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Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil-derived fungus, Aspergillus sp. SDC28

JR. Gubiani, DI. Bernardi, CCP. De Paula, MHR. Seleghim, AG. Ferreira, ANL. Batista, JM. Batista, LFP. Oliveira, SP. Lira, JE. Burdette, RGS. Berlinck

. 2022 ; 355 (4) : e2100441. [pub] 20220131

Language English Country Germany

Document type Journal Article

Persistent link   https://www.medvik.cz/link/bmc22018905

Grant support
2019/17721-9 Fundação de Amparo à Pesquisa do Estado de São Paulo
P01CA125066 NIH HHS - United States
P01 CA125066 NCI NIH HHS - United States
2019/22319-5 Fundação de Amparo à Pesquisa do Estado de São Paulo
2016/21341-9 Fundação de Amparo à Pesquisa do Estado de São Paulo
2013/50228-8 Fundação de Amparo à Pesquisa do Estado de São Paulo
2017/06014-4 Fundação de Amparo à Pesquisa do Estado de São Paulo
2017/12436-9 Fundação de Amparo à Pesquisa do Estado de São Paulo

Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil-derived fungus Aspergillus sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (1) and versiconol (2). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of 1 and 2 was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of 2. Compounds 1 and 2 showed cytotoxic activity against human ovarian cancer cells (OVCAR3).

References provided by Crossref.org

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$a Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil-derived fungus Aspergillus sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (1) and versiconol (2). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of 1 and 2 was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of 2. Compounds 1 and 2 showed cytotoxic activity against human ovarian cancer cells (OVCAR3).
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