Ellagitannins and Related Compounds from Penthorum chinense Penthorum chinenseのエラジタンニンおよび関連化合物

Four new ellagitannin metabolites, penthorumnins A?D (1?3 and 5), were isolated from the dried stem of Penthorum chinense. The structures were determined using spectroscopic and chemical analysis as well as using computations that revealed the following: (1) the acyl group of penthorumnin A (1) has a unique cyclopentane carboxylic acid structure that is derived from a hexahydroxydiphenoyl (HHDP) group; (2) penthorumnin B (2) has a 2-carboxymethyl-2,3-dihydro-3-oxo-1H-indene-1-carboxylic acid structure that originates from the acyl group of penthorumnin A; (3) penthorumnin C (3) is a glucoside of trihydroxyacetophenone with an acyl group that is oxidatively derived from the HHDP group. This acyl group is closely related to that of balanophotannin F (4), which has been previously isolated from Balanophora japonica and whose absolute configuration has been revised using the DFT method; and (4) penthorumnin D (5) is defined as 2′,4′,6′-trihydroxyacetophenone 4′-O-[4,6-(S)-dehydrohexahydroxydiphenoyl]-β-glucoside. The variety of acyl groups in these ellagitannins is indicative of the occurrence of a unique metabolism in this plant involving the HHDP ester.

長崎大学学位論文 学位記番号:博(医歯薬)甲第1148号 学位授与年月日:平成31年3月20日

Author: Manami Era, Yosuke Matsuo, Yoshinori Saito, Koyo Nishida, Zhi-Hong Jiang, Takashi Tanaka

Citation: Journal of Natural Products, 82(1), pp.129-135; 2019

Nagasaki University (長崎大学), 博士(薬学) (2019-03-20)

http://hdl.handle.net/10069/39037

長崎大学学位論文 [学位記番号]博（医歯薬）甲第1148号 [学位授与年月日]平成31年3月20日

(2019-03-20)