Natural Bioactive Sterol 5α,8α-endoperoxides as Drug Lead Compounds

Bu, Ming

doi:10.4172/2161-0444.1000217

Cited by 11 publications

(10 citation statements)

References 46 publications

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“…In particular, steroidal endoperoxides are a subgroup of steroids which are ubiquitously found in marine invertebrates, such as sponges, and sea hares, among others [5]. These marine sterols have been reported to possess diverse biological properties like anti-tumor, immunomodulatory, antiviral, and antifouling activities, being considered as lead drug compounds in the development of new pharmacological agents [6]. The 5α,8α-endoperoxides belong to a group of oxidized sterols derivatives resulting from the addition of an oxygen to a 5,7-diene system in the molecule of the precursor sterol [6].…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Effects of 5α,8α-Epidioxycholest-6-en-3β-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis

Pereira

Jiménez

et al. 2019

Marine Drugs

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Sea hares of Aplysia genus are recognized as a source of a diverse range of metabolites. 5α,8α-Endoperoxides belong to a group of oxidized sterols commonly found in marine organisms and display several bioactivities, including antimicrobial, anti-tumor, and immunomodulatory properties. Herein we report the isolation of 5α,8α-epidioxycholest-6-en-3β-ol (EnP(5,8)) from Aplysia depilans Gmelin, based on bioguided fractionation and nuclear magnetic resonance (NMR) analysis, as well as the first disclosure of its anti-inflammatory properties. EnP(5,8) revealed capacity to decrease cellular nitric oxide (NO) levels in RAW 264.7 macrophages treated with lipopolysaccharide (LPS) by downregulation of the Nos2 (inducible nitric oxide synthase, iNOS) gene. Moreover, EnP(5,8) also inhibited the LPS-induced expression of cyclooxygenase-2 (COX-2), interleukin 6 (IL-6), and tumor necrosis factor alpha (TNF-α) at the mRNA and protein levels. Mild selective inhibition of COX-2 enzyme activity was also evidenced. Our findings provide evidence of EnP(5,8) as a potential lead drug molecule for the development of new anti-inflammatory agents.

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Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Effects of 5α,8α-Epidioxycholest-6-en-3β-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis

Pereira

Jiménez

et al. 2019

Marine Drugs

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“…Those characteristic features are often found in marine invertebrates, particularly soft corals [33,34,38,39]. The 5α,8αendoperoxides 44-51 are oxidized sterols which can be formed during photooxidation reaction by addition of an oxygen molecule to a conjugated 5,7-diene system in the precursor molecule which contains the steroidal core [40][41][42][43]. This 5α,8α-endoperoxide bond is exactly responsible for the observed biological activities [40].…”

Section: Steroidsmentioning

confidence: 99%

“…The 5α,8α-endoperoxides 44-51 are oxidized sterols which can be formed during photooxidation reaction by addition of an oxygen molecule to a conjugated 5,7-diene system in the precursor molecule which contains the steroidal core [40][41][42][43]. This 5α,8α-endoperoxide bond is exactly responsible for the observed biological activities [40]. Sterol 48 has a structure almost identical to ergosterol peroxide, one of the most characteristic epidioxysteroidal derivatives found in both marine and terrestrial organisms.…”

Section: Steroidsmentioning

confidence: 99%

Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

et al. 2019

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Gorgonian corals, which belong to the genus Eunicella, are known as natural sources of diverse compounds with unique structural characteristics and interesting bioactivities both in vitro and in vivo. This review is focused primarily on the secondary metabolites isolated from various Eunicella species. The chemical structures of 64 compounds were divided into three main groups and comprehensively presented: a) terpenoids, b) sterols, and c) alkaloids and nucleosides. The observed biological activities of depicted metabolites with an impact on cytotoxic, anti-inflammatory, and antimicrobial activities were reviewed. The most promising biological activities of certain metabolites point to potential candidates for further development in pharmaceutical, cosmetic, and other industries, and are highlighted. Total synthesis or the synthetic approaches towards the desired skeletons or natural products are also summarized.

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“…Isolated from a variety of fungi and sponges, as well as vascular plants, ergosterol peroxide 8 possesses broad bioactivity, including anti-tumor, immunomodulatory, inhibitory hemolytic, anti-inflammatory, antioxidant, and antimicrobial properties. Several other endoperoxides of other phytosterols and of cholestenols have been reported to have similar properties, as well [ 30 , 31 , 32 , 33 , 34 ]. Squalamine 9 is a non-microbially derived natural steroidal, which has demonstrated antimicrobial and antiangiogenic properties and has led to interest in synthetic analogues for structure-activity improvement [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Microbial Sterolomics as a Chemical Biology Tool

Haubrich

2018

Molecules

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Metabolomics has become a powerful tool in chemical biology. Profiling the human sterolome has resulted in the discovery of noncanonical sterols, including oxysterols and meiosis-activating sterols. They are important to immune responses and development, and have been reviewed extensively. The triterpenoid metabolite fusidic acid has developed clinical relevance, and many steroidal metabolites from microbial sources possess varying bioactivities. Beyond the prospect of pharmacognostical agents, the profiling of minor metabolites can provide insight into an organism’s biosynthesis and phylogeny, as well as inform drug discovery about infectious diseases. This review aims to highlight recent discoveries from detailed sterolomic profiling in microorganisms and their phylogenic and pharmacological implications.

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Natural Bioactive Sterol 5α,8α-endoperoxides as Drug Lead Compounds

Cited by 11 publications

References 46 publications

Anti-Inflammatory Effects of 5α,8α-Epidioxycholest-6-en-3β-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis

Anti-Inflammatory Effects of 5α,8α-Epidioxycholest-6-en-3β-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis

Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

Microbial Sterolomics as a Chemical Biology Tool

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