Literature DB >> 27680770

Chevalone C analogues and globoscinic acid derivatives from the fungus Neosartorya spinosa KKU-1NK1.

Oue-Artorn Rajachan1, Kwanjai Kanokmedhakul2, Wareerat Sanmanoch3, Sophon Boonlue3, Supa Hannongbua4, Patchreenart Saparpakorn4, Somdej Kanokmedhakul1.   

Abstract

Four meroterpenoids, 1-hydroxychevalone C, 1-acetoxychevalone C, 1,11-dihydroxychevalone C, and 11-hydroxychevalone C and two ester epimers, 2S,4S-spinosate and 2S,4R-spinosate, together with seven known compounds, chevalones B, C, and E, tryptoquivaline, nortryptoquivaline, tryptoquivaline L, and quinadoline A were isolated from the fungus Neosartorya spinosa. Their structures were established based on spectroscopic data analyses. The theoretical ECD spectra of epimers, 2S,4S-spinosate and 2S,4R-spinosate were calculated to support the experimental results of their CD spectra. 1-hydroxychevalone C exhibited antimycobacterial activity against Mycobacterium tuberculosis with a MIC value of 26.4 μM. 1-Acetoxychevalone C and tryptoquivaline showed antimalarial activity against Plasmodium falciparum with IC50 values of 6.67 and 2.65 μM, respectively. In addition, 1-hydroxychevalone C, 1-acetoxychevalone C, 1,11-dihydroxychevalone C and quinadoline A showed cytotoxicity against KB and NCI-H187 cancer cell lines with IC50 values in the range of 32.7-103.3 μM.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antimalarial; Chevalones; Cytotoxicity; ECD calculations; Globoscinic acid derivatives; Meroterpenoids; Neosartorya spinosa

Mesh:

Substances:

Year:  2016        PMID: 27680770     DOI: 10.1016/j.phytochem.2016.09.008

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


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