Phyllospongianes A–E, Dinorscalarane Sesterterpenes from the Marine SpongePhyllospongia foliascens

Abstract

Phyllospongianes A–E (1–5), five new scalarane derivatives featuring an unprecedented 6/6/6/5 tetracyclic dinorscalarane scaffold, along with the known probable biogenetic precursor, 12-deacetylscalaradial (6), were isolated from the marine sponge Phyllospongia foliascens. The structures of the isolated compounds were determined by analysis of spectroscopic data and electronic circular dichroism experiments. Compounds 1–5 are the first 6/6/6/5 tetracyclic scalarane derivatives to be reported within the scalarane family. Compounds 1, 2, and 4 exhibited antibacterial activity against Vibrio vulnificus, Vibrio parahemolyticus, Escherichia coli, Staphylococcus aureus, Enterococcus faecalis, Bacillus subtilis, and Pseudomonas aeruginosa with MIC values ranging from 1 to 8 μg/mL. Furthermore, compound 3 exhibited significant cytotoxic activity on MDA-MB-231, HepG2, C4-2-ENZ, MCF-7, H460, and HT-29 cancer cell lines with IC50 values in the range between 0.7 and 13.2 μM.

Nor-24-homoscalaranes, Neutrophilic Inflammatory Mediators from the Marine Sponge Lendenfeldia sp.

“…Previous research on Lendenfeldia sponges revealed a rich diversity of secondary metabolites, with sesterterpenoids being particularly prominent [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. These sesterterpenoids exhibit a broad spectrum of biological activities, including cytotoxicity [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ], anti-inflammatory properties [ 5 , 7 , 18 , 32 , 33 , 34 , 35 , 36 ], anti-HIV effects [ 3 , 37 ], anti-microbial [ 15 , 16 , 22 , 38 , 39 , 40 , 41 ] and anti-neurofibroma activity [ 42 ]. Anti-n...…”

Phyllofenones F–M, Scalarane Sesterterpenes from the Marine Sponge Phyllospongia foliascens

“…Scalaranes can be divided into homoscalaranes (methylated at C-20 or C-24) and bishomoscalaranes (methylated at both C-20 and C-24) [2,3]. They are exclusively obtained from nudibranchs and their food chain, marine sponges [3,4]. The majority (around 90%) of scalaranes have been isolated from various marine sponges, including Hyrtios sp., Phyllospongia (previously identified as Carteriospongia) sp., Dysidea sp., Lendenfeldia sp., hippospongia sp., Scalarispongia sp., Spongia sp., Psammocinia sp., Ircinia sp., Euryspongia sp., Hyatella sp., Hyattlla sp., Coscinoderma sp., Smenospongia sp., and Collospongia sp.…”

“…The majority (around 90%) of scalaranes have been isolated from various marine sponges, including Hyrtios sp., Phyllospongia (previously identified as Carteriospongia) sp., Dysidea sp., Lendenfeldia sp., hippospongia sp., Scalarispongia sp., Spongia sp., Psammocinia sp., Ircinia sp., Euryspongia sp., Hyatella sp., Hyattlla sp., Coscinoderma sp., Smenospongia sp., and Collospongia sp. [2,4]. Since the first scalarane, scalarin, was reported in 1972 [5], approximately 500 scalaranes have been identified [2,3].…”

“…Since the first scalarane, scalarin, was reported in 1972 [5], approximately 500 scalaranes have been identified [2,3]. Moreover, extensive research has been conducted on the synthesis or semi-synthesis of scalarane derivatives due to their diverse bioactivity, including cytotoxic [6], anti-inflammatory [7], antimicrobial [4,8], and enzyme-inhibitory activity [9].…”

“…During our ongoing research on bioactive secondary metabolites from marine sponges in the South China Sea [4,7,10], we discovered that an extract obtained from the sponge P. foliascens demonstrated potent cytotoxic activity against human cancer cells. Following a comprehensive chemical investigation of the bioactive extracts, we successfully isolated…”