Chevalone C analogues and globoscinic acid derivatives from the fungus Neosartorya spinosa KKU-1NK1.
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 IC50values 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 IC50values in the range of 32.7-103.3 μM.
Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
Oue-Artorn
OA
Rajachan
Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. Electronic address: kwanjai@kku.ac.th.
Kwanjai
K
Kanokmedhakul
Department of Microbiology, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
Wareerat
W
Sanmanoch
Department of Microbiology, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
Sophon
S
Boonlue
Department of Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok, 10900, Thailand.
Supa
S
Hannongbua
Department of Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok, 10900, Thailand.
Patchreenart
P
Saparpakorn
Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
Somdej
S
Kanokmedhakul
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007211:Indoles / Q000737:chemistry; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D055326:Neosartorya / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000962:Antimalarials; D000970:Antineoplastic Agents; D007211:Indoles; D013729:Terpenes; C000614474:chevalone C; C010522:tryptoquivaline
Antimalarial; Chevalones; Cytotoxicity; ECD calculations; Globoscinic acid derivatives; Meroterpenoids; Neosartorya spinosa