Terpenoids from the Soft Coral Sinularia sp. Collected in Yongxing Island

Five new oxygenated sesquiterpenes, molestins A–D (1, 3–5) and epi-gibberodione (2), three new cyclopentenone derivatives, ent-sinulolides C, D, and F ((+)-9–(+)-11), one new butenolide derivative, ent-sinulolide H ((+)-13), and one new cembranolide, molestin E (14), together with 14 known related metabolites (6–8, (–)-9–(–)-11, (±)-12, (–)-13, 15–19) were isolated from the Paracel Islands soft coral Sinularia cf. molesta. The structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, quantum chemical calculations, and comparison with the literature data. Compound 5 is the first example of a norsesquiterpene with a de-isopropyl guaiane skeleton isolated from the genus Sinularia. Molestin E (14) exhibited cytotoxicities against HeLa and HCT-116 cell lines with IC50 values of 5.26 and 8.37 μM, respectively. Compounds 4, 5, and 8 showed significant inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 218, 344, and 1.24 μM, respectively.

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“…[50], and the South China Sea soft corals Sinularia sp. [51,52]. Our present study on the soft coral S. cf.…”

Section: Discussionmentioning

confidence: 90%

Metabolites from the Paracel Islands Soft Coral Sinularia cf. molesta

et al. 2018

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“…Compared with its analogue, tehranolide, the positions of the isopropyl and methyl groups were quite different. In in vitro antimalarial activity against P. falciparum 3D7, endoperoxide, sinuketal (1) showed mild activity (IC 50 = 80 µmol/L) as well as weak cytotoxicity against Jurkat, MDA-MB-231 (24.9 μmol/L), U2OS (32.3 μmol/L), and A549 (> 50 μmol/L) cell lines, and mild inhibitory acetylcholinesterase activity [37].…”

Section: μMol/l)mentioning

confidence: 99%

Potentials of marine natural products against malaria, leishmaniasis, and trypanosomiasis parasites: a review of recent articles

et al. 2021

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Background Malaria and neglected communicable protozoa parasitic diseases, such as leishmaniasis, and trypanosomiasis, are among the otherwise called diseases for neglected communities, which are habitual in underprivileged populations in developing tropical and subtropical regions of Africa, Asia, and the Americas. Some of the currently available therapeutic drugs have some limitations such as toxicity and questionable efficacy and long treatment period, which have encouraged resistance. These have prompted many researchers to focus on finding new drugs that are safe, effective, and affordable from marine environments. The aim of this review was to show the diversity, structural scaffolds, in-vitro or in-vivo efficacy, and recent progress made in the discovery/isolation of marine natural products (MNPs) with potent bioactivity against malaria, leishmaniasis, and trypanosomiasis. Main text We searched PubMed and Google scholar using Boolean Operators (AND, OR, and NOT) and the combination of related terms for articles on marine natural products (MNPs) discovery published only in English language from January 2016 to June 2020. Twenty nine articles reported the isolation, identification and antiparasitic activity of the isolated compounds from marine environment. A total of 125 compounds were reported to have been isolated, out of which 45 were newly isolated compounds. These compounds were all isolated from bacteria, a fungus, sponges, algae, a bryozoan, cnidarians and soft corals. In recent years, great progress is being made on anti-malarial drug discovery from marine organisms with the isolation of these potent compounds. Comparably, some of these promising antikinetoplastid MNPs have potency better or similar to conventional drugs and could be developed as both antileishmanial and antitrypanosomal drugs. However, very few of these MNPs have a pharmaceutical destiny due to lack of the following: sustainable production of the bioactive compounds, standard efficient screening methods, knowledge of the mechanism of action, partnerships between researchers and pharmaceutical industries. Conclusions It is crystal clear that marine organisms are a rich source of antiparasitic compounds, such as alkaloids, terpenoids, peptides, polyketides, terpene, coumarins, steroids, fatty acid derivatives, and lactones. The current and future technological innovation in natural products drug discovery will bolster the drug armamentarium for malaria and neglected tropical diseases.

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“…The carbon skeletons of the four methyl type bicyclo [6.3.0] sesquiterpenoids can be carried out by cyclization reaction and Wagner–Meerwein rearrangements from the farnesyl diphosphate (FPP) [54,55]. However, an unexpected cycloheptane to cyclooctane ring expansion process [56], a key step, may determine the occurrence rate of isopropyl type bicyclo [6.3.0] undecane sesquiterpenoids.…”

Section: Isopropyl Type Bicyclo [630] Undecane Sesquiterpenoidsmentioning

confidence: 99%

“…undecane sesquiterpenoid sinuketal ( 42 , Figure 6) from soft coral Sinularia sp. [56]. Its relative and absolute configurations were determined on the basis of the NOESY spectrum in combination with a conformational analysis, density functional theory-NMR, and the TDDFT/ECD method.…”

Section: Isopropyl Type Bicyclo [630] Undecane Sesquiterpenoidsmentioning

confidence: 99%

Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses

Qin

Liang²,

Liu³

et al. 2019

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Sesquiterpenoids constitute a marvelously varied group of natural products that feature a vast array of molecular architectures. Among them, the unusual bicyclo [6.3.0] undecane sesquiterpenoids are one of the most representative. To date, only approximately 42 naturally occurring compounds with this unique scaffold, which can be classified into seven different groups, have been reported. As the first-found member of each type, dactylol, asteriscanolide, dumortenol, toxicodenane C, and capillosanane S are characteristic of the four methyl groups on the five-eight-membered ring system. Only 11-hydroxyjasionone and sinuketal decorate the core with an isopropyl group. These natural products exhibit a wide range of bioactivities, including antifouling, anti-inflammatory, immune suppression, cytotoxic, antimutagenic, antiplasmodial, and antiviral activities. It was noted that some total syntheses of precapnellane-sesquiterpenoids (dactylol, poitediol, precapnelladiene), asteriscanolide, and 11-hydroxyjasionone have been achieved, because their cyclooctanoid core represents an important target for the development of synthetic strategies to prepare eight-membered ring-containing compounds. This review focuses on these natural sesquiterpenoids and their biological activities and synthesis, and aims to provide a foundation for further research of these interesting compounds.

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Terpenoids from the Soft Coral Sinularia sp. Collected in Yongxing Island

Cited by 29 publications

References 41 publications

Metabolites from the Paracel Islands Soft Coral Sinularia cf. molesta

Metabolites from the Paracel Islands Soft Coral Sinularia cf. molesta

Potentials of marine natural products against malaria, leishmaniasis, and trypanosomiasis parasites: a review of recent articles

Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses

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