Sarcophytonins F and G, New Dihydrofuranocembranoids from a Dongsha Atoll Soft Coral <i>Sarcophyton</i> sp.

Chen, Shin Pin; Chen, Bo Wei; Dai, Chang‐Feng; Sung, Ping Jyun; Wu, Yang Chang; Sheu, Jyh‐Horng

doi:10.1246/bcsj.20120100

Cited by 11 publications

(9 citation statements)

References 16 publications

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“…The DEPT spectra of 6 showed the presence of eight methyls, twelve sp 3 methylenes, six sp 3 oxygenated methines, four sp 2 methines, two sp 3 and eight sp 2 nonprotoned carbons (including two ester carbonyls). NMR signals resonating at δ C 114.3 (CH), 141.4 (C), 124.9 (C), 82.7 (CH) and 10.2 (CH 3 ), and δ H 5.28 (1H, d, J = 10.0 Hz) and δ H 1.72 (3H, s), and another group of signals observed at δ C 114.4 (CH), 141.5 (C), 124.9 (C), 81.9 (CH) and 10.2 (CH 3 ), and δ H 5.50 (1H, d, J = 10.0 Hz) and δ H 1.73 (3H, s), revealed the presence of two slightly different 2,5-dihydrofuran rings with a peroxyl group by comparison of the similar NMR data of five-membered rings in the literature [35]. Also, two groups of signals resonating at δ C 61.2 (C), 62.1 (CH) and δ H 2.51 (1H, m), and δ C 61.3 (C), 62.2 (CH) and δ H 2.51 (1H, m) showed the presence of two trisubstituted epoxides.…”

Section: Resultsmentioning

confidence: 65%

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

et al. 2018

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Six new cembranoids, cherbonolides A−E (1–5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 1–7 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils.

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Section: Resultsmentioning

confidence: 65%

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

et al. 2018

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“…Following bioassay-guided fractionation of the cytotoxic organic extract of N. pacifica, four prenylcyclogermacrane diterpenoids, pacificins C (27), E (28), G (29), and H (30) were isolated ( Figure 14). [22] The structures of germacranes 27-30 were determined by spectral data analysis.…”

Section: Nephthea Pacifica (Family Nephtheidae)mentioning

confidence: 99%

“…The structure of 46 was elucidated by spectral analysis, although the configuration of the stereogenic center at C-16 could not be elucidated at that stage. [30] In addition, a 8-hydroperoxycembranoid, (1S*,2E,4R*,6E,8S*,11S*,12S*)-11,12-epoxy-8-hydroperoxy-4-hydroxy-2,6-cembradiene (47) (Figure 21), was isolated from Sarcophyton sp., collected from Bohey Dulang, Semporna, Sabah, Malaysia. The structure of cembranoid 47 was elucidated by spectral analysis, and this compound was found to show strong inhibition of seaweed pathogens Alteromonas sp., Cytophaga-Flavobacterium, and Vibrio sp., at an antibiosis index of 0.5, 1.25, and 1.75, respectively.…”

Section: Sarcophyton Spmentioning

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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“…Sarcophytonins F and G 129 and 130, another two dihydrofuranocembranoids, were reported from Sarcophyton sp. [55]. Nineteen compounds from Sarcophyton sp., of which five cembrane diterpenoids were isolated and identified as 7-acetyl-8-epi-sinumaximol G 131, 8-episinumaximol G 132, 12-acetyl-7,12-epi-sinumaximol G 133, 12-hydroxysarcoph-10-ene 134, and 8-hydroxy-epi-sarcophinone 135, together with sinumaximol G 136, were reported [56].…”

Section: Introductionmentioning

confidence: 99%

Chemical Diversity in Species Belonging to Soft Coral Genus Sacrophyton and Its Impact on Biological Activity: A Review

et al. 2020

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One of the most widely distributed soft coral species, found especially in shallow waters of the Indo-Pacific region, Red Sea, Mediterranean Sea, and also the Arctic, is genus Sacrophyton. The total number of species belonging to it was estimated to be 40. Sarcophyton species are considered to be a reservoir of bioactive natural metabolites. Secondary metabolites isolated from members belonging to this genus show great chemical diversity. They are rich in terpenoids, in particular, cembranoids diterpenes, tetratepenoids, triterpenoids, and ceramide, in addition to steroids, sesquiterpenes, and fatty acids. They showed a broad range of potent biological activities, such as antitumor, neuroprotective, antimicrobial, antiviral, antidiabetic, antifouling, and anti-inflammatory activity. This review presents all isolated secondary metabolites from species of genera Sacrophyton, as well as their reported biological activities covering a period of about two decades (1998–2019). It deals with 481 metabolites, including 323 diterpenes, 39 biscembranoids, 11 sesquiterpenes, 53 polyoxygenated sterols, and 55 miscellaneous and their pharmacological activities.

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Sarcophytonins F and G, New Dihydrofuranocembranoids from a Dongsha Atoll Soft Coral Sarcophyton sp.

Abstract: The absolute configuration of compounds (I) and (II) is deduced from the configuration of known compounds isolated together with (I) and (II) from the same organism and with the same carbon skeleton.

Cited by 11 publications

References 16 publications

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

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

Hydroperoxyditerpenoids from Octocorals

Chemical Diversity in Species Belonging to Soft Coral Genus Sacrophyton and Its Impact on Biological Activity: A Review

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