Sapium sebiferum

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. 

Sapium sebiferum (L.) Roxb. S. discolor Mueller-Arg. Wu Jiu Shan Jiu (Chinese tallow tree, Chinese vegetable tallow) (Leaf, root bark) Xanthoxylin, corilagin, sebiferic acid, lauric acid, margaric acid, palmitic acid.33-50 Antihypertensive activity, for constipation, poisoning, skin diseases. 

There are several species known as the tallow tree. In western Africa, Pentadesma butyracea is called the tallow tree or the butter-and-tallow tree because the oil derived from its fruit is used like butter. In India, the tallow tree is Vateria indica, the seeds of which produce an oily wax. The tallow tree of China is Sapium sebiferum, in the family Euphorbiaceae. The waxy oil from the seeds of this tree is used to make candles. 

Stillingia oil Sapium sebiferum seed oil. Section 3.3.34) is unusual in that some of its glycerides contain four acyl groups including two conventional Cig acids, a Cg allenic hydroxy acid (Section 1.6) and deca-2Mc-dienoic acid (stillingic). 

When triacylglycerols contain a hydroxy fatty acid then the hydroxyl group can be esterified with further fatty acids. Examples of these glycerides have been found in plants (Hitchcock, 1975) with the occurrence of tetra-, penta- and hexa- acid glycerides. The tetra-acid triacylglycerol from Sapium sebiferum oil (Sprecher etal., 1965) is an example. 

Euphorbiaceae Sapium sebiferum Chinese vegetable 27-33 tallow 199-204 38-44 5 60 2 33 — — 26 56 18... 

A complex lipid from the seed oil of the Chinese tal-lowtree, Sapium sebiferum (Euphorbiaceae), appears to have arisen in this manner (Fig. 3.8). Although acetylenic compounds are not commonly found in the Euphorbiaceae, the presence of an allenic linkage is suggestive of dieir presence. 

Fig. 3.8. An unusual allenic lipid from Sapium sebiferum seed oil.

Whereas the usual polyenoic fatty acids contain methylene-interrupted bonds, a group of ethylene-interrupted acids also exists in some plants. They have been reviewed (Gardner et al., 1973 Hitchcock and Nichols, 1971 Hopkins, 1972 Hopkins and Chisholm, 1968) and are found in about a quarter of the different plant orders. Hitchcock and Nichols (1971) have grouped them into four classes characterized by cis-9, cis-12, trans-9, and trans-12 double-bond positions. These acids are shown in Table III, and it will be noted that certain seed oils contain very high amounts of these unusual fatty acids. The 2,4-ethylenic acids cannot be thus classified. rra/i -2,cis-4-Deca-dienoate is a constituent of oil from the seeds of Sapium sebiferum (Crossley and Hildritch, 1949) where it occurs as an ester with an unusual hydroxyal-lenic acid. It is also present in peas (Jennings et al., 1964), and the trans-... 

With the aid of adsorption TLC, it has been discovered that the seed oil of the Chinese tallow tree (Sapium sebiferum) contains up to about 25% of a fraction only a little more polar than normal triglycerides. These compounds have been characterised as mono-estolide triglycerides, i. e. (mono)hydroxy-triglycerides, esterified with ordinary fatty acids [192]. The following types of estolide-triglyceride have been... 

Although some 50 compounds with hopane skeleton (556) have been obtained so far from nature, their occurrence in woody tissues is quite rare. Hydrox-yhopanone (561) is a component of dammar from Hopea micrantha (229). Moretenol (562), from bark of Sapium sebiferum, is an example of a C-21aH hopane apparently this compound results from C-C-C-C-B folding of squalene. To date, none of the rearranged hopane types depicted in Fig. 8.1.33 has been reported to occur in woody parts of plants. 

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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