Sterols from the Madagascar Sponge Fascaplysinopsis sp.

Aknin, Maurice; Gros, Emmanuelle; Vacelet, Jean; Kashman, Yoel; Gauvin‐Bialecki, Anne

doi:10.3390/md8122961

Cited by 12 publications

(7 citation statements)

References 36 publications

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“…In previous studies, the 5α,8α-epidioxy sterols were supposed to have arisen from ∆ 5,7 -sterols by photooxidization during storage and/or chromatographic separation [21,22,23] with a self-perpetuating mechanism [23]. ∆ 5,7 -Sterol analogues were not obtained from S. gaweli ; at this point it is difficult to infer whether epidioxysterol 1 from S. gaweli is a natural product or an artifact.…”

Section: Resultsmentioning

confidence: 99%

A New 5α,8α-Epidioxysterol from the Soft Coral Sinularia gaweli

et al. 2013

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Abstract:A new sterol, (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methylcholest-6,9(11)-dien-3β-ol (1), and two known sterols, (22R,23R,24R)-5α,8α-epidioxy- OPEN ACCESSMolecules 2013, 18 2896 22,23-methylene-24-methylcholest-6-en-3β-ol (2) and 24-methylenecholestane-1α,3β,5α, 6β,11α-pentol (3), were isolated from the soft coral Sinularia gaweli. The structure of sterol 1 was established by spectroscopic methods and by comparison of the spectral data with those of known analogues. The cytotoxicity of sterols 1-3 towards various tumor cells is reported.

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Section: Resultsmentioning

confidence: 99%

A New 5α,8α-Epidioxysterol from the Soft Coral Sinularia gaweli

et al. 2013

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“…Furthermore, sterols isolated from the sponge Fascaplysinopsis sp . are found to display antioxidant activity [ 43 ].…”

Section: Discussionmentioning

confidence: 99%

Evaluation of the Anti-Inflammatory, Antioxidant and Immunomodulatory Effects of the Organic Extract of the Red Sea Marine Sponge Xestospongia testudinaria against Carrageenan Induced Rat Paw Inflammation

et al. 2015

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Marine sponges are found to be a rich source of bioactive compounds which show a wide range of biological activities including antiviral, antibacterial, and anti-inflammatory activities. This study aimed to investigate the possible anti-inflammatory, antioxidant and immunomodulator effects of the methanolic extract of the Red Sea marine sponge Xestospongia testudinaria. The chemical composition of the Xestospongia testudinaria methanolic extract was determined using Gas chromatography-mass spectroscopy (GC-MS) analysis. DPPH (2, 2-diphenyl-1-picryl-hydrazyl) was measured to assess the antioxidant activity of the sponge extract. Carrageenan-induced rat hind paw edema was adopted in this study. Six groups of rats were used: group1: Control, group 2: Carrageenan, group 3: indomethacin (10 mg/kg), group 4–6: Xestospongia testudinaria methanolic extract (25, 50, and 100 mg/kg). Evaluation of the anti-inflammatory activity was performed by both calculating the percentage increase in paw weight and hisopathologically. Assessment of the antioxidant and immunomodulatory activity was performed. GC-MS analysis revealed that there were 41 different compounds present in the methanolic extract. Sponge extract exhibited antioxidant activity against DPPH free radicals. Xestospongia testudinaria methanolic extract (100 mg/kg) significantly decreased % increase in paw weight measured at 1, 2, 3 and 4 h after carrageenan injection. Histopathologically, the extract caused a marked decrease in the capillary congestion and inflammatory cells infiltrate. The extract decreased paw malondialdehyde (MDA) and nitric oxide (NO) and increased the reduced glutathione (GSH), glutathione peroxidase (GPx), and catalase (CAT) activity. It also decreased the inflammatory cytokines, tumor necrosis factor-α (TNF-α), interleukin-1 β(IL-1β) and IL-6. The results of this study demonstrated the anti-inflammatory, antioxidant, and immunomodulatory effects of the methanolic extract of the Red Sea sponge Xestospongia testudinaria (100 mg/kg).

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“…5a,8a-Epidioxysterols, which are proposed to be formed by the photooxidation reaction of conjugated D 5,7 -sterols (Aknin et al, 2010), reportedly inhibit the growth of many human and murine cancer cell lines (Ioannou et al, 2009). The IC 50 values (4.9-6.8 mg/mL) of the inhibitory activities against HMGCR-GFP showed that 5a,8a-epidioxysterols 3-5 may be effective for cholesterol metabolism disorder.…”

Section: Resultsmentioning

confidence: 99%

Bioactivities of six sterols isolated from marine invertebrates

Zhou

Sun

et al. 2013

Pharmaceutical Biology

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Context: Epidioxy sterols and sterols with special side chains, such as hydroperoxyl sterols, usually obtained from marine natural products, are attractive for bioactivities. Objective: To isolate and screen bioactive and special sterols from China Sea invertebrates. Materials and methods: Two hydroperoxyl sterols (1 and 2) from the sponge Xestospongia testudinaria Lamarck (Petrosiidae), three epidioxy sterols (3-5) from the sea urchin Glyptocidaris crenularis A. Agassiz (Glyptocidaridae), sponge Mycale sp. (Mycalidae) and gorgonian Dichotella gemmacea Milne Edwards and Haime (Ellisellidae) and an unusual sterol with 25-acetoxy-19-oate (6) also from D. gemmacea were obtained and identified. Using high-throughput screening, their bioactivities were tested toward Forkhead box O 3a (Foxo3a), 3-hydroxy-3-methylglutaryl CoA reductase gene fluorescent protein (HMGCR-GFP), nuclear factor kappa B (NF-kB) luciferase, peroxisome proliferator-activated receptor-g co-activator 1a (PGC-1a), protein-tyrosine phosphatase 1B (PTP1B), mitochondrial membrane permeabilization (MMP) and adenosine monophosphate-activated protein kinase. Results: Their structures were determined by comparing their nuclear magnetic resonance data with those reported in the literature. Three epidioxy sterols (3-5) showed inhibitory activities toward Foxo3a, HMGCR-GFP and NF-kB-luciferase with the IC 50 values 4.9-6.8 mg/mL. The hydroperoxyl sterol 29-hydroperoxystigmasta-5,24(28)-dien-3-ol (2) had diverse inhibitory activities against Foxo3a, HMGCR-GFP, NF-kB-luciferase, PGC-1a, PTP1B and MMP, with IC 50 values of 3.8-19.1 mg/mL. Discussion and conclusion: The bioactivities of 3-5 showed that 5a,8a-epidioxy is the active group. Otherwise, the most plausible biosynthesis pathway for 1 and 2 in sponge involves the abstraction of an allylic proton by an activated oxygen, such as O 2 , along with migration of carbon-carbon double bond. Therefore, the bioactive and unstable steroid should be biosynthesized in sponge under a special ecological environment to act as a defensive strategy against invaders.

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Sterols from the Madagascar Sponge Fascaplysinopsis sp.

Cited by 12 publications

References 36 publications

A New 5α,8α-Epidioxysterol from the Soft Coral Sinularia gaweli

A New 5α,8α-Epidioxysterol from the Soft Coral Sinularia gaweli

Evaluation of the Anti-Inflammatory, Antioxidant and Immunomodulatory Effects of the Organic Extract of the Red Sea Marine Sponge Xestospongia testudinaria against Carrageenan Induced Rat Paw Inflammation

Bioactivities of six sterols isolated from marine invertebrates

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