Four New Cuparene‐Type Sesquiterpenes from Flammulina velutipes

Abstract

Flamvelutpenoids A -D (1 -4), four new cuparene-type sesquiterpenes, were isolated from the solid culture of Flammulina velutipes. Their structures were elucidated by NMR experiments. The absolute configurations of 1 and 2 were assigned via the circular dichroism data of the [Rh 2 (OCOCF 3 ) 4 ] complex, whereas that of C(3) of 3 was determined by applying the octant rule for the a,b-unsaturated ketone moiety. Compounds 1 -4 showed weak antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillin-resistant Staphylococcus aureus with MIC values larger than 100 mm.Introduction. . To further exploit the potential of F. velutipes in producing bioactive natural products, the solid culture of F. velutipes was chemically investigated. Herein, we report the isolation and characterization of the four new cuparene-type sesquiterpenes 1 -4 from F. velutipes (Fig. 1). Their antibacterial activity against Escherichia coli, Bacillus subtilis, and methicillinresistant Staphylococcus aureus was also evaluated.

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“…(Ou et al, 2005; Chung et al, 2010; Jeff et al, 2013). F. velutipes has also been shown to contain bioactive compounds with antitumor and anticancer properties (Gu and Leonard, 2006; Smiderle et al, 2006; Wang et al, 2012b; Yi et al, 2013b). …”

“…In addition to the discovery of enokipodins A–D (22, 23, 35, 36) , another research group from China isolated new cuparene-type sesquiterpenes from the solid culture of F. velutipes which also demonstrated antibacterial activities (Wang et al, 2012b). The chemical structures of these sesquiterpenes were elucidated and named as flamvelutpenoids A–D (37 to 40) .…”

“…The chemical structures of these sesquiterpenes were elucidated and named as flamvelutpenoids A–D (37 to 40) . They were shown to exhibit antibacterial activity against E. coli, B. subtilis and methicillin-resistant S. aureus with MIC measuring more than 100 μM (Wang et al, 2012b). Furthermore, Wang et al (2012d) also revealed the isolation of six new cuparene sesquiterpenes, enokipodins E–J (25 to 30) with antibacterial and antifungal activities.…”

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“…Compound 7 is deduced, tentatively, to be an epimer of compound 6 at C-3 and a novel compound. Very recently, compounds 5 and 6 and related compounds were isolated from a solid culture of F. velutipes growing on cooked rice (Wang et al , 2012a, 2012b). The 1 H and 13 C spectral data for compound 6 are identical to those reported for flamvelutpenoid C (Wang et al , 2012a).…”

“…Very recently, compounds 5 and 6 and related compounds were isolated from a solid culture of F. velutipes growing on cooked rice (Wang et al , 2012a, 2012b). The 1 H and 13 C spectral data for compound 6 are identical to those reported for flamvelutpenoid C (Wang et al , 2012a). Compound 5 showed weak antibacterial activity against B. subtilis (Wang et al , 2012a).…”