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New Bicyclic Sesquiterpene and Labdane Diterpenes from the Culture Extract of the Sea Grass-Derived Fungus Penicillium verruculosum KUFA1509
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New Bicyclic Sesquiterpene and Labdane Diterpenes from the Culture Extract of the Sea Grass-Derived Fungus Penicillium verruculosum KUFA1509
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Journal Article
New Bicyclic Sesquiterpene and Labdane Diterpenes from the Culture Extract of the Sea Grass-Derived Fungus Penicillium verruculosum KUFA1509
2026
Overview
An unreported bicyclic sesquiterpene acid, verruculosic acid (
), was isolated together with the previously reported labdane diterpenes, (+)-agathic acid (
) and hypoxyterpenoid A (
), one 3-
-2,3-seco-labdane, penioxalicin (
), and 5-carboxyphthalide (
), from a sea grass-associated fungus,
KUFA1509. The structures of the isolated compounds were elucidated by detailed analyses of 1D and 2D NMR and HRMS data. The absolute configurations of the stereogenic carbons in
and
were established by X-ray crystallography. The crystal structure of
, which was obtained for the first time, was used to prove its structure and confirm its stereochemistry. The crystal structure of
was also obtained; however, the value of its flack parameter does not allow us to determine the absolute configuration. Compound
exhibited stronger inhibitory activity than the positive control, diclofenac sodium, against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, while
and
were slightly less active than the positive control. In contrast,
exhibited much weaker activity than
. Compounds
-
were also assayed for antibacterial activity against reference and multidrug-resistant strains, but none exhibited antibacterial activity against the tested strains. Thus, the labdane skeleton could be considered as a potential scaffold for the development of anti-inflammatory agents through NO inhibition.
Publisher
MDPI AG,Multidisciplinary Digital Publishing Institute (MDPI)
Subject
/ Acids
/ Animals
/ Anti-Bacterial Agents - chemistry
/ Anti-Bacterial Agents - pharmacology
/ Anti-Inflammatory Agents - chemistry
/ Anti-Inflammatory Agents - isolation & purification
/ Anti-Inflammatory Agents - pharmacology
/ Antiinfectives and antibacterials
/ Carbon
/ Crystals
/ Diterpenes - isolation & purification
/ Enzymes
/ Fungi
/ Grasses
/ Mice
/ NMR
/ Penicillium verruculosum KUFA1509
/ Sesquiterpenes - isolation & purification
/ Sesquiterpenes - pharmacology
/ Sodium
