Sinugyrosanolide A, an unprecedented C-4 norcembranoid, from the Formosan soft coral Sinularia gyrosa

Cheng, Shi‐Yie; Shih, Neng Lang; Chuang, Cheng-Ta; Chiou, Shu‐Fen; Yang, Chia‐Ning; Wang, Shang‐Kwei; Duh, Chang‐Yih

doi:10.1016/j.bmcl.2014.01.073

Cited by 8 publications

(3 citation statements)

References 19 publications

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“…Soft corals, in particular, those belonging to the genus Sinularia, have proven to be rich sources of bioactive norcembranoids. − Previous bioassay results of these macrocyclic metabolites demonstrated cytotoxic, − ,− antifungal, antiviral, and anti-inflammatory activities. ,, Furthermore, some cembranoids , and steroids , with attractive bioactivities have also been discovered from corals of this genus. A literature search showed that previous chemical investigations of the soft coral Sinularia erecta (Klunzinger, 1877) afforded only a limited number of sesquiterpenes, cembranoids, and 18-norcembranoids, − and until now, the biological activities of these compounds have not been investigated.…”

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confidence: 99%

Bioactive Isoprenoid-Derived Natural Products from a Dongsha Atoll Soft Coral Sinularia erecta

et al. 2016

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Four new isoprenoids, including two norcembranoids sinulerectols A and B (1 and 2), a cembranoid sinulerectol C (3), and a degraded cembranoid sinulerectadione (4), along with three known isoprenoids, an unnamed norcembrene (5), sinularectin (6), and ineleganolide (7), and a known nitrogen-containing compound (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (8), were isolated from an extract of the marine soft coral Sinularia erecta. The structure of sinularectin (6) was revised, too. Compounds 3, 4, and 8 exhibited inhibitory activity against the proliferation of a limited panel of cancer cell lines, whereas 1, 2, and 8 displayed potent anti-inflammatory activity in fMLP/CB-stimulated human neutrophils.

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confidence: 99%

Bioactive Isoprenoid-Derived Natural Products from a Dongsha Atoll Soft Coral Sinularia erecta

et al. 2016

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“…Sesquiterpen capillosananes S-Z (1-8) diproduksi S. capillosa (Chen et al, 2014). Norcembran sinugyrosanolide dihasilkan S. gyrosa (Cheng et al, 2014). Senyawa diterpen Numerosol A-D (1-4) diperoleh pada S. numerosa dari perairan Taiwan (Tseng et al, 2014).…”

Section: Pembahasanunclassified

BACTERIAL SYMBIONT BIOACTIVE COMPOUND OF SOFT CORAL Sinularia flexibilis AND S. polydactyla

Rozirwan

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Chaidir

et al. 2016

J. Ilmu dan Teknologi Kelautan Tropis

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Symbiont bacteria on soft coral can produce bioactive compounds that plays an important role in chemical ecology and as a marine natural product. The purpose of this study was to find and characterize the antibacterial activities of active compounds extracted from bacterial symbionts of soft coral S. flexibilis and S. polydactyla. The methods used in this study were culture and isolation of bacterial symbionts, extraction of compounds, antibacterial bioassay, and identification of bioactive compounds using the LC-MS analyses. Four isolates of bacterial symbionts were obtained from two samples of soft corals, 2 isolates of Pseudomonas diminuta (A1) and Edwardsiellla hoshinae (A2) from soft coral S. flexibilis, and 2 isolates of E. hoshinae (B1) and P. acidovorans (B4) from S. polydactila. Antibacterial activity were found only from the extracts of bacterial symbionts P. diminuta (A1) and from S. flexiblis about 10.16 ± 0.3mm (for B. subtilis), 8.66 ± 0.8 mm (E. coli) and 9.86 ± 1.7mm (S. dysentri). No antibacterial activity found from the extracts of S. polydactyla. The results of LC MS analysis showed that the group of diterpenes sinularin produced by soft corals S. flexibilis and bacterial symbionts isolates of P. diminuta (A1).Keywords: Bacterial Symbiont, Bioactive Compound, Antibacterial Activity, Soft Coral, Sinularia flexibilis, Sinularia polydactyla

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“…Our interest in rameswaralide ( 1 ) stems from its complex architecture coupled with an interest in applying pharmacophore-directed retrosynthesis (PDR) to this and related cembranoids to gain a greater understanding of their SARs. We chose the common, densely functionalized 5,5,7 core ring system (Figure , blue) as the minimal structure required for bioactivity since family members that maintained this core generally displayed greater bioactivity (ineleganolide: 11.6 μM ED 50 P388 cells and sinugyrosanolide: 11.8 μM ED 50 P388 cells) than 5,5,6-tricyclic congeners (Figure , red) which to the best of our knowledge have weak to no activity. ,,− Thus, we hypothesized that the 5,5,7-tricyclic core present in rameswaralide ( 1 ), ineleganolide ( 2 ), and sinugyrosanolide A ( 3 ) is critical for their bioactivity, while variations in the D ring may impact the bioactivity to a lesser extent. These considerations guided the application of PDR to rameswaralide, leading to the synthesis of several targeted derivatives en route to the first total synthesis of this cembranoid.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy

et al. 2022

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A pharmacophore-directed retrosynthetic strategy was applied to the first total synthesis of the cembranoid rameswaralide in order to simultaneously achieve a total synthesis while also developing a structure−activity relationship profile throughout the synthetic effort. The synthesis utilized a Diels−Alder lactonization process, including a rare kinetic resolution to demonstrate the potential of this strategy for an enantioselective synthesis providing both the 5,5,6-and, through a ring expansion, 5,5,7-tricyclic ring systems present in several Sinularia soft coral cembranoids. A pivotal synthetic intermediate, a tricyclic epoxy αbromo cycloheptenone, displayed high cytotoxicity with interesting selectivity toward the HCT-116 colon cancer cell line. This intermediate enabled the pursuit of three unique D-ring annulation strategies including a photocatalyzed intramolecular Giese-type radical cyclization and a diastereoselective, intramolecular enamine-mediated Michael addition, with the latter annulation constructing the final D-ring to deliver rameswaralide. The serendipitous discovery of an oxidation state transposition of the tricyclic epoxy cycloheptenone proceeding through a presumed doubly vinylogous, E1-type elimination enabled the facile introduction of the required α-methylene butyrolactone. Preliminary biological tests of rameswaralide and precursors demonstrated weak cytotoxicity; however, the comparable cytotoxicity of a simple 6,7-bicyclic β-keto ester, corresponding to the CD-ring system of rameswaralide, to that of the natural product itself suggests that such bicyclic β-ketoesters may constitute an interesting pharmacophore that warrants further exploration.

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Sinugyrosanolide A, an unprecedented C-4 norcembranoid, from the Formosan soft coral Sinularia gyrosa

Cited by 8 publications

References 19 publications

Bioactive Isoprenoid-Derived Natural Products from a Dongsha Atoll Soft Coral Sinularia erecta

Bioactive Isoprenoid-Derived Natural Products from a Dongsha Atoll Soft Coral Sinularia erecta

BACTERIAL SYMBIONT BIOACTIVE COMPOUND OF SOFT CORAL Sinularia flexibilis AND S. polydactyla

Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy

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