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 no ...

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 as ...

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 poi ...

) and having various substituents. They can be classified into linear (

curcuminoid A curcuminoid is a linear diarylheptanoid, a relatively small class of plant secondary metabolites that includes curcumin, demethoxycurcumin, and bisdemethoxycurcumin, all isolated from turmeric (curcuma longa). These compounds are natural p ...

s) 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, cos ...

, 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'' 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 ...

'' 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 ...

''. A diarylheptanoid is an intermediate in the biosynthesis of phenylphenalenones in '' Anigozanthos preissii'' or '' Wachendorfia thyrsiflora'' (Haemodoraceae).

Cyclic diarylheptanoids

Cyclic diarylheptanoids formed from myricanone 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 ''Ostryopsis nobilis'' () is a shrub species in the genus ''Ostryopsis ''Ostryopsis'' is a small genus of deciduous shrubs belonging to the birch family Betulaceae. The species have no common English name, though hazel-hornbeam has been sugg ...

'' (Betulaceae). Acerogenin M can be found in '' Acer nikoense'' (Sapindaceae). Jugcathayenoside and (+)-

galeon Galeon is a discontinued Gecko-based web browser that was created by Marco Pesenti Gritti with the goal of delivering a consistent browsing experience to GNOME desktop environment. It gained some popularity in the early 2000s due to its speed, ...

can be found in the root bark of '' Juglans cathayensis'' (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