Briareins C−L, 10 New Briarane Diterpenoids from the Common Caribbean Gorgonian <i>Briareum asbestinum</i>

Rodrı́guez, Abimael D.; Ramı́rez, Catherine; Cóbar, Oscar M.

doi:10.1021/np960001y

Cited by 27 publications

(36 citation statements)

References 25 publications

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“…Its 13 C and 1 H NMR data (Tables 1 and 2) were similar to those of 11 with the difference of some additional signals for an acetate ester, an isovalerate ester, and an oxymethyl (d C 53.0, q). In 4, the 1 H and 13 C NMR spectra showed the existence of four acetate and one isovalerate groups which were assigned to C-2, C-9, C-12, C-14, and C-13 because their carbonyl carbons were correlated with the corresponding oxymethine protons in the HMBC spectrum.…”

Section: Resultsmentioning

confidence: 58%

“…Its 13 C and 1 H NMR data (Tables 1 and 3) were closely similar to those of 11 with the only difference of an additional acetate group attached to the oxymethylene C-16 because of the HMBC correlations of d H 4.75, 5.04 (each d, J¼15.6 Hz, H-16) and 2.12 (3H, s) with d C 170.5 (s). Based on complete NMR study, the structure of juncin W (6) was inferred as shown in Figure 1, and its relative stereochemistry was proved to be the same as that of 1.…”

Section: Resultsmentioning

confidence: 62%

“…According to a summary about the chemical shifts of exocyclic 11,20-epoxy groups in briarane derivatives, that while the 13 C NMR data for C-11 and C-20 appeared at d C 62-63 and 58-60 ppm, respectively, the epoxy group was b-oriented and the cyclohexane ring existed in a boat conformation; however, if the 13 C NMR data for C-11 and C-20 were shifted upfield and signals appeared at d C 55-61 and 47-52 ppm, respectively, the epoxy group was a-oriented and the cyclohexane ring had a chair conformation, 14 the stereochemistry of 11,20-epoxide [d C 58.4 (C-11), 49.1 (C-20)] in 1 should be a-oriented, and the cyclohexane ring was in a boat conformation. The Z configuration of the disubstituted double bond at C-3 was determined by the proton coupling constant (J¼10.5 Hz) between the olefinic protons H-3 and H-4.…”

Section: Resultsmentioning

confidence: 99%

“…Its 13 73.1 (t, C-16). Based on complete NMR studies, the structure of juncin V (5) was elucidated as shown in Figure 1, and its relative stereochemistry was proved to be the same as that of 1.…”

Section: Resultsmentioning

confidence: 99%

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Ten New Antifouling Briarane Diterpenoids from the South China Sea Gorgonian Junceella juncea

Zhang

Qian

et al. 2007

ChemInform

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Abstract-Ten new antifouling briarane diterpenoids, juncins R-ZI (1-10) were isolated from the South China Sea gorgonian coral Junceella juncea. The structures of these new compounds were established by extensive spectroscopic analysis, including 1D and 2D NMR data. Compounds 1-10 all showed potent antifouling activities against the larval settlement of barnacle Balanus amphitrite at nontoxic concentrations with EC 50 values of 0. 004, 0.34, 2.65, 1.61, 3.77, 21.06, 0.004, 0.14, 1.47, and 0.51 mg mL À1 . The structure-activity relationship was discussed.

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Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 62%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Ten New Antifouling Briarane Diterpenoids from the South China Sea Gorgonian Junceella juncea

Zhang

Qian

et al. 2007

ChemInform

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“…1,2) The majority of these compounds are endowed with biological activities that ranges from cytotoxic [3][4][5] to anti-inflammatory, 6,7) immunomodulatory, 8) antiviral, 9) and insecticidal 10,11) actions. In continuation of our interest in the chemistry and potential medicinal importance of briaranes, [12][13][14] we investigated the gorgonian octocoral Junceella juncea collected in Taiwan.…”

mentioning

confidence: 99%

Juncenolides F and G, Two New Briarane Diterpenoids from Taiwanese Gorgonian Junceella juncea

Lin

Huang

Khalil

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Briaranes are diterpenoid g-lactones of highly substituted bicyclic six-and ten-membered rings that are extensively produced by marine octocorals including gorgonians.1,2) The majority of these compounds are endowed with biological activities that ranges from cytotoxic [3][4][5] to anti-inflammatory, 6,7) immunomodulatory, 8) antiviral, 9) and insecticidal 10,11) actions. In continuation of our interest in the chemistry and potential medicinal importance of briaranes, [12][13][14] we investigated the gorgonian octocoral Junceella juncea collected in Taiwan. Several juncins, 15,16) gemmacolides, 16) junceelolides 13) and juncenolides 12,14) have been reported from this species. The current study resulted in the isolation of the two novel briarane-type diterpenoidal compounds, juncenolides F (1) and G (2) from the acetone extract of Junceella juncea. The structures were defined on the basis of spectral studies, especially 1D and 2D NMR.The HR-ESI-MS of 1 revealed a quasi-molecular ion peak at m/z 693 [MϩNa] ϩ consistent with the molecular formula C 33 H 47 O 12 Cl and ten degrees of unsaturation. The IR spectrum displayed absorption bands diagnostic of hydroxyl, 5-membered lactone and ester groups. Both 1 H-and 13 C-NMR spectral data (Table 1 15,16) Besides the previous four ester carbonyls, the carbon signal at d 174.5 was assigned to a 5-membered lactone ring together with the oxygenated methine at d 81.2 (C-7). The two proton singlets at d 5.81 and 5.52 along with the CH 2 signal at d 121.2 were ascribed to an exocyclic methylene group. The 1 H-NMR spectrum contained two mutually coupled signals at d 2.82, 2.35 (each 1H, d, Jϭ4.0 Hz) together with the corresponding d C 50.5 (t) and d C 57.4 (s) that were appropriate for an exocyclic epoxide. The two remaining degrees of unsaturation required a bicyclic carbon skeleton which fits a briarane diterpene. ϩ were strong evidence of the presence of a chlorine atom in 1.7) Consequently, the CH signal at d 51.7 was confidently assigned to a chlorinated carbon (C-6) that was correlated to d (Fig. 1). On the other hand, the HMBC displayed correlations between H-10/C-8, C-20; H-7/C-5; H- * To whom correspondence should be addressed. Chemical investigation of the gorgonian coral Junceella juncea collected in Taiwan has resulted in the isolation of the two novel briarane-type diterpenoid compounds, juncenolides F (1) and G (2). The structures were determined on the basis of spectral studies, especially 1D and 2D NMR.

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Cnidaria and Ctenophora–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Membrane Constituents and Secondary Metabolites of Hexacorallia (Anthozoa) Fatty Acids, Oxylipins, and Acetylenic Derivatives Sterols and Ecdysteroids Terpenes Carotenoids of Sea Anemones Aromatic Derivatives Ceramides and Lipidic α‐Amino Acids Examples of Nitrogenous Pigments: Zoanthoxanthins and Calliactine Palytoxins ( PTXs ) Mycosporines Betaines, Phosphobetaines, Purines, and Other Nitrogen‐Containing Derivatives Zoanthamine Alkaloids Cytolysins, Neuropeptides, and Other Venoms of Sea Anemones Venoms and Other Metabolites of Medusozoa Some Data on the Cubozoa and Other Jellyfish Bioluminescence of Jellyfish and Other Cnidaria Some Results on the Secondary Metabolites of Other Hydrozoa Ctenophora

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Briareins C−L, 10 New Briarane Diterpenoids from the Common Caribbean Gorgonian Briareum asbestinum

Cited by 27 publications

References 25 publications

Ten New Antifouling Briarane Diterpenoids from the South China Sea Gorgonian Junceella juncea

Ten New Antifouling Briarane Diterpenoids from the South China Sea Gorgonian Junceella juncea

Juncenolides F and G, Two New Briarane Diterpenoids from Taiwanese Gorgonian Junceella juncea

Cnidaria and Ctenophora–2

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