TAILIEUCHUNG - Prototane-type triterpenes from the rhizomes of alisma plantago-aquatica

Three terpenes with Protostane type were isolated from the rhizomes of Alisma plantago- aquatica. The chemical structures of isolated compounds were characterized as 11 ,23S,24R,25- tetrahydroxyprotost-13(17)-en-3-one (alisol A, 1), 11 ,23S,25-trihydroxyprotost-13(17)-en-3- one-24R-yl acetate (alisol A acetate, 2), and 11 ,23S,24S-trihydroxyprotost-13(17),25-dien-3-one (alisol G, 3), by detailed analysis of the 1D- and 2D-NMR spectra such as 1 H-, 13 C-NMR, DEPT 90, DEPT135, HSQC, HMBC, 1 H- 1 H COSY, and by the Electronspray Ionization (ESI) mass spectrum. This is the first report of alisol G from Alisma plantago-aquatica. | Journal of Chemistry Vol. 45 1 P. 120 -125 2007 PROTOTANE-TYPE TRITERPENES FROM THE RHIZOMES OF ALISMA PLANTAGO-AQUATICA Received 30 August 2006 CHAU VAN MINH1 11 PHAN VAN KIEM1 PHAM HAI YEN1 TRAN THU HUONG2 ALESSANDRA BRACA3 institute of Natural Products Chemistry VAST 2Department of Chemical Technology Hanoi University of Technology Department of Bioorganic Chemistry and Biopharmaceutics University of Pisa Italia SUMMARY Three terpenes with Protostane type were isolated from the rhizomes of Alisma plantago-aquatica. The chemical structures of isolated compounds were characterized as 17 -en-3-one alisol A 1 11 3 23S 25-trihydroxyprotost-13 17 -en-3-one-24R-yl acetate alisol A acetate 2 and 11 3 23S 24S-trihydroxyprotost-13 17 25-dien-3-one alisol G 3 by detailed analysis of the 1D- and 2D-NMR spectra such as 1H- 13C-NMR DEPT 90 DEPT135 HSQC HMBC 1H-1H COSY and by the Electronspray Ionization ESI mass spectrum. This is the first report of alisol G from Alisma plantago-aquatica. I - INTRODUCTION The dried rhizome of Alisma plantago-aquatica L. var. orientalis Samuelsson is a crude drug and has been used as a folk medicine for diabetes and swellings 1 . From the phytochemical investigations including its physiological active principles it was reported to contain protostane-type triterpenoids . alisol A and its 24-acetate alisol B and its 23-acetate and alisol C and its 23-acetate 2 - 5 and many other components isolated from fresh rhizome Alismatis orientale and the crude drug Alismatis rhizoma of Japanese and Chinese origins 6 . Here we report the isolation and structural determination of three terpenes with Protostane type as 1 1p 23S 24R 25-tetrahy-droxyprotost-13 17 -en-3-one alisol A 1 11p 23S 25-trihydroxyprotost-13 17 -en-3-one-24R-yl acetate alisol A acetate 2 and 11 p 23S 24S-trihydroxyprotost-13 17 25-dien- 3-one alisol G 3 from the rhizomes of this plant. II - EXPERIMENTAL 1. General experimental procedures The .

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