北玄参根中的一个新环烯醚萜衍生物_英文_
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药学学报 Acta Pharmaceutica Sinica 2014, 49 (7): 1019−1021 · 1019 · A new iridoid derivative from the roots of Scrophularia buergeriana
WU Xi-min1†, ZHANG Liu-qiang1†, CHEN Xiao-chong1, FENG Li1, XING Wang-xing2*, LI Yi-ming1*
(1. School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; 2. School of Medicine, Hangzhou Normal University, Hangzhou 310036, China)
Abstract: Phytochemical investigation of the roots of Scrophularia buergeriana Miq. (Scrophulariaceae), resulted in the isolation of a new iridoid derivative named as buergerinin (1). Its structure was elucidated as rel-(1R, 5R, 6R)-(2-oxa-bicyclo[3.3.0]oct-7-en-6, 7-diyl)dimethoxypropane based mainly on MS and 1D and 2D NMR spectroscopic analyses. Key words: Scrophularia buergeriana; iridoid derivative; buergerinin CLC number: R284 Document code: A Article ID: 0513-4870 (2014) 07-1019-03
北玄参根中的一个新环烯醚萜衍生物 吴喜民1†, 张刘强1†, 陈小冲1, 冯 丽1, 邢旺兴2*, 李医明1* (1. 上海中医药大学中药学院, 上海 201203; 2. 杭州师范大学医学院, 浙江 杭州 310036) 摘要: 从北玄参块根中发现了一个新的环烯醚萜衍生物, 命名为buergerinin (1)。通过质谱和一、二维核磁共振谱等分析, 鉴定了该新化合物结构, 并命名为rel-(1R, 5R, 6R)-(2-oxa-bicyclo[3.3.0]oct-7-en-6, 7-diyl)dimethoxy
propane。 关键词: 北玄参; 环烯醚萜衍生物; buergerinin
The genus Scrophularia (Scrophulariaceae)
comprises about 200 species, about 36 species of which occur in China. The root of Scrophularia ningpoensis Hemsl. has been used as a traditional Chinese medicine called “Xuan-Shen”, for the
Received 2014-01-14; Accepted 2014-02-19. Project supported by Funding Scheme for Training Young Teachers in Shanghai Colleges (ZZszy13057); Shanghai Municipal Education Commission (2013JW11); the Program for Professors of Special Appointment (Eastern Scholar) in Shanghai Institutions of Higher Learning (for Y M Li), the “XingLin” Scholars and Outstanding Team Training Plan of SHUTCM and the National Natural Science Foundation of China (81173518). †Joint first authors.
*Corresponding author Tel / Fax: 86-21-51322191, E-mail: ymlius@163.com; Tel: 86-571-28865674, Fax: 86-571-51322191, E-mail: xwx117@sina.com
treatment of fever, swelling, constipation, neuritis, pharyngitis and laryngitis[1]. Scrophularia buergeriana is a perennial plant native in northern China with an important role in the traditional medicine of several oriental cultures. In northern China, the root of S.buergeriana was used as “Xuan-shen” in clinic and called as “Bei Xuan-shen”. We have reported on the isolation, structure elucidation[2, 3], as well as antioxidation[4], anti-inflammation[5], and anti-platelet aggregation[6] effects of iridoid and phenylpropanoid glycosides from S. ningpoensis. We also reported nine novel iridoid derivatives, two with new carbon skeleton among them, from S. buergeriana[7]. In our continuous chemical work on S. buergeriana, here we reported the isolation and identification of a new iridoid derivative from the titled plant. · 1020 · 药学学报 Acta Pharmaceutica Sinica 2014, 49 (7): 1019−1021 Results and discussion Compound 1 was obtained as light yellow oil. HR-EI-MS exhibited the molecular-ion peak at m/z [M]+ 210.125 5, corresponding to the molecular formula C12H18O3 (calculated for 210.125 6). Its degree of unsaturation was 4, the signals at δC 146.7 and 126.8 in the 13C NMR spectrum (Table 1), as well as the signal at δH 5.46 (1H, br s) in the 1H NMR spectrum (Table 1) indicated that 1 contained only one double bond, which was trisubstituted. In addition, 1 contained neither sugar moieties, nor carbonyl and carboxyl groups. Thus, there should be three rings in this structure. According to its DEPT spectrum and chemical shifts, one CH- group at δC 88.4 and three CH2-groups at δC 67.6, 62.4 and 60.6, should be associated with oxygen atoms. The carbon at δC 102.1 indicated an aldehyde acetal existed in its empirical formula, such as C-1 of harpagide. Finally, two methyl groups at δH 1.32 (3H, s), 1.36 (3H, s) and δC 24.5, 25.0 were observed in the NMR spectra. Based on the above spectroscopic evidence, the chemical shifts of 1 were the most plausible according with ningpogenin, which was obtained from S. ningpoensis[8], except for δC 24.5, 25.0 and 102.1, which suggested that there was a more aldehyde acetal group in 1. The above conclusion was further elucidated by 2D NMR spectroscopy, including HMQC, HMBC, 1H-1H COSY and NOESY. In HMBC, there was a long-range coupling between δH 1.32 (3H, s) and δC 25.0, between δH 1.36 (3H, s) and δC 24.5, as well as between protons of two methyl groups (δH 1.32, 1.36) and the carbon at δC 102.1, so the connection of the two methyl groups to the carbon at δC 102.1 was confirmed. In the meantime, there were two long-range couplings between H-9, H-10 and the carbon at δC 102.1, implicating that C-9 and C-10 were each connected through the oxygen atom to the carbon at δC 102.1, which formed the third ring together with C-6, 7. Hence the structure of compounds 1 is elucidated as rel-(1R, 5R, 6R)-(2-oxa-bicyclo[3.3.0] oct-7-en-6, 7-diyl)dimethoxypropane (Figure 1), namely buergerinin. Figure 1 Structure of compound 1 Experimental General experimental procedures Column chromatography (CC): silica gel (SiO2, 200−300 mesh, Qingdao Haiyang Co., China), Sephadex LH-20 (Pharmacia Biotech AB, Uppsala, Sweden). ODS (Greenberbs Science & Technology Development Co., Ltd., Beijing, China). TLC: silica gel HSGF254 (Yantai
