Sesquiterpene

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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]

  1. ^ 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]


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