Two new pyridine monoterpene alkaloids by chemical conversion of a commercial extract of Harpagophytum procumbens

被引：21

作者：

Baghdikian, B

Ollivier, E

Faure, R

Debrauwer, L

Rathelot, P

Balansard, G

机构：

[1] Univ Aix Marseille 2, Fac Pharm, Lab Pharmacogonosy, F-13397 Marseille 5, France

[2] Univ Aix Marseille 2, Fac Pharm, Organ Chem Lab, F-13397 Marseille 5, France

[3] Univ Aix Marseille 3, ESA 6009, F-13397 Marseille 20, France

[4] INRA, Ctr Res Toulouse, Lab Xenobiot, F-31931 Toulouse, France

来源：

JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 02期

关键词：

D O I：

10.1021/np980149c

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The treatment of harpagide (1), harpagoside (2), or 8-O-p-coumaroylharpagide (3), the main iridoids of Harpagophytum procumbens and Harpagophytum zeyheri, with NH3 and HCl led to aucubinine B(4), a pyridine monoterpene alkaloid (PMTA). A similar procedure applied to a commercial extract of H. procumbens yielded 4 and two new PMTAs named beatrine A (5) and beatrine B (6). The structures of these new PMTAs were established using ESIMS and 2D NMR. Their semisynthesis was analyzed in terms of reaction mechanisms.

引用

收藏

页码：211 / 213

页数：3

相关论文

共 12 条

[1] An analytical study, anti-inflammatory and analgesic effects of Harpagophytum procumbens and Harpagophytum zeyheri [J].

Baghdikian, B ;

Lanhers, MC ;

Fleurentin, J ;

Ollivier, E ;

Maillard, C ;

Balansard, G ;

Mortier, F .

PLANTA MEDICA, 1997, 63 (02) :171-176

[2] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].

BAX, A ;

SUMMERS, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094

[3] SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].

BAX, A ;

SUBRAMANIAN, S .

JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569

[4] SELECTION OF COHERENCE-TRANSFER PATHWAYS IN NMR PULSE EXPERIMENTS [J].

BODENHAUSEN, G ;

KOGLER, H ;

ERNST, RR .

JOURNAL OF MAGNETIC RESONANCE, 1984, 58 (03) :370-388

[5]

DRODDELL DM, 1982, J MAGN RESON, V48, P323

[6] METABOLISM OF SWERTIAMARIN FROM SWERTIA-JAPONICA BY HUMAN INTESTINAL BACTERIA [J].

ELSEDAWY, AI ;

SHU, YZ ;

HATTORI, M ;

KOBASHI, K ;

NAMBA, T .

PLANTA MEDICA, 1989, (02) :147-150

[7] Synthesis of monoterpene piperidines from the iridoid glucoside antirrhinoside [J].

Franzyk, H ;

Frederiksen, SM ;

Jensen, SR .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (10) :1012-1016

[8] Pyridine monoterpene alkaloid formation from iridoid glycosides. A novel PMTA dimer from geniposide [J].

Frederiksen, SM ;

Stermitz, FR .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (01) :41-46

[9] TRANSFORMATION OF AUCUBIN TO NEW PYRIDINE MONOTERPENE ALKALOIDS, AUCUBININE-A AND AUCUBININE-B, BY HUMAN INTESTINAL BACTERIA [J].

HATTORI, M ;

KAWATA, Y ;

INOUE, K ;

SHU, YZ ;

CHE, QM ;

NAMBA, T ;

KOBASHI, K .

PHYTOTHERAPY RESEARCH, 1990, 4 (02) :66-70

[10] FORMATION OF NITROGEN-CONTAINING METABOLITES FROM GENIPOSIDE AND GARDENOSIDE BY HUMAN INTESTINAL BACTERIA [J].

KAWATA, Y ;

HATTORI, M ;

AKAO, T ;

KOBASHI, K ;

NAMBA, T .

PLANTA MEDICA, 1991, 57 (06) :536-542