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| Spiroketals of Pestalotiopsis fici Provide Evidence for a Biosynthetic Hypothesis Involving Diversified Diels-Alder Reaction Cascades | |
| Liu, L; Li, Y; Li, L; Cao, Y; Guo, LD; Liu, G; Che, YS | |
| 2013 | |
| Source Publication | JOURNAL OF ORGANIC CHEMISTRY
 |
| ISSN | 0022-3263 |
| Volume | 78Issue:7Pages:2992-3000 |
| Abstract | Chloropestolides B-G (1-6), six new metabolites featuring the chlorinated spiro[benzo[d][1,3]dioxine-2,7'-bicyclo[2.2.2]octane]-4,8'-dione (1-3) and spiro[benzo[d][1,3]dioxine-2,1'-naphthalene]-2',4-dione (4-6) skeletons, and their putative biosynthetic precursor dechloromaldoxin (7) were isolated from the scale-up fermentation cultures of the plant endophytic fungus Pestalotiopsis fici. The structures of 1-7 were determined mainly by NMR experiments. The absolute configurations of 1-3 were deduced by analogy to the previously isolated metabolites from the same fungus (9 and 13-18), whereas those of 4, 5, and 7 were assigned by electronic circular dichroism (ECD) calculations. Structurally, the spiroketal skeletons found in 1-3 and 4-6 could be derived from 2,6-dihydroxy-4-methylbenzoic acid with chlorinated bicyclo[2.2.2]oct-2-en-5-one and 4a,5,8,8a-tetrahydronaphthalen-2(1H)-one, respectively. Biogenetically, compounds 1-6 were derived from the same Diels-Alder precursors as the previously isolated 9 and 12-18. In addition, compounds 2 and 3 were proposed as the biosynthetic intermediates of 17 and 16, respectively. Compound 1 was cytotoxic to three human tumor cell lines. |
| Keyword | Electronic Circular-dichroism Obtusa Var.-formosana Antifungal Metabolites Organic-synthesis Endophytic Fungi Natural-products A-c Derivatives Skeleton Maldoxin |
| Language | 英语 |
| Document Type | 期刊论文 |
| Identifier | https://ir.xtbg.ac.cn/handle/353005/10228 |
| Collection | 文献共享 |
| Recommended Citation GB/T 7714 | Liu, L,Li, Y,Li, L,et al. Spiroketals of Pestalotiopsis fici Provide Evidence for a Biosynthetic Hypothesis Involving Diversified Diels-Alder Reaction Cascades[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(7):2992-3000. |
| APA | Liu, L.,Li, Y.,Li, L.,Cao, Y.,Guo, LD.,...&Che, YS.(2013).Spiroketals of Pestalotiopsis fici Provide Evidence for a Biosynthetic Hypothesis Involving Diversified Diels-Alder Reaction Cascades.JOURNAL OF ORGANIC CHEMISTRY,78(7),2992-3000. |
| MLA | Liu, L,et al."Spiroketals of Pestalotiopsis fici Provide Evidence for a Biosynthetic Hypothesis Involving Diversified Diels-Alder Reaction Cascades".JOURNAL OF ORGANIC CHEMISTRY 78.7(2013):2992-3000. |
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| Spiroketals of Pesta（904KB） | 开放获取 | CC BY-NC-SA | View Download | |||
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