Def. a "nutrient or food believed to have curative properties"[1] or a "food used as a drug"[1] is called a nutraceutical.

Various foods are displayed. Credit: Unknown author.

Def. "a source of nourishment, such as food, that can be metabolized by an organism to give energy and build tissue"[2] is called a nutrient.

Def. "any [solid][3] substance [that][4] can be consumed by living organisms, especially [by eating][4], [in order to sustain life][5]"[6] or "anything that nourishes or sustains"[7] is called a food.



Alpha-lipoic acidsEdit

"Alpha-Lipoic Acid is a naturally occurring micronutrient, synthesized in small amounts by plants and animals (including humans), with antioxidant and potential chemopreventive activities. Alpha-lipoic acid acts as a free radical scavenger and assists in repairing oxidative damage and regenerates endogenous antioxidants, including vitamins C and E and glutathione. This agent also promotes glutathione synthesis. In addition, alpha-lipoic acid exerts metal chelating capacities and functions as a cofactor in various mitochondrial enzyme complexes involved in the decarboxylation of alpha-keto acids."[8]


Artichoke contains the bioactive agents apigenin and luteolin.[9]

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides.

Apigenin is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources.[10] Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of total flavonoids.[11] Dried parsley can contain about 45 mg/gram and dried chamomile flower about 3-5 mg/gram apigenin.[12] The apigenin content of fresh parsley is reportedly 215.5 mg/100 grams, which is much higher than the next highest food source, green celery hearts providing 19.1 mg/100 grams.[13]

Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.[14] Luteolin can function as either an antioxidant or a pro-oxidant and plants rich in luteolin have been used in Chinese traditional medicine[15]

Luteolin is most often found in leaves, but it is also seen in rinds, barks, clover blossom, and ragweed pollen.[14] It has also been isolated from the aromatic flowering plant, Salvia tomentosa in the mint family, Lamiaceae.[16]

Dietary sources include celery, broccoli, artichoke, Bell pepper (green pepper), parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano.[17][18] It can also be found in the seeds of the palm Aiphanes aculeata.[19]

The total antioxidant capacity of artichoke flower heads is one of the highest reported for vegetables.[20] Cynarine is a chemical constituent in Cynara. The majority of the cynarine found in artichoke is located in the pulp of the leaves, though dried leaves and stems of artichoke also contain it.

Cynarine is a hydroxycinnamic acid derivative and a biologically active chemical constituent of artichoke (Cynara cardunculus).[21]

Fatty acidsEdit

Three-dimensional representations of several fatty acids are shown. Saturated fatty acids have perfectly straight chain structure. Unsaturated ones are typically bent, unless they have a trans configuration. Credit: phma.

Def. any "of a class of aliphatic carboxylic acids, of general formula CnH2n+1COOH, that occur combined with glycerol as animal or vegetable oils and fats"[22] is called a fatty acid.

"Only those with an even number of carbon atoms are normally found in natural fats"[23]

Usage notes: "The above general formula applies to the saturated fatty acids. Remove 2 hydrogen atoms for an unsaturated fatty acid, and 2 hydrogen atoms for every double bond in a polyunsaturated faty acid."[24]

In biochemistry, a fatty acid is a carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28.[25] Fatty acids are a major component of the lipids (up to 70 wt%) in some species such as microalgae[26] but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters.

Types of fatty acidsEdit

Comparison of the trans isomer Elaidic acid (top) and the cis isomer oleic acid (bottom). Credit: .{{free media}}

Fatty acids are classified in many ways: by length, by saturation vs unsaturation, by even vs odd carbon content, and by linear vs branched.

Length of fatty acidsEdit

  • Short-chain fatty acids (SCFA) are fatty acids with aliphatic tails of five or fewer carbons (e.g. butyric acid).[27]
  • Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12[28] carbons, which can form medium-chain triglycerides.
  • Long-chain fatty acids (LCFA) are fatty acids with aliphatic tails of 13 to 21 carbons.[29]
  • Very long chain fatty acids (VLCFA) are fatty acids with aliphatic tails of 22 or more carbons.

Saturated fatty acidsEdit

Saturated fatty acids have no C=C double bonds. They have the same formula CH3(CH2)nCOOH, with variations in "n". An important saturated fatty acid is stearic acid (n = 16), which when neutralized with lye is the most common form of soap.

Arachidic acid, a saturated fatty acid. Credit: .{{free media}}
Examples of saturated fatty acids
Common name Chemical structure C:D[30]
Caprylic acid CH3(CH2)6COOH 8:0
Capric acid CH3(CH2)8COOH 10:0
Lauric acid CH3(CH2)10COOH 12:0
Myristic acid CH3(CH2)12COOH 14:0
Palmitic acid CH3(CH2)14COOH 16:0
Stearic acid CH3(CH2)16COOH 18:0
Arachidic acid CH3(CH2)18COOH 20:0
Behenic acid CH3(CH2)20COOH 22:0
Lignoceric acid CH3(CH2)22COOH 24:0
Cerotic acid CH3(CH2)24COOH 26:0

Unsaturated fatty acidsEdit

Unsaturated fatty acids have one or more C=C double bonds. The C=C double bonds can give either cis or trans isomers.

A cis configuration means that the two hydrogen atoms adjacent to the double bond stick out on the same side of the chain. The rigidity of the double bond freezes its conformation and, in the case of the cis isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more double bonds the chain has in the cis configuration, the less flexibility it has. When a chain has many cis bonds, it becomes quite curved in its most accessible conformations. For example, oleic acid, with one double bond, has a "kink" in it, whereas linoleic acid, with two double bonds, has a more pronounced bend. α-Linolenic acid, with three double bonds, favors a hooked shape. The effect of this is that, in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer or triglycerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore can affect the melting temperature of the membrane or of the fat. Cis unsaturated fatty acids, however, increase cellular membrane fluidity, whereas trans unsaturated fatty acids do not.
A trans configuration, by contrast, means that the adjacent two hydrogen atoms lie on opposite sides of the chain. As a result, they do not cause the chain to bend much, and their shape is similar to straight saturated fatty acids.

In most naturally occurring unsaturated fatty acids, each double bond has three (omega-3 fatty acid (n-3), six (omega-6 fatty acid (n-6), or nine (omega-9 fatty acid n-9) carbon atoms after it, and all double bonds have a cis configuration. Most fatty acids in the trans configuration (trans fats) are not found in nature and are the result of human processing (e.g., hydrogenation). Some trans fatty acids also occur naturally in the milk and meat of ruminants (such as cattle and sheep). They are produced, by fermentation, in the rumen of these animals. They are also found in dairy products from milk of ruminants, and may be also found in breast milk of women who obtained them from their diet.

The geometric differences between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes).

Examples of Unsaturated Fatty Acids
Common name Chemical structure Δx[31] C:D[30] IUPAC[32] nx[33]
Myristoleic acid CH3(CH2)3CH=CH(CH2)7COOH cis9 14:1 14:1(9) n−5
Palmitoleic acid CH3(CH2)5CH=CH(CH2)7COOH cis9 16:1 16:1(9) n−7
Sapienic acid CH3(CH2)8CH=CH(CH2)4COOH cis6 16:1 16:1(6) n−10
Oleic acid CH3(CH2)7CH=CH(CH2)7COOH cis9 18:1 18:1(9) omega-9 fatty acid (n−9)
Elaidic acid CH3(CH2)7CH=CH(CH2)7COOH trans9 18:1 18:1(9t) omega-9 fatty acid (n−9)
Vaccenic acid CH3(CH2)5CH=CH(CH2)9COOH trans11 18:1 18:1(11t) n−7
Linoleic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH cis,cis912 18:2 18:2(9,12) omega-6 fatty acid (n−6)
Linoelaidic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH trans,trans912 18:2 18:2(9t,12t) omega-6 fatty acid (n−6)
α-Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH cis,cis,cis91215 18:3 18:3(9,12,15) omega-3 fatty acid (n−30)
Arachidonic acid CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOHNIST cis,cis,cis,cis5Δ81114 20:4 20:4(5,8,11,14) n−6
Eicosapentaenoic acid CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH cis,cis,cis,cis,cis58111417 20:5 20:5(5,8,11,14,17) omega-3 fatty acid (n−3)
Erucic acid CH3(CH2)7CH=CH(CH2)11COOH cis13 22:1 22:1(13) omega-9 fatty acid (n−9)
Docosahexaenoic acid CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)2COOH cis,cis,cis,cis,cis,cis4710131619 22:6 22:6(4,7,10,13,16,19) omega-3 fatty acid (n−3)

Oleic acidEdit

Oleic acid is the most common fatty acid in nature.[34] The salts and esters of oleic acid are called oleates.

Oleic acid is found in fats (triglycerides), the phospholipids that make membranes, cholesterol esters, and wax esters.[35]

Oleic acid makes up 59–75% of pecan oil,[36] 61% of canola oil,[37] 36–67% of peanut oil,[38] 60% of macadamia oil, 20–80% of sunflower oil,[39] 15–20% of grape seed oil, sea buckthorn oil, 40% of sesame oil,[40] and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed.[39] It also comprises 22.18% of the fats from the fruit of the durian species, Durio graveolens.[41] Karuka contains 52.39% oleic acid.[42] It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat,[43] and 44 to 47% of lard.

Oleic acid is the most abundant fatty acid in human adipose tissue,[44] and second in abundance in human tissues overall, following palmitic acid.

Even- vs odd-chained fatty acidsEdit

Most fatty acids are even-chained, e.g. stearic (C18) and oleic (C18), meaning they are composed of an even number of carbon atoms. Some fatty acids have odd numbers of carbon atoms; they are referred to as odd-chained fatty acids (OCFA). The most common OCFA are the saturated C15 and C17 derivatives, pentadecanoic acid and heptadecanoic acid respectively, which are found in dairy products.[45][46] On a molecular level, OCFAs are biosynthesized and metabolized slightly differently from the even-chained relatives.

Carbon atom numberingEdit

Numbering of carbon atoms. The systematic (IUPAC) C-x numbers are in blue. The omega-minus "ω−x" labels are in red. The Greek letter labels are in green.[47] Note that unsaturated fatty acids with a cis configuration are actually "kinked" rather than straight as shown here. Credit: .{{free media}}

Most naturally occurring fatty acids have an unbranched chain of carbon atoms, with a carboxyl group (–COOH) at one end, and a methyl group (–CH3) at the other end.

The position of the carbon atoms in the backbone of a fatty acid are usually indicated by counting from 1 at the −COOH end. Carbon number x is often abbreviated C-x (or sometimes Cx), with x=1, 2, 3, etc. This is the numbering scheme recommended by the IUPAC.

Another convention uses letters of the Greek alphabet in sequence, starting with the first carbon after the carboxyl. Thus carbon α (alpha) is C-2, carbon β (beta) is C-3, and so forth.

Although fatty acids can be of diverse lengths, in this second convention the last carbon in the chain is always labelled as ω (omega), which is the last letter in the Greek alphabet. A third numbering convention counts the carbons from that end, using the labels "ω", "ω−1", "ω−2". Alternatively, the label "ω−x" is written "n−x", where the "n" is meant to represent the number of carbons in the chain.[47]

In either numbering scheme, the position of a double bond in a fatty acid chain is always specified by giving the label of the carbon closest to the carboxyl end.[47] Thus, in an 18 carbon fatty acid, a double bond between C-12 (or ω−6) and C-13 (or ω−5) is said to be "at" position C-12 or ω−6. The IUPAC naming of the acid, such as "octadec-12-enoic acid" (or the more pronounceable variant "12-octadecanoic acid") is always based on the "C" numbering.

The notation Δx,y,... is traditionally used to specify a fatty acid with double bonds at positions x,y,.... (The capital Greek letter "Δ" (delta) corresponds to Roman "D", for Double bond). Thus, for example, the 20-carbon arachidonic acid is Δ5,8,11,14, meaning that it has double bonds between carbons 5 and 6, 8 and 9, 11 and 12, and 14 and 15.

In the context of human diet and fat metabolism, unsaturated fatty acids are often classified by the position of the double bond closest to the ω carbon (only), even in the case of polyunsaturated fatty acid multiple double bonds such as the essential fatty acids. Thus linoleic acid (18 carbons, Δ9,12), γ-linolenic acid (18-carbon, Δ6,9,12), and arachidonic acid (20-carbon, Δ5,8,11,14) are all classified as "ω−6" fatty acids; meaning that their formula ends with –CH=CH–CH

Fatty acids with an odd number of carbon atoms are called odd-chain fatty acids, whereas the rest are even-chain fatty acids. The difference is relevant to gluconeogenesis.

Naming of fatty acidsEdit

The following table describes the most common systems of naming fatty acids.

Nomenclature Examples Explanation
Trivial Palmitoleic acid Trivial names (or common names) are non-systematic historical names, which are the most frequent naming system used in literature. Most common fatty acids have trivial names in addition to their systematic names (see below). These names frequently do not follow any pattern, but they are concise and often unambiguous.
Systematic Oleic acid cis-9-octadec-9-enoic acid
Oleic acid (9Z)-octadec-9-enoic acid
Systematic names (or International Union of Pure and Applied Chemistry (IUPAC) names) derive from the standard IUPAC Rules for the Nomenclature of Organic Chemistry, published in 1979,[48] along with a recommendation published specifically for lipids in 1977.[49] Carbon atom numbering begins from the carboxylic end of the molecule backbone. Double bonds are labelled with cis-/trans- notation or E-Z notation (E)-/E-Z notation (Z)- notation, where appropriate. This notation is generally more verbose than common nomenclature, but has the advantage of being more technically clear and descriptive.
Δx Linoleic acid cis9, cis12 octadecadienoic acid In Δx (or delta-x) nomenclature, each double bond is indicated by Δx, where the double bond begins at the xth carbon–carbon bond, counting from carboxylic end of the molecule backbone. Each double bond is preceded by a cis- or trans- prefix, indicating the configuration of the molecule around the bond. For example, linoleic acid is designated "cis9, cis12 octadecadienoic acid". This nomenclature has the advantage of being less verbose than systematic nomenclature, but is no more technically clear or descriptive.
(or ω−x)
Omega-3 fatty acid (n−3)
(or Omega-3 fatty acid (ω−3)
nx (n minus x; also ω−x or omega-x) nomenclature both provides names for individual compounds and classifies them by their likely biosynthetic properties in animals. A double bond is located on the xth carbon–carbon bond, counting from the Methyl group (methyl) end of the molecule backbone. For example, α-Linolenic acid is classified as a omega-3 fatty acid (n−3) or (omega-3) fatty acid, and so it is likely to share a biosynthetic pathway with other compounds of this type. The ω−x, omega-x, or "omega" notation is common in popular nutritional literature, but IUPAC nomenclature (IUPAC) has deprecated it in favor of nx notation in technical documents.[48] The most commonly researched fatty acid biosynthetic pathways are omega-3 fatty acid (n−3) and omega-6 fatty acid (n−6).
Lipid numbers 18:3
Alpha-linolenic acid (18:3n3)
Alpha-linolenic acid (18:3, cis,cis,cis91215)
Alpha-linolenic acid (18:3(9,12,15)
Lipid numbers take the form C:D,[30] where C is the number of carbon atoms in the fatty acid and D is the number of double bonds in the fatty acid. If D is more than one, the double bonds are assumed to be interrupted by methylene bridge CH
units, i.e., at intervals of 3 carbon atoms along the chain. For instance, α-Linolenic acid is an 18:3 fatty acid and its three double bonds are located at positions Δ9, Δ12, and Δ15. This notation can be ambiguous, as some different fatty acids can have the same C:D numbers. Consequently, when ambiguity exists this notation is usually paired with either a Δx or nx term.[48] For instance, although α-Linolenic acid and γ-Linolenic acid are both 18:3, they may be unambiguously described as 18:3n3 and 18:3n6 fatty acids, respectively. For the same purpose, IUPAC recommends using a list of double bond positions in parentheses, appended to the C:D notation.[32] For instance, IUPAC recommended notations for α-and γ-Linolenic acid are 18:3(9,12,15) and 18:3(6,9,12), respectively.

Free fatty acidsEdit

When circulating]] in the plasma (plasma fatty acids), not in their ester, fatty acids are known as non-esterified fatty acids (NEFAs) or free fatty acids (FFAs). FFAs are always bound to a transport protein, such as albumin.[50]

Coconut oilsEdit

The approximate concentration of fatty acids in coconut oil (midpoint of range in source):

Approximate concentration of fatty acids in coconut oil
Type of fatty acid Saturation Percentage
caprylic acid saturated C8 7
capric acid saturated C10 8
lauric acid saturated C12 48
myristic acid saturated C14 16
palmitic acid saturated C16 9.5
oleic acid monounsaturated C18:1 6.5
Other polyunsaturated 5


Def. "any of many compounds that are plant metabolites, being formally derived from flavone; they have antioxidant properties,[51] and sometimes contribute to flavor[52]" is called a flavonoid.


Rhodiolin, a flavonolignan, is the product of the oxidative coupling of coniferyl alcohol with the 7,8-dihydroxy grouping of herbacetin. It can be found in the rhizome of Rhodiola rosea.[53]

Bioactivity of dietary polyphenolsEdit

Dietary source[54] Proanthocyanidin


Grape seeds 3532
Blueberries 332
Apples 70-141
Pears 32-42
Hazelnuts 501
Cinnamon bark 8108
Sorghum grains 3965
Baking chocolate 1636
Red wine 313

Grape seeds are rich in unsaturated fatty acids, which helps lowering levels of total cholesterol and LDL cholesterol in the blood.[55]


Glycosides Aglycone Glycone Plants Genus species
Alcohol glycosides Alcohol Glycone Common name Genus species
Rosavin cinnamyl alcohol arabinose Rhodiola Rhodiola rosea
Salicin salicyl alcohol glucose Willow Salix
Salidrosides tyrosol glucose Rhodiola Rhodiola rosea
Anthraquinone glycosides Anthraquinone derivative Glycone Common name Genus species
Sennosides reduced anthraquinone glucose Legume Senna
Chromone glycosides Benzo-gamma-pyrone Glycone Common name Genus species
3,5,7-trihydroxylchromone-3-O-alpha-L-arabinopyranoside chromone arabinose Rhododendron Rhododendron spinuliferum
Eucryphin chromone rhamnoside Eucryphia Eucryphia cordifolia
Coumarin glycosides coumarin Glycone Common name Genus species
Aesculin coumarin glucose Horse chestnut Aesculus hippocastanum
Cyanogenic glycosides Cyanogin Glycone Common name Genus species
Amygdalin cyanohydrin glucose Apricot kernels Prunus armeniaca
Flavonoid glycosides Flavonoid Glycone Common name Genus species
Hesperidin Hesperetin Rutinose Bitter Orange Citrus aurantium
Naringin Naringenin Neohesperidose Grapefruit Citrus × paradisi
Rutin Quercetin Rutinose Common rue Ruta graveolens
Quercitrin Quercetin Rhamnose American white oak Quercus alba
Iridoid glycosides iridoid Glycone Common name Genus species
Aucubin cyclopentan-[C]-pyran glucose spotted laurel Aucuba japonica
Phenolic glycosides Phenol Glycone Common name Genus species
Arbutin Phenol glucose Common Bearberry Arctostaphylos ova-ursi
Steroidal glycosides Steroid Glycone Common name Genus species
Digitonin saraponin glucose foxglove Digitalis purpurea
Steviol glycosides Steviol Glycone Common name Genus species
Steviosides Steviol isosteviol candyleaf Stevia rebaudiana
Iridoid glycosides
Thioglycosides Thiod Glycone Common name Genus species
Sinigrin sulfur glucose Black mustard Brassica nigra
Triterpene glycosides Triterpene Glycone Common name Genus species
Saponins Triterpene glucose soapbark tree Quillaja saponaria


Chemical compounds that have been isolated from the extract include corosolic acid, lager-stroemin, flosin B, and reginin A.[56]

Corosolic acid is a pentacyclic triterpene acid found in Lagerstroemia speciosa, similar in structure to ursolic acid, differing only in the fact that it has a 2-alpha-hydroxy attachment.[57]

In Vietnam the plant's young leaves are consumed as vegetables, and its old leaves and mature fruit are used in traditional medicine for reducing glucose in blood.[58]

Banaba plant, Lagerstroemia speciosa (giant crepe-myrtle, Queen's crepe-myrtle, banabá plant, or pride of India[59]) is a species of Lagerstroemia native to tropical southern Asia.


The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables.[60] The name derives from the Latin word for "wood".[61] Lignans are precursors to phytoestrogens.[60][62] They may play a role as antifeedants in the defense of seeds and plants against herbivores.[63]

Lignans and lignin differ in their molecular weight, the former being small and soluble in water, the latter being high polymers that are undigestable:

  1. both are polyphenolic substances derived by oxidative coupling of monolignols
  2. most lignans feature a C18 cores, resulting from the dimerization of C9 precursors
  3. coupling of the lignols occurs at C8
  4. classes of lignans: "furofuran, furan, dibenzylbutane, dibenzylbutyrolactone, aryltetralin, arylnaphthalene, dibenzocyclooctadiene, and dibenzylbutyrolactol."[64]

Many lignans are metabolized by mammalian gut microflora, producing enterolignans.[65][66]

Flax seeds and sesame seeds contain high levels of lignans.[60][67]

The principal lignan precursor found in flaxseeds is secoisolariciresinol diglucoside.[60][67]

Other foods containing lignans include cereals (rye, wheat, oat and barley), soybeans, tofu, cruciferous vegetables, such as broccoli and cabbage, and some fruits, particularly apricots and Strawberry|strawberries.[60]

Lignans are not present in seed oil, and their contents in whole or ground seeds may vary according to geographic location, climate, and maturity of the seed crop, and the duration of seed storage.[60]

Secoisolariciresinol and matairesinol were the first plant lignans identified in foods.[60]

Lariciresinol and pinoresinol contribute about 75% to the total lignan intake, whereas secoisolariciresinol and matairesinol contribute only about 25%.[60]

Foods containing lignans:[60][68]

Source Lignan amount
Flaxseeds 85.5 mg per oz (28.35 g)
Sesame seeds 11.2 mg per oz
Brassica vegetables cup (125 ml)
Strawberries 0.2 per half cup


The aromatic bark contains magnolol, honokiol, 4-O-methylhonokiol, and obovatol.[69][70][71][72][73][74] Magnolol[75] and honokiol[76] activate the nuclear receptor peroxisome proliferator-activated receptor gamma.

Magnolol is an organic compound, classified as lignan, a bioactive compound found in the bark of the Houpu magnolia (Magnolia officinalis) or in Magnolia grandiflora.[77] The compound exists at the level of a few percent in the bark of species of magnolia, the extracts of which have been used in traditional Chinese and Japanese medicine. In addition to magnolol, related lignans occur in the extracts including honokiol, which is an isomer of magnolol.

It is known to act on the GABAA receptors in rat cells in vitro[78] as well as having antifungal properties.[79] Magnolol has a number of osteoblast-stimulating and osteoclast-inhibiting activities in cell culture and has been suggested as a candidate for screening for anti-osteoporosis activity.[80] It has anti-periodontal disease activity in a rat model.[81] Structural analogues have been studied and found to be strong allosteric modulators of GABAA.[82]

Magnolol is also binding in dimeric mode to PPARγ, acting as an agonist of this nuclear receptor.[83]

Prickly ash barkEdit

Historically, Zanthoxylum (Prickly ash) bark was used in traditional medicine.[84]

Plants in the genus Zanthoxylum contain the lignan sesamin.


While sometimes used interchangeably with "terpenes", terpenoids have additional functional groups, usually containing oxygen.[85] Terpenoids are the largest class of plant secondary metabolites, representing about 60% of known natural products.[86] Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.[87] Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes.[88]

See alsoEdit


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  3. Pppery (12 July 2018). "food". San Francisco, California: Wikimedia Foundation, Inc. Retrieved 17 July 2021.
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  13. Delage, PhD, Barbara (November 2015). "Flavonoids". Linus Pauling Institute, Oregon State University, Corvallis, Oregon. Retrieved 2021-01-26.
  14. 14.0 14.1 Mann, John (1992). Secondary Metabolism (2nd ed.). Oxford, UK: Oxford University Press. pp. 279–280. ISBN 978-0-19-855529-2. 
  15. Yong Lin; Ranxin Shi; Xia Wang; Han-Ming Shen (2008). "Luteolin, a flavonoid with potentials for cancer prevention and therapy". Curr Cancer Drug Targets 42 (7): 634–646. doi:10.2174/156800908786241050. PMC 2615542. // 
  16. Ayhan Ulubelen; M. Miski; P. Neuman; T. J. Mabry (1979). "Flavonoids of Salvia tomentosa (Labiatae)". Journal of Natural Products 42 (4): 261–3. doi:10.1021/np50003a002. 
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  30. 30.0 30.1 30.2 “C:D“ is the numerical symbol: total amount of (C)arbon atoms of the fatty acid, and the number of (D)ouble (unsaturated) bonds in it; if D > 1 it is assumed that the double bonds are separated by one or more methylene bridge(s).
  31. Each double bond in the fatty acid is indicated by Δx, where the double bond is located on the xth carbon–carbon bond, counting from the carboxylic acid end.
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    Another common mistake is to say that the position of a bond in omega-notation is the number of the carbon closest to the END.
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    However, for substitutions and other purposes, they don't: a hydroxyl "at ω−3" is on carbon 15 (4th from the end), not 16. See for example this article. doi:10.1016/0005-2760(75)90089-2
    Note also that the "−" in the omega-notation is a minus sign, and "ω−3" should in principle be read "omega minus three". However, it is very common (especially in non-scientific literature) to write it "ω-3" (with a hyphen/dash) and read it as "omega-three". See for example Karen Dooley (2008), Omega-three fatty acids and diabetes.
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