sesquiterpenoid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/07 13:24:03」(JST)

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Big Sagebrush (Artemisia tridentata) contains sesquiterpene lactones which are sesquiterpenoids (built from three isoprene units) and contain a lactone ring, hence the name. These compounds are found in many other plants and can cause allergic reactions and toxicity if overdosed, particularly in grazing livestock.

Phallus indusiatus, in Cooktown, Queensland, Australia, which produces two novel sesquiterpenes

Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the empirical formula C₁₅H₂₄. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.

Sesquiterpenes are found naturally in plants and insects, as semiochemicals, e.g. defensive agents or pheromones.

Acyclic

The reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15-carbon farnesyl pyrophosphate which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Oxidation of farnesene then provides sesquiterpenoids such as farnesol.

Farnesyl pyrophosphate

Monocyclic

There are more cyclic sesquiterpenes than cyclic monoterpenes because of the increased chain length and additional double bond. In addition to common six-membered ring systems such as is found in zingiberene (a constituent of the oil from ginger), cyclization of one end of the chain to the other end can lead to macrocyclic rings such as humulene.

Bicyclic

δ-Cadinene, a sesquiterpene

The cadinenes contain two fused six-membered rings. Caryophyllene, a component of many essential oils such as clove oil, contains a nine-membered ring fused to a cyclobutane ring.

Vetivazulene and guaiazulene are aromatic bicyclic sesquiterpenoids.

Tricyclic

With the addition of a third ring, the possible structures become increasingly varied. Examples include longifolene, copaene and the alcohol patchoulol.

Dictyophorine A and B

Two sesquiterpenes named dictyophorine A and B were identified from the fungus Phallus indusiatus. These compounds are based on the eudesmane skeleton (a common structure found in plant-derived flavors and fragrances), and they are the first eudesmane derivatives isolated from fungi. The dictyophorines promote the synthesis of nerve growth factor in astroglial cells.^[1]

Footnotes

^ Kawagishi, Hirokazu (July 1997). "Dictyophorines A and B, two stimulators of NGF-synthesis from the mushroom Dictyophora indusiata". Phytochemistry (Elsevier) 45 (6): 1203–1205.

External links

Sesquiterpenes at the US National Library of Medicine Medical Subject Headings (MeSH)

English Journal

Farnesides A and B, Sesquiterpenoid Nucleoside Ethers from a Marine-Derived Streptomyces sp., strain CNT-372 from Fiji.

Zafrir Ilan E, Torres MR, Prudhomme J, Le Roch K, Jensen PR, Fenical W.SourceCenter for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego , La Jolla, California 92093-0204, United States.
Journal of natural products.J Nat Prod.2013 Sep 27;76(9):1815-8. doi: 10.1021/np400351t. Epub 2013 Aug 29.
Farnesides A and B (1, 2), linear sesquiterpenoids connected by ether links to a ribose dihydrouracil nucleoside, were isolated from a marine-derived Streptomyces sp., strain CNT-372, grown in saline liquid culture. The structures of the new compounds were assigned by comprehensive spectroscopic ana
PMID 23987585

3-O-methylthespesilactam, a new small-molecule anticancer pan-JAK inhibitor against A2058 human melanoma cells.

Li MY, Tian Y, Shen L, Buettner R, Li HZ, Liu L, Yuan YC, Xiao Q, Wu J, Jove R.SourceMarine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, PR China.
Biochemical pharmacology.Biochem Pharmacol.2013 Sep 7. pii: S0006-2952(13)00570-4. doi: 10.1016/j.bcp.2013.08.065. [Epub ahead of print]
Natural product-inspired discovery of new drug leads plays a key role in drug development. Recently, small-molecule JAK inhibitors have been pursued for the development of anticancer therapeutics. However, most of these inhibitors reported up to now are multi-nitrogen polycyclic aromatic heterocycle
PMID 24021352

Norbisabolane and eremophilane sesquiterpenoids from cultures of the Basidiomycete Polyporus ellisii.

Wang S, Li ZH, Dong ZJ, Liu JK, Feng T.SourceState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; Graduate University of Chinese Academy of Sciences, Beijing 100049, PR China.
Fitoterapia.Fitoterapia.2013 Sep 6. pii: S0367-326X(13)00231-1. doi: 10.1016/j.fitote.2013.08.023. [Epub ahead of print]
Three new 11,12,15-norbisabolane sesquiterpenoids, polisins A-C (1-3), and four new eremophilane sesquiterpenoids, polylisins A-D (4-7), were isolated from cultures of the Basidiomycete Polyporus ellisii. These new structures were elucidated based on extensive spectroscopic studies and the structure
PMID 24013036

Japanese Journal

Two New Sesquiterpenoids Including a Sesquiterpenoid Lactam from Curcuma wenyujin

Qiu Guanguan,Yan Pengcheng,Shao Weiwei,Zhou Jie,Lin Weiwei,Fang Lianglian,Zhao Xiaowei,Dong Jianyong
Chemical and Pharmaceutical Bulletin 61(9), 983-986, 2013
Two new sesquiterpenoids, namely elema-1,3,7(11),8-tetraen-8,12-lactam (1) and 7β,8α-dihydroxy-1α,4αH-guai-9,11-dien-5β,8β-endoxide (2), together with five known analogs were isolated from the EtOAc e …
NAID 130003360831

中国横断山脈地域におけるキク科リグラリア属植物の化学的・遺伝的多様性に関する研究

齋藤義紀
薬学雑誌 132(12), 1451-1459, 2012-00-00
NAID 40019510722

中国横断山脈地域におけるキク科リグラリア属植物の化学的・遺伝的多様性に関する研究

齋藤義紀
YAKUGAKU ZASSHI 132(12), 1451-1459, 2012
The Hengduan Mountains area of China is rich in plant resources. The Ligularia species, which belong to Senecioneae and Asteraceae, distributed in this area are highly diversified and contain 6 sect …
NAID 130002489523

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