Steroidal Alkaloids from the Marine Sponge Corticium niger That Inhibit Growth of Human Colon Carcinoma Cells

Abstract

Bioinformatic analysis of data from the NCI-60 cell cytotoxicity screen revealed a subset of extracts that showed selective cytotoxic activity toward human colon carcinoma cell lines. Bioassay-guided fractionation of a colon cancer selective extract from a Philippines collection of the marine sponge Corticium niger provided two new steroidal alkaloids, plakinamines N (1) and O (2), along with two known compounds of the plakinamine class (3, 4). The structures of these compounds were elucidated by interpretation of combined MS and NMR spectroscopic data. Plakinamines N (1), O (2), and J (4) were tested for antiproliferative activity in the NCI-60 screen, and they showed enhanced inhibitory effects against all of the colon cell lines with mean GI50 values of 11.5, 2.4, and 1.4 μM, respectively.

Mechanism of antiproliferative action of a new d -secoestrone-triazole derivative in cervical cancer cells and its effect on cancer cell motility

“…Natural and natural-related compounds are the most commonly used drugs worldwide; hence, the first anticancer agents with a steroid structure were of herbal origin [49][50][51][52][53][54][55]. Besides natural plant steroids, some endogenous steroid metabolites are also reported to be potent antiproliferative agents [10][11][12][13][14][15][16]56].…”

Plakinamine P, A Steroidal Alkaloid with Bactericidal Activity against Mycobacterium tuberculosis

“…The presence of two dimethylamino groups in 1 was suggested by the resonances observed as two broadened singlets (δ H 2.84 and δ H 2.85) integrating for 12 protons attached to carbon resonances observed at δ C 42.7 and 40.5. A literature search suggested that similar resonances are found in the plakinamine class of natural products [5][6][7][8][9][10][11][12][13][14][15] and comparison of the NMR data to the published data suggested that 1 is most similar to plakinamines L and M [14,15]. Other characteristic resonances observed in the 1 H NMR spectrum of 1 were the methyl resonances observed at δ H 0.59 (H 3 -18, s) and δ H 0.86 (H 3 -19, s), which are consistent with the angular methyl groups of a steroidal alkaloid.…”

New 3‐alkylpyridine marine alkaloid analogues as promising antitumor agents against the CD44+/high/CD24−/low subset of triple‐negative breast cancer cell line

“…Different classes of marine alkaloids, such as plakinamine and fascaplysin, have been described in the literature with similar in vitro cytotoxic effects . However, few studies have demonstrated the cytotoxic effects of marine alkaloids against breast cancer cell lines .…”