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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 PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume78Issue:7Pages:2992-3000
AbstractChloropestolides 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.
KeywordElectronic 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
Identifierhttp://ir.xtbg.org.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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