Anti-inflammatory Sesquiterpenoids from a Sponge-Derived Fungus Acremonium sp.

Abstract

In the course of our search for bioactive metabolites from a sponge-derived fungus Acremonium sp., new sesquiterpenoids (1-4) were isolated along with known derivatives by bioactivity-guided fractionation. The unique cyclic skeleton of compounds 2 and 3 is unprecedented. The absolute configurations were determined by modified Mosher's method and CD spectroscopy, along with comparison of (1)H and (13)C NMR spectroscopic data and specific optical rotation values with those reported. The anti-inflammatory activity of the isolated compounds (1, 5, 7-13) was evaluated by measuring their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in RAW 264.7 murine macrophage cells. Among the compounds tested, compounds 7 and 9 significantly inhibited the production of NO and TNF-alpha at the concentration of 100 microM, while compounds 11 and 12 showed selective inhibition of NO production at the same concentration.

Spirocyclic Drimanes from the Marine Fungus Stachybotrys sp. Strain MF347

“…Furthermore, six known spirocyclic drimanes, chartarlactam O [23], chartarlactam K [23], F1839A ( 7 ) [21], stachybotrylactam ( 8 ) [3], stachybotramide ( 9 ) [3] and 2α-acetoxystachybotrylactam acetate ( 10 ) [1], and two known spirocyclic drimanes featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue, stachybocin B ( 11 ) [16] and stachybocin A ( 12 ) [16], and a known sesquiterpene, ilicicolin B ( 13 ) [24] were identified by comparison of their spectroscopic data with those reported in the literature [3,16,21,23,24]. …”

Microbial metabolism of cannflavin A and B isolated from Cannabis sativa

“…The absolute configuration at C-6″ was determined through application of the modified Mosher’s method (Δ δ = δ S − δ R ) for 5 (Ahmed et al, 2008a; Murata et al, 2008; Nakamura et al, 2009; Zhang et al, 2009). The 1 H NMR resonances for the H 3 -8″ and H 3 -9″ protons of the S -MTPA ester ( 5a ) were observed downfield compared to those of the R -MTPA ester ( 5b ) [Δ δ (H 3 -8″) = +0.02 and Δ δ (H 3 -9″) = +0.03], indicating S absolute configuration at C-6″.…”

Produtos naturais marinhos: isolamento e identificação de metabólitos inéditos a partir de fungos endofíticos e cianobactérias utilizando técnicas de eliciação química epigenética e desreplicação via redes moleculares

“…O gênero Acremonium já foi relatado como fungo endofítico associado a inúmeros organismos marinhos como, por exemplo, esponjas (Boot et al, 2006;Izumikawa et al, 2009;Zhang et al, 2009), tunicados (Belofsky et al, 2000), e…”

“…Em relação ao metabolismo secundário, espécies deste gênero já foram descritas como produtoras de substâncias bioativas, as quais apresentam origens biossintéticas variadas, como por exemplo, policetídeos, terpenóides, esteróides, peptídeos e glicosídeos fenólicos (Boot et al, 2006;Izumikawa et al, 2009;Zhang et al, 2009). Algumas destas substâncias mostraram propriedades biológicas antifúngica (Belofsky et al, 2000), antimicrobiana (Belofsky et al, 2000;Jang et al, 2006a), antiinflamatória (Zhang et al, 2009), dentre outras.…”

“…Algumas destas substâncias mostraram propriedades biológicas antifúngica (Belofsky et al, 2000), antimicrobiana (Belofsky et al, 2000;Jang et al, 2006a), antiinflamatória (Zhang et al, 2009), dentre outras.…”