Novel Cytotoxic, Polyprenylated Heptacyclic Xanthonoids from Indonesian Garcinia gaudichaudii (Guttiferae)
| Autor: | Yuan-Jian Xu, Yip Sc, Soleh Kosela, Swee-Hock Goh, Hana M, Fitri E, Sim Ky |
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| Rok vydání: | 2000 |
| Předmět: |
Bridged-Ring Compounds
Magnetic Resonance Spectroscopy Plants Medicinal biology Chemistry Stereochemistry Organic Chemistry Spectrometry Mass Fast Atom Bombardment biology.organism_classification Antineoplastic Agents Phytogenic Biochemistry Forbesione Mass Spectrometry Plant Epidermis Xanthenes Indonesia visual_art visual_art.visual_art_medium Organic chemistry Bark Spectral analysis Physical and Theoretical Chemistry Garcinia Morellic acid |
| Zdroj: | Organic Letters. 2:3945-3948 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The structures of novel gaudichaudiic acids F − I(1 − 4), isolated from the bark of Indonesian Garcinia gaudichaudii , have been elucidated bydetailed spectral analysis. Gaudichaudiic acid I (4) is probably derived from 1 as a result of allylic oxidation at C-24 and C-21, followed byaromatization. Garcinia gaudichaudii is found mainly in Indo-China, theMalay Peninsula, and Borneo. The leaf juice of the planthas been used as a native medicine to rub on cuts and minorwounds. 1 The Malaysian species G. gaudichaudii is a pro-lific producer of polyprenylated xanthonoids and was previ-ously reported to contain 15 novel cytotoxic compounds;gaudichaudiones A-H, gaudichaudiic acids A-E, includingthe known morellic acid, and forbesione. 2 The isolation anddetailed characterization of 4 novel gaudichaudiic acids F-I(1-4) from the barks of Indonesian G. gaudichaudii haveprovided a substantially different profile of caged prenylatedxanthonoids. Gaudichaudiic acids F-I, which are cytotoxic,form a unique class of heptacyclic xanthonoids, and threeof them contain an unusual toluene-fused dimethylpyran ring(Figure 1).The dichloromethane-soluble fraction of the dried groundbark of G. gaudichaudii was fractionated on a silica gelcolumn, affording two major fractions. Fraction 1 yielded63 mg (1 10 |
| Databáze: | OpenAIRE |
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