Diarylheptanoid
{{Short description|Class of chemicals found in plants}}
File:Curcumin structure (keto).svg, a linear diarylheptanoid]]
The diarylheptanoids (also known as diphenylheptanoids) are a class of plant secondary metabolites. Diarylheptanoids consist of two aromatic rings (aryl groups) joined by a seven carbons chain (heptane) and having various substituents.{{cite book|last=Brahmachari|first=Goutam|title=Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds|url=https://books.google.com/books?id=lG8LGWC5KFsC&pg=PA285|accessdate=5 July 2013|date=2013-02-20|publisher=CRC Press|isbn=9781439891674|pages=285–}} They can be classified into linear (curcuminoids) and cyclic diarylheptanoids. The best known member is curcumin, which is isolated from turmeric (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 and Zingiberaceae.
A diarylheptanoid is an intermediate in the biosynthesis of phenylphenalenones in Anigozanthos preissii{{Cite journal|pages=525–526|doi=10.1039/C39950000525|title=A diarylheptanoid intermediate in the biosynthesis of phenylphenalenones in Anigozanthos preissii|year=1995|last1=Hölscher|first1=Dirk|last2=Schneider|first2=Bernd|journal=Journal of the Chemical Society, Chemical Communications|issue=5}} or Wachendorfia thyrsiflora (Haemodoraceae).{{Cite journal| pages= 413–428 |pmid=16496097| year= 2006| last1= Brand| first1= S| last2= Hölscher| first2= D| last3= Schierhorn| first3= A| last4= Svatos| first4= A| last5= Schröder| first5= J| last6= Schneider| first6= B| title= A type III polyketide synthase from Wachendorfia thyrsiflora and its role in diarylheptanoid and phenylphenalenone biosynthesis| volume= 224| issue= 2| doi= 10.1007/s00425-006-0228-x| journal= Planta|s2cid=38508249 }}
Cyclic diarylheptanoids
File:Myricanone.svg, a cyclic diarylheptanoid]]
Cyclic diarylheptanoids formed from myricanone can be isolated from the bark of Myrica rubra (Myricaceae).{{Cite journal|pages= 213–221|pmid=20299768|year= 2010|last1= Akazawa|first1= H|last2= Fujita|first2= Y|last3= Banno|first3= N|last4= Watanabe|first4= K|last5= Kimura|first5= Y|last6= Manosroi|first6= A|last7= Manosroi|first7= J|last8= Akihisa|first8= T|title= Three new cyclic diarylheptanoids and other phenolic compounds from the bark of Myrica rubra and their melanogenesis inhibitory and radical scavenging activities|volume= 59|issue= 4|journal= Journal of Oleo Science|doi= 10.5650/jos.59.213|doi-access= free}} Two cyclic diarylheptanoids, named ostryopsitrienol and ostryopsitriol, can be isolated from the stems of endemic Chinese medicinal plant Ostryopsis nobilis (Betulaceae).{{Cite journal|pages =512–514|doi =10.1016/j.cclet.2013.03.035|title =Two new cyclic diarylheptanoids from the stems of Ostryopsis nobilis|year =2013|last1 =Zhang|first1 =Yan-Xia|last2 =Xia|first2 =Bing|last3 =Zhou|first3 =Yan|last4 =Ding|first4 =Li-Sheng|last5 =Peng|first5 =Shu-Lin|journal =Chinese Chemical Letters|volume =24|issue =6|s2cid =95251161|url =http://210.75.237.14/handle/351003/24168|access-date =2018-10-27|archive-date =2020-05-29|archive-url =https://web.archive.org/web/20200529032226/http://210.75.237.14/handle/351003/24168|url-status =dead}} Acerogenin M can be found in Acer nikoense (Sapindaceae).{{Cite journal| pages =735–739|pmid=16651781| year =2006| last1 =Akihisa| first1 =T| last2 =Taguchi| first2 =Y| last3 =Yasukawa| first3 =K| last4 =Tokuda| first4 =H| last5 =Akazawa| first5 =H| last6 =Suzuki| first6 =T| last7 =Kimura| first7 =Y| title =Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor-promoting effects| volume =54| issue =5| journal =Chemical & Pharmaceutical Bulletin| doi =10.1248/cpb.54.735| doi-access =free}} Jugcathayenoside and (+)-galeon can be found in the root bark of Juglans cathayensis (Juglandaceae).{{Cite journal|pages=521–523|doi=10.1016/j.cclet.2013.03.050|title=Diarylheptanoids from the root bark of Juglans cathayensis|year=2013|last1=Li|first1=Juan|last2=Sun|first2=Jia-Xiang|last3=Yu|first3=Heng-Yi|last4=Chen|first4=Zu-Yu|last5=Zhao|first5=Xiao-Ya|last6=Ruan|first6=Han-Li|journal=Chinese Chemical Letters|volume=24|issue=6}}
Health effects
The antioxidant activity of diarylheptanoids isolated from rhizomes of Etlingera elatior (Zingiberaceae) is greater than that of α-tocopherol.{{cite journal
|year=2005
|title=Antioxidative constituents of Etlingera elatior
|journal=Journal of Natural Products
|volume=68
|issue=2
|pages=285–288
|pmid=15730265
|doi=10.1021/np040098l
|last1=Mohamad
|first1=Habsah
|last2=Lajis
|first2=Nordin H.
|last3=Abas
|first3=Faridah
|last4=Ali
|first4=Abdul Manaf
|last5=Sukari
|first5=Mohamad Aspollah
|last6=Kikuzaki
|first6=Hiroe
|last7=Nakatani
|first7=Nobuji}}
References
{{reflist}}
External links
- [http://www.genome.jp/kegg-bin/show_pathway?map00945 Stilbenoid, diarylheptanoid and gingerol biosynthesis pathway at genome.jp]
- {{cite web |url= https://www.ncbi.nlm.nih.gov/mesh/68036381|title= Diarylheptanoids|last1= |first1= |last2= |first2= |date= |website= |publisher= National Center for Biotechnology Information|accessdate=3 July 2013}}
{{natural phenol}}
{{Diarylheptanoid}}