Auroside, a Xylosyl-sterol, and Patusterol A and B, two Hydroxylated Sterols, from two Soft Corals Eleutherobia aurea and Lobophytum patulum

Yeffet, Dina; Rudi, Amira; Ketzinel, Sharon; Benayahu, Yehuda; Kashman, Yoel

doi:10.1177/1934578x1000500207

Cited by 5 publications

(3 citation statements)

References 29 publications

(29 reference statements)

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“…Steroid triol patusterol A 877 and tetraol patusterol B 878 were found in Lobophytum patulum (Shundo, Kenya) while auroside 879 was isolated from Eleutherobia aurea (KwaZulu-Natal, South Africa). 753 Patusterol A exhibited modest toxicity in the brine shrimp assay.…”

Section: Cnidariansmentioning

confidence: 98%

Marine natural products

et al. 2012

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Covering: 2010. Previous review: Nat. Prod. Rep., 2011, 28, 196. This review covers the literature published in 2010 for marine natural products, with 895 citations (590 for the period January to December 2010) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1003 for 2010), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Cnidariansmentioning

confidence: 98%

Marine natural products

et al. 2012

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“…Detailed analysis of the 1 H- 1 H COSY spectrum in combination with HMQC and HMBC ( Figure 2 ) experiments allowed the assignment of all of the chemical shifts in the 1 H and 13 C-NMR spectra and led to structure 1 . Comparison of 1 H-NMR and 13 C-NMR of 1 with those of the known compound 7 (patusterol A) [ 19 ], a hydroxylated steroid from the Kenyan soft coral Lobophytum patulum , further confirmed the structure of 1 . The obvious differences between the two compounds are the chemical shifts at δ H 3.71 (1H, ddd, J = 12.0, 8.4, 3.0 Hz, H-23) in 1 vs. 3.71 (1H, br t, J = 2.6 Hz, H-1) in 7 , and δ C 75.8 (CH) in 1 vs. 72.5 (CH) in 7 , indicating that the hydroxyl group in 1 is at C-23 not as 7 at C-1.…”

Section: Resultsmentioning

confidence: 73%

Polyoxygenated Sterols from the South China Sea Soft Coral Sinularia sp.

Shao

et al. 2012

Marine Drugs

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Chemical investigation of the ethanol extract of soft coral Sinularia sp. collected from the South China Sea led to the isolation of three new polyoxygenated sterols, (3S,23R,24S)-ergost-5-ene-3β,23α,25-triol (1), (24S)-ergostane-6-acetate-3β,5α,6β,25-tetraol (2), (24S)-ergostane-6-acetate-3β,6β,12β,25-tetraol (3) together with three known ones (4–6). The structures, including relative configurations of the new compounds (1–3), were elucidated by detailed analysis of spectroscopic data (IR, UV, NMR, MS) and by comparison with related reported compounds. The absolute configuration of 1 was further determined by modified Mosher’s method. Compound 5 exhibited moderate cytotoxicity against K562 cell line with an IC50 value of 3.18 μM, but also displayed strong lethality toward the brine shrimp Artemia salina with a LC50 value of 0.96 μM.

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“…They produce a wealthy biochemical repository of secondary metabolites [ 13 ] ranging from terpenoids [ 14 ], steroids [ 15 ], prostaglandins [ 16 ], and amides [ 17 ] to quinones [ 18 ]. Among these chemical constituents, steroids are one major group of metabolites that were found in many species of the genus Lobophytum , including Lobophytum sarcophytoides [ 9 , 17 ], Lobophytum pauciflorum [ 15 ], Lobophytum michaelae [ 19 ], Lobophytum crassum [ 20 , 21 ], Lobophytum lobophytum [ 22 ], Lobophytum compactum [ 23 ], Lobophytum patulum [ 24 ], and Lobophytum spp. [ 10 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Lobosteroids A–F: Six New Highly Oxidized Steroids from the Chinese Soft Coral Lobophytum sp.

Xia,

Sun,

Jin

et al. 2023

Marine Drugs

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To explore the steroidal constituents of the soft coral Lobophytum sp. at the coast of Xuwen County, Guangdong Province, China, a chemical investigation of the above-mentioned soft coral was carried out. After repeated column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC, six new steroids, namely lobosteroids A–F (1–6), along with four known compounds 7–10, were obtained. Their structures were determined by extensive spectroscopic analysis and comparison with the spectral data reported in the literature. Among them, the absolute configuration of 1 was determined by X-ray diffraction analysis using Cu Kα radiation. These steroids were characterized by either the presence of an α,β-α′,β′-unsaturated carbonyl, or an α,β-unsaturated carbonyl moiety in ring A, or the existence of a 5α,8α-epidioxy system in ring B, as well as diverse oxidation of side chains. The antibacterial bioassays showed that all isolated steroids exhibited significant inhibitory activities against the fish pathogenic bacteria Streptococcus parauberis FP KSP28, Phoyobacterium damselae FP2244, and Streptococcus parauberis SPOF3K, with IC90 values ranging from 0.1 to 11.0 µM. Meanwhile, compounds 2 and 6–10 displayed potent inhibitory effects against the vancomycin-resistant Enterococcus faecium bacterium G7 with IC90 values ranging from 4.4 to 18.3 µM. Therefore, ten highly oxidized steroids with strong antibacterial activities were isolated from the Chinese soft coral Lobophytum sp., which could be developed as new chemotypes of antibacterial drug leads.

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Auroside, a Xylosyl-sterol, and Patusterol A and B, two Hydroxylated Sterols, from two Soft Corals Eleutherobia aurea and Lobophytum patulum

Cited by 5 publications

References 29 publications

Marine natural products

Marine natural products

Polyoxygenated Sterols from the South China Sea Soft Coral Sinularia sp.

Lobosteroids A–F: Six New Highly Oxidized Steroids from the Chinese Soft Coral Lobophytum sp.

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