Two new rearranged clerodane diterpenes from Thai Tinospora baenzigeri
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Two new rearranged clerodane diterpenes from Thai Tinospora baenzigeri Sujitra Hanthanong1 · Siwattra Choodej2 · Thammarat Aree2 · Khanitha Pudhom2 Received: 26 July 2020 / Accepted: 14 September 2020 © The Japanese Society of Pharmacognosy 2020
Abstract A new rearranged clerodane-type diterpene (1), tinobaenzigeride, and a new rearranged clerodane glucoside (2) were isolated from the stems of Tinospora baenzigeri, along with four known compounds (3‒6). Their structures were elucidated by spectroscopic data analysis. In addition, the structure and configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 1 are a rare example of rearranged clerodanes, since it contains a fully oxygenated tetrahydrofuran moiety. The isolated compounds were evaluated for their cytotoxicity against Hep-G2 and MCF-7 cancer cells, none of them did show any significant activity at 25 μM.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11418-020-01450-5) contains supplementary material, which is available to authorized users. * Khanitha Pudhom [email protected] 1
Graduate Program in Biotechnology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
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Vol.:(0123456789)
Journal of Natural Medicines
Graphic abstract
Keywords Tinospora baenzigeri · Rearranged clerodane · Diterpene · Cytotoxicity
Introduction The genus Tinospora (Family Menispermacae) contains about 30 species, widely distributed in tropical and subtropical areas of Asia, Africa, Australia, and the Pacific [1, 2]. T. baenzigeri, known as “Chingcha Chalee”, is one of the two species well-known in Thailand and has long used for antipyretic and antimalarial treatment; however, its chemical investigation has not been extensively studied. Previous studies on the chemical constituents of Tinospora sp. have resulted in the isolation of several phytochemical classes with the clerodane-type furanoditerpenes as typical secondary metabolites [3–8], while those of T. baenzigeri provided the difference in that the main chemicals are rearranged clerodane furanoditerpenes. To date, there have been a few phytochemical investigations on the plant [9, 10], and more recently, we have reported the isolation and characterization of a series of rearranged clerodanes from T. baenzigeri collected from the central part of Thailand [11]. Since it is well known that the production of the secondary metabolites is
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also effected by environmental and geographical factors, we have decided to study the chemical constituents of the plant collected from Bueng Kan province, far northeastern Thailand due to its different chemical profile observed. Phytochemical investigation of the stems of T. baenzigeri yielded two new rearranged clerodane diterpenes (1‒2) and four known compounds including three flavonoids (3‒5) and one lignan (6) (Fig. 1). Herein, details of the isolation, struct
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