Marine antitumor agents: 14-deoxycrassin and pseudoplexaurol, new cembranoid diterpenes from the Caribbean gorgonianPseudoplexaura porosa

Abstract

Two new cytotoxic antitumor diterpenoids of the cembrane class, named 14-deoxycrassin (3) and pseudoplexaurol (4), have been isolated from the Caribbean gorgonian octocoral Pseudoplexaura porosa. The structure of lactone 3, possessing the infrequently encountered alpha-methylene-delta-lactone ring, has been established from spectral and chemical data and that of alcohol 4 has been established from spectral data.

Cell Survival and Apoptosis Signaling as Therapeutic Target for Cancer: Marine Bioactive Compounds

“…Marine organisms, including sponges [98], sponge-microbe symbiotic association [99], gorgonian [100], actinomycetes [101] and soft coral [102], have been widely explored for potential anticancer agents. The effects of marine nutraceuticals on apoptotic pathways, signaling pathways and/or different targets in cancer mean that they could be helpful starting points in the design and development of novel cancer preventive agents.…”

Identification of crassin acetate as a new immunosuppressant triggering heme oxygenase-1 expression in dendritic cells

“…This compound was originally isolated from whole dried gorgonians in 1960 15 and later found to exhibit modest in vitro cytotoxicity against fibroblasts, human leukemic cells, and HeLa cells in the anti-cancer drug discovery program at the National Cancer Institute. [16][17][18] CRA dose dependently inhibited the proliferation of C57BL/6-derived T cells triggered by BALB/c-derived DCs, with a significant effect (P Ͻ .01) observed at 2 M and almost complete (Ͼ 95%) inhibition achieved at 5 M ( Figure 1C). We also tested the impact of CRA on OVA-specific CD4 ϩ T cells freshly isolated from the DO11.10 TCR transgenic mice (BALB/c background).…”

Cembranoid-Related Metabolites and Biological Activities from the Soft Coral Sinularia flexibilis

“…In previous studies of the chemical constituents of Taiwanese soft corals, numerous marine metabolites with cytotoxic [14,15], neuroprotective [16], and anti-inflammatory activities [17,18,19] were also found from Sinularia flexibilis . Some cembranolides, possessing an α-methylene lactone ring, have been discovered as potent cytotoxic agents to a limited panel of cancer cell lines, for example, 14-deoxycrassin [20], and as significant anti-inflammatory agents, for example, sinulariolone acetate [21]. Additionally, cembranoids and related compounds from other coral species were also found to have notable antiviral [22], anti-inflammatory [23,24], and antiproliferative [25,26,27,28] activities.…”

“…flexibilis , collected off the waters of Taiwan. Herein, we report the isolation of five new cembrane-related metabolites, namely, flexbilisins D and E ( 1 and 2 ), secoflexibilisolides A and B ( 3 and 4 ), and a cembranolide flexibilisolide H ( 5 ) (Figure 1), and nine known compounds, including 6 R -hydroxysinulariolide ( 6 ) [3], 11-dehydrosinulariolide ( 7 ) [18], 11- epi -sinulariolide acetate ( 8 ) [13], 14-deoxycrassin ( 9 ) [20], 3,4:8,11-bisepoxy-7-acetoxycembra-15(17)-en-1,12-olide ( 10 ) [6], sinulariolide ( 11 ) [2], sinulaflexiolide E ( 12 ) [10], querciformolide A ( 13 ) [21], and flexibilisquinone ( 14 ) [19] (Figure 2). Their structures were established by spectroscopic analysis including infrared (IR), mass spectrometry (MS), and nuclear magnetic resonance (NMR) data (Figures S1–S14), as well as chemical transformation.…”