Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities

Abstract

Thirty-three metabolites including five phenalenone derivatives (1-5), seven cytochalasins (6-12), thirteen butenolides (13-25), and eight phenyl derivatives (26-33) were isolated from Aspergillus sp. CPCC 400735 cultured on rice. The structures of all compounds were elucidated by NMR, MS, and CD experiments, of which 1-5 (asperphenalenones A-E), 6 (aspochalasin R), and 13 (aspulvinone R) were identified as new compounds. Specifically, asperphenalenones A-E (1-5) represent an unusual structure composed of a linear diterpene derivative linked to a phenalenone derivative via a C-C bond. Compounds 1, 4, 10, and 26 exhibited anti-HIV activity with IC values of 4.5, 2.4, 9.2, and 6.6 μM, respectively (lamivudine 0.1 μM; efavirenz, 0.4 × 10 μM).

Expanding the chemical diversity of an endophytic fungusBulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

“…In our study, bulgarialactone B (1) revealed no cytotoxicity against the tested L5178Y cell line, albeit in a previous study it was reported to possess antitumor activity against an ascitic ovarian carcinoma xenogra. 30 Butyrolactone analogues similar to the derivatives isolated in this study were previously described from Aspergillus species, 58,62,[66][67][68] Here we report B. inquinans as a source of this type of metabolites for the rst time. Moreover, the results obtained upon application of the OSMAC approach employing a mixture of salts (MgSO 4 , NaNO 3 and NaCl) highlighted the usefulness of this strategy not only for diversifying secondary metabolites produced by this strain, but also to afford rare natural product scaffolds, as exemplied by the isolation of 1,3oxazine derivatives (7 and 8) and of an unusual a-pyrone dimer 13.…”

Secondary metabolites of Phlebopus species from Northern Thailand

“…Prominent representatives are the trihydroxypulvinones (Edwards and Gill 1973) isolated from Suillus grevillei or the group of aspulvinones from Aspergillus spp. (Ojima et al 1973;Golding and Rickards 1975;Pang et al 2017). However, substitution of the butenolide unit by a third phenyl group at C-9′ has not been found in nature so far and provides a new subclass of pulvinones.…”

In vitro activity of 1H-phenalen-1-one derivatives against Leishmania spp. and evidence of programmed cell death

“…Many PHs have been described recently to possess different biological activities ranging from antifungal to antiHIV. For example, Li et al [28] described the antifungal activity of some PHs isolated from Auxarthron pseudauxarthron against Cryptococcus and Candida and Pang et al [29] isolated some PHs with antiHIV activity from Aspergillus . Other studies have shown antibacterial activities against many species such as Pseudomonas aeruginosa , Escherichia coli , Staphylococcus aureus and Bacillus subtilis [30].…”