The following gives an overview of the chemistry of medicinal herbs along with examples of main herbs containing them.1. Alkaloids
Alkaloids are organic nitrogenous compounds which tend to have pronounced physiological activity.
Alkaloids in common medicinal herbs
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Less Commonly used Alkaloids
Narcotic & Stimulant Alkaloids
Pyrrolizidine Alkaloids: This is an important class medicinally as they have been reported to cause Liver damage and are banned for internal use in some countries:
Steroidal Alkaloids These alkaloids are closely related to sterols, and are found in 2 major groups: Solanum and Veratrum Alkaloids. The Solanum alkaloids have anti-inflammatory, anti-bacterial and anti-cancer effects, amongst others. The Veratrum alkaloids are very toxic, affecting cardiovascular, respiratory and neuromuscular systems. They have been used for myasthenia gravis, hypotension, eclampsia etc.
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2. Terpenoids
Large class of organic hydrocarbon compounds including Terpenes, diterpenes, triterpenes and sesquiterpenes; They are formed from linked isoprenes and tend to be aromatic.
Triterpenoids
Carotenoids (Tetraterpenoids) Carotenes (Orange pigments)
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Xanthophylls (Yellow pigments)
Monoterpenes
Steroids
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3. Phenols (Phenolic compounds)
Phenols are organic compounds with a hydroxyl group combined with carbon. They include phenols (eg. gallic acid), biphenols (eg. resveratrol), and polyphenols (eg tannic acid). Polyphenols are the most common anti-oxidants.
Natural Monophenols
- Apiole –
- Celery
- Parsley.
- Carnosol –
- Rosemary (Rosmarinus officinalis)
- Mountain desert sage (Salvia pachyphylla).
- Carvacrol –
- Oregano (Origanum vulgare)
- Thyme (Thymus vulgaris)
- bee balm (Monarda fistulosa
- Dittany of Crete (Origanum dictamnus)
- Marjoram (Origanum majorana),
- Dillapiole – Fennel (Foeniculum Vulgare), Dill (Anethum graveolens), etc.
- Rosemarinol – Rosemary and various plants of the mint family
Polyphenols
Flavonoids (Red, blue, purple pigments)
- Flavonols
- Quercetin – Various fruits, vegetables, leaves and grains; widley found in Asteraceae, Passifloraceae, Rhamnaceae, and Solanaceae families.
- Evening Primrose (Oenothera biennis)–up to 200,000 ppm
- Onion–up to 48,000 ppm
- Tea–up to 10,000 ppm
- Neem–up to 1000 ppm
- also Cabbage, Kale, Brussel Sprouts, Spinach
- Pear, Apple, Cranberry
- Kaempferol – Very common, found in numerous plants.
- Marshmallow, Dill, Calendula, Horsetail, Camomile, Basil, Thyme, Violet
- Myricetin – Vegetables, fruits, nuts, berries, etc.
- Fisetin – various fruits: Strawberries, Mango, Cucumber, Apple, Persimmons, Peach, Grape
- Rutin – Anti-inflammatory, Free Radical Scavenger
- Rue, Yarrow, Calendula, Shepherd’s Purse, Meadowsweet, St. John’s wort, Motherwort, Camomile, Peppermint, Violet
- Garlic, Onion
- Buckwheat
- Orange, Grapefruit, Lemon, Cranberries
- Rhubarb, Wormwood, Neem
- Isorhamnetin – Ginkgo biloba, Goldenrod, Mustard leaf.
- Quercetin – Various fruits, vegetables, leaves and grains; widley found in Asteraceae, Passifloraceae, Rhamnaceae, and Solanaceae families.
- Flavanones
- Hesperidin – Citrus fruits (Citron, Tangerine, Orange, Lemon etc.), Schizonepeta Jing Jie
- Naringenin – Antibacterial, anti-fungal, antihepatotoxic, antioxidant, antispasmodic, and antiulcerogenic properties
- Citrus fruits and Tomatoes
- Silybin – Milk thistle (Silybum marianum)
- Eriodictyol – Yerba santa (Eriodictyon californicum), liana (Millettia duchesnei), eupatorium (Eupatorium arnottianum)
- Flavones
- Acacetin – Damiana (Turnera diffusa), silver birch (Betula pendula).
- Apigenin – Phytochemicals found in many plants. Has anti-inflammatory, an- tibacterial, diuretic, and hypotensive properties.
- Parsley (Petroselinum crispum)
- Celery (Apium graveolens), Celeriac (Apium graveolens var. rapaceum)
- Camomile (Matricaria recutita, Chamaemelum nobile).
- Chrysin – Purple passionflower (Passiflora incarnata), blue passionflower (Passiflora caerulea), chamomile (Matricaria recutita, Anthemis nobilis), midnight horror (Oroxylum indicum).
- Diosmetin – Found in citrus fruits and juices, such as oranges, lemons, grapes and grapefruit. Also found in herbs like spearmint, oregano, sage, tansy and thyme.
- Tangeritin Found in tangerine and various citrus peels.
- Luteolin – Celery, broccoli, basil, green pepper, parsley, artichoke, thyme, dandelion, perilla, chamomile tea, carrots, peppermint, olive oil, rosemary, rooibos, navel oranges, and oregano.
- Flavanols
- Catechins – Green tea (Camellia sinensis), cocoa tree (Theobroma cacao), blackberries, red raspberries, cranberries, cherries, barley, rhubarb
- Theaflavin – Black tea.
- Thearubigins – Black tea extracts.
- Anthocyanins (flavonals)
- Pelargonidin – Plant pigment found in many flowers and fruit. (orange color)
- Peonidin – Primary plant pigment (purple-red color).
- Cyanidin – Plant pigment (reddish-purple color). Found in Grapes, bilberry, red cabbage, blackberry, blueberry, cranberry, elderberry, hawthorn, loganberry, açai berry, raspberry, apples, red onion. etc.
- Delphinidin – Primary plant pigment (blue color).
- Malvidin – Primary plant pigment (blue color).
- Petunidin – Plant pigment (dark red or purple color).
- Isoflavones (phytoestrogens)
- Daidzein –
- Soy (Glycine max)
- Kudzu (Pueraria lobata) (Ge Gen)
- Dyer’s broom (Genista tinctoria)
- Genista tinctoria (dyers broom)
- Psoralea corylifolia (Bu Gu Zhi)
- Red Clover (Trifolium pratense)
- Genistein –
- Dyer’s broom (Genista tinctoria)
- Kudzu (Pueraria lobata) (Ge Gen)
- Wild Indigo (Baptisia tinctoria)
- Scotch broom (Cytisus scoparius)
- Soy (Glycine max)
- Licorice (Glycyrrhiza glabra)
- White Lupine (Lupinus albus)
- Alfalfa (Medicago sativa)
- Butter Bean (Phaseolus lunatus)
- Kidney Bean (Phaseolus vulgaris)
- Pea (Pisum sativum)
- Sour Cherry (Prunus cerasus)
- Chickweed (Stellaria media)
- Red Clover (Trifolium pratense)
- Adzuki bean (Vigna angularis)
- Glycitein – Soybeans.
- Other herbs containing isoflavones: Belamcanda She Gan, Licorice, Astragalus Huang Qi
- Daidzein –
- Isoflavandiols
- Isoflavenes
- Pterocarpans / Coumestans (phytoestrogens) – Phytochemicals found in plants in the Fabaceae family. Anti-fungal
- Coumestrol – Clover, alfalfa, sunflower seeds, lima and pinto beans.
- Rotenoids – Mullein, Jamaica Dogwood (Piscidia erythrina).
- Silymarin – Milk thistle (Silybum marianum)
- Aloe – aloe ernodin, aloin, isobarbaloin, chrysophanol, chrysophanol glucoside, anthranol, aloenin, aloesaponol
- Cassia seed – emodin, aloe-emodin, rhein, chrysophanol, physcion, obtusin
- Dodder
- Hedyotis Bai Hua She She Cao –
- Madder – alizarin, purpurin, pseudopurpurin, rubiadin, rnunjistin
- Morinda Ba Ji Tian
- Polygonum rnultiflorum He Shou Wu – chrysophanol, chrysophanol anthrone, rhein, emodin, emodin monomethylether, physcion
- Rhubarb – emodin, aloe emodin, chrysophanol, physcion, rhein; palmidin A, B, C, rheidin A, B, C, sennidin A, C
- Senna
- Soloman’s Seal
- Highest amounts are found in flax seed and sesame seed (sesamin, sesamolin, sesamol)
- also in bran of wheat, oats, rice, barley
- Albizzia He Huan Pi
- Amenarrhena Zhi Mu
- Acanthopanax Wu Jia Pi, Siberian Ginseng (Acanthopanax Ci Wu Jia) – syringaresinol, sesarnin
- Eucommia Du Zhong –numerous lignans and lignan glycosides
- Forsythia Lian Qiao – phillyrin (forsythin), phillygenin
- Long Pepper (and other Piper spp.) – sesamin, asarinin, pluviatilol, fargesin
- Magnolia flower (Xin Yi), Magnolia bark (Hou Po) – magnolol, honokiol, isomagnolol, tetrahydromagnolol, bornylmagnolol, magnaldehyde, magnolignan
- Schisandra Wu Wei Zi
- Matairesinol – Seeds, whole grains, vegetables, and fruits.
- Secoisolariciresinol
- Pinoresinol – Found in plants in the Genus Styrax. Also present in sesame seed and in olive oil.
- Lariciresinol – Phytochemicals commonly found in plants in the Genus Brassica, ect.
- Resveratrol – White hellebore (Veratrum album), grape seed (Vitis vinifera), Japanese knotweed (Fallopia japonica), etc.
- Pterostilbene – Almonds, various berries of plants in the Genus Vaccinium, grape leaves, blueberries
- Piceatannol – Grapes, passion fruit, white tea, Japanese knotweed (Fallopia japonica).
- Pinosylvin – Present in the heartwood of plants in the Genus Pinaceae.
- Curcumin – Turmeric (Curcuma longa).
- Vanillin – Vanilla (Vanilla planifolia).
- Punicalagins – Pomegranates (Punica granatum), Bengal almond (Terminalia catappa), East Indian almond (Terminalia myriocarpa), velvet bushwillow (Combretum molle).
- Castalagins – Oak (Quercus spp.), chestnut (Castanea spp.), African birch (Anogeissus leiocarpa).
- Vescalagins – Oak.
- Castalins – Broad-leaved paperbark (leaves) (Melaleuca quinquenervia), Oak (Quercus spp.).
- Casuarictins – Found in plants in the Genus Casuarina and Stachyurus.
- Grandinins – North American white oak (Quercus alba), European red oak (Quercus robur), broad-leaved paperbark (leaves) (Melaleuca quinquenervia).
- Punicalins – Pomegranate (Punica granatum), dooki (Combretum glutinosum), Bengal almond (Terminalia catappa).
- Roburin – Oak wood, oak cork.
- Terflavin – Yellow or chebulic myrobalan (Terminalia chebula).
- Proanthocyanidins – Maritime pine bark (Pinus pinaster, Pinus maritima), cinnamon (Cinnamomum verum), bilberry (Vaccinium myrtillus), green tea/black tea (Camellia sinensis), Irish oak (Quercus petraea), etc.
Aromatic acids
Phenolic Acids
- Salicylic acid –
- Willow bark (Salix spp.)
- Meadowsweet (Filipendula ulmaria).
- Licorice
- Knotgrass
- Cimifuga Sheng Ma
- Artemisia Yin Chen
- Vanillin – Flat-leaved vanilla (Vanilla planifolia), bicolored leptotes (Leptotes bicolor), Chinese red pine (Pinus tabuliformis).
- Vanillic acid – Dong Gui (Angelica sinensis)
- Gallic acid – Oak gall (Quercus Spp.).
- Ellagic acid – Present in many fruits and vegetables with the highest levels in blackberries, cranberries, grapes, pomegranates, raspberries, strawberries, walnuts, wolf-berries and peach.
- Tannic acid – Oak (bark, leaves) and oak gall (Quercus Spp.).
- Caffeic acid –
- Eucalyptus bark (Eucalyptus globulus),
- Rosemary (Rosmarinus officinalis)
- Caraway (Carum carvi)
- Thyme (Thymus vulgaris)
- Sage (Salvia Officinalis)
- Spearmint (Mentha spicata).
- Chlorogenic acid – Peach (Prunus persica), capillaris (Artemisia capillaris), heather (Calluna vulgaris), coffee beans, etc.
- Cinnamic acid – Cinnamon (Cinnamomum verum).
- Ferulic acid – Dong quai (Angelica sinensis), common centaury (Centaurium erythraea).
- Coumarin – Sweet, vanilla-like scent, with a bitter Taste. Anticoagulant effect by inhibiting Vitamin K production
Examples: coumarin, ostruthin, bergapten, umbelliferone, scopoletin- Angelica, Angelica Bi Zhi, Angelica Du Huo – angelol, imperatorin, bergaptene, xanthotoxine, umbelliferon, scopoletin
- Asafetida
- Astragalus Huang Qi
- Agrimony, Agrimonia Xian He Cao
- Aniseed, Caraway, Dill, Fennel
- Artemisia Qing Hao – scoparine, scoparone, scopoletin
- Artemisia Yin Chen – sopoletin, isoscopoletin, capillarin
- Ash tree, Korean Ash (Qin Pi) – aesculin
- Camomile
- Citrus peel (Tanergine [Chen Pi, Qing Pi], Citron, Orange, Lemon) – linonin, citropten
- Cleavers
- Dittany, Dictamnus Bai Xian Pi – psoralen, xanthotoxin, scopoletin
- Eclipta Han Lian Cao – wedelolactone, demethylwedelolactone
- Forsythia Lian Qiao
- Ganoderma Ling Zhi
- Glehnia Bei Sha Shen – psoralen, bergapten, xanthotoxin, imperatorin, cnidilin, xanthotoxol, marmesin, scopoletin
- Hawthorn, Shan Zha
- Licorice, Gan Cao
- Lovage
- Lycium Gou Qi Zi – scopoletin
- Clover, Meliot
- Mullein (Verbascum thapsus)
- Marshmallow
- Parlsley
- Psoralea Bu Gu Zi – psoralen, isopsoralen, isopsoralidin, bakuchicin, angelicin, xanthotoxin, psoralidin
- Puecedanum – scopolin, scopoletin, skimmin, apiosylskimmin, umbelliferone
- Pueraria Ge Gen
- Purslane
- Cassia, Cinnamon (Cinnamomum cassia)
- Rue
- Saposhnikovia Fang Feng – psoralen. bergapten, imperatorin, phellopterin, deltoin, xanthotoxin, anomalin, scopoletin
- Sea Holly
- Self Heal,, Xia Ku Cao – umbelliferone, scopoletin, esculetin
- St. John’s wort
- Wormwood
- Strawberry, Cherries, Apricots, Black Currants
- Coumarin types:
- Aglycones – Aesculetin, Ferujol, Umbelliferone
- O-methylated – Fraxetin, Herniarin, Scopoletin
- Glycosides – Aesculin, Fraxin, Skimmin, Scopolin, Umbelliferone 7-apiosylglucoside
- Furanocoumarins – mostly in Apiaceae and Rutaceae – Angelicin, Psoralen, Imperatorin, Xanthotoxol, Bergapten, Methoxsalen
- Angelica, Angelica Bai Zhi – imperatorin
- Figs
- Celery, Coriander seed
- Citrus peel
- Peucedanurn
- Psoralea Bu Gu Zi
- Dihydrofuranocoumarins – Anthogenol, Felamidin, Marmesin, Rutaretin
- Pyranocoumarins (inc. xanthyletin, Grandivittin, Agasyllin, Inophyllum) – Rue, Peucedanurn
- Phenylcoumarins – Isodispar, Mammea, Disparinol
- Methoxycoumarins – Rue
- Hydroxycoumarins –
- Fennel
- Yarrow
- Aglycones – Aesculetin, Ferujol, Umbelliferone
- Rosmarinic acid –
- Basil, Holy Basil
- Marjoram, Rosemary, Lemon Balm, Sage, Self Heal
Phenylethanoids
- Tyrosol – Olive oil, argan oil, green tea.
- Hydroxytyrosol – Olive leaf and olive oil.
- Oleocanthal – Extra-virgin olive oil.
- Oleuropein – Olive leaf.
Others Aromatic Acids
- Capsaicin – Chili pepper (Capsicum spp.).
- Gingerol – Ginger (Zingiber officinale).
- Alkylresorcinols – Phytochemicals found in wheat, rye, barley, ginkgo (Ginkgo biloba).
4. Glucosinolates
These are hot and pungent chemicals producing mustard oil when oxidised (chewed, cut or crushed)
Indoles
- Indole-3-carbinol – Found in high concentrations in vegetables such as broccoli, cabbage, cauliflower and brussels sprouts.
- 3,3′-Diindolylmethane or DIM – Broccoli, cabbage, kale, etc.
- Allicin – Garlic (Allium sativum).
- Alliin – Fresh garlic (Allium sativum).
- Allyl isothiocyanate – Mustard plant (Brassica nigra, Brassica juncea, Sinapis alba), horseradish (Armoracia rusticana), wasabi (Eutrema japonicum).
- Syn-propanethial-S-oxide – Onion (Allium cepa).
5. Betalains
These are red and yellow indole-derived pigments that replace anthocyanins; found in Caryophyllales and some Fungii.
Betacyanins – reddish to violet pigments
- Betanin – Beet (Beta vulgaris)
- Isobetanin – Vine spinach (Basella alba)
- Probetanin – Red and yellow pigments found in plants in the Order Caryophyllales.
- Neobetanin – Beet (Beta vulgaris), barbary fig (Opuntia ficus-indica).
- Indicaxanthin – Beet (Beta vulgaris), marvel of Peru (Mirabilis jalapa), red dragonfruit (Hylocereus costaricensis).
- Vulgaxanthin – Chard (Beta vulgaris subsp. vulgaris), beets (Beta vulgaris).
6. Chlorophylls
- Chlorophyllin – widely found in Green leafy vegetables
7. Organic acids
- Aconitic acid – Aconite, Yarrow, Horsetail
- Anacardic acid – Cashew nut (Anacardium occidentale).
- Caftaric acid – Grapes (Vitis vinifera), common chicory (Cichorium intybus), Echinacea
- Coutaric acid – Grapes (Vitis vinifera).
- Fertaric acid – Grapes (Vitis vinifera).
- Fumaric acid – Fumitory, Shepherd’s Purse, Horsetail, Fennel,
- Malic acid – Fruits and vegetables, often associated with apples.
- Oxalic acid – Common sorrel (Rumex acetosa), etc.
- Phytic acid – Seeds and grains.
- Quinic acid – Cinchona (Cinchona officinalis), Coffee beans (Coffea spp.).
- Succinic acid – Amber; Wormwood, Horsetail, Ground Ivy, Lemon Balm, Plantain, Rose Hip
- Tartaric acid – Grape (Vitis spp.), etc.
8. Amines
- Betaine – Sugar beet (Beta vulgaris subsp. vulgaris).
9. Polysaccharides
Polysaccharides are complex carbohydrates composed of a number of monosaccharides bound together. Upon hydroloysis they break down to their monosaccharides.. The most important class are the beta-glucans. They tend to be Immunomodulatory and some are anti-tumor and anti-cancer.
They are sweet and are found in many tonic medicines, especially Yin and Qi tonics.
- Beta-glucan
- Chitin – Fungi. Found in the fungal cell wall; exoskeletons of arthropods; not found in plants.
- Lentinan – Shiitake Mushroom (Lentinula edodes).
- Chitin – Fungi. Found in the fungal cell wall; exoskeletons of arthropods; not found in plants.
- Fructan
- Inulins – Phytochemicals found in common chicory (Cichorium intybus), etc.
- Lignin – Occurs in vascular plants and some algae.
- Pectins – Mostly found in ripe fruits and non-woody parts of terrestrial plants.
Polysaccharide Research:
–The Anti-Oxidant and Antitumor Properties of Plant Polysaccharides.
Major Polysaccharide-containing Herbs:
In the following list, some are names of the polysaccharides, some of the individual sugar released on hydrolysis
- Aconite spp. (Aconitum napellus, Aconitum Fu Zi, Aconitum Chuan Wu, Aconitum Wu Tou etc)
- Adenophora Nan Sha Shen
- Agrimony
- Aloe
- Anemarrhea Zhi Mu – anernaran
- Asparagus root (all, Indian [Shatavari], Chinese [Tian Men Dong], Western)
- Astragalus Huang Qi – astragalin I, II, III, AH-1, AH-2
- Burdock root & seed – Inulin, fructan, rharnnogalacturonan, xylan, galactan, arabinogalactan
- Calendula
- Camomile (both types)
- Cistanche Rou Cong Rong
- Codonopsis Dang Shen – inulin, fructose, Cp-1 – Cp-4.
- Dioscorea Shan Yao
- Elecampane – Inulin (to 40%)
- Gentian – pectin, inulin
- Ginseng (both Chinese Ren Shen, & American Xi Yang Shen) – fructose, glucose, arabinose, rhamnose, mannose, xylose; sucrose, maltose; raffinose, ginsengtrisaccharides
- Glehnia Bei Sha Shen – glehnia-polysaccharide
- Job’s Tear (Coix Yi Yi Ren)
- Jujube (Da Zao)
- Kelp, Laminaria – alginic acid, alginates, fucansulfates
- Knotgrass (Polygonum Bian Xu)
- Linseed – rhamnose, arabinose, galactose
- Lobelia (incl. Ban Bian Lian) – inulin, lobelinin
- Luffa Si Gua Lou – xylan, mannan, galactan
- Mallow seed (Dong Kui Guo)
- Marshmallow – basorine, galacturonic rhamnans, arabinogalactans, arabans, glucans
- Mistletoe (Viscum) – viscin, inc. galacturonans, arabino galactans
- Nettle – glucans, glucogalacturonans, arabino galactans
- Pepper (White, Black, Long)
- Platycodon Jie Geng – piatycodinin
- Polyporus Zhu Ling
- Poria Fu Ling – pachyrnan, pachyrnaran, pachyrnose, glucan
- Saposhnikovia Fang Feng – saposhnikovan
- Sargassum Hai Zao –
- Self Heal – glucose, galactose, mannose, rhamnose, xylose, arabinose, galacturonic acid
- Senna leaf
- Soloman’s Seal (incl. Yu Zhu & Huang Jing)– odoratan, polygonaturn fructanfructose, mannose, glucose, galacturonic acid
- Tabasheer (Tian Zhu Huang) –
- Tetrapanax Tong Cao – a-galacturonic acid, galactose, glucose, xylos
- Turmeric (Jiang Huang) –
- Thyme – galacturonic acid, glucuronic acid, arabinose, rhamnose, galactose, glucose, xylose, mannose, fructose
- Trichosanthes root – trichosan
- Violet (Western & Chinese)
- Turtle shell
Mucopolysaccharides
Also called glycosaminoglycans, are long-chained polysaccharides found throughout the body, especially in mucus membranes:
- Borage
- Comfrey
- Coltsfoot – galactose, fructose, arabinose, xylose, mucin, inulin
- Violet
- Snail
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