanobacteria, Rhodophyta
16.3.5.2.5 Phycobiliproteins, nitrogen-fixing cyanobacteria, Anabaena azollae
16.3.5.2.7 Phytochromes, red light sensitive
16.3.5.2.8 Polyvinyl pyrrolidene, povidone
16.3.5.2.2 Porphyrins, porphine

16.3.5.3.0 Betalains, betains
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
Betanin
2. Betaxanthins yellow-orange
Indicacaxanthin, C14H16N2O8, antioxidant, in beets, prickly pears, Red dragonfruit

16.3.4.2.19 Alkylmethoxyphenols
4-Ethylguaiacol, C9H12O2
4-Vinylguaiacol, C9H10O2

16.3.4.2.20 Alkylphenols
3-Methylcatechol, C7H8O2
4-Ethylcatechol

16.3.4.2.21 Curcuminoids
Bisdemethoxycurcumin, C19H16O4
Curcumin, C21H20O6
Demethoxycurcumin, C20H18O5

16.3.4.2.22 Furanocoumarins
Bergapten, C12H8O4
Isopimpinellin, C13H10O5
Psoralen, C11H6O3
Xanthotoxin, C12H8O4

16.3.4.2.23 Hydroxybenzaldehydes
4-Hydroxybenzaldehyde, C7H6O2
Gallic aldehyde, C7H6O4
p-Anisaldehyde, C8H8O2
Protocatechuic aldehyde, C7H6O3
Syringaldehyde, C9H10O4
Vanillin, C8H8O3

16.3.4.2.14 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

16.3.4.2.24 Hydroxybenzoketones
2,3-Dihydroxy-1-guaiacylpropanone, C10H12O5
3-Methoxyacetophenone, C9H10O2

16.3.4.2.25 Hydroxycinnamaldehydes
Ferulaldehyde, C10H10O3
Sinapaldehyde, C11H12O4

16.3.4.2.15 Hydroxycinnamic acids
Caffeic acid, C9H8O4
Chicoric acid, C22H18O12
Cinnamic acid, C9H8O2
Ferulic acid, C10H10O4
Isoferulic acid, C10H10O4
m-Coumaric acid, C9H8O3
Rosmarinic acid, C18H16O8
Schottenol ferulate, C39H58O4
Sinapic acid, C11H12O5
Sinapine, C16H24NO 5

16.3.4.2.25a Hydroxycoumarins
4-Hydroxycoumarin, C9H6O3
Coumarin, C9H6O2
Esculetin, C9H6O4
Esculin, C15H16O9
Mellein, C10H10O3
Scopoletin, C10H8O4
Umbelliferone, C9H6O3

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

16.3.4.2.17 Hydroxyphenylpropanoic acids
Dihydro-p-coumaric acid, C9H10O3
Dihydrocaffeic acid, C9H10O4

16.3.4.2.26 Hydroxyphenylpropenes
Acetyl eugenol, C12H14O3
Anethol, C10H12O
Estragole, C10H12O
Eugenol, C10H12O2
[6]-Gingerol, C17H32O4

16.3.4.2.18 Lignans
Arctigenin, C21H24O6
Conidendrin, C20H20O6
Episesamin, C20H18O6
Lariciresinol, C20H24O6
Matairesinol, C20H22O6
Medioresinol, C21H24O7
Nortrachelogenin, C20H22O7
Pinoresinol, C20H22O6
Sesamin, C20H18O6
Sesamol, C7H6O3
Syringaresinol, C22H26O8
Todolactol A, C20H24O7

16.3.4.2.18a Stilbenes
d-Viniferin, C28H22O6
e-Viniferin, C28H22O6
Pallidol, C28H22O6
Piceatannol, C14H12O4
Piceatannol 3-O-glucoside, C20H22O9
Pinosylvin, C14H12O2
Pterostilbene, C16H16O3
Resveratrol, C14H12O3
Resveratrol 3-O-glucoside, C20H22O8
Resveratrol 5-O-glucoside, C20H22O8

16.3.4.2.27 Methyoxyphenols
Guaiacol, C7H8O2, 2-methoxyphenol, yellow aromatic oil, disinfectant,
expectorant, dental pulp anaesthetic, induces cell proliferation, used to prepare
synthetic vanillin, in wood smoke by pyrolysis of lignin, in wood creosote,
in Guaiacum

16.3.4.2.28 Naphtoquinones
1,4-Naphtoquinone, C10H6O2
Juglone, C10H6O3

16.3.4.2.29 Phenolic terpenes
Carnosic acid, C20H28O4
Carnosol, C20H26O4
Carvacrol, C10H14O11
Epirosmanol, C20H26O5
Rosmadial, C20H24O5
Rosmanol, C20H26O5
Thymol, C10H14O

16.3.4.2.30 Tyrosols
O-leuropein, C25H32O13
Tyrosol, C8H10O2

16.3.4.2.31 Other polyphenols
3,4-Dihydroxyphenylglycol, C8H10O4
Arbutin, C12H16O7
Catechol, C6H6O2
Coumestrol, C15H8O5
Phenol, C6H6O
Phlorin, C12H16O8
Pyrogallol, C6H6O3

16.3.4.2.0 Flavonoids, (Bioflavonoids)
See diagram 16.3.4.2: Flavonoids (apigenin-7-monoglucoside), flavones, riboflavin, anthicyanin
Plant pigments, based on flavone or similar to flavone, C15H10O2, including anthocyanins.
Vasodilating actions, antioxidant, anti-allergenic, anti-inflammatory and antiviral properties.
Colour, flavour and aroma for many foods and are found in fruits and vegetables, tea, red wine, cacao and some nuts.
Flavonoids are 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
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, in citrus fruits, e.g. kumquat, lemon, lime, grapefruit, orange, tangerine, artichoke, red and white wine.

16.3.4.2.1 Anthoxanthins, glycosides, similar to and associated with anthocyanin
Water-soluble white to yellow flavonoid pigments, antioxidants, in potatoes, cauliflower, onions, parsnips, bananas.
Anthoxanthins cause bright white colour of food in acid medium, yellow in alkaline medium.
Canthaxanthin, C40H52O2

16.3.4.2.1a Flavones, condensed tannins
Acacetin, C16H12O5
Apigenin, C15H10O5, in parsley
Apigenin 6-C-glucoside, C21H20O10
Baicalein, C15H10O5
Chrysin, C15H10O4
Diosmin, C28H32O15
Diosmetin, C16H12O6?
Eupatorin, C18H16O7
Gardenin B, C19H18O7
Geraldone, C16H12O5
Herbacetin, C15H10O7?
Hispidulin, C16H12O6
Isorhoifolin, C27H30O14
Jaceosidin, C17H14O7
Luteolin, C15H10O6 in thyme
Neodiosmin, C28H32O15
Nepetin, C16H12O7
Nobiletin, C21H22O8
Pebrellin, C18H16O7
Rhoifolin, C27H30O14
Scutellarein, C15H10O6
Sinensetin, C20H20O7
Tangeritin, C20H20O7
Tetramethylscutellarein, C19H18O6

16.3.4.2.1b Flavan-3-ols, flavanols
34 flavanols
1. Monomers - catechins, in chocolate, cinnamon, red wine
(+)-Catechin, C15H14O6
Catechin, C15H14O6, cyanidanol, bioflavonoid, tannin, antioxidant, anti-viral, anti-bacterial, in woody plants, in willow catkin Salix
Sengalia catechu, Fabaceae,
Mimosa catechu, Uncaria rhynchophylla, in green tea and wine, cocoa, argan oil, used as haemostatic drug to treat liver diseases
(+)-Catechin 3-O-glucose, C21H24O11
Cinnamtannin A2 C60H50O24
Epicatechin C15H14O6, epicatechol, antioxidant, in woody plants, in cacao bean, green tea
(-)-Epicatechin 3-O-, C22H18O10
Epicatechin gallate (ECG), C22H18O10, in green tea, buckwheat, grapes, rhubarb
Epigallocatechin (EGC),C15H14O7, in almond, broard beans, green tea, black tea
Epigallocatechin gallate (EGCG), C22H18O11, antioxidant, in green tea, the main catechin in black tea, Tea plant
Gallocatechin, C15H14O7
2. Dimers and polymers, in chocolate, cinnamon
3. Proanthrocyinidins - Flavon-3-ol polymers
4. Theaflavins
Theaflavin, C29H24O12
Theaflavin-3-gallate

16.2.1.1 Flavonols
Fisetin, C15H10O6
Galangin, C15H10O5
Isorhamnetin, C16H12O7, O-methylated flavonol, in kale
Kaempferol, C15H10O6, in kale, broccoli
Myricetin, C15H10O8
Pachypodol, C18H16O7
Methylgalangin, C16H12O5
Morin, C15H10O7
Myricetin, C15H10O8, in parsley, red onion, blueberry
Quercetin, C15H10O7 bioflavonoid, in rocket, red onion, kale
Rhamnetin, C16H12O7
Rhamnazin, C17H14O7
Rutin, C27H30O16
Spinacetin 3-O-glucoside, C44H50O25

16.3.4.2.2 Flavanones
22 flavanones
Butin, C15H12O5, in seeds of Vernonia anthelmintica, Dalbergia odorifera
Didymin, C28H34O14
Eriocitrin, C27H32O15
Eriodictyol, C15H12O6, in lemons
Eriodictyol 7-O-glucoside, C21H22O11
Hesperetin , C16H14O6, in lemon, orange
Hesperidin (aglycone hesperetin) C28H34O15
Isoxanthohumol, C21H22O5
Neoeriocitrin, C27H32O15
Neohesperidin, C28H34O15
Naringenin, C15H12O5 (4,5,7-Trihydroxyflavone), in grapefruit
Naringin, C27H32O14, flavanone-7-0-glycoside, in citrus fruit, especially grapefruit, pomelo, orange
Naringin 4'-O-glucoside, C33H42O19
Narirutin, C27H32O14, flavanone-7-0-glycoside, in Orange juice
Pinocembrin, C15H12O4
Poncirin, C28H34O14
Silibinin, C25H22O10
Sinensetin, C20H20O7
Sakuranetin, C16H14O5

16.3.4.2.3 Flavanonols
Taxifolin, C15H12O7

16.3.4.2.4 Flavans, Benzopyran derivatives, 2-phenyl-3,4-dihydro-2H-chromene skeleton, flavan-3-ols, flavan-4-ols and
flavan-3,4-diols (leucoanthocyanidin).
A C-glycosidic from cocoa liquor.
Casuarina glauca is an actinorhizal plant producing root nitrogen-fixing nodules infested by Frankia, containing flavans.

1. Flavan-3-ols, flavanols (NOT "Flavonols"!)
In fruits and vegetables, e.g. apples, apricots, berries, cherries, grapes, nectarines, peaches, pears, plums, Swiss chard.
In nuts, e.g. almonds, cashews, hazelnuts, pecans and pistachios.
In green, black and oolong teas, cacao, red and white wine.
Catechin, C15H14O6, bioflavonoid
Catechin hydrate (+)-Catechin hydrate, C15H16O7, C15H14O6.xH2O, polyphenolic antioxidant, Chinese medicine, antioxidant, free
radical scavenger, suppresses DNA strand breaks
Catechin gallate, C22H18O10, bioflavonoid, green tea extract
Epicatechin, (EC), C15H14O6, bioflavonoid
Epicatechin gallate, bioflavonoid
Epigallocatechin (EGC), C15H14O7, bioflavonoid
Epigallocatechin gallate (EGCG), bioflavonoid
Catechol, C6H4(OH)2

2. Flavan-4-ols
Apiforol, C15H14O4

3. Flavan-3.4.diols, Leucanthocyanidins,
Leucanthocyanidin, C15H14O3, from enzymes, in many plants, e.g. Zea mays

Rutin hydrate, C27H30O16.xH2O, poly flavonoid

16.3.4.2.5 Anthocyanins, anthocyanidins
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 in plants, in vacuoles of outer layers of plant cells as signalling colours.
In chokeberry, black currant, blueberry, blackberry, red cabbage, black plum, radish , rasberry, apple, eggplant, grapes, pears, red
onions, hazelnuts, pecans, pistachios, potatos, red wine.

List of anthocyanins
Aurantinidin, in Impatiens polypetala, subsp. aurantiaca
Aureusidin, in Snapdragon (Antirrhinum majus)
Bracteatin, in Snapdragon (Antirrhinum majus)
Butein, a chalcone, C15H12O5
Cyanidin, C15H11O6, red-purple pigment in berries, apple, plum, red cabbage, red onion
Cyanidin 3-O-galactoside
Cyanidin 3-O-glucoside, 3G, Cyanidin-3-rutinoside, decrease blood sugar levels
Cyanin, in Sambucus species (elders)
Delphinidin, C15H11O7, blue pigment, Viola,
Delphinium, grape, cranberry
Delphinidin 3-O-glucoside, C21H21O12
Delphinidin chloride, C15H11ClO7, pigment in grapes cranberies, pomegranates
Hydroxycyanidin, in Alstroemeria species
Isobutrin, in Flame-of-the-forest (Butia monosperma)
Malvidin, C17H15O7 (O-methylated anthocyanidin), blue pigment, Primula, Anagallis, blue pimpernel, in (Lathyrus odoratus), Sweet pea
Malvidin 3-O-glucoside
Pelargonidin, C15H11O5, orange pigment, in berries, kidney beans, Philodendron, in Snapdragon (Antirrhinum majus)
Pelargonidin, Pelargonidin 3-O-glucoside
Pelargonin, in Mukul myrrh tree (Comiphora mukul)
Peonidin, C16H13O6, in Lowbush blueberry (Vaccinium angustifolium)
Peonidin, Peonidin 3-O-glucoside
Petunidin, in (Lathyrus odoratus), Sweet pea
Petunidin 3-O-glucoside
Pigment A
Pinotin A
Rosinidin, C17H15O6, in Madagascar periwinkle
Vitisin A

16.3.4.2.6 Isoflavonoids, isoflavones, phytoestrogens
Isoflavones, C15H10O2, almost only in Fabaceae, oestrogenic activity, e.g. Psoralea
Isoflavones, related to isoflavonoids, phytestrogens and antioxidants, soy isoflavones may prevent breast cancer, only in legumes.
In soybeans, pistachios.
Astragaloside 4, C41H68O14, anti-inflammatory, in Astragali radix
Daidzein, C15H10O4, isoflavone, soybean, tofu, anti-inflammatory, anti-microbial
Coumestrol
Betavulgarin, antifungal isoflavonoid, C17H12O6, in Beta vulgaris
Biochanin A, C16H12O5
Daidzein, C15H10O4
Daidzin, C21H20O9, isoflavone, anti-oxidant, daidzoside, anti-carcinogenic, anti-antheroscerotic, in TCM Chinese medicine,
Pueraria lobata, kudzu, alcohol abuse
Formononetin, C16H12O4
Genistein, C15H10O5, [C6-C3-C6], prunetol, genisteol, isoflavone, (a trihydroxyisoflavone), phytoestrogen, in Genista tinctoria, dyer's
broom, Fabaceae
Genistein is an isoflavonoid derived from soy product, which inhibits protein-tyrosine kinase and topoisomerase-II, leading to DNA
fragmentation and apoptosis, has antioxidant, antiangiogenic, and immunosuppressive activities, so it is used as an antineoplastic and
antitumor agent.
Genistein and daidzein are isoflavones compounds found in a number of plants, but mainly in soybeans and soy products like tofu and
textured vegetable protein are the primary food source.
Genistein's has potentially beneficial effects on some human degenerative diseases.
It has a weak estrogenic effect and lessens the risk of cardiovascular diseases, but the mechanism is not known.
Genistein also is a relatively poor antioxidant, however, it protects against inflammatory-related vascular disease and atherosclerosis.
Genistein is a biomarker for the consumption of soy beans and other soy products
Pueraria mirifica, Kwao, Krua, Pueraria lobata, kudzu, Glycine max
Genistin, C21H20O10, genistine, isoflavone, in soya, kudzu
Glycitein, C16H12O5, isoflavone, O-methylated isoflavone, weak oestrogen activity, soybean, Centrosema haiense, C. Pubescens,
Glycine max
Glycitin, C22H22O10
Onion in C22H22O9, isoflavone glucoside, in Radix astragali, Chinese medicine
Puerarin, C21H20O9, isoflavone, in kudzu, reduces alcohol withdrawal anxiety

2. Isoflavanes, C15H14O, in Lonchcarpus laxiflorus, Fabaceae

3. Pterocarpans, only in Fabaceae, e.g. Phaseolin, C20H10O4, in Phaseolus vulgaris, French bean, Fabaceae

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

16.3.4.2.8a Other flavonoids, bioflavonoids
Proanthocyanidin
Proanthocyanidin, rotenone, pisatin, isoflavan, pisatin, proanthocyanidins, orcein, vulpinic acid, taxol, urushiol (pentadecyl-catechol),
(phytoalexins: resveratrol, psoralen) (flavone alkaloids: ficine, vochysine).

Brazilin
Brazilin, red pigment (C16H14O5), from Caesalpinia echinata, "Brazil wood" originally "bresel wood", Natural Red 24

Haematoxylin
Haematoxylin, log wood (C16H14O6), from Haematoxylum campechianum, logwood tree, Natural Black

16.3.4.2.8 Chalcones
Two chalcones 1. Butein, C15H12O5
2. Xanthohumol, C21H22O5

16.3.4.2.9 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

16.3.4.2.10 Dihydroflavonols
Dihydromyricetin 3-O-rhamnoside, C21H22O12
Dihydroquercetin, C15H12O7
Dihydroquercetin 3-O-rhamnoside, C21H22O11

16.3.4.2.12 Flavanones
22 flavanones
Didymin, C28H34O14
Eriocitrin, C27H32O15
Eriodictyol, C15H12O6
Eriodictyol 7-O-glucoside, C21H22O11
Hesperetin, C16H14O6
Hesperidin, C28H34O15
Isoxanthohumol, C21H22O5
Naringenin, C15H12O5
Naringin, C27H32O14
Naringin 4'-O-glucoside, C33H42O19
Narirutin, C27H32O14
Neoeriocitrin, C27H32O15
Neohesperidin, C28H34O15
Pinocembrin, C15H12O4
Poncirin, C28H34O14
Sakuranetin, C16H14O5

Apigenin, C15H10O5, flavone, antioxidant, anti-inflammatory and anti-tumor, inhibit melanoma growth, lower inflammation, inhibits
growth of cancer cells
Occurs in parsley, thyme, peppermint, chamomile, lemon balm, vervain, yarrow, Anthemis nobilis, Limonium axillare
Yellow crystalline solid, aglycone of apiin (C26H28O14)

Baicalin, C21H18O11 flavone glycoside, (baicalein 7-O-glucuronide, the glucuronide of the flavone baicalein), in leaves of
Scutellaria lateriflora (blue skullcap), and Scutellaria galericulata leaves (common skullcap), in Chinese medicinal herb
Huang-chin (Scutellaria baicalensis) to treat cancer, in herbal supplement Sho-Saiko-To and in bark of Oroxylum indicum.
See diagram: Baicalin

Catechins, Bioflavonoids
Catechins are plant-derived polyphenolic antioxidants with phytotonic properties, used for treating obesity.
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 occur in many plant species
Catechin gallate
Catechin hydrate
Epicatechin">Epicatechin (EC), C15H14O6, bioflavonoid
Epicatechin gallate, bioflavonoid
Epigallocatechin (EGC), C15H14O7, bioflavonoid
Epigallocatechin gallate (EGCG), bioflavonoid
Catechol, C6H4(OH)2

Catechin (C), C15H14O6, flavan-3-ol, colourless monomer (isomer epicatechin), major constituent
of catechu, the astringent tannin-rich extract of acacia, in green tea, cocoa, vinegar, in catechu, black grapes, fava bean, black tea
haemostatic, in Potentilla fragarioides, See diagram 16.21.6: anthocyanin, catechin
Catechin gallate, C22H18O10, bioflavonoid, green tea extract, antioxidant, free radical scavenger, may treat breast cancer.
(2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)
Catechin hydrate, (+)-Catechin hydrate, C15H16O7, C15H14O6.xH2O, polyphenolic antioxidant, Chinese medicine, antioxidant, free
radical scavenger, suppresses DNA strand breaks

Epicatechin (EC), C15H14O6, flavan-3-ol, in green tea, cocoa (Theobroma cacao), black grapes, tea, kola nut, peach,
Polyphenol catechins: green tea, black tea, fava bean
Epicatechin gallate, C22H18O10, in green tea.

Gallocatechin (GC), C15H14O7, bioflavonoid, flavan-3-ol, polyphenolic compound, in green tea, free radical scavenger
Gallocatechin gallate, C22H18O11, bioflavonoid, in green tea.

Polyphenol flavonoids:
Epigallocatechin (EGC), C15H14O7, bioflavonoid, flavan-3-ol,antioxidant, from green tea, St John's wort
Epigallocatechin gallate, Epigallocatechin-3-gallate (EGCG), C22H18O11, bioflavonoid, flavan-3-ol, from green tea, antioxidant,
most abundant catechin in green tea

Catechol, C6H6O2, C6H4(OH)2, pyrol catechol, 1,2-dihydroxybenzene, flavan-3-ol, from catechin, causes dermatitis, possible
carcinogen, in Argania spinosa

Geosmin, C12H22O, bicyclic alcohol, earth smell, muddy fish smell, after rain smell, cut grass smells, from, Streptomyces and
Calothrix cyanobacterium.
See diagram 16.3.4.1: Coumarin, isocoumarin, cycloalkyls, geosmin
1. The degraded sesquiterpene geosmin, C12H22O, a bicyclic alcohol, causes the "earth smell" of moist soil, produced by
Streptomyces is species, Streptomyces antibioticus and Streptomyces coelicolor and blue-green algae.
The "earth smell", "rain smell" noticed after rain and in wet rugby dressing rooms, causes the earthy taste of beetroot, and "off tastes"
in water and wine.
Blue-green algae in water can also produce geosmin.
In Australia, when heavy rain occurs after a long period of dry weather, a bad taste, "off taste", may develop in the drinking water
caused by the high concentration of geosmin washed into water supply dams.
Actinomycetes bacteria grows in damp soil but produces survival spores during hot weather.
During the first rainfall, wind suspends the spores in the air as an aerosol causing the "after the rain smell" from geosmin, C12H22O,
(trans-1,10-dimethyl-trans-9-decalol).
The smell occurs after you have breathed in tiny particles of soil containing the bacteria.
Another explanation for the after rain smell is that volatile chemicals in the air spaces between soil particles are washed out by the rain
and become relatively concentrated just above the soil.
Some people call the earth smell "petrichor" and say that is caused by plant oils that become adsorbed to clay minerals to produce an
argillaceous odour.
Some people say they can smell ozone in the smell before rain and this may be true after severe lightning from thunderstorms.

2. Geosmin also causes the earthy taste of beetroot and off-flavours in wine and drinking water.
It can be isolated from Streptomyces antibioticus.
Also, Streptomyces coelicolor may be involved in producing the smell.

3. Geosmins are also produced by blue-green algae and anaerobic bacteria when they die.
Geosmins may cause the muddy smell of fish, e.g. catfish, carp and mullet.
Geosmins breakdown in acid solutions so fish is generally eaten with lemon juice.

4. The sweet smell of new mown hay is because of a coumarin from cut clover, e.g. white clover (Melilotus alba), when a glucosidase
reacts with glycosylated cinnamic acid to produce hydroxycinnamic acid that esterifies to form coumarin.
Newly cut grass produces a variety of volatile organic compounds depending on the species of the grass and when it is cut during its
life cycle.
The compounds include methanol, ethanol, acetaldehyde, acetone, butane, 1,8-cineole, aldehydes of hexanoic acid (caproic acid,
CH3(CH2)4COOH), and so-called hexenyl compounds.
These emitted compounds may be a significant proportion of atmospheric pollution emitted during motorized grass cutting and grazing.

Kaempferol, C15H10O6, flavonol, chromogenic agent for antimony, gallium, indium, antioxidant and oestrogenic activity, inhibits
bone resorption, possible anti-cancer, and treat cardiovascular disorders
Common in ferns and angiosperms, vegetable foods, Aloe vera, apples, onions, leeks, citrus fruits, grapes, red wines, Ginkgo biloba, St. John's wort,
apricots, blueberries, blackberries, arugula, asparagus, green and oolong tea, cocoa, broccolli, cabbage, kale, beens, endive, tomatoes, strawberries.
In Ginkgo biloba, Tilia spp, Equisetum arvense, Moringa oleifera, Sophora japonica.

Luteolin, C15H10O6, flavone
Yellow crystalline antioxidant, anti-inflammatory, and anti-tumor, strong antioxidant, radical scavenger, possible anti-cancer
In expectorants, hypoglycaemic agent, withstand radiation and chemotherapy.
Occurs in parsley, thyme, peppermint, basil, celery, artichoke, broccoli, green pepper, dandelion, perilla, Aiphanes aculetat palm,
Salvia tomentosa, Ambrosia

Naringin, C27H32O14, flavonoid glycoside, flavanone-7-O-glycoside, antioxidant occurs in grapefruit, causing its distinctive bitter taste, and
in other citrus fruit.
Naringen has a cholesterol-lowering effect, and is an aldose reductase inhibitor so prevent retinal disease in diabetics, but it may reduce
the availability of many pharmacological agents
Naringen may improve Alzheimer's disease, increase absorption of some heart-related drugs and antihistamine terfenadine, and increase
the effects of caffeine and vitamin C.

Quercetin, C15H10O7, [C6-C3-C6], flavonol glycoside
polyphenolic flavonoid, most active of the flavonoids, many medicinal plants have high quercetin content, anti-inflammatory activity by
inhibiting release of histamine, antioxidant activity, anticancer, inhibits fatty acid synthase, phytochemical, colouring found in the skins of
apples and red onions
May protect against heart disease and cancer, prevents damage to LDL cholesterol, antioxidant, natural anti-histamine, anti-inflammatory,
anti-cancer, but unproved addition to dietary supplements, in berries, red grapes, citrus fruit, tomato, broccoli.
Do not take quercetin if taking prescribed medicines, are pregnant or breast feeding or have liver disease.

Rutin, C27H32O16, (quercetin rutinoside), citrus flavonoid glycoside
Rutin, sophorin, bioflavonoid is a yellow or greenish-yellow, needle-shaped crystals.
In many plants, fruits and vegetables, especially buckwheat, Carpobrotus, Sophora japonica, Ruta graveolens, Citrus sp (e.g. orange,
grapefruit)
Antioxidant, strengthens capillaries to prevent bruising or bleeding, anti-inflammatory, prevent atherogenesis, reduce cytotoxicity of
oxidized LDL-cholesterol, utilize vitamin C, maintain collagen.
Do not take rutin if pregnant or breastfeeding.
Rutin hydrate, C27H30O16.xH2O, polyphenolic flavonoid, antioxidant, NO scavenger, free radical scavenger, protection against
carcinogenesis

Tangeritin, C20H20O7, O-polymethylated-flavone, a "citrus bioflavonoid"
In tangerine, Citrus tangerina, and other citrus peels, strengthens the cell walls and protects from cell invasion.
Tangeritin may protect nerve cells, reduce risk of cancers, destroy cell leukaemials and lower cholesterol.

16.3.3.0 Furanocoumarin, furocoumarin glucoside
Furanocoumarin (Furan C4H4O, Coumarin, C9H6O2, 5-member aromatic ring), heterocyclic
Furanocoumarin occur in species of Apiaceae and Rutaceae, are toxic and used as defence mechanism against herbivores
Some are photoactive, e.g. bergaptene, bergamotine, with their toxicity enhanced by ultraviolet radiation.
Can be detected by their blue, violet, brown, green or yellow colours, in UV light.
In water hemlock, coriander, cow parsnip, and snakeroot, wild parsnip, giant hogweed
Lipid-soluble, can be isolated during extraction of dried plant material with ether or light petroleum.
Angelicin, C11H6O3 and Psoralen, C11H6O3 are the most common furanocoumarin isomers:

List of furanocoumarins
Angelicin, C11H6O3
Apterin, C20H24O10
Bergamottin, C21H22O4, 16.9.20
Bergapten, C12H8O4
Citropten, C11H10O4, 5,7-Dimethoxycoumarin, Limettin
DHB (6',7-Dihydroxybergamottin) C21H24O6
Psora-4, C21H18O4, 5-(4-Phenylbutoxy)psoralen, immunosuppression, suppresses memory T-cells
Psoralen, C11H6O3, psoralene, Furo[3,2-g]coumarin
Trioxsalen, C14H12O3, trimethylpsoralen
Xanthotoxin, C12H8O4, 8-methoxsalen, (8-MOP), with ultraviolet A irradiation used to study DNA repair

Apterin, C20H24O10, an O-glycosyl compound containing O-glycosidic bond, reported to dilute coronary arteries, block calcium
channels, in roots of Apiaceae, e.g. | Angelica | Coastal hogfennel | Heartleaf alexanders | Lovage |

Bergapten, C12H8O4, 5-methoxypsoralen, in citrus essential oils, in bergamot oil causes phytotoxicity, possible to treat psoriasis
may be in sun-tanning lotions to increase melanin production but is phytotoxic and may cause over-pigmentation of the skin.

DHB (6',7-Dihydroxybergamottin) C21H24O6
In grapefruit, grapefruit juice effect, DHB is a furanocoumarin that inhibits CYP3A4 and is found in grapefruit juice and Seville orange
juice.
Grapefruit juice increases the oral bioavailability of many CYP3A4 substrates, including cyclosporine.
It appears to be the primary compound in grapefruit juice that is responsible for inhibition of testosterone 6B hydroclase activity.
Grapefruit juice reduces CYP3A activity to a significantly greater extent (p < 0.05) than does orange juice.
In grapefruit, 6', 7 dihydroxybergamottin, which is implicated in drug interactions, is most concentrated in the rind or in oil extracted
from the peel.

Angelicin, C11H6O3, isopsoralen
Angelicin is an angular furanocoumarin and it and its methoxy derivatives occur in plants in the Umbelliferae family.
It occurs in dong dang gui, angelica, chervil, spear grass, dill.
It has photobiological effects, in ultraviolet A radiation it binds covalently to isolated DNA and to DNA in bacteria, yeast and cultured
mammalian cells.
It anti-proliferative, antifungal and anti-inflammatory, inhibits tumour cells and is used in treatment of psoriasis and thalassemia.

Psoralen, C11H6O3, psoralene
It is a photosensitizing agent that makes the skin more sensitive to ultraviolet light.
It is a photochemical reagent for study of nucleic acid structure and function.
Mutagen and possibly carcinogen, used with ultraviolet light in PUVA (ultraviolet light therapy therapy) treatment for psoriasis, eczema
and vitiligo.
Psoralens damage DNA and cause skin inflammation and occur in fig, celery, parsley, parsnips.

16.3.2.6.0 Glycosides
16.3.2.6.0a List of glycosides by aglycone
16.3.2.6.0b List of glycosides by name
16.3.2.6.1 Glucosides
16.3.2.6.2 Glucosinolates
A glycoside is a compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by
an alcoholic, phenolic, or other organic group.
Glycosides are named from the constituent sugar, e.g. glucoside (glucose), pentoside (pentose), fructoside (fructose).
Glycosides, unlike polysaccharides, are sugars bonded to a non-sugar, so they contain a carbohydrate and a non-carbohydrate residue
in the same molecule.
Glycone and aglycone
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, 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: Glycosyl group
e.g. Hesperetin , C16H14O6, in lemon, orange, Hesperidin (aglycone hesperetin) C28H34O15

16.3.2.6.0a List of glycosides by aglycone
1. Alcoholic glycosides, salicin in Salix
Aldehyde glycosides, vanilla pod, glucovanillin, cinnamon bark cinnamic aldehyde, vanillin in Vanilla orchid
Aminoglycosides
Anthocyanin glycosides
Anthocyanidins (aglycones of the glycoside anthocyanins), e.g. Cyanidin, C15H11O6
2. Anthraqinone glycosides (aglycone from anthraquinone), alizarin, hypericin, physcion, rhubarb, Cascara, Senna, Aloe
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,
Cymarin, C30H44O9, Apocynum cannabium, dogbane
3. Coumarin glycosides (coumarin aglycone), apterin, corylifolin, psoralin (psoralen Psoralea corylifolia)
4. Chromone glycosides
5. Cyanogenic glycosides (cyanophore glycosides), (aglycone contains CN group), amygdalin, betanin, dhurrin, linamarin, lotaus
tralin, prunisin, rose family, bamboo, cassava, sorghum
glycosides, e.g. Naringin, C27H32O14
6. Flavonoid glycosides
Hesperidin, C28H34O15, in peels of lemons, sweet oranges, aglycone: hesperetin, C16H14O5
Naringin, C27H32O14, grapefruit bitter taste, aglycone: naringenin, C15H12O5, bitter, colourless, grapefruit
Rutin, C27H30O16, capers, olive, buckwheat, Ruta graveolens, aglycone: quercetin, C15H10O7, capers, lovage, dock, dill, fennel
7. Iridoid glycosides, monoterpenes
Isothionate glycosides, wild mustard
Lactone glycosides, sweet clover , red clover

8. Phenolic glycosides, arbutin (bearberry), Uva Ursi
9. 16.3.7.0 Saponins
10. Steroidal glycosides, cardiac glycosides
11. Steviol glycosides (aglycone steviol), Stevia. 2 primary glycosides: stevioside, rebaudioside A
12. Thioglycosides (contain sulfur), Sinigrin precursor to allyl isothiocyanate, sinalbin glucosinolate

16.3.2.6.0b List of glycosides by name
Acetyldigoxin, C43H66O15, cardiac glycoside
Acolongifloroside, K, C29H44O12, cardiactive glycoside
Adoniside, cardiac glycoside
Agnuside, C22H26O11, iridoid glycoside
Aloe-emodin, C15H10O5anthraquinone glycoside
Alvonal MR, C30H44O9, cardiac glycoside
Aloin, barbaloin, C21H22O9 anthraquinone glycoside
Amarogentin, C29H30O13, secoiridoid glycoside
Amygdalin, cyanogenic glycoside
Apiin, C26H28O14, diglycoside
Arbutin, C12 H16O7, glycoside
Asiaticoside, C48H78O19, triterpene glycoside
Baicalin, C21H18O11, flavone glycoside
Bufalin, C24H34O4, cardiac glycoside, (in toad venom)
Calotropin, C29H40O9, cardiac glycoside
Cascarosides, C27H32O14 hydroxyanthracene glycoside
Convallatoxin, C24H42O10, cardiac glycoside
Cornin, C17H24O10, iridoid glycoside
Deslanoside, cardiac glycoside
Dhurrin, C14H17NO7, cyanogenic glycoside
Digitoxin, C41H64O13, cardiac glycoside
Digoxin, C41H64O14, cardiac glycoside
Echinacoside, C35H46O20, glycoside
Gentamicin, C21H43N5O7, amminoglycoside
Gentiopicrin, C16H20O9, secoiridoid glycoside
Hesperidin, C28H34O15, flavanone glycoside
Hypericin, C30H16O8, anthroquinone glycoside
Lanoxicaps, C41H64O14, cardiac glycoside
Lanatoside C, C49H76O20, cardiac glycoside
Linamarin, C10H17NO6, cyanogenic glycoside
Lotaustrain, C11H19NO6, cyanogenic glycoside
Mangiferin, C19H18O11, glycoside
Metildigoxin, C42H66O14, digitalis glycoside
Naringin, C27H32O14, flavonoid glycoside
Netilmicin, C21H41N5O7, aminoglycoside
Oleandrin, C32H48O9, cardiac glycoside
Ouabain, C29H24O12, cardiac glycoside
Phillyrin, C27H34O11, lignan
Physcion, C16H12O5, anthroquinone
Proscillaridin A, C30H42O8, cardiac glycoside
Prunasin, C14H17NO6, cyanogenic glycoside
Pseudohypericin, C30H16O9
Rutin, C27H30O16, glycoside
Rebaudioside, C44H70O13, glycoside
Rhamnazin, C17H14O7, flavonol glycoside
Rhamnetin, C16H12O7, flavonol glycoside
Rosarin, C20H28O10, cinnamyl alcohol glycoside
Scillaren A, C36H52O13, cardiac glycoside
ShatavarinIV, C45H74O17, asparanin B
Sisomycin, C19H37N5O7, aminoglycoside
Sophoricoside, C21H20O10, isoflavone glycoside
Stevioside, C38H60O18, steviol diterpene glycoside
Strophanthin, C36H54O14, cardioactive glycoside
Verbascoside, C29H36O15, glycoside

Aminoglycosides
Antibiotics, Gentamycin, tobramycin, amikacin, streptomycin, neomycin, paromomycin, treat gram-negative bacteria
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, Sisomycin, Netilmicin
Amikacin hydrate, C22H43N5O13.xH2O, broad spectrum antibiotic

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

16.3.7.0 Saponins
Saponin glycosides, plant glycosides, soluble in water and alcohol but 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
Horse chestnut tree
1. Triterpenoid glycosides, triterpenoid saponins, triterpenene glycosides, triterpene saponins, pentacyclic triterpenoid saponins
alpha-hederin, C42H68O12, Black cumin (Nigella sativa), Ranunculaceae, possibly anti-cancer
Araloside, C47H74O18, Japanese angelica tree, (Aralia alata), Araliaceae, possible anti-ulcer
Astragalosides I, II, III), Astragaloside I, C44H72O16, Mongolian milkvetch, Huang qi (Astragalus propinquus, A. membranaceus), Fabaceae, may increase
gastric pH
Astragaloside II, C43H70O15, Mongolian milkvetch, Huang qi (Astragalus propinquus, A. membranaceus), Fabaceae, stimulates bone
formation
Astragaloside IV, C41H68O14, Astragali radix, anti-inflammatory
Bacoside A3, C47H76O18
Betulinic acid
Water hyssop (Bacopa monieri), Plantaginaceae
CDDO Methyl Ester
Cycloastragenol
Cucurbitacins, Cucurbitaceae, Bryonia alba, plant taste repellents
Elaterinide
Eleutheroside B, syringin, C17H24O9, Siberian ginseng | Lilac bark
Ginsenoside RG1, C42H72NO14
Glycyrrhizin, C42H62O16, Licorice Liquorice plant, triterpenoid aglycone in Glycyrrhiza glabra.
Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice)
Gymnemic acid, C43H66O14, Gymnema sylvestre
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
Ecdysterone (20E) 20-hydroxyecdysterone, C27H44O7, Rhaponticum carthamoides, maral root, Asteraceae
Ilexsaponin A1
Jujuboside A, B
Momordin, Bitter melon
Notoginsenoside
Platycodin D
Pseudoginsenoside f11, American ginseng
Ruscogenin
Saikosaponin C from Bupleurum falcatnum
Soyasapogenol B, C30H50O3, triterpenoid saponin
Tangshenoside I, C29H42O18, in Dang Shen (bellflower)
Withanolides, in Ashwagandha
Ziziphin, C51H80O18

2. Steroid glycosides, sterol glycoside, steroidal saponins, phytosteroid saponins, tetracyclic triterpenoid saponins
Horse chestnut Aesculus hippocastanum, Saponins that foam in water
Asparagus recemosa
Charantin, β-sitosteryl glucoside, C36H60O6, white crystals, neutral, tasteless, causes low blood sugar levels, Bitter melon
Digitonin, C56H92O29, Foxglove
Diosgenin, C27H42O3, in bark of Wild yam, Discorea villosa, diosgenin contains disoscin glycoside
Eleutheroside A, daucosterol, C35H60O6, 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
Fenugreek
Indian squill, Drimia indica, steroid saponins, cardiac tonic, congestive cardiac failure.
Oleander, Nerium oleander, Oleandrin, C32H48O9, steroid saponin, from toxic sap, for suicide, formerly therapeutic uses
Alfalfa Lucerne, Medicago sativa, hederagenin, C30H48O4, soyasaponin 1
Chickpeas Cicer 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
Peas
Wavy-leafed soap plant, Chlorogalum pomeridianum

Nightshade glycosides, (solanine glycoside in Solanum nigrum) ( glycoalkaloid, α-Solanine from potato sprouts, C45H73NO15)
potato, tomato, eggplant

16.3.2.6.1 Glucosides
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, glucose + phenolic compound

List of glucosides
Aesculin (Escalin): C21H24O13, coumarin glucoside: 16.3.5.1
Aloenin, C19H22O10, bitter glucoside, in Candelabra aloe, in skin care cosmetics, possibly anti-cancer
Apterin, C20 H24O10
Arctiin, C27H34O11, anti-tumour, antiviral, glucoside of arctigenin, C21H24O3, Arctium lappa, burdock
Arjunglucoside, C36H58O11, sericoside
Benzyl-beta-D-glucoside, C13H16O7, Pteris
Betanin
, Isobetanin, C24H26N2O13
Cornuside, C24H30O14, secoiridoid glucoside, anti-inflammatory
Decyl glucoside, C16H32O6, non-ionic surfactant
Fraxin, C16H18O10: 16.3.5.5
Icariin, C33H40O15, flavonol glucoside, in horny goat weed, Epimedium grandiflora, Berberidaceae, oriental aphrodisiac.
Lauryl glucoside, C18H36O6, surfactant
Linamarin, C10H17NO6, cyanogenic glucoside, from cassava, Manihot esculanta), from linseed, flax, Linum usitatissimum, and
Lotus japonica.), lima beans
Prunin, C21H22O10 (naringenin-7-0-glucoside)
Octyl glucoside, C14H28O6, non-ionic surfactant
Piceid, C20H22O8, stilbenoid glucoside, polydatin, grape juice, Picea sitchensis, Polygonum cuspidatum, Japanese knotweed,
stilbene in medicinal herbs, antioxidant, anti-inflammatory, neuroprotective
Piceatannol, C14H12O4
Picrocrocin, C16H26O7, saffron bitter, monoterpene glucoside, bitter taste, hay-like fragrance, from catotenoid zeaxanthin, in
Saffron
Populin, C20H22O8, --> salicin, poplar
Quercitrin, C21H20O11, Fagopyrum (Quercus, --> Quercetin and Rhamnose)
Ranunculin, C11H16O8, Ranunculaceae
Rhamnetin, C16H12O7, O-methylated flavonol, from cloves, Rhamnus cathartica, buckthorn
Rhaponticin, C21H24O9, rhubarb rhizome
Salicin, C13H18O7, alcoholic β-glucoside,similar to aspirin, acetylsalicylic acid, white willow bark, Salix (digitonin, digitoxin, βcyanin)
Sakakin, C13H18O7, orcinol glucoside
Salidroside, C14H20O7, rhodioloside, 8-o- β-D glucoside of tyrosol, neuroprotective, antidepressant, anxiolytic. Rhodiola rosea
Saponarin, saponaria

Resveratrol, C14H12O3, [C6-C2-C6], stilbenoid, stilbene derivative, phenolic phytoalexin, antioxidant and free radical, synthesis
in seeds of transgenic oilseed rape (Brassica napus) (produced from Japanese knotweed, piceid), in grape skin, anti-diabetic,
neuroprotective.

16.3.2.6.2 Glucosinolates
Glucosinolates from sugar + amino acid, contain S and N.
Glucosinolates --> mustard oil glycosides, when plant cells damaged or chewed, common in Cruciferae
Mustard oil glycosides, glucosinolates
Brassica (phenethyl glucosinolate potassium salt, C15H20NO9S2K)
List of glucosinolates
Epiprogoitrin (C11H19NO10S2), in Crambe abyssinica oil, Brassicaceae
Glucobarbarin (C15H21NO10S2)
Glucocapparin, Glucocapparin (C8H14NO4S2)
in most Crucferae and in Capparaceae, during cooking lachrimatory methyl isothiocyanate (CH3=C=S forms by hydrolysis
to give characteritic flavour of horseradish
Glucocheirolin (C11H20KNO11S3), in seeds of crucifers
Glucobrassicin, indolylmethyl glucosinolate, (C16H20N2O9S2), + myrosinase --> non-pungent isothionates, in Brassica and
Raphanus species, in most cruciferous plants
Glucocapparin Glucoiberin (C11H21NO10S3), in Brassica oleracea and other crucifers
Glucoerucin (C12H23NO9S3), in seed of salad rocket and brussels sprouts
Gluconapin (C11H18NO9S2), in rapeseed and other Brassica species
Gluconasturtiin (C15H21NO9S2), precursor to phenethyl isothionate, in water cress Nasturtium officinale and other crucifers
Glucoraphanin (C12H23NO10S3), glucosinolate precursor to sulforaphane, in young sprouts of broccoli, brussels sprouts, cabbages
and cauliflower, red cabbage, anti-cancer, anti-microbial, treat arthritis glucoraphanin
(C12H22NO10S3) + myrosinase --> sulforaphane (C6H11NOS2)
Glucoraphenin (C12H21NO10S3)
Glucosibarin (C15H20KNO10S2)
Glucotropaeolin, benzyl glucosinolate (C14H19NO9S2), precursor to benzyl isothionate and benzyl thiocyanate by hydrolysis,
from Tropaeolum majus (nasturtium), garden cress
Progroitrin (C11H19NO10S2), in cabbage, peanuts, horseradish, rutabaga
Phenethyl glucosinolate potassium salt, C15H20NO9S2K, in Brassica
Raphanin (C6H9NOS2), sulphoraphene, toxic, antioxidant, antibacterial, Chinese medicine, in radish, Raphanus sativus
Sinigrin, C10H16KNO9S2, glucosinolate

Sinalbin (C14H19NO10S2), glucosinolate, in white mustard seeds, | white mustard | onion | garlic |
See diagram: Sinalbin

Sinigrin (C10H16KNO9S2), glucosinolate, black mustard
sinigrin + myrosinase --> glucose + allyl isothiocyanate, so sinigrin is precursor to allyl isothioncyanate
Sinigrin hydrate, C10H16HNO9S2.xH2O, glucosinate, in black mustard seeds, in horseradish
See diagram: Sinigrin

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

Betanin
Betanin, C24H26N2O13, Betalain alkaloid, glucopyranosylbetanidin, phytolaccanin, is cyanogenic glycoside (betacyanin) betanidin-5-O-b-glycoside,
Betalain alkaloid, glucopyranosylbetanidin, phytolaccanin, (betanidin-5-O-beta-glucoside), purple pigment, food industry colouring agent
16.3.5.3.0 Betalains, betains
in beets, Beta vulgaris (beetroot extract), Swiss chard Carpobrotus, all Azoiaceae, cactus Opuntia species, Amaranthus spinosus leaves, Bougainvillea glabra floral bracts, Phytolacca, Portulaca.
9.5.10 Tests for urine, urine tests, (See 3. Colour of urine)
Betanin may not not broken down in the body so can cause temporary red urine (beeturia and red faeces), and so cause distress in people
who think they are suffering haematuria (blood in the urine).
E162 Beetroot Red, Food additive, colorant in cosmetics and pharmaceuticals
Betanin, Red beef extract diluted with dextrin, C24H26N2O13.
Food dye, cosmetic and pharmaceutical colourant.
Betanin aglycone is betanidin, C18H16N2O8

Picrotoxin, C30H34O13 cocculin,
Picrotoxin,cocculin, is an equal mixture of picrotoxinin, C15H16O6, and picrotin, C15H18O7
Picrotoxin is bitter, poison, stimulant, convulsant, inhibits neurotransmission, desensitizing
Has been used to flavour beer.
Skin contact is dangerous
In fruit of Indian berry, fishberry.

16.3.5.2.1 Tetrapyrroles, bilin, bilirubin, biliverdin, haeme
| See diagram 16.3.5.2: Bilin, haeme (heme) | See diagram 16.3.5.2.1: Haeme (heme)
| See diagram 16.3.5.2.2 Tetrapyrroles | See diagram: Biliverdin
Tetrapyrroles are natural pigments containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to
position 5 of the next pyrrole ring.
Porphyrins are macrocyclic tetrapyrroles, e.g. bilin (a linear tetrapyrrole).
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 (heme), in haemoglobin, globular protein in animals, oxygen carriers
Haeme A, C49H56O6N4Fe (cytochrome oxidase ligand complex) tetradentate ligand],
Haeme, Constituents of blood: 9.214

16.3.5.2.2 Porphyrins, porphine
See diagram 16.3.5.01: Porphine | See diagram 16.3.5.2: Porphyrins, porphine
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 in a cyclic configuration with usually metal side chains attached, e.g. with iron to form heme (haeme).
Porphyrin chelates include haeme, in haemoglobin, bonded to iron (II) ion, and chlorophyll bonded to Mg (II) ion.
The haeme component of the protein haemoglobin has four iron porphyrins.
Porphyrins occur in iron-containing cytochrome pigments in mitochondria in plants, animals and bacteria.
For oxidative phosphorylation, electron transport system, and ATP production.

16.3.5.2.4 Legheamoglobin, nitrogen-fixing bacteria, legumes
Legheamoglobin, leghemoglobin, legoglobin, occurs in nitrogen-fixing bacteria in the root nodules of legumes.
It is an oxygen carrier and a hemoprotein, produced by legumes in response to the roots being infected by nitrogen-fixing bacteria,
Rhizobium.
Like haemoglobin, it is red in colour.
The apoprotein 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 in animals.

16.3.5.2.5 Phycobiliproteins, nitrogen-fixing cyanobacteria
Phycobiliproteins occur in cyanobacteria and red algae are composed of water-soluble phycobilin pigments and protein.
Nitrogen-fixing cyanobacteria such as Anabaena azollae live symbiotically within leaf cavities of the water fern Azolla.

16.3.5.2.6 Phycobilins, phycocyanin, phycoerythrin, Cyanobacteria, Rhodophyta.
Phycobilins include the blue-green pigment phycocyanin and the red pigment phycoerythrin to enable red algae to be photosynthetically
efficient in deep water where blue light predominates.
Phycobilin pigments are soluble in water-soluble and occur in the cytoplasm and stroma of chloroplast.
They occur only in Cyanobacteria and Rhodophyta.
The blue green pigment phycocyanin occurs in the Cyanobacteria their name.
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 fluoresce are fluorescent.

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

16.3.5.2.8 Polyvinyl pyrrolidene, povidone, PVP
See diagram 16.3.5.2: Povidone, PVP
E1201 Polyvinyl pyrrolidene, povidone, PVP, is a water-soluble polymer, used as a coating or binder in medical tablets,
e.g. povidone-iodine complex (PVD-iodine) in the antiseptic "Betadine", that nowadays has replaced tincture of iodine solution in
medicine.

16.3.8.0 Steroids, sterols, steroid alcohols, natural steroids
| See diagram 16.3.5.3: Cholesterol, cholic acid, bile salt, estradiol, progesterone, northindrone,
| See diagram: Steroid nucleus
| See diagram: Testosterone
Steroids have a nucleus of three six-member carbon rings and one five-member ring.

List of steroids
1. Sterols (steroid alcohols), include: Adosterol, Cholesterol, Daucosterol, Episterol, Fungisterol, Ganoderic acid, 22R-Hydroxycholesterol,
Inotodiol, Lanosterol, Oxycholesterol, Parkeol, Spinasterol, Zymosterol
2. Phytosterols (plant sterols) include: Brassicasterol, Campestanol, Campesterol, Charantin, Momordenol, Muldamine, Beta-Sitosterol,
Stigmastanol, Stigmasterol
3. Adrenocortical hormones
3.1 from outer layer of adrenal cortex, e.g. aldosterone
3.2 from middle layer of adrenal cortex, e.g. cortisone, prednisone
3.3 from inner layer of adrenal cortex, Sex hormones including:
3.3.1 Androgens and androgen esters, Testosterone.
3.3.2. Estrogens and estrogen esters, Estradiol.
3.3.3 Progestogens and progestogen esters.
4. Bile acids, e.g. Cholic acid, C24H40O5
5.Cardenolides
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

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.
Steroids 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), estrogen, cardiac glucosides, diosgenin, androstane, 19-norpregnane,
7-dehydrocholesterol, previtamin D3, ergocalciferol (vitamin D2), cholecalciferol, (vitamin D3).
Sterols are anti inflammatory and analgesic agents.
Plant sterols are extracts of certain plants that, when ingested, inhibit the absorption of cholesterol in the small intestine.

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 immuneenhancing 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.

16.3.8.1 Sterols
Sterols are natural products derived from the steroid skeleton and containing a hydroxy group in the 3 position, closely related to
cholestan-3-ol.
Sterols (steroids) in animal sex hormones, squalene (in shark liver oil), cephalosporin, gonane, hopane, diplotene, lupeole
Squalene, in liver oil of sharks
Sterols are solid, waxy, unsaturated steroid alcohols.
Plant sterols called phytosterols.
Some sterols exist naturally free and some exist in combination as esters or glycosides.
β-sitosterol, C29H50O, oestrogenic activity, inhibits human leukemia cells, vegetable oils, nuts, avocado
Naturally occurring non-delta-5 plant sterols include cycloartenol, 24-methylene cycloartenol, cycloeucalenol, and obtusifoliol.
List of sterols:
Alisol B acetate, Androstene, Avenacoside,
Avenasterol, C29H48O Brassicasterol, C28H46O Cholesterol, C27H46O, Beta-sitosterol (C29H50O)
Campesterol, C28H48O
Cyasterone, C29H44O8, in Ajuga, insect moulting hormone Cycloastragenol, Dehydroandrosterone, Ecdysone, Ergosterol, C28H44O Fucosterol, C29H48O, in Cocos Lupeol, C30H50O, pentacyclic triterpenoid Sitosterol, C29H50O
Stigmasterol, C29H48O
Stigmastanol, C29H52O, phytosterol

16.3.1.0 Phytochemicals
Phytochemicals are biologically active compounds found in plants.
They are not necessary for human nutrition so they are regarded as secondary metabolites.
Their function in the human body may include as antioxidants, like oestrogens, like hormones, against cancer cells and bacteria
replication, and strenthen cell walls.
There is no agreed classification of phytochemicals, so the categories in this document below are from various scientific and
commercial classification systems.

16.4.6.0, Organosulfur compounds
Allicin, C6H10OS2, in Garlic | 16.2.8.9
Allyl isothiocyanate, C4H5NS, in Horseradish
Propanethial S-oxide, C3H6OS, in cut onions: 16.2.8.9

16.4.8.0 Plant extracts
Butylphthalide, C12H14O2, celery seed, Chinese medicine, antioxidant
Creosote from beechwood tar
Lycopodium, clubmoss, Family Lycopodiaceae, fine yellow powder, Highly flammable
Mangiferin (MGF), C19H18O11, xanthoid, antimicrobial, anti-inflammatory, antioxidant, from Mangifera indica
Protopanaxadiol, C30H52O3, ginsenoside metabolite, sapogenin
Rosin, C15H20O6, 16.1.1.2.2
Pollen from Sorghum halepense, Betula fontinalis occidentalis, water birch, Juglans nigra, black walnut, Populus
deltoides
, eastern cottonwood.

Aloin, C21H22O9, barbaloin, anthracycline, anthraquinone glycosyl, bitter, Aloe barbadensis, leaves, wound healing, inhibits blood
vessel formation,
Aloenin, C19H22O10, Aloe arborescens, bitter glucoside

Beta-sitosterol (C29H50O), phytosterol, similar to cholesterol, oestrogenic activity, inhibits proliferation of human leukemia cells,
reducing serum cholesterol levels. natural prostate health. reduce the growth of human prostate and colon cancer cells.

Campesterol, C28H48O, phytosterol in wild mustard (Brassica campestris), margarines, vegetable oils, seeds, nuts, fruits,
vegetables, legumes, beans and avocados, inhibits absorption of cholesterol, treat cardiovascular diseases, so cholesterol-lowering
and anti-carcinogenic effects.

Cinnamaldehyde, flavonoid
Cinnamaldehyde, yellowish oily liquid, not soluble in water, main component in cassia oil, cinnamon bark oil, flavouring compounds for
cinnamon flavour, cinnamon bark has cinnamon and cassia aroma.
BP 246oC, Flash point 71oC, MP -8oC.
Cinnamaldehyde can be made synthetically, but is more commonly obtained from the steam distillation of the oil of cinnamon bark.

CPY3A4 (cytochrome P450 3A4), enzyme mainly in the liver and intestine, which oxidizes foreign organic molecules for removal
Grapefruit juice increases blood levels of atorvastatin (lipitor) by 80%, causing slower breakdown of drug in liver so more in the
bloodstream.
So grapefruit can affect the rate at which drugs are process by the liver, including statins used to treat blood vessel and heart conditions.
The many drugs are metabolized by CPY3A4 are called "CPY3A4 substrates", e.g. Atorvastin (Lipitor).
Some patients my develop severe toxicity when CPY3A4 inhubitors are taken concurrently.
CPY3A4 inhibitors, drugs that inhibit CPY3A4 activity, increase the plasma concentration of CPY3A4 substrate medications, e.g.
clarithromycin.
CPY3A4 inducers, drugs that increase CPY3A4 activity, decrease the plasma concentration of CPY3A4 substrate medications, e.g.
rifamprin.

Galangin, C15H10O5, 3,5,7-Trioxyflavone, flavonol, induces cell destruction, anti-oxidative and free radical scavenger activities
capable of suppressing the genotoxicity of chemicals
in Alpinia galanga, Alpinia officinarum, Heliochrysum aureonitens

Sitosterol, C29H50O, phytosterol, similar to cholesterol, extracted from wheat germ oil, corn oil, soybean and other grain or nut oils,
Amaranthus species, rice bran, soybean, Prunus africana, Serenoa repens, Lycium barbarum, Cucurbita pepo
Sitosterol use is not recommended during pregnancy
Beta-sitosterol (C29H50O), phytosterol, similar to cholesterol, oestrogenic activity, inhibits proliferation of human leukemia cells,
reducing serum cholesterol levels. natural prostate health. reduce the growth of human prostate and colon cancer cells.

Stigmasterol, C29H48O, phytosterol, stigmasterin, steroid derivative, unsaturated phytosterol, anti-cancer, anti-pyretic,
anti-inflammatory, immune-modulating, possible treatment for osteoarthrirtis, reference standard for cholesterol-lowering dietary
supplements, plant fats, soybean, calabar bean, canola seed, --> androgens, oestrogens, corticoids, vitamin D3, Ophiopogon,
vegetables, legumes.

Stigmastanol, C29H52O, phytosterol, steroid derivative, fucostanol, stigmastan-3β-ol, lipid, inhihits absorption of cholesterol from
food, possible treatment of atherosclerosis, prostate and colon cancers.

Trioxsalen, C14H12O3
Trioxsalen is a furanocoumarin and a psoralen derivative.
It is obtained from several plants, mainly Psoralea corylifolia.
Like other psoralen it causes photosensitization of the skin.
Trioxsalen is used as a very strong medicine that increases the skin's sensitivity to sunlight.
In addition to causing serious sunburns if not properly used, it has been reported to increase the chance of skin cancer and cataracts.
In albinism, trioxsalen will increase the tolerance of the skin to sunlight, although no pigment is formed.
Trioxsalen is used in conjunction with ultraviolet light A (UVA).
This mode of treatment is known as PUVA (psoralen plus ultraviolet light A).
Psoralea coryfolia


Phytochemicals
1.0 Carbohydrates and Lipids
1.1 16.3.1.3 Monosaccharides
16.3.1.0 Aliphatic compounds
1.2 Oligosaccharides
1.3 Polysaccharides
1.4 19.1.04Polyhydric alcohols, Glycerol, Mannitol, Sorbitol
1.5 16.3.8.0 Organic acids
1.6 16.3.8.1Fatty acids, lipids
1.7 Hydrocarbons and derivatives
1.8 Acetylenes
2.0 Compounds containing Nitrogen
2.1 16.3.6.1.0 Amino acids
2.2 16.3.32 Amines
2.3 Cyanogenic glycosides
2.4 Glucosinolates
2.5 16.3.33 Purines and Pyrimidines
2.6 Proteins and peptides
2.7 Nitrogen compounds
3.0 16.3.0.0 Alkaloids
4.0 Phenolics

4.1 16.3.4.2.5 Anthocyanidins
, anthocyanins, athochlors
4.2 16.3.4.1a Benzofurans, Benzofuranoids, benzopyranoids
4.3 16.3.4.1aChromones, Chromone glycosides, Chromenes
4.4 Coumarins
4.5 16.3.4.2.0 Flavonoids, Flavonols
4.6 Isoflavonoids, Neoflavonoids
4.6 16.3.4.2.18 Lignans
4.7 16.1.0 Phenols, Phenolic acids
4.8 Phenolic ketones
4.9 16.5.6.0 Phenylpropanoids
4.10 16.3.10.0 Quinones
4.11 16.3.4.2.18a Stilbenes, stilbenoids
4.12 16.2.7.0 Tannins, plant polyphenols
5.0 16.3.5.0 Terpenes and Terpenoids (Isoprenoids)