Lesson 13: Phytochemicals

Terpenoids (isoprenoids)

• α-Carotene – to vitamin A carrots, pumpkins, maize, tangerine, orange.
• β-Carotene – to vitamin A dark, leafy greens, red, orange and yellow fruits and vegetables.
• γ-Carotene – to vitamin A,
• δ-Carotene
• ε-carotene
• Lycopene Vietnam Gac, tomatoes, grapefruit, watermelon, guava, apricots, carrots, autumn olive.
• Neurosporene
• Phytofluene star fruit, sweet potato, orange.
• Phytoene sweet potato, orange.

• Canthaxanthin – Paprika & mushrooms.
• Cryptoxanthin (Converts to vitamin A) – Mango, tangerine, orange, papaya, peaches, avocado, pea, grapefruit, kiwi.
• Zeaxanthin – Wolfberry, spinach, kale, turnip greens, maize, red pepper, pumpkin, orange.
• Astaxanthin – Microalgae, yeast.
• Lutein – Spinach, turnip greens, romaine lettuce, red pepper, pumpkin, mango, papaya, oranges, kiwi, peaches, squash, brassicas, prunes, sweet potatoes, honeydew melon, rhubarb, plum, avocado, pear, cilantro.
• Rubixanthin – Rose hip.

Triterpenoid

• Saponins soybeans, beans, other legumes, maize, alfalfa.
• Oleanolic acid American pokeweed, honey mesquite, garlic, java apple, cloves, and many other Syzygium species.
• Ursolic acid apples, basil, bilberries, cranberries, elder flower, peppermint, lavender, oregano, thyme, hawthorn, prunes.
• Betulinic acid Ber tree, white birch, winged beans, tropical carnivorous plants Triphyophyllum peltatum, Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), chaga, and many other Syzygium species.
• Moronic acid Rhus javanica (a sumac), mistletoe

Diterpenes

• Cafestol Coffea arabica in unfiltered form such as French press coffee or Turkish coffee/Greek coffee.^[

Monoterpenes

• Limonene oils of citrus, cherries, spearmint, dill, garlic, celery, maize, rosemary, ginger, basil.
• Perillyl alcohol citrus oils, hops, caraway, mints.

Steroids

• Phytosterols almonds, cashews, peanuts, sesame seeds, sunflower seeds, whole wheat, maize, soybeans, many vegetable oils.
  • Campesterol buckwheat.
  • beta Sitosterol avocado, rice bran, wheat germ, corn oils, fennel, peanuts, soybeans, hawthorn, basil, buckwheat.
  • gamma sitosterol
  • Stigmasterol buckwheat.
• Tocopherols (vitamin E)

Phenolic Compounds

Natural monophenols

• Apiole parsley, celery leaf.
• Carnosol rosemary, sage.
• Carvacrol oregano, thyme, pepperwort, wild bergamot.
• Dillapiole dill, fennel root.
• Rosemarinol rosemary.

Polyphenols

• Flavonols
  • Quercetin red and yellow onions, tea, wine, apples, cranberries, buckwheat, beans, lovage.
  • Kaempferol tea, strawberries, gooseberries, cranberries, grapefruit, apples, peas, brassicates (broccoli, kale, brussels sprouts, cabbage), chives, spinach, endive, leek, tomatoes.
  • Myricetin grapes, red wine, berries, walnuts.
  • Fisetin strawberries, cucumbers.
  • Rutin citrus fruits, oranges, lemons, limes, grapefruit, berries, peaches, apples, pagoda tree fruits, asparagus, buckwheat, parsley, tomatoes, apricots, rhubarb, tea.
  • Isorhamnetin red turnip, goldenrod, mustard leaf, ginkgo biloba, onion.
• Flavanones
  • Hesperidin citrus fruits.
  • Naringenin citrus fruits.
  • Silybin milk thistle.
  • Eriodictyol citrus fruits.
• Flavones
  • Acacetin Robinia pseudoacacia, Turnera diffusa.
  • Apigenin chamomile, celery, parsley.
  • Chrysin Passiflora caerulea, Pleurotus ostreatus, Oroxylum indicum.
  • Diosmetin Vicia.
  • Tangeritin tangerine and other citrus peels.
  • Luteolin beets, artichokes, celery, carrots, celeriac, rutabaga, parsley, mint, chamomile, lemongrass, chrysanthemum.
• Flavan-3-ols (flavanols)
  • Catechins white tea, green tea, black tea, grapes, wine, apple juice, cocoa, lentils, black-eyed peas.
    • (+)-Catechin
    • (+)-Gallocatechin
    • (−)-Epicatechin
    • (−)-Epigallocatechin
    • (−)-Epigallocatechin gallate (EGCG) green tea.
    • (−)-Epicatechin 3-gallate
  • Theaflavin black tea.
    • Theaflavin-3-gallate black tea.
  • Thearubigins black tea.
  • Proanthocyanidins
• Flavanonols
• Anthocyanidins (flavonals) and Anthocyanins red wine, many red, purple or blue fruits and vegetables.
  • Pelargonidin bilberry, raspberry, strawberry.
  • Peonidin bilberry, blueberry, cherry, cranberry, peach.
  • Cyanidin red apple & pear, bilberry, blackberry, blueberry, cherry, cranberry, peach, plum, hawthorn, loganberry, cocoa.
  • Delphinidin bilberry, blueberry, eggplant.
  • Malvidin malve, bilberry, blueberry.
  • Petunidin

Isoflavonoids

• Isoflavones (phytoestrogens) use the 3-phenylchromen-4-one skeleton (with no hydroxyl group substitution on carbon at position 2).
  • Daidzein (formononetin) soy, alfalfa sprouts, red clover, chickpeas, peanuts, kudzu, other legumes.
  • Genistein (biochanin A) soy, alfalfa sprouts, red clover, chickpeas, peanuts, other legumes.
  • Glycitein soy.
• Isoflavanes
• Isoflavandiols
• Isoflavenes
• Pterocarpans or Coumestans (phytoestrogens)
• Coumestrol red clover, alfalfa sprouts, soy, peas, brussels sprouts.

Aurones

Chalconoids

Flavonolignans

• Silymarin artichokes, milk thistle.

Lignans

Phytoestrogens seeds (flax, sesame, pumpkin, sunflower, poppy), whole grains (rye, oats, barley), bran (wheat, oat, rye), fruits (particularly berries) and vegetables.^[

• Matairesinol flax seed, sesame seed, rye bran and meal, oat bran, poppy seed, strawberries, blackcurrants, broccoli.
• Secoisolariciresinol flax seeds, sunflower seeds, sesame seeds, pumpkin, strawberries, blueberries, cranberries, zucchini, blackcurrant, carrots.
• Pinoresinol and lariciresinol ^[4]  sesame seed, Brassica vegetables.

Stilbenoids

• Resveratrol grape (skins and seeds, grape wine), nuts, peanuts, Japanese Knotweed root.
• Pterostilbene grapes, blueberries.
• Piceatannol grapes.
• Pinosylvin

Curcuminoids

• Curcumin (Oxidizes to vanillin) turmeric, mustard.

Tannins

Hydrolyzable tannins

• Ellagitannins
  • Punicalagins  tea, berries.
  • Castalagins
  • Vescalagins  oak wood.^[5]
  • Castalins
  • Casuarictins
  • Grandinins
  • Punicalins
  • Roburin As
  • Tellimagrandin IIs
  • Terflavin Bs
• Gallotannins
  • Digalloyl glucose
  • 1,3,6-Trigalloyl glucose

Condensed tannins

• Proanthocyanidins horse chestnut Aesculus hippocastanum, cranberry juice, peanut skin, grape.
• Polyflavonoid tannins
• Catechol-type tannins
• Pyrocatecollic type tannins
• Flavolans

Phlorotannins

extracted from brown alga species (Ecklonia cava, Sargassum mcclurei), sea oak (Eisenia bicyclis, Fucus vesiculosus).

Flavono-ellagitannin

extracted from Mongolian Oak (Quercus mongolica).

Aromatic acid

Phenolic acids

• Salicylic acid peppermint, licorice, peanut, wheat.
• Vanillin and Vanillic acid açaí oil, vanilla beans, cloves.
• Gallic acid tea, mango, strawberries, rhubarb, soy.
• Ellagic acid walnuts, strawberries, cranberries, blackberries, guava, grapes.
• Tannic acid nettles, tea, berries.

Hydroxycinnamic acids

• Caffeic acid burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple, olive oil.
• Chlorogenic acid echinacea, strawberries, pineapple, coffee, sunflower, blueberries.
• Cinnamic acid cinnamon, aloe.
• Ferulic acid oats, rice, artichoke, orange, pineapple, apple, peanut, açaí oil.
• Coumarin citrus fruits, maize.

Phenylethanoids

• Tyrosol olive oil.
• Hydroxytyrosol olive oil.
• Oleocanthal olive oil.
• Oleuropein olive oil.

Others

• Capsaicin chilli peppers.
• Gingerol ginger.
• Alkylresorcinols wholegrain wheat, rye and barley.
• Piperine black pepper.

Glucosinolates

The precursor to isothiocyanates

• Sinigrin (the precursor to allyl isothiocyanate) broccoli family, brussels sprouts, black mustard.
• Glucotropaeolin (the precursor to benzyl isothiocyanate)
• Gluconasturtiin (the precursor to phenethyl isothiocyanate)
• Glucoraphanin (the precursor to sulforaphane) brassicas: broccoli, cauliflower, brussels sprouts, cabbages.

Aglycone derivatives

• Dithiolthiones (isothiocyanates)
  • Sulforaphane brassicas: broccoli, cauliflower, brussels sprouts, cabbages.
  • Allyl isothiocyanate
  • Phenethyl Isothiocyanate
  • Benzyl Isothiocyanate
• Oxazolidine-2-thiones
• Nitriles
• Thiocyanates

Organosulfides/ Organosulfur compounds

• Polysulfides (allium compounds)
  • Allyl methyl trisulfide garlic, onions, leeks, chives, shallots.
• Sulfides
  • Diallyl disulfide garlic, onions, leeks, chives, shallots.
• Allicin garlic.
• Alliin garlic.
• Allyl isothiocyanate horseradish, mustard, wasabi.
• Syn-propanethial-S-oxide cut onions.

Indoles

• Indole-3-carbinol cabbage, kale, brussels sprouts, rutabaga, mustard greens, broccoli.
• 3,3′-Diindolylmethane or DIM broccoli family, brussels sprouts, cabbage, kale.

Betalains

• Betacyanins beets, chard, Amaranthus tricolor.
  • betanin
  • isobetanin
  • probetanin
  • neobetanin
• Betaxanthins (non glycosidic versions)
  • Indicaxanthin beets, sicilian prickly pear.
  • Vulgaxanthin beets.

Chlorophylls

• Chlorophyllin: Dark green leafy vegetables like spinach, wheatgrass

Other organic acids

• Saturated cyclic acids
  • Phytic acid (inositol hexaphosphate) cereals, nuts, sesame seeds, soybeans, wheat, pumpkin, beans, almonds.
  • Quinic acid
• Oxalic acid orange, spinach, rhubarb, tea and coffee, banana, ginger, almond, sweet potato, bell pepper.
• Tartaric acid apricots, apples, sunflower, avocado, grapes, tamarind.
• Anacardic acid cashews, mangoes.
• Malic acid apples.
• Caftaric acid grapes.
• Coutaric acid grapes.
• Fertaric acid

Amines

• Betaine – beetroot.

Carbohydrates

Monosaccharides

• Hexose wheat, barley.
• Pentose rye, oat.

Polysaccharides

• Beta-glucan
  • Chitin – fungi includes other edible mushrooms.
  • Lentinan – fruit body of shiitake (Lentinula edodes mycelium (LEM)) and other edible mushrooms.

• Fructan
  • Inulins – diverse plants, e.g. topinambour, chicory.

• Lignin – stones of fruits, vegetables (filaments of the garden bean), cereals.

• Pectins – the fruit skin (mainly apples, quinces), vegetables.

Protease inhibitors

• Protease inhibitors soybean, seeds, legumes, potatoes, eggs, cereals.