Structure and occurrence of unusual fatty acids in minor seed oils

The biochemistry of plant cuticular lipids.

Ethnopharmacological survey on medicinal plants used in herbal drinks among the traditional communities of Pakistan

A number of sapindaceous seed oils have been investigated with respect to their cyanolipid constituents. All but one of the oils have this new class of lipids in amounts ranging from 13% to 55%. These cyanolipids are of four different types, but all consist of long-chain fatty acids esterified with an unsaturated isoprenoid hydroxy- or dihydroxynitrile. The large amounts of C20 acids usually found in these oils indicate an appreciable cyanolipid content because such acids are preferentially incorporated in nitrile-containing fractions.Cardiospermum halicacabum L. seed oil was shown to contain 49% of a diester having two fatty acid moieties esterified with 1-cyano-2-hydroxymethylprop-2-ene-1-ol and 6% of another diester derived from 1-cyano-2-hydroxymethylprop-1-ene-3-ol. Treatment of the latter diester with methanolic hydrogen chloride produces methyl 4,4-dimethoxy-3-(methoxymethyl) butyrate from the dihydroxynitrile moiety.

Cyanolipids ofCardiospermum halicacabum L. and other sapindaceous seed oils

Koelreuteria paniculata Laxm. (Sapindaceae) seed oil is a mixture of cyanolipids (42%) and ordinary triglycerides. The cyanolipid portion contains two classes of components. One of these (25% of the oil) is a mixture of diesters composed of two fatty acid moieties (predominantly C18 and C20 monoenoic) esterified with an unsaturated five-carbon dihydroxynitrile (1-cyano-2-hydroxymethylprop-1-ene-3-ol). The other class (17% of the oil) consists of cyanolipids having one fatty acid moiety (predominantly C20 monoenoic) esterified with 1-cyano-2-methylprop-1-ene-3-ol. Monoesters based on this same hydroxynitrile were previously isolated fromStocksia brahuica seed oil and characterized. Hydrogenation of the diesters was accompanied by varying degrees of hydrogenolysis of the ester groups. The hydrogenated diester was reduced with lithium borohydride and the dihydroxynitrile portion was isolated. Acetolysis of the hydrogenated diester in glacial acetic acid with sulfuric acid catalyst yielded an acetylated γ-lactone. The double bond of the dihydroxynitrile moiety in the diester does not react with bromine in carbon tetrachloride.

Cyanolipids ofKoelreuteria paniculata Laxm. seed oil

Fatty acids of Monnina emarginata seed oil.

Cyanolipids of Stocksiabrahuica benth. Seed oil

Aus obiger Spezies konnte das makrocyclische Lacton (I) isoliert werden, das bei der katalytischen Hydrierung zu (II) gesattigt wird.

L.W. Tjarks

Papers

Fatty acids of Monnina emarginata seed oil.

Cyanolipids of Stocksiabrahuica benth. Seed oil

(s)‐13‐hydroxy‐cis‐9, trans‐11‐octadecadiensaeure‐lacton, eine 14gliedrige ringverbindung aus monnina‐emarginata‐samenoel