Phytochemicals, Plant extracts, Alkylphenols to Tyrosols.

School Science Lessons
(topic16g)
2024-09-16

Phytochemicals
Contents
Charantin
Flavans
Glycone and aglycone
Glycosides
Hydroxy compounds
Isoflavones
Napththoquinones
Phenols and Phenolic acids
Phenol, carbolic acid
Phenolic compounds, by name
Phenylpropanoids
Phytochemicals
Phytosterols
Proanthocyanidin

Proanthocyanidin
Proanthocyanidin, polyphenols, flavonoids, condensed tannins
They occur in different parts of many plants and have defence functions for plants and a health benefit for humans.
Proanthocyanidin, C31H28O12
psoralen), (flavone alkaloids: ficine, vochysine)
See: Vestitol
Flavonoids.
Fisetin
Galangin
Isorhamnetin
Myricetin

Flavanols, (Flavan-3-ols)
1. Monomers - catechin, occurs in chocolate, cinnamon, red wine.
Catechin
Epicatechin, (EC), Flavonoid
ECG Epicatechin gallate (ECG), Flavonoid
EGC Epigallocatechin (EGC), Bioflavonoid
EGCG Epigallocatechin gallate (EGCG), Bioflavonoid
2. Dimers and polymers, occurs in chocolate, cinnamon.
3. Proanthrocyinidins - Flavon-3-ol polymers
4. Theaflavins
Theaflavin, C29H24O12
Theaflavin-3-gallate
Butin
Hesperetin, C16H14O6, occurs in lemon, orange
Hesperidin, (aglycone hesperetin)
Naringin
Naringin 4'-0-glucoside, C33H42O19, Flavanone Glycoside
Narirutin, C27H32O14, flavanone-7-0-glycoside, Flavanone Glycoside, occurs in Orange juice.
Poncirin
Silibinin
Sinensetin

Flavans, fruits, vegetables
Flavans, Benzopyran derivatives, 2-phenyl-3,4-dihydro-2H-chromene skeleton, (leucoanthocyanidin)
A C-glycosidic from cocoa liquor.
Casuarina glauca is an actinorhizal plant producing root nitrogen-fixing nodules infested by Frankia, containing flavans.
1. Flavanols (NOT "Flavonols"!)
Occurs in fruits and vegetables, e.g. apples, apricots, berries, cherries, grapes, nectarines, peaches, pears, plums, Swiss chard.
Occurs in nuts, e.g. almonds, cashews, hazelnuts, pecans and pistachios.
Occurs in green, black and oolong teas, cacao, red and white wine.
Catechin
Epicatechin, (EC), Flavonoid
ECG Epicatechin gallate (ECG), Flavonoid
Epigallocatechin (EGC), bioflavonoid
Epigallocatechin gallate (EGCG), bioflavonoid
Catechol, C6H6O2, a phenol
Apiforol, C15H14O4
Leucanthocyanidin, C15H14O3, from enzymes, occurs in many plants, e.g. Zea mays
Rutin hydrate, C27H30O16.xH2O, poly flavonoid

Glycosides, glucoside (glucose)
1. A glycoside contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other organic group.
Glycosides are named from the constituent sugar, e.g. glucoside (glucose), pentoside (pentose), fructoside (fructose).
Glycosides, unlike polysaccharides, are sugars bonded to a non-sugar, so they contain a carbohydrate and a non-carbohydrate residue occurs in the same molecule.
2. Anthoxanthins, glycosides, are similar to and associated with anthocyanin.
They are water-soluble white to yellow flavonoid pigments, antioxidants, occur occurs in potatoes, cauliflower, onions, parsnips, bananas.
Anthoxanthins cause bright white colour of food occurs in acid medium, yellow occurs in alkaline medium.
Canthaxanthin
3. Anthraqinone glycosides, (aglycone from anthraquinone), alizarin, hypericin, physcion, rhubarb, Cascara, Senna, Aloe
4. Cardiac glycosides, (steroidal glycosides, digitalis glycosides, cardiovascular glycosides), heart stimulants, occurs in Digitalis, Convallaria.
Cardenolide, C23H34O2 is a steroid molecule, but "cardenolides" are usually cardenolide glycosides
For example:
Cymarine
Digitoxin
Digoxin
Ouabain
Strophanthin|
Cardenolides are cardiac-active steroids, and occur mainly occurs in toxic latex of Asclepidaceae.
Apocynaceae, Moraceae, e.g. ouabain C29H44O12.8H2O, occurs in Acokanthera ouabaio (Apocynaceae).
See diagram: Cardenolide
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

Isoflavones, phytoestrogens, (Isomer of flavone)
Isoflavones, C15H10O2, almost only occurs in Fabaceae, oestrogenic activity, e.g. Psoralea
Isoflavones are related to isoflavonoids, phytestrogens and antioxidants, soy isoflavones may prevent breast cancer.
They only occurs in legumes, especially in soybeans, and pistachios.
Astragaloside 4, C41H68O14, anti-inflammatory, occurs in Astragali radix.
Daidzein, C15H10O4, Dihydroxyisoflavone, occurs in soybean and tofu, anti-inflammatory, anti-microbial, antioxidant, phytoestrogenic, estrogenic metabolite Equol is the main active product of daidzein metabolism produced by microflora occurs in the gut, It is a biomarker for the consumption of soy beans and other soy products, antineoplastic, phytoestrogen.
Betavulgarin, antifungal, C17H12O6, (Isoflavonoid)
Betavulgarin, (2'-Hydroxy-5-methoxy-6, 7-methylenedioxyisoflavone), an hydroxyisoflavone, hydroxyisoflavone, methoxyisoflavone)
It occurs in Beta vulgaris,
See diagram 16.3.5.4: Betavulgarin
Daidzin,
Daidzin, C21H20O9, isoflavone, anti-oxidant, daidzoside, anti-carcinogenic, anti-antheroscerotic
It occurs in TCM Chinese medicine and it is used to treat alcohol abuse.
It occurs in Pueraria lobata, kudzu.
Formononetin, C16H12O4
Genistein
Genistein, C15H10O5, isoflavone, phytoestrogen, antineoplastic, from soy product, induces apoptosis, antioxidant, antiangiogenic, immunosuppressive, anti-inflammatory, anti-atherosclerosis
It is biomarker for soy consumption, an antitumor, and may lessens risk of cardiovascular diseases.
It occurs in Pueraria mirifica, Kwao, Krua, Pueraria lobata, kudzu, Glycine max, tofu, fava beans, soybeans, lupin occurs in dyer's broom, (Genista tinctoria), and in Felmingia vestita anti-cestode medicine.
Genistin, C21H20O10, genistine, isoflavone, occurs in soya, occurs in kudzu.
Glycitein
Glycitein, C16H12O5, isoflavone, O-methylated isoflavone, weak oestrogen activity, occurs in soybean, Centrosema haiense, C. Pubescens, occurs in Glycine max.
Irilone
Irilone, C16H10O6, a methylenedioxyisoflavone, an hydroxyisoflavone, immunomodulator, antineoplastic agent, inhibits growth of malignant cells
It occurs in Trifolium pratense (red clover), and Iris species
Ononin
Ononin, C22H22O9, isoflavone glucoside, formononetin-7-O-glucoside, Chinese medicine.
It occurs in Radix astragali, Daphnia pulex, and Astragalus hoantchy.
, Puerarin, C21H20O9, isoflavone, occurs in kudzu, reduces alcohol withdrawal anxiety.
Pterocarpans, derivatives of isoflavonoids, occurs only occurs in Fabaceae, e.g. Phaseolin, C20H10O4, phytoalexin
It occurs in Phaseolus vulgaris, French bean, Fabaceae, and occurs in the stems of Erythrina subumbrans.

Glycone and aglycone
glycoside (hydrolysis) --> glycone (sugar group) + aglycone (non-sugar group)
The sugar group is called a "glycone" and the non-sugar group is called an "aglycone" or genin part of the glycoside.
Upon hydrolysis, a sugar and non-sugar component (aglycone) are formed.
Cadenolide glycosides are usually potentially heart toxic, but Digitalis species are used medically.
An aglycone, is the non-sugar component formed when a glycoside is hydrolysed.
It is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom.
See diagram: Fructose, Glycosyl group.
Vanilla species --> pods -->glucovanillin, [4-O-(3-methoxy-benzaldehyde)-β-D-glucoside] + β-glucosidase enzyme --> vanillin
glucovanillin + (hydrolysis) --> glycone glucose + aglycone vanillin
C14H18O8 + (glucosidase) --> C6H12O6 + C8H8O3

Glycosides
1. Alcoholic glycosides, salicin occurs in Salix.
* Aldehyde glycosides, vanilla pod, glucovanillin, cinnamon bark cinnamic aldehyde
Anthocyanidins (aglycones of the glycoside anthocyanins), e.g. Cyanidin
2. Flavonoid glycosides
Hesperidin, C28H34O15, occurs in lemon peel, sweet oranges, aglycone: hesperetin, C16H14O5.
Naringin
Rutin
* Iridoid glycosides, monoterpenes
* Isothionate glycosides, wild mustard
* Lactone glycosides, sweet clover, red clover
* Phenolic glycosides, arbutin (bearberry), Uva Ursi
* Steroidal glycosides, cardiac glycosides
* Steviol glycosides (aglycone steviol), Stevia, has 2 primary glycosides: stevioside, rebaudioside A.
* Thioglycosides (contain sulfur), Sinigrin precursor to allyl isothiocyanate, mustard oil
appendix G, Phytochemicals by trivial names
Steroid glycosides, sterol glycoside, steroidal saponins, phytosteroid saponins, tetracyclic triterpenoid saponins

Charantin
Charantin, β-sitosteryl glucoside, C36H60O6, white crystals, neutral, tasteless, causes low blood sugar levels
Bitter melon
Digitonin
Diosgenin occurs in bark of Wild yam, Discorea villosa, diosgenin contains disoscin glycoside.
Eleutheroside A, daucosterol, C35H60O6, occurs in Siberian ginseng.
Esculeoside A, C56H95NO29, occurs in Solanum lycopersicum
Osladin|
Protodioscin, C51H84O22, Puncture vine, Solanine, Hedera, Ruscus, Smilax, Withania, Yucca schidigera
Agavaceae, steroidal saponins
Allium, Beth root, Trillium erectum
Climbing oleander, rose oleander, Stropanthus gratus, steroid saponins, cardiac tonic
Foxglove, Digitalis purpurea, steroid saponins, cardiac tonic
Indian squill, Drimia indica, steroid saponins, cardiac tonic, congestive cardiac failure
Oleander, Nerium oleander, Oleandrin, C32H48O9, steroid saponin, from toxic sap, used for suicide, formerly therapeutic uses.
Alfalfa Lucerne, Medicago sativa, hederagenin, C30H48O4, soyasaponin 1
Chickpeas Cicer arietinum
Horse chestnut, Aesculus hippocastanum, saponins that foam occurs in water.
Maesa balansae occurs 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).
Wavy-leafed soap plant, Chlorogalum pomeridianum

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

Phenols and Phenolic acids, (Phenolics, Polyphenols)
Phenols | 16.1.0
1. Phenol crystals, C6H5OH, Highly toxic by all routes, lung irritant, corrosive to skin
Phenol solution < 1%, Not hazardous
Phenol red, C19H14O5S: 28 (indicator)
Phenol, phenolic, is a derivative of an aromatic hydrocarbon where a hydroxyl group is attached to a benzene ring.
Phenolic compounds occur occurs in seeds, grape skins occurs in citronella, clove oil, dicoumarin, eucalyptol, ubiquinone, urushiol and extracted from oak barrels.
Prepare carbol xylol solution: 1.4
Phenylpropanoids
Quinones, Alizarin, Alkannin, Barbaloin, Juglone. Stilbenoids, resveratrol
Sugars
Tannins
Xanthones, Gentisin
Deoxykaempferol
Phenolic acids
16.5.2.1 Hydroxybenzoic acids
Note: "hydroxybenzoic acid" may refer to different compounds:
Salicyclic acid, C7H6O3 2-hydroxybenzoic acid
3-hydroxybenzoic acid, C7H6O3, occurs in gut microfauna.
4-hydroxybenzoic acid, C7H6O3 --> esters --> parabens
trihydroxybenzoic acid Gallic acid, C7H6O5, hydrolysable tannin, pseudotannin
Benzoic acid, C6H5COOH, C7H6O2
Ellagic acid, C14H6O8

Phenolic compounds, by name
Anethole
Arbutin
Bergenin
Caffeic acid
Capsaicin
Carvacrol
Catechol, C6H6O2, a phenol
Chlorogenic acid
< a href="../topics/topicIndexCarbon.html#CichoricacidH">Cichoric acid
Cinnamaldehyde
Cinnamic acid
Coumaric acid
Coumarin
Cresol
Curcumin
Cyanidin
Emodin
Ethylphenol
Estradiol, (oestradiol), C18H24O2
Estragole
Eugenol
Ferulic acid
Furanocoumarins
Gallic acid
Genistein, C15H10O5
Guaiacol, Methyoxyphenol
Juglone
Mangiferin
Methyl salicylate
Myristicin
Nordihydroguaiaretic acid
O-leuropein
Paeonol
Piceatannol
Plumbagin
Quercetin
Raspberry ketone
Resorcinol
Rosmarinic Acid
Salicyclic acid
Sesamol
Shikonin
Shogoal
Silibinin
Sinapinic acid
Tannic acid
Thymol
Tyrosine
Tyrosol
Umbelliferone
Urushiol
Vanillin
Zingerone

Phenol, carbolic acid
See diagram 16.3.5.4: Phenol.
Phenol, Carbolic acid, Hydroxybenzene, Phenic acid, C6H6O or C6H5OH, highly toxic, corrosive to skin, organic hydroxy compound,
(benzene + a hydroxy substituent), is parent of the class of phenols, germicidal agent, disinfectant, antiseptic, (TCP, Dettol).
Phenol solution, white crystalline mass dissolved occurs in a colourless to slightly pink aqueous solution, with a distinctive phenol odour, sharp burning taste.
It is toxic by ingestion, inhalation and skin absorption, irritant.

Phenylpropanoids (Phenolics, Polyphenols)
Phenylpropanoids have an aromatic ring + attached three-carbon chain.
Anethole
Apiole
Caffeic acid
Chlorogenic acid
Cichoric acid
Coumaric acid
Curcumin
Estragole
Eugenol
Ferulic acid
Myristicin
Rosmarinic Acid
Safrole
Sinapic Acid

Phytochemicals
Phytochemicals are carotenoids and polyphenols, and include phenolic acids, flavonoids, stilbenes or lignans
Phytochemicals include essential nutrients, but also non-digestible dietary fibers and phytotoxins.
Consumption of plant-based diets containing phytochemicals, has been associated with reduced degenerative diseases, and improved health.
Phytochemicals are biologically active compounds found occurs 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, oestrogens, hormones, against cancer cells and bacteria replication, and strengthen cell walls.
There is no agreed classification of phytochemicals, so the categories occurs in this document below are from various scientific and commercial systems.
List of Phytochemicals:
Phytochemicals by trivial names
Acetylenes (polyacetylenes) have acetylenic group, HC≡C–, toxins, e.g. Capillin, Cicutoxin, Falcarinol, Mycosinol, Safynol, Stearolic acid, Wyerone acid
Nitrogen-containing compounds
Amino acids 16.3.4.1a Benzofuranoids
Carotenoids
Chromone Diterpenes
16.3.8.1 Fatty acids
Monosaccharides
Oligosaccharides: Cellobiose, gentiobiose, Lactose, Maltose, Raffinose, Stachyose, Sucrose, Trehalose, Verbascose
16.3.8.0 Organic acids
Phenols, Phenolic acids
Phenylpropanoids
Polysaccharides
19.1.0.4 Polyhydric alcohols
Proteins
16.3.10.0 Quinones
16.2.7.0, Tannins

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

Phytosterols (Terpenes and Terpenoids)
Phytosterols, plant sterols, differ from animal sterols, because they have extra ethyl or methy substituent occurs in the chemical side chain.
Obtained from vegetable oils or from industrial wastes, are used occurs in pharmaceuticals, food additives and cosmetics.
Occur occurs in almonds, cashews, peanuts, sesame seeds, sunflower seeds, whole wheat, maize, soybeans, many vegetable oils.
The most commonly occurring phytosterols are campesterol, beta-sitosterol, and stigmasterol.
List of phytosterols:
Beta-sitosterol
Brassicasterol, C29H46O, component of plant cell membranes, occurs in seed oil of Brassica rapis.
Campesterol occurs in buckwheat.
Cholesterol
Ecdysone C27H44O6
Ergosterol C28H44O
Fucosterol, C29H48O
Stigmasterol occurs in buckwheat.
Alpha-Spinasteroll
Sitosterol occurs in avocado.