Scalarane-Type Bishomosesterterpenes from the Sponge Phyllospongia foliascens

Guo²,

Gu³

2006

CMC

The increasing demand for new lead compounds in the pharmaceutical and agrochemical industries has driven scientists to search for new sources of bioactive natural products. Marine invertebrates are a rich source of novel, bioactive secondary metabolites and they have attracted a great deal of attention from scientists in the fields of chemistry, pharmacology, ecology, and molecular biology. During the past 25 years, many complex and structurally unique secondary metabolites have been isolated from the invertebrates inhabiting the South China Sea. These metabolites are responsible for various bioactivities such as anti-tumor, anti-inflammation and antioxidant activities, and/or they act on the cardiovascular system. This review will focus on the marine natural product chemistry of invertebrates from the South China Sea, aiming to give the reader a brief view of the compounds isolated from these invertebrates, as well as their biological activities. The article covers the literature published during the period from the beginning of 1980 to the end of 2005, with 340 citations and 811 compounds from invertebrates from the South China Sea, including sponges, coelenterates, molluscs and echinoderms.

Section: Spongesmentioning

confidence: 99%

Section: Spongesmentioning

confidence: 99%

See 1 more Smart Citation

Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Guo²,

Gu³

2006

CMC

“…Several carbolactone-based bishomoscalarane sesterterpenes have been isolated from marine sponges, which only limited to three different sponge genera, namely Carteriospongia [4–6], Phyllospongia [7–16], and Strepsichordaia [17]. And some Phyllospongia sponges were found to metabolite 20, 24-bishomoscalarane sesterter-penes with moderate in vitro cytotoxic activities against KB, BS-C-1, P388, NIH 3T3 cell lines and HIV-1 [11, 15, 16]. Therefore, this type sesterterpene has attracted worldwide attention in the field of marine natural product chemistry.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Phyllactone Analogs from the Marine Sponge Phyllospongia papyrecea

Crews

Tenney

et al. 2017

Background A growing evidence indicates that marine sponge Phyllospongia sp. is one of rich sources of 20, 24-bishomoscalarane sesterterpenes with potent biological activities. In order to search more bioactive 20, 24-bishomoscalarane sesterterpenes for new drug discovery, chemical investigation was carried out on an Indonesian marine sponge P. papyrecea. Methods Bioassay-guided fractionation was carried out on its dichloromethane extract. And nine compounds were purified and isolated using HPLC. Their chemical structures were determined by a combination of spectroscopic and spectrometric data, including 1D-, 2D-NMR and HRESI-MS. Their cytotoxic activities were performed on three human tumor cell lines A549, MCF-7 and HeLa using the CCK-8 method. Results One new 20, 24-bishomoscalarane sesterterpene, phyllactone H (9), was isolated and elucidated together with phyllactones A-B (1–2) and D-G (3–6), 12α, 24-dihydroxy-20, 24-dimethyl-15, 17-scalaradien-25, 24-olides (7–8). Compounds 1 and 2, 3 and 4, 5 and 6, 7 and 8 were C-24 anomers and inseparable mixtures, respectively. The 1H and 13C-NMR data for 7/8 were firstly reported in this paper. Conclusion Compounds 1–9 possessed in vitro moderate cytotoxicities against A549, MCF-7 and HeLa cells with IC50 values of less than 25 μM.

“…-Marine sponges of the order Dictyoceratida are rich resources of bioactive scalarane-based sesterterpenes [1], and some of them were characterized by a 20(24)-(bis)homoscalarane skeleton and were considered to be ideal chemotaxonomic markers for the foliose sponges of the family Spongiidae [2]. The sponge Phyllospongia foliascens has proven to possess novel sesterterpenes with cytotoxic, antimicrobial, anti-inflammatory and anti-HIV activities, such as foliaspongin [3] [4], phyllofoliaspongin [5], phyllactones [6], phyllofenones [7], and phyllofolactones [7] [8]. In our continuing studies on bioactive constituents of marine sponges collected from the South China Sea, the acetone extract of P. foliascens showed significant antineoplastic activity in vitro.…”

mentioning

confidence: 99%

Scalarane Sesterterpenes from the Chinese Sponge Phyllospongia foliascens

Tang

et al. 2009

Helvetica Chimica Acta

Three new scalarane sesterterpenes, phyllofolactone L (1), phyllofenone D (2) and phyllofenone E (3), were isolated from the acetone extract of the South China Sea sponge Phyllospongia foliascens. Their structures were elucidated on the basis of spectroscopic analysis. Phyllofenone D (2) was cytotoxic against the P388 leukemia cell line with an IC 50 value of 6.5 mg/ml. [7], and phyllofolactones [7] [8]. In our continuing studies on bioactive constituents of marine sponges collected from the South China Sea, the acetone extract of P. foliascens showed significant antineoplastic activity in vitro. Bioassay-guided separation led to the isolation of two new 24-homoscalarane sesterterpenes, phyllofolactone L (1) and phyllofenone D (2), and a new 20,24-bishomo-25-norscalarane sesterterpene, phyllofenone E (3), from this sponge. The details of isolation and structure elucidation are reported in this work.