Pregna-1,4,20-triene-3-one, a novel marine steroid from the sea raspberry gersemia rubiformis

Kingston, John F.; Fallis, Alex G.

doi:10.1016/s0040-4039(01)83480-8

Cited by 18 publications

(12 citation statements)

References 22 publications

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“…For chemical background to soft corals, see: Coll (1992); Sarma et al (2009). For the initial isolation of the title compound, see: Kingston et al (1977); Higgs & Faulkner (1977). For further isolations of the title compound from other organisms, see: Maia et al (1998); Ciavatta et al (2004); Zhang et al (2003Zhang et al ( , 2005.…”

Section: Related Literaturementioning

confidence: 99%

“…Pregna-1,4,20-triene-3-one was first isolated independently in parallel by the groups of Fallis (Kingston et al, 1977) and…”

Section: S1 Commentmentioning

confidence: 99%

“…The methyl substituents at atoms C-10 and C-13 are oriented to the same side of the steroid nucleus. The vinyl group at C17 is attached equatorially to ring D. The absolute configuration could not be determined by x-ray, but could be established by direct comparison of optical rotation and 1 H NMR and 13 C NMR data with literature data (Ciavatta et al, 2004;Higgs & Faulkner, 1977;Kingston et al, 1977 and1979).…”

Section: S1 Commentmentioning

confidence: 99%

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Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

2010

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The title compound, C21H28O, was isolated from the cytotoxic lipid extract of the Fidjian soft coral Nephthea sp. The steroid showed inhibitory activity to human colon adenocarcinoma SW480 cells (IC50 = 2.5 µg ml−1). The molecular structure indicates that the A ring is almost planar (r.m.s. deviation = 0.032 Å), the B and C rings adopt chair conformations and the five-membered D ring is a half-chair. The B/C and C/D ring junctions are trans-fused.

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Section: Related Literaturementioning

confidence: 99%

“…Pregna-1,4,20-triene-3-one was first isolated independently in parallel by the groups of Fallis (Kingston et al, 1977) and…”

Section: S1 Commentmentioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

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Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

2010

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“…attracted our attention because the EtOAc crude extract displayed significant toxicity toward the larvae of the brine shrimp Artemia salina , with a mortality rate of 88.6% at a concentration of 25 μg/mL. Chemical investigation on the active extract led to the isolation of four pregnanes with a 3-one framework: 15 β -hydroxypregna-1,4,20-trien-3-one ( 1 ), 15 β -acetoxypregna-1,4,20-trien-3-one ( 2 ) [13], 18-acetoxypregna-1,4,20-trien-3-one ( 3 ) [13], and pregna-1,4,20-trien-3-one ( 4 ) [14,15] (Figure 1). Their structures were elucidated by NMR spectroscopic methods and comparison with data previously reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Bioactive Pregnane Steroids from a South China Sea Gorgonian Carijoa sp.

Zhao

Shao

et al. 2013

Molecules

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Abstract:A new pregnane steroid, 1, and three known analogues 2-4, have been isolated from a gorgonian Carijoa sp. collected from the South China Sea. The planar structure and relative configuration of 1 were elucidated from comprehensive spectroscopic data. Its absolute configuration was determined by application of the modified Mosher method. Compounds 1, 3 and 4 exhibited cytotoxicity against the human hepatoma cell line Bel-7402, with IC 50 values of 9.33, 11.02 and 18.68 µM, respectively. Additionally, compound 1 exhibited promising antibacterial activity against Pseudomona puido, with a MIC value of 31 nM, which is approximately 5-fold more potent than ciprofloxacin (MIC = 156 nM).

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“…, a new sterol, dendrotriol(71), along with the wellknown metabolites, cholesterol(26) [30] (Figure 4) and hexitol (72)[66]. The structures of new compounds 70 and 71 were established by spectroscopic methods, although the stereocehmsitry for C-24 stereogenic center in 71 was not determined[66].…”

mentioning

confidence: 99%

Natural Products from Octocorals of the Genus Dendronephthya (Family Nephtheidae)

Chen¹,

Chang

Chen

et al. 2020

Molecules

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In this review, 170 natural substances, including steroid, diterpenoid, sesquiterpenoid, peptide, prostaglandin, base, chlorolipid, bicyclolactone, amide, piperazine, polyketide, glycerol, benzoic acid, glycyrrhetyl amino acid, hexitol, pentanoic acid, aminoethyl ester, octadecanone, alkaloid, and a 53-kD allergenic component from octocorals belonging to genus Dendronephthya, were listed. Some of these compounds displayed potential bioactivities.

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Pregna-1,4,20-triene-3-one, a novel marine steroid from the sea raspberry gersemia rubiformis

Cited by 18 publications

References 22 publications

Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

Bioactive Pregnane Steroids from a South China Sea Gorgonian Carijoa sp.

Natural Products from Octocorals of the Genus Dendronephthya (Family Nephtheidae)

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