Novel Benzil and Isoflavone Derivatives from Millettia dielsiana

被引:46
作者
Gong, Ting [1 ,2 ,3 ]
Wang, Dong-Xiao [4 ]
Chen, Ruo-Yun [1 ,2 ,3 ]
Liu, Ping [4 ]
Yu, De-Quan [1 ,2 ,3 ]
机构
[1] Chinese Acad Med Sci, Inst Mat Med, Beijing 100050, Peoples R China
[2] Minist Educ, Key Lab Bioact Subst & Resources Utilizat Chinese, Beijing, Peoples R China
[3] Peking Union Med Coll, Beijing 100021, Peoples R China
[4] Gen Hosp Chinese PLA, Dept Clin Pharmacol, Beijing, Peoples R China
基金
中国国家自然科学基金;
关键词
Millettia dielsiana Harms; Leguminosae; benzil; prenylated isoflavones; millesianins A-E; Snatzke's method; ABSOLUTE-CONFIGURATION; ROOT BARK; FLAVONOIDS; STEM;
D O I
10.1055/s-0028-1112203
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The analysis of vine stem extract from Millettia dielsiana Harms yielded a novel benzil (1) and five new prenylated isoflavones (2-6) together with three known isoflavones (7-10) and one known flavone (11), and their structures were elucidated on the basis of chemical and spectral analysis. The absolute configuration of the 3 '',4 '' diols in 6 was determined by observing the CD induced after addition of dimolybdenum tetraacetate in DMSO solution (Snatzke's method). Some isolates were tested for their anti-inflammatory and antithrombase activities and cytotoxicities. Compound 2, barbigerone, and genistein showed significant anti-inflammatory activity, with inhibitory ratios 59.1%, 59.5%, and 58.5%, respectively, at 10 mu M, while compound 4 exhibited moderate cytotoxicity.
引用
收藏
页码:236 / 242
页数:7
相关论文
共 25 条
[1]   Determination of absolute configuration of acyclic 1,2-diols with Mo2(OAc)4.: 1.: Snatzke's method revisited [J].
Di Bari, L ;
Pescitelli, G ;
Pratelli, C ;
Pini, D ;
Salvadori, P .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4819-4825
[2]  
Dominguez X.A., 1991, REV LATINOAM QUIM, V22, P94
[3]   Cube resin insecticide: Identification and biological activity of 29 rotenoid constituents [J].
Fang, NB ;
Casida, JE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (05) :2130-2136
[4]   Comparison of five thrombin time reagents [J].
Flanders, MM ;
Crist, R ;
Rodgers, GM .
CLINICAL CHEMISTRY, 2003, 49 (01) :169-172
[5]  
Gong Ting, 2007, Zhongguo Zhong Yao Za Zhi, V32, P2138
[6]  
Górecki M, 2006, POL J CHEM, V80, P523
[7]   Practical method for the absolute configuration assignment of tert/tert 1,2-diols using their complexes with Mo2(OAc)4 [J].
Gorecki, Marcin ;
Jablonska, Ewa ;
Kruszewska, Anna ;
Suszczynska, Agata ;
Urbanczyk-Lipkowska, Zofia ;
Gerards, Michael ;
Morzycki, Jacek W. ;
Szczepek, Wojciech J. ;
Frelek, Jadwiga .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :2906-2916
[8]   Synthesis and antitumor activity of cholest-4α-methyl-7-en-3β-ol derivatives [J].
He, Lan ;
Liu, Yumei ;
Shi, Jiangong ;
Pei, Qiang .
STEROIDS, 2006, 71 (06) :476-483
[9]   Chemical constituents of Millettia taiwaniana:: Structure elucidation of five new isoflavonoids and their cancer chemopreventive activity [J].
Ito, C ;
Itoigawa, M ;
Kojima, N ;
Tokuda, H ;
Hirata, T ;
Nishino, H ;
Furukawa, H .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07) :1125-1130
[10]   Isolation and structure determination of bioactive isoflavones from callus culture of Dipteryx odorata [J].
Januário, AH ;
Lourenço, MV ;
Domézio, LA ;
Pietro, RCLR ;
Castilho, MS ;
Tomazela, DM ;
da Silva, MFGF ;
Vieira, PC ;
Fernandes, JB ;
França, SD .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (07) :740-742