Chemical studies on monoterpenoid indole alkaloids from medicinal plant resources Gelsemium and Ophiorrhiza

被引:72
作者
Kitajima, Mariko [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
基金
日本学术振兴会;
关键词
indole alkaloid; Gelsemium; gelsedine; anti-tumor; camptothecin; Ophiorrhiza;
D O I
10.1007/s11418-006-0101-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We have proved that the plant of origin of "Yakatsu", one of the ancient medicines stored in Shosoin Repository, is Gelsemium elegans (Loganiaceae). Exhaustive investigation of the alkaloids in this plant as well as its closely related plant, G. sempervirens, resulted in the isolation of more than 50 compounds, including new gelsedine-, sarpagine-, and yohimbane-type. alkaloids. Pharmacological study of representative and new Gelsemium alkaloids revealed that the gelsedine-type alkaloids exhibit potent cytotoxic activity against the A431 human epidermoid carcinoma cell line. It was found that Ophiorrhiza pumila (Rubiaceae) produces a remarkable anti-tumor alkaloid, camptothecin, and its related alkaloids, including new compounds that might be the biogenetic precursors of camptothecin. Chemical investigation of callus cultures, regenerated plants, and hairy roots of O. pumila revealed that the regenerated plants and the hairy roots produce almost the same alkaloids, including camptothecin, as do the wild-type plants.
引用
收藏
页码:14 / 23
页数:10
相关论文
共 33 条
[1]  
AIMI N, 1986, CHEM PHARM BULL, V34, P3064
[2]   SYNTHESIS AND ABSOLUTE-CONFIGURATION OF CHABOSIDE, 1ST NATURAL GLUCO-CAMPTOTHECIN [J].
AIMI, N ;
UENO, M ;
HOSHINO, H ;
SAKAI, S .
TETRAHEDRON LETTERS, 1992, 33 (37) :5403-5404
[3]   STRUCTURE OF OPHIORINE-A AND OPHIORINE-B - NOVEL TYPE GLUCO INDOLE ALKALOIDS ISOLATED FROM OPHIORRHIZA SPP [J].
AIMI, N ;
TSUYUKI, T ;
MURAKAMI, H ;
SAKAI, S ;
HAGINIWA, J .
TETRAHEDRON LETTERS, 1985, 26 (43) :5299-5302
[4]   PUMILOSIDE AND DEOXYPUMILOSIDE - PLAUSIBLE INTERMEDIATES OF CAMPTOTHECIN BIOSYNTHESIS [J].
AIMI, N ;
NISHIMURA, M ;
MIWA, A ;
HOSHINO, H ;
SAKAI, S ;
HAGINIWA, J .
TETRAHEDRON LETTERS, 1989, 30 (37) :4991-4994
[5]   CHABOSIDE, 1ST NATURAL GLYCOCAMPTOTHECIN FOUND FROM OPHIORRHIZA-PUMILA [J].
AIMI, N ;
HOSHINO, H ;
NISHIMURA, M ;
SAKAI, SI ;
HAGINIWA, J .
TETRAHEDRON LETTERS, 1990, 31 (36) :5169-5172
[6]   THE ALKALOIDS OF OPHIORRHIZA-FILISTIPULA [J].
ARBAIN, D ;
PUTRA, DP ;
SARGENT, MV .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (07) :977-985
[7]  
CHIN DB, 2003, ACAD J 1 MED COLL PL, V23, P911
[8]   BIOSYNTHESIS OF CAMPTOTHECIN .3. DEFINITION OF STRICTOSAMIDE AS THE PENULTIMATE BIOSYNTHETIC PRECURSOR ASSISTED BY C-13 AND H-2 NMR-SPECTROSCOPY [J].
HUTCHINSON, CR ;
HECKENDORF, AH ;
STRAUGHN, JL ;
DADDONA, PE ;
CANE, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (12) :3358-3369
[9]   Isolation and partial synthesis of 3(R)- and 3(S)-deoxypumiloside; Structural revision of the key metabolite from the camptothecin producing plant, Ophiorrhiza pumila [J].
Kitajima, M ;
Masumoto, S ;
Takayama, H ;
Aimi, N .
TETRAHEDRON LETTERS, 1997, 38 (24) :4255-4258
[10]   Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila [J].
Kitajima, M ;
Yoshida, S ;
Yamagata, K ;
Nakamura, M ;
Takayama, H ;
Saito, K ;
Seki, H ;
Aimi, N .
TETRAHEDRON, 2002, 58 (45) :9169-9178