Marine-Derived Lead Fascaplysin: Pharmacological Activity, Total Synthesis, and Structural Modification

Abstract

Fascaplysin is a planar structure pentacyclic alkaloid isolated from sponges, which can effectively induce the apoptosis of cancer cells. In addition, fascaplysin has diverse biological activities, such as antibacterial, anti-tumor, anti-plasmodium, etc. Unfortunately, the planar structure of fascaplysin can be inserted into DNA and such interaction also limits the further application of fascaplysin, necessitating its structural modification. In this review, the biological activity, total synthesis and structural modification of fascaplysin will be summarized, which will provide useful information for pharmaceutical researchers interested in the exploration of marine alkaloids and for the betterment of fascaplysin in particular.

Current Status of Indole-Derived Marine Natural Products: Synthetic Approaches and Therapeutic Applications

“…Reduced DHβC and THβC analogs of compounds 217-237 (Figure 50) have similar therapeutic activity compared to their unsaturated counterparts. Eudistomidins B (238), G (239), H (240), and I (241), isolated from Eudistoma glaucus, exhibited cytotoxicity against L1210, L5178Y, P388, and KB cancer cells, although weaker than related compounds 223-237. Ingenine F (242), obtained from Acanthostrongylophora ingens, showed similar levels of cytotoxic activity against MCF-7, HCT-116, and A549 lines compared to compound 230 [172].…”

“…Namely, anticancer activity against Human Alveolar Rhabdomyosarcoma cells, leukemia, liver cancer cells, melanoma, small lung cancer cells, and ovarian cancer cells, among others. Further, they also exert analgesic, anti-thrombotic, anti-Alzheimer’s, and antimalarial activity [ 238 ]. Thorectandramine ( 333 ), from the marine sponge Thorectandra sp., had weak cytotoxicity against MCF-7, OVCAR-3, and A549 cell lines (EC 50 27.0–55.0 μg/mL) [ 239 ].…”

Current Scenario of Indole Marine-Derivatives: Synthetic Approaches and Therapeutic Applications

“…Namely, anticancer activity against Human Alveolar Rhabdomyosarcoma cells, leukemia, liver cancer cells, melanoma, small lung cancer cells, and ovarian cancer cells, among others. Further, they also exert analgesic, anti-thrombotic, anti-Alzheimer's, and antimalarial activity [238]. Thorectandramine (333), from the marine sponge Thorectandra sp., had weak cytotoxicity against MCF-7, OVCAR-3, and A549 cell lines (EC 50 27.0-55.0 µg/mL) [239].…”

Recent Advances in the Synthesis of the Marine-Derived Alkaloid Fascaplysin and Its Metabolites Homofascaplysins A–C

“…Fascaplysin inhibits AChE noncompetitively, with IC50 and Ki values of 1.49 and 2.28 µM, respectively [20]. At 1 mM, fascaplysin displays promising P-gp activation and AChE inhibition, which together with good medication safety demonstrates the potential of this compound as an anti-Alzheimer agent [21]. Furthermore, fascaplysin shows potential antiplasmodial activity, inhibiting Plasmodium falciparum strains NF54 and K1 with IC50 values of 34 and 50 ng/mL, respectively [22].…”