Chemical Constituents and Anti-inflammatory Activity from the Root of Beilschmiedia tsangii

• Main Authors: Yun-Ting Huang, 黃筠婷
• Other Authors: Ih-Sheng Chen
• Format: Others
• Language: zh-TW
• Published: 2011
• Online Access: http://ndltd.ncl.edu.tw/handle/63218697579865746687

碩士 === 高雄醫學大學 === 天然藥物研究所 === 99 === Beilschmiedia tsangii Merr. (Lauraceae) is a medium sized evergreen tree, distributed in Vietnam to Yunnan, Kwangsi, Kwangtung in China, and Taiwan, which is only in Kaohsiung and Pingtung Counties. Beilschmiedia genus in Taiwan only has 2 species: B. tsangii and B. erythrophloia. The root of B. erythrophloia has been studied and isolated many endiandric acid derivatives previously. However, previous studies on stem and leaves of B. tsangii didn’t discover endiandric acid derivatives. On the other hand, the phytochemistry and biological activities of its root have never been conducted. Recently, over 40 species of Formosan Lauraceous plants have been screened for anti-inflammatory activity with inducible nitric oxide synthase (iNOS) assay and the methanolic extract of root of this species showed potent inhibition of NO production without any cytotoxicity against RAW 264.7 cells. Based on the phytochemistry and biological activity investigation, the aim of this study is the isolation of chemical constituents and their iNOS inhibitory activities. Bioassay-guided fractionation of the active ethyl acetate extract of the root of this species led to the isolation of ten new endiandric acid analogues: tsangibeilin A (1), tsangibeilin B (2), tsangibeilin C (3), tsangibeilin D (4), endiandramide A (5), endiandric acid K (6), endiandramide B (7), endiandric acid L (8), endiandric acid M (9), and tricyclotsangibeilin (10), two new tetrahydrofuran-type lignans: beilschminol A (11), beilschminol B (12), one new benzenoid: tsangin C (13), one new sesquiterpene: (+)-5-hydroxybarbatenal (14), and one sesquiterpene first isolated from nature: (4R,5R)- 4,5-dihydroxycaryophyll-8(13)-ene (15), together with ten known compounds: rel-(7R,8R,7''R,8''R)-3'',4''-methylenedioxy-3,4,5,5''-tetramethoxy-7,7''-epoxylignin (16), rel- (7R,8R,7''R,8''R)-3,4,3'',4''-dimethylenedioxy-5,5''-dimethoxy-7,7''-epoxylignan (17), rel- (7S,8S,7''R,8''R)-3,3'',4,4'',5,5''-hexamethoxylignan (18), 3,4,5-trimethoxybenzaldehyde (19), octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)-1H-indene-1- methanol (20), eudesm-4(15)-ene-1β,6α-diol (21), ursolic acid (22), vanillin (44), β-sitosterol (102) and 6β-hydroxystigmast-4-en-3-one (106). The structures of isolates were determined by spectroscopic techniques. Endiandric acids derivatives and lignans both showed iNOS inhibitory activity. Among the isolates, endiandramides A, B (5, 7) exhibited potent iNOS inhibitory activity with IC50 values of 9.59 and 16.40 μM, respectively, which are even better than positive controls.