Melongenaterpenes A-L, Vetispirane-Type Sesquiterpenoids from the Roots of Solanum melongena

被引:20
作者
Yin, Xin [1 ,2 ]
Liu, Yan [1 ]
Pan, Juan [1 ]
Ye, Hong-Liang [1 ]
Sun, Yan [1 ]
Zhao, Dong-Ying [1 ]
Kuang, Hai-Xue [1 ]
Yang, Bing-You [1 ]
机构
[1] Heilongjiang Univ Chinese Med, Minist Educ, Key Lab Chinese Mat Med, Harbin 150040, Peoples R China
[2] Guizhou Univ Tradit Chinese Med, Guiyang 550000, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2019年 / 82卷 / 12期
基金
中国博士后科学基金;
关键词
GLYCOSIDES; STEREOCHEMISTRY; METABOLITES; DERIVATIVES; LUBIMIN;
D O I
10.1021/acs.jnatprod.9b00206
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Melongenaterpenes A-L (1-12), 12 new sesquiterpenoids with rare spiro[4.5]decane skeletons, were isolated from the roots of Solanum melongena. Their 2D structures and relative configurations were determined based on NMR and HRESIMS data. The absolute configuration of melongenaterpene A (1) was defined by X-ray crystallographic analysis. The absolute configurations of the remaining compounds were determined by comparison of their NMR data with 1 and consideration of the biosynthetic pathway. This is the first report of the crystal structure of a vetispirane-type sesquiterpenoid. None of the compounds exhibited cytotoxic activity against the three human cancer cell lines HepG2, HeLa, and MCF-7.
引用
收藏
页码:3242 / 3248
页数:7
相关论文
共 20 条
[1]   VETISPIRANE SESQUITERPENE GLUCOSIDES FROM FLUE-CURED VIRGINIA TOBACCO - STRUCTURE, ABSOLUTE STEREOCHEMISTRY, AND SYNTHESIS - X-RAY STRUCTURE OF PARA-BROMOBENZENESULFONATE OF ONE OF DERIVED AGLYCONES [J].
ANDERSON, RC ;
GUNN, DM ;
MURRAYRUST, J ;
MURRAYRUST, P ;
ROBERTS, JS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (01) :27-28
[2]  
[Anonymous], CHINESE MATERIA MED
[3]  
Engström K, 1998, PHYTOCHEMISTRY, V47, P985, DOI 10.1016/S0031-9422(97)00699-7
[4]   Post-infectional metabolites from infected potato tubers [J].
Engström, K .
PHYTOCHEMISTRY, 1998, 49 (06) :1585-1587
[5]   Antifungal activity to Phytophthora infestans of sesquiterpenoids from infected potato tubers [J].
Engström, K ;
Widmark, AK ;
Brishammar, S ;
Helmersson, S .
POTATO RESEARCH, 1999, 42 (01) :43-50
[6]   H-1-NMR STUDY OF THE STEREOCHEMISTRY OF LUBIMIN AND RELATED VETISPIRANE SESQUITERPENOIDS [J].
EWING, DF ;
WHITEHEAD, IM ;
ATKINSON, A ;
THRELFALL, DR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (02) :343-348
[7]   Bioactive Sesquiterpenoids from the Rhizomes of Acorus calamus [J].
Hao, Zhi-You ;
Liang, Dong ;
Luo, Huan ;
Liu, Yan-Fei ;
Ni, Gang ;
Zhang, Qing-Jian ;
Li, Li ;
Si, Yi-Kang ;
Sun, Hua ;
Chen, Ruo-Yun ;
Yu, De-Quan .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (06) :1083-1089
[8]   STUDIES ON PHYTOALEXINS .14. LUBIMIN AND OXYLUBIMIN - STRUCTURE ELUCIDATION [J].
KATSUI, N ;
MATSUNAGA, A ;
KITAHARA, H ;
YAGIHASHI, F ;
MURAI, A ;
MASAMUNE, T ;
SATO, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (05) :1217-1225
[9]   New sesquiterpenes from Capsicum annuum [J].
Kawaguchi, Y ;
Ochi, T ;
Takaishi, Y ;
Kawazoe, K ;
Lee, KH .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (11) :1893-1896
[10]   New sesquiterpenoid derivatives from Solanum lyratum and their cytotoxicities [J].
Li, Gui-Sheng ;
Yao, Fang ;
Zhang, Lei ;
Yue, Xi-Dian ;
Dai, Sheng-Jun .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2014, 16 (02) :129-134