関: diterpenoid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/18 11:44:44」(JST)

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Geranylgeranyl pyrophosphate, the starting material for the biosynthesis of diterpenes

Diterpenes are a class of chemical compounds composed of two terpene units with the molecular formula C₂₀H₃₂; they may also be thought of as consisting of four isoprene units. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and antiinflammatory.

Diterpene structures

Taxadiene: a tricyclic diterpene

As with most terpenes a huge number of potential structures exists, which may be broadly divided according to the number of rings present.

Number of rings	Examples
0	Phytane
1	Cembrene A
2	Sclarene, Labdane
3	Abietane, Taxadiene
4	Stemarene, Stemodene

Diterpenoids

Retinol: one of the animal forms of vitamin A

Phytol: usedin the biosynthesis of vitamin E and vitamin K1

Diterpenes are formally defined as being hydrocarbons and thus contain no heteroatoms. Functionalized structures should instead be called diterpenoids, although in scientific literature the two terms are often used interchangeably. Although a wide range of terpene structures exist few of them are biologically significant, by contrast diterpenoids possess a rich pharmacology and include important compounds such as retinol and phytol.

Taxanes

Taxanes are class of diterpenoids featuring a taxadiene core. They are produced by plants of the genus Taxus (yew trees) and are widely used as chemotherapy agents.^[1]

Other

Dodonaea petiolaris yields the diterpene ent-3β-acetoxy-15,16-epoxylabda-8(17),13(16),14-trien-18-oic acid (C₂₂H₂₈O₆) or its enantiomer.^[2]
Salvia divinorum yields Salvinorin A, a psychotropic drug

References

^ Rowinsky, MD, Eric K. (February 1997). "THE DEVELOPMENT AND CLINICAL UTILITY OF THE TAXANE CLASS OF ANTIMICROTUBULE CHEMOTHERAPY AGENTS". Annual Review of Medicine 48 (1): 353–374. doi:10.1146/annurev.med.48.1.353.
^ Jefferies, P. R.; Payne, T. G.; Raston, C. L.; White, A. H. "The chemistry of Dodonaea spp. VIII. Isolation and crystal structure of a diterpene acid from Dodonaea petiolaris". Australian Journal of Chemistry 34 (5): 1001–1007. doi:10.1071/CH9811001.

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1. LSDおよび他の一般的な幻覚剤による中毒 intoxication from lsd and other common hallucinogens

English Journal

New approaches on the analyses of thermolabile coffee diterpenes by gas chromatography and its relationship with cup quality.

Novaes FJ1, Oigman SS2, de Souza RO3, Rezende CM2, de Aquino Neto FR4.
Talanta.Talanta.2015 Jul 1;139:159-66. doi: 10.1016/j.talanta.2014.12.025. Epub 2015 Jan 12.
A new gas chromatography method using pulsed split injector (PS-GC) was validated to quantify thermolabile diterpenes cafestol, kahweol and isokahweol in methanolysed Arabica coffee oils. Linearity was 0.99 from 8 to 69mgmL(-1), recovery ranged from 99% to 101% and precision of less than 4% was obta
PMID 25882422

Synthesis of new ent-labdane diterpene derivatives from andrographolide and evaluation on cytotoxic activities.

Luo Y1, Wang K2, Zhang MH2, Zhang DY3, Wu YC4, Wu XM2, Hua WY2.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2015 Jun 1;25(11):2421-4. doi: 10.1016/j.bmcl.2015.03.086. Epub 2015 Apr 4.
There are many reports for andrographolide modification regarding antitumor effects. Transformation of the five-membered lactone ring to furan aromatic ring still results in compounds with good cytotoxicity. To determine further the importance of the five-membered lactone ring and to obtain better l
PMID 25913115

A bioguided identification of the active compounds that contribute to the antiproliferative/cytotoxic effects of rosemary extract on colon cancer cells.

Borrás-Linares I1, Pérez-Sánchez A2, Lozano-Sánchez J1, Barrajón-Catalán E2, Arráez-Román D3, Cifuentes A4, Micol V5, Carretero AS1.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2015 Jun;80:215-22. doi: 10.1016/j.fct.2015.03.013. Epub 2015 Mar 20.
Rosemary extracts have exhibited potential cytostatic or cytotoxic effects in several cancer cell models but their bioactive compounds are yet to be discovered. In this work, the anticancer activity of a rosemary-leaf extract and its fractions were assayed to identify the phenolic compounds responsi
PMID 25801906

Japanese Journal

Radical-Mediated Three-Component Reaction: A Study toward the Total Synthesis of Resiniferatoxin

Urabe Daisuke
Chemical and Pharmaceutical Bulletin 63(8), 565-572, 2015
… This review summarizes the efforts to develop a radical-mediated three-component reaction and its application to a convergent approach to synthesize the 5/7/6-tricyclic framework (ABC-rings) of the densely functionalized dephnane diterpene, resiniferatoxin. …
NAID 130005090108