New Communesin Derivatives from the Fungus Penicillium sp. Derived from the Mediterranean Sponge Axinella verrucosa

Abstract

The ethyl acetate extract of Penicillium sp., derived from the Mediterranean sponge Axinella verrucosa, yielded the known compound communesin B (1) and its new congeners communesins C (2) and D (3), as well as the known compounds griseofulvin, dechlorogriseofulvin, and oxaline. All structures were unambiguously established by 1D and 2D NMR and MS data. In several bioassays performed on different leukemia cell lines, the communesins exhibited moderate antiproliferative activity.

Molybdenum‐Catalyzed Asymmetric Allylic Alkylation of 3‐Alkyloxindoles: Reaction Development and Applications

“…37–38 Communesin B, in particular, shows both potent cytotoxicity against P-388 leukemia (ED 50 = 0.45 µg/mL) and insecticidal activity against silk worms (LD 50 5 µg/mL). 39 Perophoramidine is cycotoxic against the HCT-116 colon carcinoma cell line (IC 50 60 µM) and induces apoptosis via PARP cleavage. 40 …”

Evolution of a Strategy for Total Synthesis of the Marine Fungal Alkaloid (±)-Communesin F

“…Recently, several other communesins have been isolated, including communesin C ( 6 ), D ( 7 ), E ( 2 ), F ( 8 ), G ( 3 ) and H ( 4 ) 3. These metabolites differ only in the substituents at N15 and N16, except for communesin F, which has a double bond instead of an epoxide at C21,22.…”

Cytotoxic Natural Products from Marine Sponge-Derived Microorganisms

“…Communesin 34 was observed to be most active on the human acute T lymphoblastic leukemia cell line MOLT-3 with an ED 50 value of 8.6 µg/mL. Conversely, 35 possessed a strong inhibitory effect on the human acute B lymphoblastic leukemia cell line SUP-B15 with an ED 50 value of 9.0 µg/mL [22]. A new sorbicillin-derived compound, 36 , metabolized by Penicillium chrysogenum associated with the Mediterranean sponge Ircinia fasciculata was found to exhibit a strong cytotoxic activity against L5178y cells and low toxicity to cervical carcinoma HeLa S3 cells and pheochromocytoma PC12 cells [23].…”