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).

Biology Centre CAS Institute of Hydrobiology České Budějovice Czech Republic

Departamento de Ciências Exatas Escola Superior de Agricultura Luiz de Queiroz Universidade de São Paulo Piracicaba Brazil

Departamento de Ecologia e Biologia Evolutiva Universidade Federal de São Carlos São Carlos Brazil

Departamento de Química Universidade Federal de São Carlos São Carlos Brazil

Instituto de Ciência e Tecnologia Universidade Federal de São Paulo São José dos Campos Brazil

Instituto de Química de São Carlos Universidade de São Paulo São Carlos Brazil

Instituto de Química Universidade Federal Fluminense Niterói Brazil

Pharmaceutical Sciences College of Pharmacy University of Illinois Ashland Oregon USA

Zobrazit více v PubMed

Paula CCP, Montoya QV, Meirelles LA, Sanchez CF, Rodrigues A, Seleghim MHR, An. Acad. Bras. Cienc 2019, 91 (3): e20180583. DOI 10.1590/0001-3765201920180583. PubMed DOI

Paula CCP, Montoya QV, Rodrigues A, Bichuette ME, Seleghim MHR, J. Cave Karst Stud 2016, 78 (3), 208.

Northup DE, Lavoie KH, Geomicrobiol. J 2001, 18, 199.

S Taylor EL, Stoianoff MAAR, Ferreira RL, Int. J. Speleol 2013, 42 (3), 267.

Nováková A, Int. J. Speleol 2009, 38 (1), 71.

Zhang ZF, Zhao P, Cai L, Front. Microbiol 2018, 9, 1407. PubMed PMC

Vanderwolf KJ, Malloch D, McAlpine DF, Forbes GJ, Int. J. Speleol 2013, 42 (1), 77.

Jurado V, Laiz L, Rodriguez-Nava V, Boiron P, Hermosin B, Sanchez-Moral S, Saiz-Jimenez C, Int. J. Speleol 2010, 39 (1), 15.

Belyagoubi L, Belyagoubi-Benhammou N, Jurado V, Dupont J, Lacoste S, Djebbah F, Ounadjela FZ, Benaissa S, Salim H, Abdelouahid DE, Saiz-Jimenez C, Int. J. Speleol 2018, 47 (2), 189.

Taylor ELS, Ferreira GF, De Freitas GJC, Ferreira RL, Santos DA, Resende-Stoianoff MA, Int. J. Speleol 2017, 46 (3), 369.

Tavares DG, Barbosa BVL, Ferreira RL, Duarte WF, Cardoso PG, Biocatal. Agric. Biotechnol 2018, 16, 148.

Costa Souza PN, Tavares DG, Souza CRF, Martinez MLL, Oliveira WP, Guimarães LHS, Cardoso PG, Braz. Arch. Biol. Technol 2020, 63, 1.

Gupta VK, New and Future Developments in Microbial Biotechnology and Bioengineering - Aspergillus System Properties and Applications. Elsevier, Amsterdam, 2016.

Subhan M, Faryal R, Macreadie I, J. Fungi 2016, 2, 13. 10.3390/jof2020013. PubMed DOI PMC

Xu W-F, Chao R, Hai Y, Guo Y-Y, Wei M-Y, Wang C-Y, Shao C-L, J. Nat. Prod, 2021, 84 (4), 1353. PubMed

Li W, Ding L, Wang N, Xu J, Zhang W, Zhang B, He S, Wu B, Jin H, Mar. Drugs, 2019, 17 (5), 283. 10.3390/md17050283. PubMed DOI PMC

Fukuyama K, Tsukihara T, Katsube Y, Hamasaki T, Hatsuda Y, Bull. Chem. Soc. Jpn 1975, 48 (10), 2648.

Schabort JC, Roberts HA, Biochem. Pharmacol 1971, 20 (1), 243. PubMed

Shier WT, Lao Y, Steele TWJ, Abbas HK, Bioorg. Chem 2005, 33, 426. PubMed

Kozlovskii AG, Antipova TV, Zhelifonova VP, Baskunov BP, Ivanushkina NE, Kochkina GA, Ozerskaya SM, Microbiology, 2017, 86 (2), 176. PubMed

Steyn PS, Vleggaar R, Wessels PL, Cole RJ, Scott DBJ, Chem. Soc., Perkin Trans. 1 1979, 451.

Petersen F, Dredenhagen A, Mett H, Lydon NB, Delmendo R, Jenny H-B, Peter HH, J. Antibiot 1995, 48 (3), 191. PubMed

Lee YM, Li H, Hong J, Cho HY, Bae KS, Kim MA, Kim D-K, Jung JH, Arch. Pharmacal Res 2010, 33 (2), 231. PubMed

Tian Y-Q, Lin S-T, Kumaravel K, Zhou H, Wang S-Y, Liu Y-H, Phytochem. Lett 2018, 27, 74.

Steyn PS, Vleggaar R, Wessels PL, Scott DB, J. Chem. Soc., Perkin Trans. 1, 1979, 460.

Yabe K, Ando Y, Hamasaki T, Microbiology, 1991, 137 (10), 2469. PubMed

Grau MF, Entwistle R, Oakley CE, Wang CC, Oakley BR, ACS Chem. Biol. 2019, 14 (7), 1643. PubMed PMC

Hatsuda Y, Hamasaki T, Ishida M, Yoshikawa S, Agric. Biol. Chem 1969, 33 (1), 131.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ, in Gaussian 09, Revision A.02; Gaussian, Wallingford, CT: 2009.