New polyhydroxydinostane sterols from the Caribbean gorgonian octocoral Pseudopterogorgia americana

Rodrı́guez, Abimael D.; Rivera, Jocelyn; Boulanger, Anna

doi:10.1016/s0040-4039(98)01695-5

Cited by 18 publications

(6 citation statements)

References 10 publications

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“…The downfield shift of H 3 -28 from δ 0.77 in 10 to δ 0.93 in 4 supported the above conclusion. The 1 H NMR and 13 C NMR assignments of the side chain were identical to those of model compounds [29,30,31,32,33,34]. An S absolute stereochemistry at C-24 in 4 was proposed by careful comparison of 1 H NMR data with those of in dinosterol and its C-24 epimer [31], where the 1 H signals for H 3 -21 ( δ 0.921, d, J = 6.9 Hz)), H 3 -27 ( δ 0.779, d, J = 6.8 Hz) and H 3 -26( δ 0.836, d, J = 6.5 Hz) were close to those of dinosterol ( δ 0.919, d, J = 6.5 Hz, H 3 -21; 0.778, d, J = 6.5 Hz, H 3 -26; 0.837, d, J = 6.5 Hz, H 3 -27) rather than its C-24 epimer ( δ 0.910, d, J = 6.8 Hz, H 3 -21; 0.772, d, J = 6.8 Hz, H 3 -26; 0.848, d, J = 6.5 Hz, H 3 -27).…”

Section: Resultsmentioning

confidence: 68%

Bioactive Polyoxygenated Steroids from the South China Sea Soft Coral, Sarcophyton sp.

et al. 2013

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Seven new polyoxygenated steroids (1–7) were isolated together with seven known analogues (8–14) from the South China Sea soft coral, Sarcophyton sp. The structures of the new compounds were identified on the basis of extensive spectroscopic analysis and comparison with reported data. All the steroids are characterized with 3β,5α,6β-hydroxy moiety, displaying carbon skeletons of cholestane, ergostane, gorgostane and 23,24-dimethyl cholestane. In the in vitro bioassay, metabolites exhibited different levels of antimicrobial activity against bacterial species Escherichia coli and Bacillus megaterium, and fungal species Microbotryum violaceum and Septoria tritici. No inhibition was detected towards microalga Chlorella fusca. Preliminary structure-activity analysis suggests that the 11α-acetoxy group may increase both antibacterial and antifungal activities. The terminal-double bond and the cyclopropane moiety at the side chain may also contribute to the bioactivity.

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Section: Resultsmentioning

confidence: 68%

Bioactive Polyoxygenated Steroids from the South China Sea Soft Coral, Sarcophyton sp.

et al. 2013

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“…P. americana from Puerto Rico gave the 4R-methyl sterols A10.10g 2 and the 9,11-seco product A10.11g 2 . 100 A ∆ 5 sterol, the known secogorgosterol A6.09h 1 (Figure 6), was isolated as the major sterol. 100 From P. acerosa, A10.12g 2 , named as acerosterol, is reported.…”

Section: Activation Of Allylic Carbons: C(4) (Figure 10)mentioning

confidence: 99%

“…100 A ∆ 5 sterol, the known secogorgosterol A6.09h 1 (Figure 6), was isolated as the major sterol. 100 From P. acerosa, A10.12g 2 , named as acerosterol, is reported. 101 From Pseudopterogorgia sp.…”

Section: Activation Of Allylic Carbons: C(4) (Figure 10)mentioning

confidence: 99%

Marine Metabolites: The Sterols of Soft Coral

et al. 2009

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“…475 Two polyhydroxylated dinostane sterols 662 and 663 were obtained from Pseudopterogorgia americana from Puerto Rico. 476 An Indonesian Lophogorgia species contained 3b,7b,11-trihydroxy-5a,6a-epoxy-9,11-secogorgostan-9-one 664. 477 3b,6a,11-Trihydroxy-9,11-seco-5a-cholest-7-ene-9-one 665 and both 24S-and 24R-methyl-3b,6a,11-trihydroxy-9,11-seco-5a-cholest-7,22E-diene-9-ones 666 and 667 were isolated from the gorgonian Subergorgia suberosa from the Indian Ocean.…”

Section: Spongesmentioning

confidence: 99%