New Metabolites from the Endophytic Fungus Mollisia sp.

Abstract

Two new metabolites, mollisinols A and B (1 and 2), and one first isolated from nature, mollisilactone (3), along with 13 known compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16), were isolated from the EtOAc-soluble fraction of the solid-state fermentation of the endophytic fungus Mollisia sp., derived from the root bark of Ardisia cornudentata Mez (Myrsinaceae). Their structures were elucidated by spectroscopic analyses, including 1D and 2D NMR experiments, and by HR-ESI-MS mass spectrometry. Among the isolates, ergosterol peroxide (12) inhibited NO production in activated macrophages, and emodin (8) showed IL-6 inhibitory activity in LPS activated RAW 264.7 cells with IC 50 values of 36.99 and 5.97 PM, respectively.Plant endophytes are a group of microorganisms, including fungi and bacteria, which not only live within the plantsc internal tissues or organs, without causing any apparent symptoms of disease in the host plant [1-3], but also serve as important sources of bioactive compounds, presumably owing to the symbiotic relationship with their hosts [1-3]. Research on endophytes from different plant sources has yielded many structurally diverse and pharmacologically active natural products [4][5][6][7][8][9][10]. During a program of investigation on potentially bioactive secondary metabolites from Formosan endemic plant endophytes, an endophytic fungal strain, Mollisia sp. (Dermateaceae) BCRC 09F0002, was isolated from the root bark of Ardisia cornudentata Mez (Myrsinaceae). Previous chemical investigations of the genus Mollisia have received less attention, and only a few articles have been reported [11][12][13][14][15]. In the course of our search for potentially diverse secondary metabolites from natural fungal sources, and to further understanding the minor metabolites of the genus Mollisia, we examined an EtOAc-soluble fraction of Mollisia sp., which showed inhibitory activity on lipopolysaccharide (LPS)-induced nitric oxide (NO) release and interleukin-6 (IL-6) production in RAW 264.7 murine macrophages, as determined by our primary screening (approximately 90% inhibition at a concentration of 10 Pg/mL). Current phytochemical investigation of the above-mentioned fungus has led to the isolation of two new metabolites, mollisinols A, B (1, 2), with one compound, mollisilactone (3), isolated for the first time from nature, together with 13 known compounds (4-16). The structures of compounds 1-3 were established by spectroscopic analysis, and the inhibitory effects of some isolates on NO and IL-6 production by macrophages are described herein.The EtOAc-soluble fraction of the MeOH extract of rice produced by the endophytic fungus Mollisia sp. was fractionated by a combination of silica gel, RP-18 columns, Sephadex LH-20, and prep. TLC to furnish 16 compounds 1-16, the structures of which were elucidated by 1D and 2D NMR spectra and comparison with literature data.

Chemical Constituents and Antimicrobial Activity of Soil Fungus Aspergillus sp. FRIZ12

“…16 The sterols ergosterol (5), ergosterol peroxide (6), cerivisterol (7), sitosterol (8), and stigmasterol (9) were isolated by chromatographic procedures and identified by NMR and with literature data. [17][18][19] Analysis of the control extracts by MS showed the absence of the isolated compounds in the culture medium, confirming that the isolated compounds are secondary metabolites produced by the fungus Aspergillus FRIZ12 and not from the culture medium.…”

Pyrrole-2-carboxaldehydes: Origins and Physiological Activities

“…The chemical structures of the known Py-2-Cs ( 25 , 26 , 27 , 3 , 21 , and 12 ) were determined based on the spectroscopic analyses [ 23 ]. From the endophytic fungus Mollisia sp., among many metabolites, one known Py-2-C ( 15 ) was isolated and identified [ 24 ]. From the edible mushroom Basidiomycetes-X ( Echigoshirayukitake ), three Py-2-C derivatives ( 3 , 4 , and 28 ) have been isolated and identified [ 25 ].…”

New Chlorinated Metabolites and Antiproliferative Polyketone from the Mangrove Sediments-Derived Fungus Mollisia sp. SCSIO41409

“…Mangrove forests are a complex ecosystem, and the microbes in mangrove sediments play an important role in the biogeochemical cycles of mangrove ecosystems [ 1 ]. The high diversity of mangrove environments has contributed to high microbial diversity, which is an important source of bioactive natural products [ 2 , 3 , 4 ]. Research on secondary metabolites from mangrove sediments-derived microbes has yielded many natural products with novel structures and significant pharmacological activities [ 5 , 6 , 7 , 8 ].…”

“…The natural products from the genus Mollisia were not well explored and were limited to few publications. Mollisinols A and B, two new metabolites were isolated from the endophytic fungus Mollisia sp., derived from the root bark of Ardisia cornudentata Mez [ 3 ]. Ophiobolin C, isolated from Mollisia sp.…”