Sapium japonicum

A number of closely related linear allenes have also been isolated from seed oils (Scheme 18.8). Examples are laballenic acid (18) [27], lamenallenic acid (19) [28] and phlomic acid (20) [29]. The hydroxy acid 21 was isolated as part of a triglyceride from the Chinese tallow tree Sapium sebiferum [30] and as its methyl ester 22 from the related species Sapium japonicum [31], which is found in Japan. 

The major stmctural types known are the phorbol esters [e.g., a tigliane from Sapium japonicum (17)] Croton, Sap-ium, Aleurites, Mancinella, Baliospermum, and Euphorbia), ingenol esters [e.g., ingenane (18)] Euphorbia), and daph-nanes [e.g., daphnetoxin (19)] Euphorbia, Hura, Hip-pomane, Excoecaria, Baliospermum, Thymelaeaceae) (Fig. 22.7) most of the plants that contain these diterpenes are in subfamilies Crotonoideae and Euphorbioideae (Kinghom, 1979 Webster, 1975). 

Illicium religiosum Casuarina equisetifolia Anogeissus tatifolia Sapium japonicum S. siebiferum Aleurites cordata Quercus stenophylla Q. pedunculata Ginkgo biloba Mammea americana Hama metis spp. 

The structure of an allenic antifungal constituent isolated from the leaves of Sapium japonicum (Euphorbiaceae) has been shown to be (55), Compound (56), which incorporates (55) as part of its structure, was isolated previously from a member of the same genus, Sapium sebiferum. ... 

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