Penicilindoles A–C, Cytotoxic Indole Diterpenes from the Mangrove-Derived Fungus Eupenicillium sp. HJ002

Abstract

Three new indole diterpenes, penicilindoles A-C (1-3), were isolated from the mangrove-derived fungus Eupenicillium sp. HJ002. Their planar structures and absolute configurations were determined by interpretation of NMR spectroscopic data, HR-ESIMS, and X-ray diffraction analysis using Cu Kα radiation. The cytotoxic and antibacterial activities were evaluated in vitro; penicilindole A (1) showed cytotoxic activity against human A549 and HepG2 cell lines with IC values of 5.5 and 1.5 μM, respectively.

Four New Chromone Derivatives from Colletotrichum gloeosporioides

“…Compound 2 was obtained as a brown oil, with the molecular formula of C 12 2), and one carbonyl carbon (δ(C) 180.2). The 1 H, 1 H COSY-correlations revealed two coupling systems, CH(5)À CH 2 (6)À CH (7)À CH 2 (8) and CH 2 (9)À CH 2 (10)À Me (11). The HMBC spectrum showed correlations from HÀ C(3) to C(2) and C(4a), HÀ C(5) to C(4a), C (7) and C(6), HÀ C(8) to C(7), HÀ C(6) to C(7), HÀ C(9) to C(2), C(3), C(10) and C(11) ( Figure 2).…”

“…The (E)-configuration of the C=C bond at C(9) and C(10) was inferred from the large coupling constant of J H9-H10 = 15.7 Hz. A sole methyl group at δ(H) 1.91(d, J = 7.0, HÀ C(11), 3 H) was connected to an olefinic bond according to the 1 H, 1 H-COSY correlations of CH(9)À CH(10)À Me (11), and the HMBC of HÀ C(11) to C(9) (Figure 2). The relative configuration of 4 was also determined by NOESY correlation from HÀ C(5) to HÀ C (7).…”

“…[4 -7] Many bioactive secondary metabolites, such as aspergillomarasmims A and B, colletotric acid phytotoxins, gloeosporone, colletotricone A, cytochalasin D, and many other compounds, were produced by Colletotrichum species. [8 -10] Recently, in the research on new bioactive secondary metabolites from mangrove-derived fungi, [11][12][13] four new chromone derivatives with a known one were isolated from the culture broth of Colletotrichum gloeosporioides, which was isolated from the mangrove Ceriops tagal. It produced a series of new chromone compounds with similar structures but different biological activities, which were evaluated for their cytotoxic activity against A549 (human lung adenocarcinoma cell line) cell line.…”

Bioactive Secondary Metabolites from the Culture of the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004

“…In our ongoing research on mangrove-derived fungi, we have found some new bioactive metabolites (including metabolites with inhibitory activity against α-glucosidase) [9][10][11][12][13][14].…”

“…Mangrove-derived fungi can produce secondary metabolites with novel structures and biological activities [8]. In our ongoing research on mangrove-derived fungi, we have found some new bioactive metabolites (including metabolites with inhibitory activity against α-glucosidase) [9][10][11][12][13][14]. A mangrove-derived fungus Daldinia eschscholtzii HJ004 attracted our attention due to the inhibitory activity against α-glucosidase of its EtOAc extract, and three polyketide derivatives with strong inhibitory activity against α-glucosidase have been isolated [9].…”