New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri

Peng, Chia-Chi; Huang, Chiung‐Yao; Ahmed, Atallah F.; Hwang, Tsong‐Long; Dai, Chang‐Feng; Sheu, Jyh‐Horng

doi:10.3390/md16080276

Cited by 21 publications

(36 citation statements)

References 49 publications

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“…Key HMBC correlations observed from H 3 -18 to C-3 and C-5; H 3 -19 to C-7 and C-9; H 2 -20 to C-11 and C-13; H-15 to C-2 were used to connect the four COSY correlated partial structures and to further establish the 3,7-linkage in the capnosane molecular skeleton. Moreover, the NMR signals at δ H 7.64 (1H, br s) and δ C 90.7 (CH) pointed out the presence of an allylic hydroperoxy group [39,40,41]. Finally, the detailed HMBC correlation analysis confirmed the hydroperoxyl, the two hydroxyls, the exomethylene, and the trisubstituted double bond to be at C-11, C-4, C-8, C-12, and C-1/C-2, respectively, and consequently the planar structure of 1 as shown in Figure 2.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

et al. 2019

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Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.

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Section: Resultsmentioning

confidence: 99%

Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

et al. 2019

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“…[23] The structures, including the absolute configurations, of cembranoids 31 and 32 were elucidated by spectroscopic analysis and chemical methods. [23]…”

Section: Sarcophyton Cherbonnieri (Family Alcyoniidae)mentioning

confidence: 99%

“…Two hydroperoxycembranoids, cherbonolides B ( 31 ) and E ( 32 ) (Figure ), were obtained from the Formosan soft coral S. cherbonnieri , collected from Jihui Fish Port, Taiwan . The structures, including the absolute configurations, of cembranoids 31 and 32 were elucidated by spectroscopic analysis and chemical methods …”

Section: Alcyonaceamentioning

confidence: 99%

Hydroperoxyditerpenoids from Octocorals

Sheu

Peng

Fang

et al. 2019

Israel Journal of Chemistry

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The structures, names, bioactivities, and references of 75 marine diterpenoids from octocorals possessing a hydroperoxy group, including 46 cembranes, 8 eunicellins, 5 briaranes, 5 dolabellanes, 4 germacranes, 3 xenicins, 2 caryophyllanes, 1 decalin, and 1 pseudopterosin, are summarized in this review article. All the hydroperoxyditerpenoids mentioned in this review were isolated from octocorals from Alcyonacea (Briareum excavatum, Briareum polyanthes, Briareum violaceum, Briareum sp., Cespitularia sp., Cladiella tuberculosa, Cladiella sp., Clavularia inflata, Klyxum simplex, Lemnalia sp., Lobophytum crassum, Lobophytum sp., Nephthea pacifica, Sarcophyton cherbonnieri, Sarcophyton crassocaule, Sarcophyton glaucum, Sarcophyton mililatensis, Sarcophyton trocheliophorum, Sarcophyton sp., Sinularia arborea, Sinularia erecta, Sinilaria flexibilis, Sinularia gibberosa, Sinularia manaarensis, Xenia umbellata) and Gorgonacea (Astrogorgia sp., Eunicea calyculata, Eunicea pinta, Eunicea succinea, Eunicea sp., Pseudopterogorgia sp.). Among these isolates, 41 compounds exhibited potential biomedical activities, including cytotoxicity, antimalarial activity, anti‐inflammatory activity, and antibacterial activity.

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“…Subsequently, a series of analogs were discovered from different Sarcophyton species. Importantly, these compounds have been proven to display diverse biological activities, including cytotoxic [ 4 , 5 , 6 , 7 , 8 , 9 , 10 ], anti-inflammatory [ 11 , 12 , 13 , 14 ], and antiviral [ 15 ] activities. In our study of discovering bioactive natural products, we focused on the investigation of secondary metabolites obtained from the soft coral Sarcophyton tenuispiculatum and examined the biological activities of the isolates.…”

Section: Introductionmentioning

confidence: 99%

New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral Sarcophyton tenuispiculatum

Huang

Chen

et al. 2020

Marine Drugs

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Chemical investigation of the marine soft coral Sarcophyton tenuispiculatum resulted in the isolation of a 1,4-dihydrobenzoquinone, sarcotenuhydroquinone (1), three new cembranoids, sarcotenusenes A‒C (2‒4), and ten previously reported metabolites 5–14. The chemical structures of all isolated metabolites were determined by detailed spectroscopic analyses. In biological assays, anti-inflammatory, cytotoxic, and peroxisome proliferator-activated receptor γ (PPAR-γ) transcription factor assays of all compounds were performed. None of the isolated compounds were found to exhibit activity in the PPAR-γ transcription factor assay. The anti-inflammatory assays showed that (+)-7α,8β-dihydroxydeepoxysarcophine (13) inhibited the production of IL-1β to 56 ± 1% at a concentration of 30 µM in lipopolysaccharide (LPS)-stimulated J774A.1 macrophage cells. In addition, 1 and 2 were found to exhibit cytotoxicity towards a panel of cancer cell lines.

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New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri

Cited by 21 publications

References 49 publications

Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

Hydroperoxyditerpenoids from Octocorals

New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral Sarcophyton tenuispiculatum

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