FN Archimer Export Format PT J TI Asperopiperazines A and B: Antimicrobial and Cytotoxic Dipeptides from a Tunicate-Derived Fungus Aspergillus sp. DY001 BT AF YOUSSEF, Diaa T. A. SHAALA, Lamiaa A. GENTA-JOUVE, Gregory AS 1:1;2:2,3;3:4; FF 1:;2:;3:; C1 King Abdulaziz Univ, Fac Pharm, Dept Nat Prod, Jeddah 21589, Saudi Arabia. Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia Department of Medical Laboratory Sciences, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia 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 C2 UNIV KING ABDULLAH KAUST, SAUDI ARABIA UNIV KING ABDULLAH KAUST, SAUDI ARABIA UNIV KING ABDULLAH KAUST, SAUDI ARABIA IRD, FRANCE UM LEEISA IN WOS Cotutelle UMR DOAJ copubli-int-hors-europe IF 5.4 TC 5 UR https://archimer.ifremer.fr/doc/00786/89823/95399.pdf https://archimer.ifremer.fr/doc/00786/89823/95400.zip LA English DT Article DE ;red sea tunicate;Didemnum sp;associated fungi;Aspergillus sp;DY001;marine dipeptides;asperopiperazines A and B;antimicrobial activity;cell lines' growth inhibition AB 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. PY 2022 PD JUN SO Marine Drugs SN 1660-3397 PU Mdpi VL 20 IS 7 UT 000833308300001 DI 10.3390/md20070451 ID 89823 ER EF