Hydnocarpate

Chaulmoogric and hydnocarpic acids (Figure 3.15) are cyclopentenyl fatty acids found in chaul-moogra oil expressed from seeds of Hydnocar-pus wightiana (Flacourtiaceae). These acids are known to arise by malonate chain extension of the... 

Chief constituents Glycerides of chaulmoogric and hydnocarpic acids. 

Ethyl ester, eluiulmestroL Moogrol. Essentially a mist of the ethyl esters of the unsaturated fatty acids (chanlmoogric and hydnocarpic) of chaulmoogra oil. Pale yellow, clear liquid slight fruity odor not unpleasant taste. Iodine no. 90-100, dg about 0.904. [a]J +44,5° (chloroform). Insol in water mi sc with ale, chloroform. 

Sodium salt, sodium hydnocarpate, hydnocarpate sodium, sodium gynocardate, Alepol. Yellowish powder. Sol in water, ale. The aq soln is alkaline. MLD i.v. in rats 100-125 mg/kg (Spector),... 

Hydnocarpic acid see chaulmoogric acid. Hydnufermgin, hydnufemiginin. 

Oils containing cyclopentenoid fatty acids such as chaul-moogric and hydnocarpic acids (Fig. 2.18) have long been used for the treatment of leprosy. 

Figure 5.1 Structures of naturally occurring cyclic fatty acids. I, Cyclopropane acids a, 9,10-methylenehexadecanoic acid b, 11,12-methyleneoctadecanoic (lactobacillic) acid c, 8,9-methy-leneheptadecanoic (dihydromalvalic) acid d, 9,10-methyleneoctadecanoic (dihydrosterculic) acid. II, Mycolic (2-alkyl-3-hydroxy) acid. Ill, Cyclopropene acids a, 9,10-methyleneoctadec-9-enoic (sterculic) acid b, 8,9-methyleneheptadec-8-enoic (malvalic) acid. IV, Cyclopentenyl acids a, ll-cyclopent-2-enyl-undecanoic (hydnocarpic) acid b, 13-cyclopent-2-enyl-tridecanoic (chaulmoogric) acid c, 13-cyclopent-2-enyl-tridec-6-enoic (gorlic) acid. V a, 11-cyclohexyl-undecanoic acid b, 11-cycloheptylundecanoic acid.

In this category, fatty acids with a terminal cyclopentenyl ring are best known (Sebedio and Grandgirard, 1989). There are three main types hydnocarpic (ll-cyclopent-2-enyl-undecanoic) acid (structure IVa, Fig. 5.1), chaulmoogric (13-cyclopent-2-enyl-tridecanoic) acid (structure IVb) and gorlic (13-cyclopent-2-enyl-tridec-6-enoic) acid (structure IVc) and its positional isomers (13-cyclopent-2-enyl-tridec-4-enoate and 13-cyclopent-2-enyl-tridec-9-enoate). They usually occur in varying proportions as major components (up to 90% of total fatty acids) in seed oils along with smaller amounts of saturated, oleic and linoleic acids. 

A terminal cyclopentenyl group is evident in the mass spectra of the methyl esters. For example, for methyl hydnocarpate the base peak at m/z (mass per... 

Fig. 4. Structures of cyclopentenyl fatty acids. Homologues of chaulmoogric acid, CsHt—(CH,)n—COOH, are, withn = 0, 2, 4, 6, 8, 10, 14, aleprolic, alepraic, aleprestic, alepry-lic, alepric, hydnocarpic, and hormelic acids, respectively. A homologue of gorlic acid is onco-bic acid, 15-(2 -cyclopentenyl)-8-pentadecenoic acid.

Chaulmoogra oils, individual cyclopentenyl fatty acids, and their derivatives have been used for centuries in the treatment of leprosy. Yet, satisfactory results have not been achieved, even in modem times (Schlossberger, 1938). However, activity against Mycobacterium leprae has been reported for the sodium salts of hydnocarpic and chaulmoogric acids (Levy, 1975). 

Figure 4.5. Phases Cr 62.5 (S 56.5 Sa 58.9 N 61.7) is, prepared from hydnocarpic acid.

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