Eupatorium jhanii

Some new diterpenoid oxides have been obtained from Eupatorium jhanii. They are jhanol (12) and its 18-acetate together with jhanidiol (13) and its 18-monoacetate and diacetate. Their structures were established by correlation with manoyl oxide and by an examination of their C n.m.r. spectra. 11/3-Hydro-xymanoyl oxide (14) has been isolated from Juniperus oxycedrus ° A group of new 11-oxomanoyl oxide derivatives (15a—e) has been obtained from Coleus forskohlii (Labiatae). Their oxygenation pattern is reminiscent of that of the tricyclic diterpenoids which have beemobtained from other Coleus species. 

The structure of the epoxy-dialdehyde (15), from Afromomum daniellii (Zingiberaceae), was established by correlation with c -12-norambreinolide. The hydroxy-acid (16), salvic acid from Eupatorium salvia,and the ring B seco-labdane jhanic acid (17) from Eupatorium jhanii are two further diterpenoids from these species of the Compositae. The structure of the latter rests on interpretation of the H and C n.m.r. data. Gutierrezia lucida (Compositae) contains the 13-epimeric acids (18) related to agathic acid together with the butenolide (19). Some esters of 6-hydroxylabdane-17-carboxylic acids were detected in G. mandonii. The investigation of Cistus species has continued. The ent-labdane acetyl-laurifolic acid (20) is a component of Cistus laurifolius ... 

Gonzalez, A.G., J.M. Artega, J.L. Breton, and B.M. Fraga Five new labdane diterpene oxides from Eupatorium jhanii, Phytochem. 16, 107 (1977). 

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