SUBMICROMOLE STRUCTURE ELUCIDATION - CRYPTOLEPICARBOLINE - A NOVEL DIMERIC ALKALOID FROM CRYPTOLEPIS-SANGUINOLENTA

被引:36
作者
SHARAF, MHM
SCHIFF, PL
TACKIE, AN
PHOEBE, CH
HOWARD, L
MEYERS, C
HADDEN, CE
WRENN, SK
DAVIS, AO
ANDREWS, CW
MINICK, D
JOHNSON, RL
SHOCKCOR, JP
CROUCH, RC
MARTIN, GE
机构
[1] BURROUGHS WELLCOME CO,BIOANALYT SCI,RES TRIANGLE PK,NC 27709
[2] UNIV PITTSBURGH,SCH PHARM,DEPT PHARMACEUT SCI,PITTSBURGH,PA 15261
[3] CTR SCI RES PLANT MED,MAMPONG AKWAPIM,GHANA
[4] WATERS INC,MILFORD,MA 01757
[5] VARIAN NMR INSTRUMENTS,PALO ALTO,CA 94303
关键词
ALKALOID STRUCTURE; CRYPTOLEPICARBOLINE; MICROPROBE; NANO-PROBE;
D O I
10.1002/mrc.1260331003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cryptolepis sanguinolenta (Lindl.) Schlechter (Asclepiadaceae), a shrub indigenous to West Africa, has been employed by traditional healers in the treatment of various fevers, including malaria, Column chromatography of the alkaloid fraction obtained from a defatted ethanolic extract of the roots of the plant afforded the previously characterized alkaloids cryptolepine, quindoline and cryptospirolepine. Continued extensive column chromatography, followed by preparative high-performance liquid chromatography, resulted in the isolation of nine new alkaloids, including approximately 100 mu g of a novel indoloquinoline-beta-carboline dimeric alkaloid, cryptolepicarboline. The structure was elucidated through the use of a combination of spectroscopic techniques which included UV, Fourier transform, electron impact mass spectrometry, and 500 MHz NMR spectroscopy. NMR data included 1D H-1 and C-13 reference spectra, the latter recorded in 40 mu l of DMSO-d(6) using a new Varian heteronuclear Nano-probe and in 140 mu l of DMSO-d(6) using a Nalorac carbon-optimized microprobe. These C-13 NMR spectra allow the first direct comparison of these two probe formats. Homonuclear 2D NMR data acquired included both COSY and ROESY spectra. The homonuclear 2D experiments were variously performed in both a homonuclear Nano-probe and micro-inverse detection probes. Heteronuclear shift correlation experiments included HMQC, HMBC and IDR (inverted direct response)-HMQC-TOCSY spectra, which were uniformly performed using a 500 MHz Nalorac micro inverse-detection probe.
引用
收藏
页码:767 / 778
页数:12
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