Cyberlipid
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SESTERTERPENES

They are derived from geranylfarnesol pyrophosphate and have 25 carbon atoms (the sester- prefix means half to three, i.e. two and a half.). These relatively rare lipids were first isolated from insect protective waxes and from fungal sources. Now, they are known to be widespread, they have been isolated from terrestrial fungi, lichens, higher plants, insects, and various marine organisms, especially sponges.

geranylfarnesol


They exhibit diverse biological properties such as anti-inflammatory, cytotoxic, anticancer, antimicrobial, and anti-biofilm activities. The structure of the most recent sesterterpenoids and their activities have been reviewed (Wang L et al., Nat prod Rep 2013, 30, 455).

Three examples of sesterterpenes are shown below.

ophiobolin, gascardic acid, ceroplastol

Ophiobolin A, a fungal metabolite and a phytotoxin stimulates the net leakage of electrolytes and glucose from maize seedling roots and was found to be a potent inhibitor of calmodulin-activated cyclic nucleotide phosphodiesterase (Leung PC et al., J Biol Chem 1984, 259, 2742-7).
Gascardic acid is the first sesterterpenes that was isolated in 1965 from the secretion of an insect, Gascardia madagascariensis.

Variously unsaturated and branched sesterterpenes, known as Haslenes, were found in species of diatomaceous algae (