Asperopiperazines A and B: Antimicrobial and Cytotoxic Dipeptides from a Tunicate-Derived Fungus Aspergillus sp. DY001
| Type | Article | ||||||||||||
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| Date | 2022-07 | ||||||||||||
| Language | English | ||||||||||||
| Author(s) | Youssef Diaa T. A.1, Shaala Lamiaa A.2, 3, Genta-Jouve Gregory4 | ||||||||||||
| Affiliation(s) | 1 : King Abdulaziz Univ, Fac Pharm, Dept Nat Prod, Jeddah 21589, Saudi Arabia. 2 : Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia 3 : Department of Medical Laboratory Sciences, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia 4 : UAR3456 CNRS LEEISA, Laboratoire Ecologie, Evolution, Interactions des Systèmes Amazoniens, Centre de Recherche de Montabo, IRD, 275 Route de Montabo, CEDEX BP 70620, 97334 Cayenne, France |
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| Source | Marine Drugs (1660-3397) (Mdpi), 2022-07 , Vol. 20 , N. 7 , P. 451 (13p.) | ||||||||||||
| DOI | 10.3390/md20070451 | ||||||||||||
| WOS© Times Cited | 5 | ||||||||||||
| Note | This article belongs to the Special Issue Antimicrobial and Antiviral Agents from Marine Sources | ||||||||||||
| Keyword(s) | red sea tunicate, Didemnum sp, associated fungi, Aspergillus sp, DY001, marine dipeptides, asperopiperazines A and B, antimicrobial activity, cell lines' growth inhibition | ||||||||||||
| Abstract | Investigation of the cytotoxic fractions of the ethyl acetate extract of the fermentation broth of the tunicate-derived Aspergillus sp. DY001 afforded two new dipeptides, asperopiperazines A and B (1 and 2), along with the previously reported compounds (+)-citreoisocoumarin (3) and (-)-6,8-di-O-methylcitreoisocoumarin (4). Analyses of the 1D and 2D NMR spectroscopic data of the compounds supported their structural assignments. Asperopiperazine A (1) is a cyclic dipeptide of leucine and phenylalanine moieties, which are substituted with an N-methyl and an N-acetyl group, respectively. On the other hand, asperopiperazine B (2) is a cyclic dipeptide of proline and phenylalanine moieties with a hydroxyl group at C-2 of the proline part. The absolute configuration of the amino acid moieties in 1 and 2 were determined by Marfey's analyses and DFT NMR chemical shift calculations, leading to their assignment as cyclo(l-NMe-Leu-l-NAc-Phe) and cyclo(d-6-OH-Pro-l-Phe), respectively. Asperopiperazines A and B displayed higher antimicrobial effects against Escherichia coli and Staphylococcus aureus than Candida albicans. Furthermore, compounds 1-4 displayed variable growth inhibitory effects towards HCT 116 and MDA-MB-231 cells, with asperopiperazine A as the most active one towards HCT 116. |
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