Abstract
Three new polyene compounds, talacyanols A–C (1–3), along with two known compounds, ramulosin (4) and eurothiocin A (5), were isolated from the marine fungus Talaromyces cyanescens derived from a seaweed Caulerpa sp. Structures of 1–5 were established by one-dimensional and two-dimensional (1D/2D) NMR, HR-ESIMS, and the modified Mosher’s methods, as well as comparison with previously reported literature data. All the compounds (1–5) were tested for their in vitro cytotoxic and anti-neuroinflammatory activities. Among them, 1 showed moderate cytotoxic activity against a panel of cancer cell lines (HCT-15, NUGC-3, NCI-H23, ACHN, PC-3, and MDA-MB-231) with GI50 values ranging from 44.4 to 91.6 μM, whereas compounds 2 and 5 exhibited anti-neuroinflammatory effect without cytotoxicity against all the tested cell lines.
Highlights
Despite developing new therapeutic agents is a long, intricate, and costly process, the discovery and development of the new drugs are urgently needed due to the increase in the annual number of deaths caused by cancer, cardiovascular, respiratory, and neurodegenerative diseases, as well as the emergence and rapid growth of multidrug resistant pathogenic microbes [1,2]
The structures of the known compounds were identified as ramulosin (4), and eurothiocin A (5) by comparison of their spectroscopic data with those reported in the literature [19,20,21]
The fungus was identified as Talaromyces cyanescens Stchigel & Guarro on the basis of DNA amplification and ITS gene sequencing (GenBank accession number MK 072976.1)
Summary
Despite developing new therapeutic agents is a long, intricate, and costly process, the discovery and development of the new drugs are urgently needed due to the increase in the annual number of deaths caused by cancer, cardiovascular, respiratory, and neurodegenerative diseases, as well as the emergence and rapid growth of multidrug resistant pathogenic microbes [1,2]. By comparing 1H NMR data of bis-S- and -R-MTPA esters of 2, the absolute configurations at C-6 and C-7 were assigned as 6S and 7R (Figure 3B), and the structure of 2 was determined as (2E,4E,6S,7R)-6,7-dihydroxy-2-((Z)-prop-1-en-1-yl)octa-2,4-dienal and named talacyanol B. The absolute configurations at C-6 and C-7 of pinophol A had not been determined yet and their relative configurations were reported as syn-1,2-diols (6R, 7R or 6S, 7S) Comparison of their optical rotation values ([α]2D5 − 10 (c 0.2, MeOH) for 3 and [α]2D6 +32.6 (c 0.1, MeOH) for pinophol A) and 1H NMR data in CDCl3 of 3 and pinophol A (δH-6 4.12 and δH-7 3.88 for 3 and δH-6 3.87 and δH-7 3.63 for pinophol A, Figure S22) suggested that they could be a pair of diastereomers. The structures of the known compounds were identified as ramulosin (4), and eurothiocin A (5) by comparison of their spectroscopic data with those reported in the literature [19,20,21]
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