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Xylogranatins A-D: novel tetranortriterpenoids with an unusual 9,10-seco scaffold from marine mangrove Xylocarpus granatum.
- Source :
-
Organic letters [Org Lett] 2006 Oct 12; Vol. 8 (21), pp. 4935-8. - Publication Year :
- 2006
-
Abstract
- [reaction: see text] Four novel tetranortriterpenoids, xylogranatins A-D (1-4), with an unusual 9,10-seco skeleton were isolated from the seeds of a Chinese marine mangrove Xylocarpus granatum. Their structures were determined by spectroscopic and chemical means. Xylogranatin A (1) featured by a unique 1,9-oxygen bridge was confirmed by single-crystal X-ray diffraction, and xylogranatin D (4) with an unprecedented skeleton of C-30-C-9 linkage was postulated biogenetically from 3 via an alpha-hydroxyl ketone rearrangement and was chemically mimicked.
- Subjects :
- Animals
Antineoplastic Agents, Phytogenic pharmacology
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Leukemia P388
Limonins pharmacology
Mice
Molecular Conformation
Molecular Structure
Antineoplastic Agents, Phytogenic chemistry
Antineoplastic Agents, Phytogenic isolation & purification
Limonins chemistry
Limonins isolation & purification
Meliaceae chemistry
Plants, Medicinal chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 8
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 17020340
- Full Text :
- https://doi.org/10.1021/ol062101t