School Science Lessons
Appendix G
Phytochemicals
2019-02-21
Please send comments to: J.Elfick@uq.edu.au

Phytochemicals

Table of contents
Acetyldigoxin, C43H66O15, N-Acetyltyramine
Acolongifloroside K, C29H44O12
Aesculetin, C9H6O4
Agnuside, C22H26O11
Agrimophol, C26H34O8
Alvonal MR, C30H44O9
Amarogentin, C29H30O13
Amygdalin, C20H27NO11
Annonacin, C35H64O7
Apiin, C26H28O14
Arbutin, C12H16O7
Aristolochic acid B, C17H11NO7
Asiaticoside, C48H78O19
Asparanin A, C39H64O13
Asparanin B, C45H74O17
Aucubin, C15H22O9
Benzyl benzoate, C14H12O2
Bromelain
Calotropin, C29H40O9
Canthaxanthin, C40H52O2
Carnosol, C20H26O4
Carthamin, C43H42O22, formerly carthamine
Cascarosides, C27H32O14
Casticin, C19H18O8
Convallatoxin, C24H42O10
Curcumin, C21H20O6
Cymarine, C30H44O9
Cynarin, C25H24O12
Deslanoside, C47H74O19
Digitoxigenin, C23H34O4
Digitoxin, C41H64O13
Digoxin, C41H64O14
Dihydroxyflavan, C15H14O3
Dihydroxy-7-methoxyflavan, C16H16O4
Diindolylmethane, C17H14N2
DisogeninC27H42O3
Docetaxel, C43H53NO14
Dhurrin, C14H17NO7
Echinacoside, C35H46O20
Emodin, C15H10O5
Etoposide, C29H32O13
Fisetin, C15H10O6
Galegine, C6H13N3
Gentiopicrin, C16H20O9
Ginsenoside RG1, C42H72NO14
Glaucarubin, C25H36O10
Glycyrrhizin C42H62O16
Gossypol, C30H30O8
Guanidine, CH5N3
Herbacetin, C15H10O7
Hesperidin, C28H34O15
Hyperforin, C35H52O4.C12H23N
Hypericin, C30H16O8
Indole-3-carbinol, C9H9NO
Irinotecan, C33H38N4O6
Iridomyrmecin, C10H16O2
Kainic acid, C10H15NO4
Kawain, C14H14O3
Kheltin, C14H12O5
Lamiidoside, C26H32O14
Lanatoside C, C49H76O20
Lanoxicaps, C41H64O14
Lapachol, C15H14O3
Levodopa, C9H11NO4
Linamarin, C10H17NO6
Loganin, C17H26O10
Lotaustrain, C11H19NO6
Mangiferin, C19H18O11
Melatonin, C13H16N2O2
Methyl salicylate, C8H8O3
Metildigoxin, C42H66O14
Monocrotaline, C16H23NO6
Myricetin, C15H10O8
N-Methylcytisine, C12H16N2O
N-Methylephedrine, C11H17NO
Narcissin, C28H32O16
Neoandrographolide, C26H40O8
Netilmicin, C21H41N5O7
Nipagin, C8H8O3
Nordihydroguaiaretic acid, C18H22O4
Norepinephrine, C8H11NO3
Octopamine hydrochloride, C8H12ClNO2
Oleandrin, C32H48O9
Oleandrigenin, C25H36O6
Ouabain, C29H24O12, C29H44O12.8H2O
Ouabagenin, C23H34O8
Octopamine, C8H11NO2
Octopamine hydrochloride
Paclitaxel, C47H51NO14
Phillyrin, C27H34O11
Phyllodulcin, C16H14O5
Physcion, C16H12O5
Picrotoxin, C30H34O13
Pinitol, C7H14O8
Pipernonaline, C21H27NO3
Plumbagin, C11H8O3
Podophyllotoxin, C22H22O8
Proscillaridin A, C30H42O8
Protostephanine, C21H27NO4
Prunasin, C14H17NO6
Pseudohypericin, C30H16O9
Quinolizidine, C9H17N
Quisqualic acid, C5H7N3O5
Rebaudioside, C44H70O13
Rhamnazin, C17H14O7
Rhamnetin, C16H12O7
Rhodionin, C15H10O7
Rhododendrol, C10H14O2
Rorifone, C11H21NO2S
Rosarin, C20H28O10
Rotundine, C15H21NO
Rutaecarpine, C18H13N3O
Sakakin, C13H18O7
Salicin, C13H18O7
Santonin, C15H18O3
Scillaren A, C36H52O13
Serotonin, C10H12N2O
Shatavarin IV, C45H74O17
Silymarin, C25H22O10
Sinensetin, C20H20O7
Sophoricoside, C21H20O10
Stevioside, C38H60O18
Strophanthin, C36H54O14
Tenisopide, C32H32O13S
Tetrahydrocannabinol, C21H30O2
Thymol, C10H14O
Trichanthin,C22H27NO7S
Verbascoside, C29H36O5
Xanthone, C13H8O2
Yuanhuacine, C37H44O10

Acacetin, C16H12O5
linarigenin, O-methylated flavone, 4-methoxy-5,7-dihydroxyflavone, anti-peroxidative, anti-inflammatory, anti-aromatase (blocks
oestrogen synthesis) flavonoid, antiproliferative agent which induces apoptosis of cancer cells, used in traditional Chinese medicine
and used by athletes and body-builders as dietary supplement to maintain testosterone levels and prevent increasing estrogen levels,
relief from menopause symptoms, tumor growth prevention, reduction of estrogen synthesis.
In | Damiana| Black locust| Silver birch tree
See Diagram: Acacetin

Acetyldigoxin, C43H66O15
cardiac glycoside, in Woolly foxglove, acetyl derivatives of digoxin from Digitalis lanata are better absorbed and longer acting than
digoxin, used to treat congestive heart failure.
See diagram: Acetyldigoxin

Acolongifloroside, K, C29H44O12,
cardiactive glycoside, used as with digitalis, in Strophanthus gratusseeds, and other Apocynaceae.
Acolongifloroside K consists of rhamnose and ouabagenin, used like Digitalis and in cell biological research.
See diagram: Acolongifloroside

Adoniside
cardiac glycoside, cardiotonic, a cardenolide, in Adonisvernalis

Aesculetin, C9H6O4
esculetin, Coumarinderivative, 6,7-dihydroxycoumarin, a lactone, anticoagulant, its glucoside is aesculetin, used in UV filters,
in | Chicory| barley |

Agnuside, C22H26O11
iridoid glycoside, ester of aucubin and hydroxybenzoic acid, used to treat premenstrual syndrome, in Chaste tree

Agrimophol, C26H34O8
a phloroglucinol, anthelmintic, kills maggots, in Agrimony, used in research on Mycobacterial tuberculosis (Mtb)
See diagram: Agrimophol

Alvonal MR, C30H44O9
cymarine, cymarin, cardiotonic glycoside, cardiac glycoside, K-strophanthin-alpha (strophanthin aglycone), cardioprotective,
in Strophanthus gratus, and Dogbane
Apocynum cannabinum, A. venetum, source of fibre

Amarogentin, C29H30O13
secoiridoid glycoside, most bitter sustance, standard of bitterness, in different kinds of bitters, possible use for cancer chemotherapy,
in gentian Gentiana lutea| Swertiachirata, with Gentiopicrin

Amygdalin, C20H27NO11
cyanogenic glycoside, cyanide poisoning, in Rosaceae seeds, e.g. apricot kernels, bitter almonds, apple seeds, peach, plum
Neither amygdalin nor modified form called laetrile are anti-cancer agents and are not vitamins, "Vitamin B17" is a misnomer.
Hydrolysis with dilute hydrochloric acid or emulsin
C20H27NO11, + H2O --> C6H6CHO + HCN + 2C6H12O6
amygdalin + water --> benzaldehyde + hydrogen cyanide + D-glucose
Almond: 16.3.6.17
Bitter almond: 16.3.6.18
See diagram: Amygdalin

Annonacin, C35H64O7
neurotoxic acetogenin in Annonaceae, e.g. American pawpaw, soursop, custard apple, cherimoya, Goniothalamus.
Acetogenins, found only in Annonaceae, are linear 32- or 34-carbon chains containing oxygenated functional groups.
Annonacin has been found to caused significant cell death in various cancers, e.g. bladder cancer.

Apiin, C26H28O14
apioside, β-D-glucoside, flavonoid (aglycone of apinogen), anti-inflammatory, in parsley, celery
See diagram: Apiin
Apiose, C5H10O5, monosaccharide, in Appiin of parsley, Petroselenum crispum

Arbutin, C12H16O7
glycoside, glycolsylated hydroquinone, Chinese medicine, inhibits melanin formation by inhibiting tyrosinase,
in bearberry, pear skin, wheat, Bergenia, Arctostaphylos

Aristolochic acid B, C17H11NO7
Chinese medicine, ma dou ling, Dutchman's pipe, carcinogenic, mutagenic, in Aristolochiaceae
birthwort, family Asiaticoside, C48H78O19, wound healing, in Centella asiatica ( gotu cola), and Aristolochia tagala
toxic to birds, anti-inflammatory, anti-fertility, carcinogenic in animals
Aristolindiquinone, C12H10O4, napthoquinone, in Aristolochia indica rootcine, in Asparagus officinalis

Asiaticoside, C48H78O19
oleanane-type triterpene glycoside, O-glucose-glucose-rhamnose, madecassol, fine white and odourless, toxic to birds, anti-inflammatory,
anti-fertility, carcinogenic in animals, powder, in green vegetables, in Gotu kola, Asiatic pennywort (Centella asiatica), and Aristolochia
tagala, antibiotic, used for wound healing tissue repair in "Madecassol" healing ointment, and anti-depressant

Asparanin A, C39H64O13
steroidal saponin, nematocidal, anticancer
Asparanin B, C45H74O17, steroidal saponin, Chinese medicine, in Asparagus officinalis

Aucubin, C15H22O9
iridoid glycoside, in Aucuba japonica, Eucommia ulmoides, Plantago species, Galium aparin, used in traditional Chinese folk medicine
See diagram: Aucubin

Bromelain
proteolytic enzymes, mixture of compounds in extract from pineapple stem, lesser in fruit, anti-inflammatory, mixture of proteolytic enzymes,
anti-inflammatory, used after bruising and surgery, used to treat burn tissue, meat tenderizer, in Pineapple
Avoid bromelain if taking aspirin or blood-thinning anticoagulants or if allergic to pineapple.

Benzyl benzoate, C14H12O2
Ascabiol, Benylate, Novoscabin, Benzoic acid, C14H12O2
Ester of benzyl alcohol + benzoic acid, acaricide, scabicide, insect repellent, in tuberose, hyacinth,
Formerly used to treat scabies and lice infestation of the head and body, but it has irritant properties.
In Balsam of Peru
C6H5CH2OH + C6H5COOH --> C6H5CH2O2CC6H5+ H2O
benzyl alcohol + benzoic acid --> benzyl benzoate + water
See diagram: Benzyl benzoate
See diagram: Benzyl benzoate

Calotropin, C29H40O9
pecilocerin, cardiac glycoside, cardenolide, cardioprotective agent, in Sodom apple
See diagram: Calotropin

Canthaxanthin, C40H52O2
orobronze, keto-carotenoid, trans-carotenoid pigment, widely distributed in nature, fat soluble, antioxidant, food colouring, oral suntanning
agent, but causes damage to the retina, food and drug colouring agent, E161g, in algae, mushrooms, bacteria.
gives farmed salmon a pink color similar to wild salmon and acts as antibiotic, so used to determine the origin of salmons for food.
See diagram: Canthaxanthin

Carnosol, C20H26O4
antioxidant, phenolic diterpene, may inhibit breast cancer, anti-inflammatory, anti-microbial anti-cancer, chemopreventive,
in | Rosemary| Mountain Desert Sage| extract of rosemary leaves contains high antioxidative activity to carnosol and carnosic acid, C20H28O4,
easily converted to carnosol by oxidation, possibly neuroprotective effects by promoting synthesis of nerve growth factor in glial cells, activates
enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose, so posibly being used clinically for treatment
of type 2 diabetes.
See diagram: Carnosol

Carthamin, C43H42O22
food additive Natural Red 26, Safflower Yellow, formerly known as carthamine, red quinonoid glycoside, flavonoid,
colouring matter of Safflower, used as dye and a food colouring, cosmetic, ancient Egypt wool dye
See diagram: Carthamin

Cascarosides, C27H32O14
Cascaroside A and Cascaroside B, hydroxyanthracene glycosides, laxatives acting on the large intestines,
Cascaroside A in Purging buckthorn
Cascaroside B in Cascara sagrada
See diagram: Cascaroside A

Casticin, C19H18O8, methyoxylated flavonol
Vitexicarpin, tetramethoxyflavone, methyoxalated flavonol (two attached methyl groups), from quercetagetin, apotosis inducer,
in Vitex trifoliata, Chaste tree(Vitex agnus-castus) seeds, Eremophila
See diagram: Casticin

Convallatoxin, C29H42O10
cardiac glycoside, in Lily-of-the-valley(Convallaria majalis), Liliaceae.
See diagram: Convallatoxin

Curcumin, C21H20O6
diferuloylmethane, Natural yellow 3, Turmeric yellow, phenolic compound, phytopolylphenol pigment, diarylheptanoid
phenolic compound, choleretic, anti-inflammatory by inhibition of cyclooxygenases (COX) , antioxidant,
yellow-orange dye, tumeric is powdered rhizome of Turmeric (Curcuma longa), easily penetrates cell cytoplasm and accumulates in plasma membrane,
endoplasmic reticulum and nuclear envelope, used to prepare curcuma paper and the detection of boron, pharmacological properties caused by
inhibitory effects on metabolic enzymes, inhibits tumor cell proliferation curcumin, dietary supplements may cause heartburn.
E100Curcumin
See diagram: Curcumin

Cynarin, C25H24O12
cynarine, cinarin, (1,5-Dicaffeoylquinic acid), phenolic compound, a hydroxycinnamic acid, ester of quinic acid +
caffeic acid, inhibits taste receptors so water tastes sweet, aids digestion, disorders of liver and gallbladder, choleretic, aids cholesterol
levels, possibly immunosuppressive agent, in Artichoke, and Artichoke thistle
See diagram: Cynarine

Deslanoside, C47H74O19
deacetyllanatoside C, desacetyllanatoside C, cardiac glycoside, cardiotonic glycoside, in leaves of Digitalis lanata
used to treat heart disorders by increasings intracellular sodium and calcium concentrations, which may promote activation of contractile
proteins (e. g. , actin, myosin), and acts on the electrical activity of the heart.
See diagram: Deslanoside

Dhurrin, C14H17NO7
cyanogenic glycoside, in leaves, and later stems, of Sorghum bicolor, may cause HCN cattle poisoning
See diagram: Dhurrin

Digitoxin, C41H64O13
cardiac glycoside, cardenolide, lipid-soluble, in plasma membrane, anti-cancer, odourless powder, mentioned as poison in stage plays,
in Foxglove, it causes 1. increased intracellular sodium and calcium levels and decreased intracellular potassium levels, leading to apoptosis
and inhibition of cancer cell growth, 2. increased intracellular concentrations of calcium to promote activation of contractile proteins
(e.g. actin, myosin), so acts on the electrical activity of the heart
Digitoxin has similar toxic effects to digoxin, sometimes used in place of it and has a longer half life,
See diagram: Digitoxin
Digitoxigenin, C23H34O4, cardiac glycoside, cardenolide, from hydrolysis of digitoxin

Digoxin, C41H64O14
cardiac glycoside (also called digitalis, digitalin), cardenolide, controls ventricular rate, used to treat congestive
heart failure, in | Digitalis lanata| Digitalis purpurea|

Dihydroxyflavan, 7,4'-Dihydroxyflavan, C15H14O3
3',4'-Dihydroxy-7-methoxyflavan, C16H16O4
In Butterfly tree, causes diarrhoea, antifungal and antibacterial activity
See diagram: Dihydroxyflavan

Diindolylmethane (3,3'-diindolylmethane), C17H14N2
Chemical compound 3,3-Diindolylmethane (DIM) is a bioactive metabolite of indole-3-carbinol, phytochemical produced by the breakdown
of glucosinolate glucobrassicin in Brassicaceae vegetables, inhibits neoplasms, an apotosis inducer which has been used in treatment of
prostate cancer and cervical dysplasia (abnormal changes in cervix cells) caused by human papilloma virus, but effectiveness not clear

Disogenin, C27H42O3
steroid sapogenin, used to treat rheumatoid arthritis, may cause death of human colon carcinoma cells.
Diosgenin occurs in yams and as the isomer yamogenin in the herb fenugreek.
Natural derivatives of disogenin are solasodine and solanine.
See diagram: Yamogenin

Docetaxel, C43H53NO14
taxotere, a taxane, anti-cancer, prevents mitosis, microtubule inhibitor, related to Paclitaxel, anhydrous
form used as a common chemotherapy drug as an inhibitor of cellular mitosis to treat solid tumors, e.g. breast and lung cancer

Echinacoside, C35H46O20,
glycoside, caffeic acid glycoside, in herbal medicine, used to treat Parkinson's disease

Emodin, C15H10O5
anthroquinone, 6-methyl-1,3,8-trihydroxyanththraquinone, purgative , laxative, catharctic, excites large intestine
smooth muscle, anticancer, in | Rheumemodi | Buckthorns| in Rhamnus cathartica|

Etoposide, C29H32O13
VP-16, topoisomerase inhibitor, irritant, antitumor agent, podophyllotoxin, in Podophyllum peltatum,
(mayapple, American mandrake, ground lemon), Etoposide phosphate, anti-cancer drug

Fisetin, C15H10O6
flavonol, flavonoid polyphenol, antioxidant, colouring agent, anticarcinogenic, neuroprotective, anti-inflammatory,
highest concentrations in strawberry, apple, persimmon, lotus root, onion, grapes, Fisetin, possibly anti-cancer agent

Galegine, C6H13N3, Amine
isoamylene guanidine, the drug metformin (C4H11N5) which can both be extracted from galegine and Guanidine, in Goat's rue,
is a biguanide, as is (C2H7N5), HN[C(NH)NH2]2, a chemical which which prevents the production of glucose in the liver, so it used to
treat type 2 diabetes.

Ginsenoside RG1, C42H72NO14
sanchinoside C1, panaxoside A, panaxoside Rg1, sanchinoside Rg1, root triterpenoid saponin
Ginsenoside RG1 is most abundant in Ginseng (Panax ginseng) (Korean ginseng), Araliaceae, improves spatial learning, estrogen-like
activity, cardioprotective agent.
Ginsenosides are a class of steroid glycosides, and triterpene saponins, found only in Panax (ginseng), appear to affect multiple
physiological pathways.

Gentiopicrin, C16H20O9
gentiopicrocide, component of secoiridoid glycosides, in gentian, anticonvulsant, anti-addiction, iridoid in Gentiana species, Gentiana lutea,
Swertia chirata, with Amarogentin
Geniposidic acid (GA), C16H22O10, anti-inflammatory, anti-cancer, jaundice, hepatic disorders, in Gardenia jasminoides

Glaucarubin, C25H36O10
triterpenoid, amoebicide, in Simarouba glauca (paradise tree)

Glycyrrhizin, C42H62O16
saponin or saponin-like compound, glycyrrhizinic acid, glycyrrhetinic acid glycoside, glycyrrhizinic acid, triterpene aglycone, , sweet
tasting, used in food and drug industry, used formerly to treat peptic ulcer, causes sweet flavour of Glycyrrhiza glabra (liquorice root),
Abrus precatorius, anti-inflammatory, expectorant, metabolized to glycyrrhetinic acid which inhibits enzymes in metabolism of
corticosteroids, possibly used to treat sodium retention and potassium loss, edema, inflammation, increased blood pressure, growth of
tumor cells, widely used anti-inflammatory agent from licorice root, may suppress growth of tumor cells.

Gossypol, C30H30O8,
phenolic compound, toxic, male contraceptive, in Gossypium sp (cotton)

Guaiacol, C6H4(OH)(OCH3),
phenolic compound, in gaiac oil, formerly used to treat syphilis, from Guaiacum officinale ("Lignum
vitae"), Zygophyllaceae.

Guanidine, CH5N3, HNC(NH2)2
polyamine, iminourea, aminomethanamidine, carbamidine, carbamamidine, crystalline compound, colourless solid, dissolves in polar
solvents, strong base that is used in the production of plastics and explosives, in urine from protein metabolism, isolated from Peruvian
guano, in Goat's rue.
Guanidine is a biguanide, as is Galegine.
Guanidine is an acetylcholine releasing agent and is used in the manufacture of plastics and explosives
Guanidine is protonated (addition of hydrogen) as guanidinium cation (C(NH2)+, so guanidine is very strong organic base in water.
Guanidinium nitrate is used as a propellant in air bags.
Guanidinium chloride is used to denature proteins.
Guanidinium hydroxide in some hair relaxers.

Herbacetin, C15H10O7
flavonol, possible cancer therapy, in Rhodiola rosea, golden root, rose root, Crassulaceae

Hesperidin, C28H34O15
flavanone glycoside (aglycone hesperetin), in citrus fruit peels, bitter orange, orange juice, hesperidin, used
to treat capillary fragility

Hyperforin, C35H52O4.C12H23N
phytochemical (dicylohexylammonium) salt, antidepressant and anxiolytic activity, anti-inflammatory, in St John's
wort

Hypericin, C30H16O8
anthroqinone glycoside, anthroqinone-derivative, anti-bacteria, Gram-positive and Gram-negative, in
Hypericum perforatum

Indole-3-carbinol (I3C), 3-Indolemethanol, C9H9NO
natural phytochemical, off-white solid, formed in cabbage family after crushing or during cooking, produced by action of myrosinase
on the glucosinolate glucobrassicin in Brassica species, e.g. cabbage, radishes, cauliflower, broccoli, Brussels sprouts, daikon, metabolized
to 3, 3'-diindolylmethane, natural chemopreventive, anticarcinogenic, antitumorigenic, may prevent development of estrogen-enhanced
cancers including breast, endometrial and cervical cancers
See diagram: Indole-3-carbinol

Iridomyrmecin, C10H16O2
simple iridoid, in Actinidia polygama, antibiotic, Plantago lanceolata, used in laxative and diuretic medicins, antidote to Amanita virosa
poisoning.

Irinotecan, C33H38N4O6
anticancer, antitumor agent, topoisomerase enzyme inhibitor, used in the treatment of colorectal cancer, "Camptosar",
in Camptotheca acuminata, "Asian Happy tree", derivative of camptothecin that inhibits the action of topoisomerase I
and causes double-strand DNA breakage and cell death.

Kainic acid, C10H15NO4
Kainic acid, C10H15NO4, ascaricide, in Digenea simplex (algae)
Kainic acid monohydrate, C10H15NO4.H2O, excess induces neurocytosis and epiliptic seizures

Kawain, C14H14O3
DL-kawain, kavain, anti-anxiety, anticonvulsant, hypnotic, sleep-quality enhancing, tranquillizer, kavalactone, in Piper methysticum
(kava kava)

Kheltin, C14H12O5
pyrone, gamma-pyrone, furanochromone derivative, bronchodilator, smooth muscle relaxant, used to treat vitiligo, kidney stones, in
Ammi visnaga, toothpick plant, bishop's weed, Apiaceae

Lamiidoside, C26H32O14
iridoid glucoside
in Phlomis fructicosa, Labiatae, Bouchea fluminensis, Verbanaceae

Loganin, an iridoid glucoside, C17H26O10
in Strychnos nux-vomica, Hydrangea species, Catharanthus roseus, used in bitter tonic folk medicines

Lanoxicaps, C41H64O14
cardiac glycoside, consists of three sugars and the aglycone digoxigenin, used to control ventricular rate in atrial fibrillation, toxic if
therapeutic drug dose is too large, in Digitalia lantana

Lanatoside C, C49H76O20
cardiac glycoside, used to treat heart failure, arrhythmia, in Digitalis lanata

Lapachol, C15H14O3, napthoquinone, antimicrobial, anti-inflammatory, analgesic, anticancer, antitumor, in Tabebuia sp (trumpet tree),
Bignoniaceae

Levodopa, C9H11NO4
L-dopa, dihydroxyphenylalinine, aromatic amino acid, in the brain levodapa is decarboxylated by opaminergic neurons to dopamine,
psychoactive drug, treat stiffness, spasms, poor muscle control of Parkinson's disease, in Mucuna pruriens, cowhage, velvet bean, Fabaceae,
Vicia faba (broad bean), Dalbergia, Mucuna, Llupinus

Lotaustrain, C11H19NO6
cyanogenic glycoside, in Lotus austral;is, lima bean, Rhodolia rosea, white clover, cassava

Mangiferin, C19H18O11
glycoside, [C6-C1-C6], xanthonoid, hydroxalated xanthone c-glycoside, in mangoes, antimicrobial, antioxidant, possibly antidiabetic,
in Iris unguicalaris, Bombax ceida, Asplenium montanum.

Melatonin, C13H16N2O2
animal hormone to anticipate darkness, used to treat insomnia disorders, sleep disorders, jet lag, headaches, in coffee, walnuts, most plants

Methyl salicylate, C8H8O3
C6H4OHCO.OCH3, 2-Hydroxybenzoic acid methyl ester, Methyl 2-hydroxybenzoate, oil of wintergreen, organic ester in many plants,
colorless / yellow / red liquid, odour and taste of wintergreens.
Occurs in vanilla, tea, clary sage, red sage cherry, apple, raspberry, papaya, plum, leaves of Wintergreen.
Used as flavouring agent in beverages, white wine, chewing gums mints, antiseptic in mouthwash solutions.
Used as a rubefacient and analgesic in deep heating liniments for acute joint and muscular pain.
Prepare methyl salicylate: 16.5.5
See diagram: Methyl salicylate

Metildigoxin, C42H66O14
digitalis glycoside, used to treat heart failure

N-Methylcytisine, C12H16N2O N-Methylcytisine, C12H16N2O, caulophylline, in Caulophyllum thalictroides

N-Methylephedrine, C11H17NO
in Ephedra distachya, (1R,2S)-(-)-N-Methylephedrine (1S,2R)-(+)-N-Methylephedrine

Monocrotaline, C16H23NO6
topical antitumor agent, in Crotalaria sessiliflora

Myricetin, C15H10O8
bioflavonoid, flavonol, antioxidant, anticarcinogen, antiviral, antithrombic, antidiabetic, antiatherosclerotic,
in vegetables, fruit, berries, tea, red wine, possible cancer therapy, in | Bayberry| Ginger| Hops|

Narcissin, C28H32O16
flavonoid,, in marigold

Neoandrographolide, C26H40O8
a glucopyranoside, used to treat dysentery, shows viricidal activity against herpes simplex virus
1 (HSV-1), in Andrographis paniculata

Netilmicin, C21H41N5O7
aminoglycoside antibiotic, 1-N-ethylsisomicin, netilmicinum, semisynthetic, action similar to gentamicin, but less ear and kidney toxicity.

Nipagin, C8H8O3 hydroxybenzoic acid derivative (benzene ring + carbpxylic acid, methyl paraben, methyl-4-hydroxy-benzoate, antimicrobial,
allegen, increases histamine release and cell-mediated immunity, in alcoholic beverages, cloudberry, yellow passionfruit, white wine
Nipagin A, propyl paraben, sodium salt, sensitizer (food preservative against fungi),
Nipagin A, Parabens: 16.3.4.0.12
Nipagin B, methyl p-hydroxybenzoate (anti-fungal agent), Parabens: 16.3.4.0.12

Nordihydroguaiaretic acid, C18H22O4
(NDGA), antioxidant, inhibitor of broad bean lipoxygenase, in Larrea divaricata, (creosote
bush, chaparral), herbal medicine but may be toxic

Norepinephrine, C8H11NO3
(NE), L-noradrenaline, noradrenalin, arterenol, a catecholamine hormone, monoamine from dopamine, directly stimulates adrenergic
receptors so adrenergic neurotransmitter, central and autonomic neurotransmitter, precursor of epinephrine, secreted from adrenal medulla
of the brain, also found in plants, used pharmacologically as a sympathomimetic.
Norepinephrine causes vasoconstriction of the smooth muscles, including the sphincter of the gastrointestinal tract.
Stimulation of beta-1 adrenergic receptors causes an increase in myocardial contractility, heart rate
Stimulation of beta-2 adrenergic receptors causes bronchiolar and vascular smooth muscle dilatation.
See diagram: Norepinephrine

Octopamine, C8H11NO2, Amine
Biogenic phenylethanolamine, tyramine, alpha-adrenergic sympathomimetic amine, from tyramine in the CNS and platelets, in invertebrate
nervous systems, Octopamine, Norsynephrine, Norsympatol, Norsympathol, NordenA, used to treat hypotension, used as cardiotonic,
produces cardiovascular adrenergic responses.

Octopamine hydrochloride, C8H12ClNO2
in weight loss supplements but possibly not effective

Oleandrin, C32H48O9
steroid saponin, toxic sap, used for suicide, formerly therapeutic uses, in Nerium oleander
Oleandrigenin, C25H36O6, steroid ester, toxic sap, for suicide, formerly therapeutic uses, in Nerium oleander

Ouabain, C29H24O12
cardiac glycoside, g-strophanthin, toxic, steroidal hormone, arrow poison, low dose used to treat hypertension arrhythmia, dangerous drug,
in Strophanthus gratus,(ouabain tree)
Ouabagenin, C23H34O8 (G-Strophanthidin), cardenolide, cardioactive steroid, steroidal lactone, cardiotonic effects

Paclitaxel, C47H51NO14 Taxol A, "taxol", taxane, cyclodecane, anticancer, antineoplastic, stabilizes microtubules to cause cell death,
kills B-cell Leukemia 2, prevent carotid artery narrowing, in bark of Taxus brevicola, Pacific yew, Taxus braccata, Eurpean yew

Phillyrin, C27H34O11
Forsythin, anti-obesity, antioxidant, anti-inflammatory, lignan, in fruit of Forsythia suspensa

Phyllodulcin, C16H14O5
dihydroisocoumarin, sweetener, in Hydrangea macrophylla (big leaf hydrangea, French hydrangea)

Physcion, C16H12O5, anthraquinone derivative, in Rheumspecies.
also in Microsporum, Psorospermum and Rhamnus, anticancer, antibiotic, anti-inflammatory,
antibacterial activity against Staphylococcus, Pseudomonas, and Escherichia, and antifungal activity
against Candida and Aspergillus.
Picrotoxin, C30H34O13
cocculin (two compounds: picrotoxinin C15H16O6 + picrotin, C15H18O7), poison, blocks nervous system,
stimulant and convulsant, affects GABA receptor channels, analeptic, non-medical use illegal, in Anamirta cocculus (fish berry)

Pinitol, C7H14O8
D-pinitol, anti-diabetic, expectorant, salt stress regulator in many plants, in Bougainvillea, Sutherlandia frutescens

Pipernonaline, C21H27NO3
in Piper longum, antifungal, mosquito larvicidal

Plumbagin, C11H8O3
genotoxic, mutagenic, from naphthoquinone, yellow pigment, anti-inflammatory, antifungal, antiviral,
antibacterial, possibly anticarcinogenic, in Plumbago| Drosera| Nepentheskhasiana | Juglansnigra black walnut | Diospyrosanisandra
| (possibly, anti-tuberculosis)

Podophyllotoxin, C22H22O8
PPT, podofilox, podophyllum resin, a lignan, antitumor, anticancer agent, used to treat genital warts,
in roots and rhizomes of Podophyllum peltatum (may apple)

Proscillaridin A, C30H42O8
cardiac glycoside, scillarenin 3-O-rhamnoside, in Scilla maritima var. alba, squill, Drimia maritima
(sugar + steroid) ( in roots of Asclepias curassavica), (steroid glycoside H.g.-12, in Hoodia gordonii)

Protostephanine, C21H27NO4
in Stephania japonica, snake vine

Prunasin, C14H17NO6
, cyanogenic glycoside, in Olinia ventosaleaves and stem

Pseudohypericin, C30H16O9 antidepressant and anxiolytic activity, in St John's wort

Quinolizidine, C9H17N
in Lupinus, Genista hirsuta, Nymphaea lotus, Nymphaceae

Quisqualic acid, C5H7N3O5
non-protogenic alpha-amino acid, anthelmintic, in Quisqualis indica, (Rangoon creeper, drunken sailor)

Rebaudioside, C44H70O13
glycoside, REBA, molecule structure based only on glucose molecules, sweetener, in Stevia rebaudiana

Rhamnazin, C17H14O7
flavonol glycoside, O-methylated flavonol, in Rhamnus petiolaris

Rhamnetin, C16H12O7
flavonol glycoside, O-methylated flavonol, from cloves, in Rhamnus petiolaris

Rhodionin, C15H10O7
rhamnoside, , in Rhodiola rosea rhizome, Crassulaceae

Rhododendrol, C10H14O2
betuligenol, may reduce fat-induced body weight gain, in Rhododendron aureum

Rhomitoxin
antihypertensive, antitachcardiac, tranquillizer, in Rhododendron molle (rhododendron)

Rorifone, C11H21NO2S
antitussive, in Rorippa indica

Rosarin, C20H28O10
reduce fatigue, increase endurance and mental performance, in Rhodiola rosea

Rotundine, C15H21NO
selective dopamine D1 receptopr agonist, analagesic, adrenergic, anti-arrhythmic, antihypertensive,
antipsychotic, sedative, tranquillizer, in Stephania sinica

Rutaecarpine, C18H13N3O
a pyridopyrimidine, i.e. a pyridine fused to a pyrimidine, inhibits platelet agregation, vasoldilator, in Chinese medicine, counteracts
breakdown of caffeine, anti-inflammatory, vasorelaxation, in Tetradium ruticarpum (previously Euodia ruticarpa), tree from China,
fruit has strong bitter taste

Sakakin, C13H18O7
orcinol glucoside, in rhizome of Curculigo orchioides

Salicin, C13H18O7
glucoside, water-soluble, analgesic, in Salix alba (white willow)

Santonin, C15H18O3
ascaricide, antihelminthic, white crystals, in dried flower heads of Artemisia maritma (wormwood), Artemisia
cima, levant wormseed, Santonica

Scillaren A, C36H52O13
cardiac glycoside, cariotonic, hair disorders, anti-cancer, rodenticide, in Scilla maritima, Urginea maritima, squill

Serotonin, C10H12N2O, Amine
5-Hydroxytryptamine, synthesized from L-tryptophan, a monoamine but serotonin is not usually classified as alkaloid because it is a primary
metabolite, neurotransmitter in in CNS, gastrointestinal tract, and blood platelets biochemical messenger and regulator, neurotransmission,
gastrointestinal motility, hemostasis, and cardiovascular integrity, biochemical mediator with broad physiological actions as messenger and
regulator local transmitter at synapses, allows wide variety of behavioral responses to different stimuli, vasoconstriction, anaphylactic shock,
circadian rhythms
See diagram: Serotonin

Shatavarin IV, C45H74O17
asparanin B

Silymarin, C25H22O10
antihepatotoxic, aids digestion, disorders of liver and gallbladder, aids cholesterol levels, in Silybum
marianum (milk thistle), artichoke

Sinensetin, C20H20O7
methylated flavone, in Java teaand Orange oil

Sophoricoside, C21H20O10
Sophoricoside, C21H20O10, anti-inflammatory, anti-cancer, immunosuppressive, in pagoda tree, Sophora japonica, huai hua,
kowhai, Sophora tetraptera

Stevioside, C38H60O18
steviol diterpene glycoside, Stevia is the calorie-free sweetener in leaves of Steviarebaudiana, sweet leaf
Asteraceae + glucose --> steviocide sweetener, relative sweetness 250 to 300

Strophanthins, C36H54O14, cardioactive glycosides in Strophanthus species
Strophanthus, g-Strophanthin,
Ouabain,ouabainAlvonal MR

Tenisopide, C32H32O13S
Vehem, ataxane, antitumor agent, inhibits DNA synthesis, topoisomerase in hibitor, prevents mitosis,
causes cell death, derivative of podophyllotoxin, in Podophyllum peltatum (may apple or mandrake)

Tetrahydrocannabinol, C21H30O2
(THC), dronabinol, a cannabinoid, psychoactive compound, in Cannabis sativa, (marijuana,
hashish), isomer delta-9-tetrahydrocannabinol is the most active form, to produce mood and perceptual changes, acts directly on
appetite and vomiting centres in the brain to stimulate appetite and prevent vomiting, decreases ocular tension.

Trichanthin,C22H27NO7S
Trichanthin B, Trichanthin A, in stem and root of Glycosmis trichanthera

Verbascoside, C29H36O15
acteoside, glycoside, in many species, Verbascum, Phlomis, olive, vervain, plantago, anti-microbial, anti-inflammatory.

Xanthone, C13H8O2
xanthonoid compound, insecticide, ovicide, in many plant families, Iris, and mangosteen fruit pericarp
See diagram: Xanthone

Yuanhuacine, C37H44O10
daphnane diterpenoid, abortifacient, anti-cancer, diuretic, expectorant, in Daphne genkwa (lilac)