Dimeric sesquiterpene

A number of sesquiterpenes have been demonstrated to have pronounced biological activity ( ) among the non-volatile compounds the sesquiterpene lactones are best known (M) but other oxygenated sesquiterpenes are also known to be active. For example, the role of gossypol, a dimeric sesquiterpene and structurally related compounds has been investigated (21,22). The oxygenated sesquiterpenes, shiromodiol monoacetate and diacetate, from Parabenzoin trilobum (=Lindera triloba Blume) possess potent anti feeding activity toward Spodoptera litura larvae (85). 

Gossypol, toxic, dimeric sesquiterpene from cottonseed... 

Gossypol (dimeric sesquiterpene) Gossypium hirsutum, Montezuma speciosissima (Malvaceae) Acrosin, Azocoll proteinase [110, 111]... 

Additionally, the aerial parts of Baccharis petiolata D. C. from a collection in Chile afforded an unusual dimeric sesquiterpene [27], while B. boliviensis, a species widely distributed from Peru across Bolivia to Chile and Argentina, also yielded new sesquiterpenes [33],... 

Two groups of macrotriolides have been reported. One is 14-membered ring parsonsine-type pyrrolizidine alkaloids, and the other is 18-membered ring dimeric sesquiterpenes, shizukaols. Parsonsine (Fig. 26, 152) was isolated from Parsonia heterophylla [179]. Shizukaols (shizukaol B, 153) were isolated from the roots of Chloranthus serratus [180],... 

CsoHjoOg, Mr 518.56, canary yellow crystals, mp. 181-184°C (+)-form, [ab+445° or 371° (CHCl,) and 199 or 214 °C (racemate), respectively. An atro-pisomeric, aromatic dimeric sesquiterpene, the (+)-form or racemate of which is contained as the main yellow pigment of cotton seeds, occurs not only in cotton seed oil but also in the root bark (ca. 1.2%) of the cotton plant (Gossypium spp., Malvaceae). G. is mildly toxic and has been developed in Brazil as a contraceptive ( pill for the man ) on account of its inhibitory activity on lactate dehydrogenase and thus also spermatogenesis, in addition activity against Herpes genitalis has been described... 

The main bitter component of wormwood Artemisia absinthium) is a dimeric sesquiterpenic lactone absinthin (8-252), which is produced by intramolecular cycloaddition (Diels-Alder reaction) probably of two molecules of astabisin (8-253), which is derived from guaiane. In wormwood extracts, absinthin is transformed into isomeric anabsinthin (8-254). The bitter taste of mugwort (A. vulgaris) is derived primarily from the related compounds estafiatin (8-255) and balchanin (8-256), which are... 

Bohlmann, F., M. Ahmed, J. Jakupovic, R.M. King, and H. Robinson Dimeric sesquiterpene lactones and kolavane derivatives from Gochnatia paniculata. Phytochem. 22, 191 (1983). 

Shizuri, Y. and Yamada, K. (1985) Laurebiphenyl, a dimeric sesquiterpene of the cyclolaurane-type from the red alga Laurencia nidifica. Phytochemistry, 24, 1385-1386. 

Gossypol is a dimeric sesquiterpene found in the immature flower buds and seed kernels of the cotton plant (Gossypium sp., Malvaceae). The compound has gained much attention as a potential male antifertility agent. In the plant it is present as a... 

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