Many fungi, lichens, and bacteria produce xanthones (derivatives of 9H-xanthen-9-one, “xanthone” from the Greek “xanthos”, for “yellow”) as secondary metabolites. Xanthones are typically polysubstituted and occur as either fully aromatized, dihydro-, tetrahydro-, or, more rarely, hexahydro-derivatives. This family of compounds appeals to medicinal chemists because of their pronounced biological activity within a notably broad spectrum of disease states, a result of their interaction with a correspondingly diverse range of target biomolecules. This has led to the description of xanthones as “privileged structures”.(1) Historically, the total synthesis of the natural products has mostly been limited to fully aromatized targets. Syntheses of the more challenging partially saturated xanthones have less frequently been reported, although the development in recent times of novel and reliable methods for the construction of the (polysubstituted) unsaturated xanthone core holds promise for future endeavors. In particular, the fascinating structural and biological properties of xanthone dimers and heterodimers may excite the synthetic or natural product chemist.

Xanthones from fungi, lichens, and bacteria : the natural products and their synthesis

Marine natural products.

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities.

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

Fungi have been proved as promising and prolific sources of functional secondary metabolites with potent agricultural applications. In this study, 14 xanthone derivatives (1-14), including six new ones, versicones I-N (1-4, 7, 11), and a biogenetically related derivative (15), were isolated from the alga-derived fungus Aspergillus versicolor D5. Their structures were elucidated by comprehensive spectroscopic methods. Versicone L (4) exhibited a broad antifungal spectrum and prominent inhibitory effects on Botrytis cinerea at a minimum inhibitory concentration (MIC) of 152 μM, 7-fold stronger than that of the positive control, carbendazim (MIC = 1.05 × 103 μM). Dihydrosterigmatocystin (13) showed strong antifungal activity toward B. cinerea at MIC = 38.3 μM, almost 30-fold stronger than that of carbendazim. Meanwhile, 13 exhibited potent herbicidal activity toward Amaranthus retroflexus L. with an MIC of 24.5 μM, approximately 4-fold stronger than that of the positive control, glyphosate (MIC = 94.7 μM). Additionally, 13 also displayed remarkable activity against other weeds belonging to Amaranth sp. Analysis of the structure-herbicidal activity relationship indicated that the bifuranic ring played an important role in xanthone phytotoxicity and the presence of a double bond in the furan ring could decrease phytotoxicity. This study indicated that xanthones can be served as promising candidates for lead compounds of agrochemicals.

Herbicidal and Antifungal Xanthone Derivatives from the Alga-Derived Fungus Aspergillus versicolor D5.

A new polyketide derivative, nafuredin C (1), a novel heterocyclic dipeptide, trichodermamide G (3), together with four known biogenetically related compounds nafuredin A (2), trichodermamide A (4), aspergillazin A (5), and peniisocoumarin H (6), were isolated from the mangrove-derived fungus Trichoderma harzianum D13 Their structures, including their absolute configurations, were determined by spectroscopic analysis and time-dependent density functional theory-electronic circular dichroism (ECD) calculations Trichodermamide G was found to be a novel epithiodiketopiperazine derivative with an unprecedented cyclic system containing a sulfur bridge, and nafuredin C represented the third nafuredin derivative of these homologous compounds The new compound nafuredin C exhibited obvious antifungal activity against Magnaporthe oryzae with a minimum inhibitory concentration (MIC) of 863 μM, which is on the same order of magnitude as the positive control carbendazim (MIC = 327 μM)

/pdf/antifungal-nafuredin-and-epithiodiketopiperazine-derivatives-3zfk2qurgo.pdf

Cai-Juan Zheng

Papers

Herbicidal and Antifungal Xanthone Derivatives from the Alga-Derived Fungus Aspergillus versicolor D5.

Antifungal Nafuredin and Epithiodiketopiperazine Derivatives From the Mangrove-Derived Fungus Trichoderma harzianum D13.