Two New Sesquiterpenes from the Marine Fungus Eutypella scoparia FS26 from the South China Sea

Abstract

A new monocyclofarnesane-type sesquiterpene, 3,7,10-trihydroxy-6,11-cyclofarnes-1-ene (1), and a new acorane-type sesquiterpene, 8-(hydroxymethyl)-1-(2-hydroxy-1-methylethyl)-4-methylspiro[4.5]-dec-8-en-7-ol (2), were isolated from the culture of Eutypella scoparia FS26 from the South China Sea, along with three known terpenes, 3 -5. The structures of these compounds were determined by extensive analysis of their spectroscopic data as well as by comparison with literature reports. The isolated compounds 1 -5 were evaluated for their cytotoxic activities against the SF-268, MCF-7, and NCI-H460 tumor cell lines.

Bioactive Pimarane Diterpenes from the Arctic Fungus Eutypella sp. D‐1

“…The HMBCs from H-C (14) to C(7), C(8), C(9), and C(13), from H-C(15) to C(12), C(13), C (14), and C (17), from Me (20) to C(1), C(9), and C(10), from HO-C(9) to C(9) and C(10), and from HO-C(6) to C(5), C(6), and C (7) corroborated the skeleton of rings B and C with Me (20) at C(10) and two hydroxy groups at C(6) and C(9), respectively. Moreover, correlations from H-C (15) and H-C(16) to C(13), and from Me (17) to C(13), C (14), and C(15) indicated that Me (17) and CH(15)=CH 2 (16) were attached to C (13). Finally, the planar structure of compound 1 was confirmed as depicted.…”

“…Fungus of the genus Eutypella have been reported to be mainly distributed the South China Sea, tropical forests of Australia and Thailand, and the soil of Arctic and Antarctica . Secondary metabolites with extensive structural diversity from this genus, including sesquiterpenoids, pimarane diterpenoids, cytochalasin derivatives, γ ‐lactones, cyclic dipeptides, and cytosporin‐related compounds, showed various bioactivities, such as antimicrobial, antitumor, and immunosuppressive activities . Eutypella sp.…”

Bioactive Terpenes from Marine-Derived Fungi

“…A new monocyclic farnesyl sesquiterpene named 3,7,10-trihydroxy-6,11-cyclofarnes-1-ene ( 61 ) together with a new acorane sesquiterpene, 8-(hydroxymethyl)-1-(2-hydroxy-1-methylethyl)-4-methylspiro[4.5]-dec-8-en-7-ol ( 62 ), were isolated from the marine-derived fungus Eutypella scoparia FS26 isolated from a sediment sample from the South China Sea ( Figure 4 ) [ 23 ]. Compounds 61 and 62 were investigated for cytotoxicity against a panel of cancer cell lines but they only showed a weak cytotoxic activity against MCF-7 cell line.…”

Cytotoxic cytochalasins from the endophytic fungus Eutypella scoparia PSU-H267

“…Chemical investigation of this fungus has resulted in the discovery of various types of metabolites, including chromenes (Pongcharoen et al, 2006;Sun et al, 2013), cytochalasins (Pongcharoen et al, 2006;Ciavatta et al, 2008;Sun et al, 2011aSun et al, , 2013, cytosporin-related compounds (Ciavatta et al, 2008), pimarane diterpenes (Pongcharoen et al, 2006;Sun et al, 2011bSun et al, , 2012a, sesquiterpenes (Sun et al, 2011a(Sun et al, , 2012b and steroids (Sun et al, 2011b). In this study, we chemically investigated secondary metabolites produced by E. scoparia PSU-H267 isolated from a leaf of Hevea brasiliensis collected in Songkhla Province, Thailand.…”