Calamenenes – aromatic bicyclic sesquiterpenes – from the Indian gorgonian<i>Subergorgia reticulata</i>(Ellis and Solander, 1786)

Mol, V. P. Limna; Raveendran, T.V.; Naik, B. G.; Kunnath, Roji J.; Parameswaran, P.S.

doi:10.1080/14786419.2010.495069

Cited by 14 publications

(6 citation statements)

References 13 publications

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“…Three double bonds accounted for three degrees of unsaturation; consequently, the remaining degrees were due to the bicyclic structure of 1 . From these data, compound 1 is assumed to be a bicyclic calamenene-type sesquiterpene [ 36 , 37 ] with two oxygenated carbons. The assignment of all carbons and protons, as well as the structure of compound 1 , was elucidated based on the extensive analysis of 2D NMR ( 1 H- 1 H COSY, HSQC, and HMBC).…”

Section: Resultsmentioning

confidence: 99%

A Comprehensive In Silico Study of New Metabolites from Heteroxenia fuscescens with SARS-CoV-2 Inhibitory Activity

et al. 2022

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Chemical investigation of the total extract of the Egyptian soft coral Heteroxenia fuscescens, led to the isolation of eight compounds, including two new metabolites, sesquiterpene fusceterpene A (1) and a sterol fuscesterol A (4), along with six known compounds. The structures of 1–8 were elucidated via intensive studies of their 1D, 2D-NMR, and HR-MS analyses, as well as a comparison of their spectral data with those mentioned in the literature. Subsequent comprehensive in-silico-based investigations against almost all viral proteins, including those of the new variants, e.g., Omicron, revealed the most probable target for these isolated compounds, which was found to be Mpro. Additionally, the dynamic modes of interaction of the putatively active compounds were highlighted, depending on 50-ns-long MDS. In conclusion, the structural information provided in the current investigation highlights the antiviral potential of H. fuscescens metabolites with 3β,5α,6β-trihydroxy steroids with different nuclei against SARS-CoV-2, including newly widespread variants.

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Section: Resultsmentioning

confidence: 99%

A Comprehensive In Silico Study of New Metabolites from Heteroxenia fuscescens with SARS-CoV-2 Inhibitory Activity

et al. 2022

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“…Cnidarian metabolites with these properties included sesquiterpenes and a nitrogenous azulene derivative (Figure 3). Only one of the source description papers reported bioactivity (barnacle cyprid inhibition and Artemia nauplii mortality in 1, [11]). This pattern of bioactivity is consistent with a view of sesquiterpenes as defensive metabolites, also reflected in activity against Vibrio harveyi [12].…”

Section: Resultsmentioning

confidence: 99%

Not Drug-like, but Like Drugs: Cnidaria Natural Products

et al. 2021

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Phylum Cnidaria has been an excellent source of natural products, with thousands of metabolites identified. Many of these have not been screened in bioassays. The aim of this study was to explore the potential of 5600 Cnidaria natural products (after excluding those known to derive from microbial symbionts), using a systematic approach based on chemical space, drug-likeness, predicted toxicity, and virtual screens. Previous drug-likeness measures: the rule-of-five, quantitative estimate of drug-likeness (QED), and relative drug likelihoods (RDL) are based on a relatively small number of molecular properties. We augmented this approach using reference drug and toxin data sets defined for 51 predicted molecular properties. Cnidaria natural products overlap with drugs and toxins in this chemical space, although a multivariate test suggests that there are some differences between the groups. In terms of the established drug-likeness measures, Cnidaria natural products have generally lower QED and RDL scores than drugs, with a higher prevalence of metabolites that exceed at least one rule-of-five threshold. An index of drug-likeness that includes predicted toxicity (ADMET-score), however, found that Cnidaria natural products were more favourable than drugs. A measure of the distance of individual Cnidaria natural products to the centre of the drug distribution in multivariate chemical space was related to RDL, ADMET-score, and the number of rule-of-five exceptions. This multivariate similarity measure was negatively correlated with the QED score for the same metabolite, suggesting that the different approaches capture different aspects of the drug-likeness of individual metabolites. The contrasting of different drug similarity measures can help summarise the range of drug potential in the Cnidaria natural product data set. The most favourable metabolites were around 210–265 Da, quite often sesquiterpenes, with a moderate degree of complexity. Virtual screening against cancer-relevant targets found wide evidence of affinities, with Glide scores <−7 in 19% of the Cnidaria natural products.

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“…Hydroquinone and its derivatives are an important class of compounds that can be found in various natural compounds, synthetic intermediates, and materials such as polymers and molecular electronics . The most straightforward synthesis of hydroquinone is reduction of the corresponding quinone with stoichiometric organic and inorganic reductants, and catalytic hydrogenation methods have been utilized for this purpose –. However, preparation and derivatization of electron‐rich hydroquinones, such as naphthoquinone and anthraquinone, are challenging because they require stronger reductive conditions that cause problems of overreduction and side reaction .…”

Section: Figurementioning

confidence: 99%

Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous‐Flow Hydrogenation‐Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts

et al. 2019

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Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi‐Al2O3)) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous‐flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation, and benzoylation were successfully performed under sequential and continuous‐flow conditions to afford the desired products in good to excellent yields. Especially, air‐sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential and continuous‐flow conditions without decomposition.

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Calamenenes – aromatic bicyclic sesquiterpenes – from the Indian gorgonianSubergorgia reticulata(Ellis and Solander, 1786)

Cited by 14 publications

References 13 publications

A Comprehensive In Silico Study of New Metabolites from Heteroxenia fuscescens with SARS-CoV-2 Inhibitory Activity

A Comprehensive In Silico Study of New Metabolites from Heteroxenia fuscescens with SARS-CoV-2 Inhibitory Activity

Not Drug-like, but Like Drugs: Cnidaria Natural Products

Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous‐Flow Hydrogenation‐Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts

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