Chemical composition of Potentilla fruticosa. II. Triterpenoids

. 5. A. A. Semenycheva and V. B. Zbarskii, Farmatsiya, 19, No. i, 46 (1970). Thin-Layer Chromatography [Russian translation, Mir, Moscow (1965)]. CHEMICAL COMPOSITION OF Potentilla fruticosa. !I. TRITERPENOIDS UDC 547.914 T. V. Ganenko and A. A. Semenov We have previously reported on the isolation from bush cinquefoil Potentilla fruticosa Lo, family Rosaceae, of five flavonoid compounds [I]. Continuing a study of the extractive substances (nonpolar fraction) of this plant, we have isolated three compounds of the triterpene type (I-III). The substances were chromatographed in the form of the native compounds or their methyl esters and were identified on the basis of the results of ~H and 13NMR spectroscopies and mass spectrometry, and also the results of a comparison of physicochemical characteristics. 22 +95 ° ( c 1.2 ; chloroform) [2]_. Substance (I) - C30H~sOz, mp 232-235 ° , [also6 This compound was epiursolic acid, although the isolation of ursolic acid itself from Potentilla fruticosa has been reported elsewhere [3]. In the IH NMR spectrum of substance (I), the signal of the H-3 proton arranged geminally to the hydroxy group appears at 3.46 ppm with SSCCs of 5 and 9 Hz, which shows the E-orientation of this proton and, consequently, the orientation of the hydroxy group. Substance (II) - C30H~sO ~, mp 242-244°, [~]s~62° +34 .3 ° (c 1.34; pyridine), melting point of the methyl ester 210-212 ° , [ a ] ~ 6 +85.7° (c 0.6; chloroform). This was identified as 2a-hydroxyursolic acid [4]. Substance (III) - C~0H4sOs, M + 488; methyl ester C31Hs00s, mp 145-148 ° , [ A ] ~ +54 ° (c 0.9; chloroform). This was identified as termentic acid (2a,19a-dihydroxyursolic acid) [5]. This is the first time that all these substances have been isolated from this plant. LITERATURE CITED i. 2. 3. 4. 5. T. V° Ganenko, V. I. Lutskii, M. F. Larin, A. L. Vereshchagin, and A. A. Semenov, Khim. Prir. Soedin., 451 (1988). S. Huneck and G. Snatzke, Chem. Ber., No. 5, 120 (1965). J. Le Men and H. Pourrat, Ann. Pharm. Franc., 13, No. 3, 169 (1955). A . T . Glen, W. Lawrie, J. McLean, and M. Ei-Garby Younes, J. Chem. Soc. (C), 510 (1967). S. Shigenaga, I. Kouno, and N. Kawano, Phytochemistry, No. i, 115 (1985). Irkutsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, p. 856, November-December, 1989. Original article submitted January 24, 1989. 0009-3130/89/2506-0727512.50 ©1990 Plenum Publishing Corporation 727  (...truncated)