NMR STRUCTURE DETERMINATION AND INTRAMOLECULAR TRANSESTERIFICATION OF 4 DIACETYL TAXININES WHICH CO-ELUTE WITH TAXOL OBTAINED FROM TAXUS X MEDIA HICKSII NEEDLES

被引：18

作者：

CHMURNY, GN ^{[1
]}

PAUKSTELIS, JV ^{[1
]}

ALVARADO, AB ^{[1
]}

MCGUIRE, MT ^{[1
]}

SNADER, KM ^{[1
]}

MUSCHIK, GM ^{[1
]}

HILTON, BD ^{[1
]}

机构：

[1] NCI,DCT,DTP,NPB,FREDERICK,MD 21702

来源：

PHYTOCHEMISTRY | 1993年 / 34卷 / 02期

关键词：

TAXUS X MEDIA; TAXACEAE; YEW; NEEDLES; NMR; TAXININES; TAXOL; TRANSESTERIFICATION;

D O I：

10.1016/0031-9422(93)80034-P

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The isolation of taxol from Taxus x. media Hicksii includes four taxinines which co-elute and interfere with HPLC analyses of taxol. Their structures: 1,9alpha-dihydroxy-2alpha,10beta-diacetoxy-5alpha-cinnamatetaxa-4(20),11-diene-13-one; 1,10beta-dihydroxy-2alpha,9alpha-diacetoxy-5alpha-cinnamatetaxa-4(20),11-diene-13-one;2alpha,9alpha-dihydroxy-10beta,13alpha-diacetoxy-5alpha-cinnamatetaxa-4(20),11-diene and; 2alpha,10beta-dihydroxy-9alpha,13alpha-diacetoxy-5alpha-cinnamatetaxa-4(20),11-diene, have been determined by 1D(H-1, C-13) and 2D(DQCOSY, TOCSY, HMQC, HMBC and TROESY) NMR spectroscopy. Transacetylation between 10beta and 9alpha on the baccatin core has been documented to occur in CDCl3 and CD3OD at 27-degrees. Interatomic distances were obtained from TROESY build-up curves of the first compound and were compared to those obtained from a computer minimized structure.

引用

页码：477 / 483

页数：7

共 28 条

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