Abstract
A new sesquiterpenoid 9,10-diolhinokiic acid (1) and a new diterpenoid roussoellol C (2), together with 4 known compounds, were isolated from the extracts of laboratory cultures of marine-derived fungus Talaromyces purpurogenus. 9,10-diolhinokiic acid is the first thujopsene-type sesquiterpenoid containing a 9,10-diol moiety, and roussoellol C possesses a novel tetracyclic fusicoccane framework with an unexpected hydroxyl at C-4. These new structures were confirmed by spectroscopic data, chemical method, NMR data calculations and electronic circular dichroism (ECD) calculations. The selected compounds were evaluated for cytotoxicities against five human cancer cell lines, including SW480, HL-60, A549, MCF-7, and SMMC-7721 and the IC50 values of compound 2 against MCF-7 and 3 against HL-60 cells were 6.5 and 7.9 μM, respectively.
Highlights
Over the past forty years, more than 60% small molecule new drugs have been directly or indirectly derived from natural product source, which demonstrates that natural products continue to play a significant role in drug discovery and development process [1]
In our screening of extracts of several fungi for their cytotoxic activities, EtOAc extract of T. purpurogenus, isolated from a mud sample, showed significant cytotoxic activity in vitro
A chemical investigation of the fungus T. purpurogenus resulted in the isolation of two new secondary metabolites 9,10-diolhinokiic acid (1) and roussoellol C (2), and four known compounds including dankasterone (3) [12,13], cyclotryprostatin E (4) [14], 6-methoxyspirotryprostatin B (5) [15], and (3S,12aS)-3-methyl-2,3,6,7,12,12ahexahydropyrazino[10,20 :1,6]pyrido[3,4-b]indole-1,4-dion (6) (Figure 1) [16]
Summary
Over the past forty years, more than 60% small molecule new drugs have been directly or indirectly derived from natural product source, which demonstrates that natural products continue to play a significant role in drug discovery and development process [1]. Fungi-derived natural products are rich sources of medicines due to their diverse chemical structures and bioactivities. Lovastatin, penicillin, echinocandin B, and cyclosporine A have been clinically used as effective medicines, illustrating the significance of fungi-derived metabolites in drug discovery [2]. The impressive structurally diverse metabolites from this fungus exhibit extensive bioactivities including anti-inflammatory [11], anti-influenza virus [7], insecticidal [4], antitumor [9], and antifungal activities [8]. A chemical investigation of the fungus T. purpurogenus resulted in the isolation of two new secondary metabolites 9,10-diolhinokiic acid (1) and roussoellol C (2), and four known compounds including dankasterone (3) [12,13], cyclotryprostatin E (4) [14], 6-methoxyspirotryprostatin B (5) [15], and (3S,12aS)-3-methyl-2,3,6,7,12,12ahexahydropyrazino[10 ,20 :1,6]pyrido[3,4-b]indole-1,4-dion (6) (Figure 1) [16].
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