np5b00969_si_002.cif (28.91 kB)
Phomanolides A and B from the Fungus Phoma sp.: Meroterpenoids Derived from a Putative Tropolonic Sesquiterpene via Hetero-Diels–Alder Reactions
dataset
posted on 2015-12-24, 00:00 authored by Jinyu Zhang, Ling Liu, Bo Wang, Yang Zhang, Lili Wang, Xingzhong Liu, Yongsheng ChePhomanolides A (1) and
B (2), unique
meroterpenoids with new pentacyclic and tetracyclic skeletons, respectively,
and phomanoxide (3), the double-epoxidation product of
a putative biosynthetic precursor of 1 and 2, were isolated from the solid substrate fermentation cultures of
the fungus Phoma sp., along with the known compound
eupenifeldin (4). The structures of 1–3 were elucidated based on NMR spectroscopic data and electronic
circular dichroism calculations and further secured by X-ray crystallography.
Biogenetically, compounds 1 and 2 could
be derived from a hypothetical monotropolonic sesquiterpene intermediate
via hetero-Diels–Alder reactions. Compound 4 showed
potent antiproliferative effects against three human glioma cell lines,
with IC50 values of 0.08–0.13 μM.
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cultureCompound 4NMR spectroscopic dataeupenifeldincrystallographydichroism calculationsphomanoxideDerivedReactionsPhomanolidebiosynthetic precursorantiproliferative effectsIC 50 valuescompounds 1Putative Tropolonic Sesquiterpenemonotropolonic sesquiterpenefungusBiogeneticallypentacyclicPhomanolidesubstrateMeroterpenoidtetracyclic skeletonsPhomaFungumeroterpenoidglioma cell lines
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