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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/03/16 08:50:03」(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 molecular 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[edit]

When geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate, which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Oxidation can then provide sesquiterpenoids such as farnesol.

Farnesyl pyrophosphate

Monocyclic[edit]

With the increased chain length and additional double bond, the number of possible ways that cyclization can occur is also increased, and there exists a wide variety of cyclic sesquiterpenes. 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[edit]

δ-Cadinene, a sesquiterpene

In addition to common six-membered rings such as in the cadinenes, one classic bicyclic sesquiterpene is caryophyllene, from the oil of cloves, which has a nine-membered ring and cyclobutane ring. Additional unsaturation provides aromatic bicyclic sesquiterpenoids such as vetivazulene and guaiazulene.

Tricyclic[edit]

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[edit]

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

Footnotes[edit]

^ Kawagashi et al., pp. 1203-1205.

References[edit]

Kawagishi et al. (1997.)"Dictyophorines A and B, two stimulators of NGF-synthesis from the mushroom Dictyophora indusiata.Phytochemistry1997, volume 45, issue 6,pp. 1203–1205. [1]

External links[edit]

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

English Journal

Chemical composition and anticancer, antiinflammatory, antioxidant and antimalarial activities of leaves essential oil of Cedrelopsis grevei.

Afoulous S, Ferhout H, Raoelison EG, Valentin A, Moukarzel B, Couderc F, Bouajila J.SourceUniversité de Toulouse, Laboratoire des Interactions Moléculaires et Réactivité Chimique et Photochimique, UMR CNRS 5623, Université Paul-Sabatier, 118 route de Narbonne, F-31062 Toulouse, France.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2013 Jun;56:352-62. doi: 10.1016/j.fct.2013.02.008. Epub 2013 Feb 28.
The essential oil from Cedrelopsis grevei leaves, an aromatic and medicinal plant from Madagascar, is widely used in folk medicine. Essential oil was characterized by GC-MS and quantified by GC-FID. Sixty-four components were identified. The major constituents were: (E)-β-farnesene (27.61%), δ-cad
PMID 23459148

Anti-inflammatory effects of tectroside on UVB-induced HaCaT cells.

Kim SB, Kang OH, Joung DK, Mun SH, Seo YS, Cha MR, Ryu SY, Shin DW, Kwon DY.SourceCollege of Pharmacy and Wonkwang-Oriental Medicines Research Institute, Institute of Biotechnology, Wonkwang University, Jeonbuk 570-749, Republic of Korea.
International journal of molecular medicine.Int J Mol Med.2013 Jun;31(6):1471-6. doi: 10.3892/ijmm.2013.1343. Epub 2013 Apr 11.
Ultraviolet B (UVB) irradiation causes skin damage and inflammation by inducing the secretion of various cytokines, which are immune regulators produced by cells. To prevent skin inflammation, keratinocytes that have been irreversibly damaged by UVB must be eliminated through apoptosis. Ixeris denta
PMID 23588209

Sesquiterpene lactones from Lactuca canadensis and their chemotaxonomic significance.

Michalska K, Szneler E, Kisiel W.SourceDepartment of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, 12 Smetna Str., Pl-31-343 Krakow, Poland.
Phytochemistry.Phytochemistry.2013 Jun;90:90-4. doi: 10.1016/j.phytochem.2013.02.005. Epub 2013 Mar 20.
A total of 19 sesquiterpene lactones were isolated from roots of Lactuca canadensis L., of which 10 were reported for the first time from Lactuca species and two were unknown. This is also the first report on the co-occurrence of three pairs of zaluzanin C-type guaianolides, epimeric at C-3, and on
PMID 23522933

Japanese Journal

Repression of Tropolone Production and Induction of a Burkholderia plantarii Pseudo-Biofilm by Carot-4-en-9, 10-diol, a Cell-to-Cell Signaling Disrupter Produced by Trichoderma virens

Wang Mengcen,Hashimoto Makoto,Hashidoko Yasuyuki
Plos one 8(11), 2013-11-04
… When exposed to catechol, this fungus dose-dependently produced carot-4-en-9,10-diol,a sesquiterpene-type autoregulatory signal molecule that promotes self-conidiation of T. …
NAID 120005365919