Constituents of Two Indonesian Gingers, Alpinia galanga and Curcuma heyneana

Abstract

trans-p-Coumaryl alcohol-O-methyl ether (11, EA205HC-11-1-K14), 1'S-1'-acetoxychavicol acetate (12, EA205HC-11-1-K11), trans-p-coumaryl diacetate (13, EA205HC-11-10-K5), and 1'R-1'-hydroxychavicol acetate (14, EA205HC-11-29-K1) were obtained from the n-hexane and EtOAc extract of Alpinia galanga (L.) Willd. (Zingiberaceae). The structures of the compounds obtained in the present investigation were identified using 1D- and 2D- NMR techniques such as DEPT, 1H-13C HSQC, 1H-13C HMBC, 1H-1H COSY, and 1H-1H NOESY experiments as well as by comparing their data with the published data. p-Coumaryl alcohol γ-O-methyl ether (11) which was found as an antioxidant compound11 previously, was isolated from A. galanga for the first time in the present study. And also 1'R-1'-hydroxychavicol acetate (14) was isolated from natural products for the fist time. To the best of our knowledge, this is also the first report on the cytotoxic activity of compound 11. A new stereoisomer, 1-epi-zedoarondiol (22, EA196H-11-40-K1), was isolated from the n-hexane and CHCl3 extract of the rhizomes of Curcuma heyneana Val. & V. Zijp (Zingiberaceae) along with four other known compounds, zedoarondiol (23, EA196C-11-42-K39), demethoxycurcumin (24, EA196C-11-42-K24), germacrone (25, EA196H-11-32-K1), and dehydrocurdione (26, EA196C-11-48-K3). The structures of the compounds obtained in the present investigation were identified using 1D- and 2D- NMR techniques such as DEPT, 1H-13C HSQC, 1H-13C HMBC, 1H-1H COSY, and 1H-1H NOESY experiments as well as by comparing their data with the published data. Compounds 23 and 24 were isolated from this plant for the first time.;Alpinia galanga (생강과) 의 근경의 헥세인과 클로로포름 추출 분획물은 인간 암세포들에 유효성을 나타내었고, 이에 근거하여 활성 추적 분획법을 실시하였다. Alpinia galanga로부터 trans-p-coumaryl alcohol-O-methyl ether (11, EA205HC-11-1-K14)가 이 식물에서 처음 분리되었으며, 이미 보고된 바 있는 1'S-1'-Acetoxychavicol acetate (12, EA205HC-11-1-K11)와 trans-p-coumaryl diacetate (13, EA205HC-11-10-K5)도 함께 분리되었다. 1'R-1'-hydroxychavicol acetate (14, EA205HC-11-29-K1)도 역시 분리되었는데, 이는 천연물 유래 물질로는 처음 보고하는 바이다. 화합물들의 구조는 각종 이화학적 및 분광학적 기법을 사용한 분석하였다. 세포 독성 시험에서, 물질 11, 12, 13은 각각의 인간 암세포들에 대하여 유효성을 보였다. 나아가 물질 11에 대한 세포 독성은 처음 보고되는 바이다. Curcuma heyneana (생강과)의 근경의 헥세인과 클로로포름 추출 분획물로부터 새로운 구조 이성체이며 Guaiane 유형의 sesquiterpenoid 중의 한 물질인 1-epi-zedoarondiol (22, EA196H-11-40-K1)이 네 개의 알려진 구조인 zedoarondiol (23, EA196C-11-42-K39), demethoxycurcumin (24, EA196C-11-42-K24), germacrone (25, EA196H-11-32-K1), dehydrocurdion (26, EA196C-11-48-K3)과 함께 분리되었다. Zedoarondiol (23, EA196C-11-42-K39)과 demethoxycurcumin (24, EA196C-11-42-K24)은 이 식물에서 처음 분리되었다. 새로운 화합물의 구조는 각종 이화학적 및 분광학적 기법을 사용하여 분석하였다.