从少药八角果实中分离得到的具有抗氧化和抗炎活性的新型倍半萜内酯及新木脂素糖苷。

New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum.

作者信息

Tang Wen-Zhao, Liu Yun-Bao, Yu Shi-Shan, Qu Jing, Su Dong-Min

机构信息

Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China.

出版信息

Planta Med. 2007 May;73(5):484-90. doi: 10.1055/s-2007-967189. Epub 2007 Apr 26.

DOI:10.1055/s-2007-967189

PMID:17458778

Abstract

Phytochemical investigations of the fruits of Illicium oligandrum resulted in a new sesquiterpene lactone, 3 beta-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7 R,8 S)-9-O-beta-D-xylopyranosyl-9'-O-alpha- L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7 R,8 S)-9-O-shikimoyl-4-O-beta-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (3) and one 8- O-4' neolignan glycoside, (7 S,8 R)-1-[4-O-(beta-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (4), together with three known sesquiterpene lactones (5 - 7) and two known neolignan glycosides (8 and 9). Their structures were elucidated on the basis of 1D, 2D NMR, HR-MS and chemical evidence. Compounds 3 and 4 showed moderate antioxidant activity with the inhibitory rates 13.30% and 9.30% at 1.0 x 10(-5) M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0% and 51.0% at 1.0 x 10(-5) M, respectively.

摘要

对少药八角果实进行的植物化学研究得到了一种新的倍半萜内酯，3β-苯甲酰氧基-10-脱氧佛罗里达内酯（1），以及三种新的新木脂素糖苷，包括两种二氢苯并呋喃新木脂素糖苷，（7R，8S）-9-O-β-D-吡喃木糖基-9'-O-α-L-吡喃鼠李糖基-（1→6）-β-D-吡喃葡萄糖基二氢去氢双松柏醇（2）和（7R，8S）-9-O-莽草酸基-4-O-β-D-吡喃葡萄糖基二氢去氢双松柏醇（3），以及一种8-O-4'新木脂素糖苷，（7S，8R）-1-[4-O-（β-D-吡喃葡萄糖基）-3-甲氧基苯基]-2-[4-（3-羟丙基）-2,6-二甲氧基苯氧基]-1,3-丙二醇（4），还有三种已知的倍半萜内酯（5 - 7）和两种已知的新木脂素糖苷（8和9）。它们的结构通过一维、二维核磁共振、高分辨质谱和化学证据得以阐明。化合物3和4在1.0×10⁻⁵ M时表现出中等抗氧化活性，抑制率分别为13.30%和9.30%。化合物3和9在1.0×10⁻⁵ M时表现出抗炎活性，抑制率分别为67.0%和51.0%。