The diarylheptanoids (also known as diphenylheptanoids) are a relatively small class of plant

secondary metabolite Secondary metabolites, also called specialised metabolites, toxins, secondary products, or natural products, are organic compounds produced by any lifeform, e.g. bacteria, fungi, animals, or plants, which are not directly involved in the norma ...

s. Diarylheptanoids consist of two aromatic rings (

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...

groups) joined by a seven carbons chain (

heptane Heptane or ''n''-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 poin ...

) and having various substituents. They can be classified into linear ( curcuminoids) and cyclic diarylheptanoids. The best known member is

curcumin Curcumin is a bright yellow chemical produced by plants of the ''Curcuma longa'' species. It is the principal curcuminoid of turmeric (''Curcuma longa''), a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmet ...

, which is isolated from

turmeric Turmeric () is a flowering plant, ''Curcuma longa'' (), of the ginger family, Zingiberaceae, the rhizomes of which are used in cooking. The plant is a perennial, rhizomatous, herbaceous plant native to the Indian subcontinent and Southeast ...

(''Curcuma longa'') and is known as food coloring E100. Some other ''Curcuma'' species, such as ''

Curcuma comosa ''Curcuma comosa'' is a species of flowering plant in the ginger family. It is native to much of Asia, including Thailand, Indonesia, and Malaysia.Qu, Y., et al. (2009)Sesquiterpenes from ''Curcuma comosa''.''Journal of Natural Medicines'' 63 10 ...

'' also produce diarylheptanoids. They have been reported from plants in 10 different families, e.g. ''

Betulaceae Betulaceae, the birch family, includes six genera of deciduous nut-bearing trees and shrubs, including the birches, alders, hazels, hornbeams, hazel-hornbeam, and hop-hornbeams numbering a total of 167 species. They are mostly natives of the ...

'' and ''

Zingiberaceae Zingiberaceae () or the ginger family is a family of flowering plants made up of about 50 genera with a total of about 1600 known species of aromatic perennial herbs with creeping horizontal or tuberous rhizomes distributed throughout tropical Af ...

''. A diarylheptanoid is an intermediate in the biosynthesis of phenylphenalenones in '' Anigozanthos preissii'' or ''

Wachendorfia thyrsiflora ''Wachendorfia thyrsiflora'', the marsh butterfly lily, is a plant species of high when flowering, that has been assigned to the bloodroot family. It is a large to very large evergreen perennial plant with an underground rootstock with cluste ...

'' (Haemodoraceae).

Cyclic diarylheptanoids

Cyclic diarylheptanoids formed from

myricanone Myricanone is a cyclic diarylheptanoid isolated from the bark of ''Myrica rubra ''Myrica rubra'', also called yangmei (; Cantonese: yeung4 mui4; Shanghainese: ), , Chinese bayberry, red bayberry, yumberry, waxberry, or Chinese strawberry (and o ...

can be isolated from the bark of ''

Myrica rubra ''Myrica rubra'', also called yangmei (; Cantonese: yeung4 mui4; Shanghainese: ), , Chinese bayberry, red bayberry, yumberry, waxberry, or Chinese strawberry (and often mistranslated from Chinese as arbutus) is a subtropical tree grown for its f ...

'' (Myricaceae). Two cyclic diarylheptanoids, named ostryopsitrienol and ostryopsitriol, can be isolated from the stems of endemic Chinese medicinal plant '' Ostryopsis nobilis'' (Betulaceae). Acerogenin M can be found in ''

Acer nikoense ''Acer maximowiczianum'' (Nikko maple; syn. ''A. nikoense'' Maxim.), is a species of maple widely distributed in China (Anhui, Hubei, Hunan, Jiangxi, Sichuan, Zhejiang) and Japan ( Honshū, Kyūshū, Shikoku).Xu, T.-z., Chen, Y., de Jong, ...

'' (Sapindaceae). Jugcathayenoside and (+)- galeon can be found in the root bark of ''

Juglans cathayensis ''Juglans mandshurica'' (), also known as Manchurian walnut, or Tigernut, is a deciduous tree of the genus ''Juglans'' (section ''Cardiocaryon''), native to the Eastern Asiatic Region ( China, Russian Far East, North Korea and South Korea). ...

'' (Juglandaceae).

Health effects

The antioxidant activity of diarylheptanoids isolated from rhizomes of ''

Etlingera elatior ''Etlingera elatior'' (also known as torch ginger, ginger flower, red ginger lily, torch lily, wild ginger, ''combrang, bunga kantan'', Philippine wax flower, ගොඩ ඕලු (goda olu), ගොඩ නෙලුම් (goda nelum), සිද් ...

'' (Zingiberaceae) is greater than that of

α-tocopherol α-Tocopherol is a type of vitamin E. It has E number "E307". Vitamin E exists in eight different forms, four tocopherols and four tocotrienols. All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free r ...

References

External links

Stilbenoid, diarylheptanoid and gingerol biosynthesis pathway at genome.jp
* {{Diarylheptanoid