Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita

被引:17
|
作者
Rahim, Abdul [1 ,2 ]
Saito, Yohei [1 ]
Miyake, Katsunori [3 ]
Goto, Masuo [4 ]
Chen, Chin-Ho [5 ]
Alam, Gemini [2 ]
Morris-Natschke, Susan [4 ]
Lee, Kuo-Hsiung [4 ,6 ]
Nakagawa-Goto, Kyoko [1 ,4 ]
机构
[1] Kanazawa Univ, Sch Pharmaceut Sci, Coll Med Pharmaceut & Hlth Sci, Kanazawa, Ishikawa 9201192, Japan
[2] Hasanuddin Univ, Dept Pharmacognosy Phytochem, Fac Pharm, Makassar, Indonesia
[3] Tokyo Univ Pharm & Life Sci, Hachioji, Tokyo 1920392, Japan
[4] Univ N Carolina, UNC Eshelman Sch Pharm, Div Chem Biol & Med Chem, Chapel Hill, NC 27599 USA
[5] Duke Univ, Med Ctr, Durham, NC 27710 USA
[6] China Med Univ & Hosp, Chinese Med Res & Dev Ctr, Taichung 401, Taiwan
来源
JOURNAL OF NATURAL PRODUCTS | 2018年 / 81卷 / 07期
关键词
IN-VITRO; LEAVES; CONSTITUENTS; INHIBITORS; BARK;
D O I
10.1021/acs.jnatprod.8b00211
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A novel cycloartane triterpenoid alkaloid, kleinhospitine E (1), six new cycloartane triterpenoids (2-7), three known cycloartane triterpenoids (8-10), and taraxerone (11) were isolated from a methanol extract of Kleinhovia hospita. Their structures were elucidated by 1D- and 2D-NMR spectroscopy as well as HRMS analysis. The absolute configurations of all isolated compounds were determined from their ECD spectra by comparison with theoretical values. Kleinhospitine E (1) is the first cycloartane alkaloid possessing an unusual gamma-lactam with an oxopropylidene side chain. Compounds 2, 3, and 6 were assigned as cycloartane triterpenoids with a 9 alpha,10 alpha-cyclopropyl ring, which is found rarely among naturally occurring compounds, while 4 and 5 were established as isomers of compound 3 containing a 21,23-diacetal side chain. Biological evaluation revealed that compounds 4 and 9 exhibited more potent antiproliferative activities against a multidrug-resistant tumor cell line compared with its parent chemosensitive cell line. Furthermore, compound 6 exhibited submicromolar anti-HIV activity.
引用
收藏
页码:1619 / 1627
页数:9
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