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

Li, Rui; Shao, Chang‐Lun; Qi, Xin; Li, Xiubao; Li, Jing; Sun, Lingling; Wang, Chang‐Yun

doi:10.3390/md10071422

Cited by 37 publications

(30 citation statements)

References 31 publications

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“…[64] and Sinularia sp. [65]), echinoderms, and sponges [62]. Interestingly, all the polyoxygenated steroids investigated for antitumor [66], antibacterial [64], antifungal [64], and reversing MDR [62] activities contain the characteristic 3β,5α,6β-hydroxyl moiety.…”

Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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Multidrug resistance (MDR) to anticancer drugs is a serious health problem that in many cases leads to cancer treatment failure. The ATP binding cassette (ABC) transporter P-glycoprotein (P-gp), which leads to premature efflux of drugs from cancer cells, is often responsible for MDR. On the other hand, a strategy to search for modulators from natural products to overcome MDR had been in place during the last decades. However, Nature limits the amount of some natural products, which has led to the development of synthetic strategies to increase their availability. This review summarizes the research findings on marine natural products and derivatives, mainly alkaloids, polyoxygenated sterols, polyketides, terpenoids, diketopiperazines, and peptides, with P-gp inhibitory activity highlighting the established structure-activity relationships. The synthetic pathways for the total synthesis of the most promising members and analogs are also presented. It is expected that the data gathered during the last decades concerning their synthesis and MDR-inhibiting activities will help medicinal chemists develop potential drug candidates using marine natural products as models which can deliver new ABC transporter inhibitor scaffolds.

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Section: Polyoxygenated Steroids and Derivativesmentioning

confidence: 99%

Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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“…Four polyoxygenated sterols were separated from a soft coral Sinularia sp., including 187 ((3S,23R,24S)ergost-5-ene-3β,23α,25-triol), 188 ((24S)-ergostane-6 -a c e t a t e -3 β , 5 α , 6 β , 2 5 -t e t r a o l ) , 1 8 9 ( ( 2 4 S )ergostane-6-acetate-3β,6β,12β,25-tetraol) and 190 (24-methylenecholestane-3β,5α,6β-triol-6-monoacetate) ( Fig. 34) (Li et al 2012b). Compound 190 showed moderate cytotoxicity against the K562 cell line (IC 50 = 3.18 μmol/L) and also demonstrated potent lethality toward brine shrimp A. salina (LC 50 = 0.96 μmol/L).…”

Section: Steroidsmentioning

confidence: 99%

Metabolites from marine invertebrates and their symbiotic microorganisms: molecular diversity discovery, mining, and application

Liu

Zheng

Shao

et al. 2019

Mar Life Sci Technol

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Metabolites from marine organisms have proven to be a rich source for the discovery of multiple potent bioactive molecules with diverse structures. In recent years, we initiated a program to investigate the diversity of the secondary metabolites from marine invertebrates and their symbiotic microorganisms collected from the South China Sea. In this review, representative cases are summarized focusing on molecular diversity, mining, and application of natural products from these marine organisms. To provide a comprehensive introduction to the field of marine natural products, we highlight typical molecules including their structures, chemical synthesis, bioactivities and mechanisms, structure-activity relationships as well as biogenesis. The mining of marine-derived microorganisms to produce novel secondary metabolites is also discussed through the OSMAC strategy and via partial chemical epigenetic modification. A broad prospectus has revealed a plethora of bioactive natural products with novel structures from marine organisms, especially from soft corals, gorgonians, sponges, and their symbiotic fungi and bacteria.

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“…Based on the coupling constants of H-6 (dd, J = 9.9, 1.9 Hz) and H-7 (d, J = 2.1 Hz), and by comparison with the reported data of hirsutosterol G [24], the protons H-5 and H-6 are in axial orientation confirming the α-OH group at C-6. Since almost all the 24-methylsterols isolated from corals have 24S stereochemistry according to the literature [5], the absolute configuration of 2 was determined as (3S,6S,24S)-ergost-7-ene-11-oxo-3β ,6α-diol, which was named zahramycin B (2).…”

Section: Zahramycin Bmentioning

confidence: 99%

“…Compound 1 has structural similarity to the recently reported (24S)-ergostane-6-acetate-3β ,5α,6β ,25-tetraol (3) isolated from the soft coral Sinularia sp. [5], and other related structures from Sarcophyton glaucum [16], except that the two oxygenated carbons C-5 and C-6 in 3 bearing hydroxy (C-5) and acetoxy (C-6) groups [5] were replaced by an oxirane ring in 1. The relative configuration of 1 was deduced on the basis of a 2D NOESY experiment.…”

Section: Zahramycin Amentioning

confidence: 99%

Zahramycins A-B, Two New Steroids from the Coral Sarcophyton trocheliophorum

Shaaban

Ghani²,

Shaaban

2013

Zeitschrift Für Naturforschung B

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Two new poly-hydroxy steroids, zahramycins A (1) and B (2), have been isolated from the polar fraction of the extract of the coral Sarcophyton trocheliophorum. Compound 1 was confirmed to bear an oxirane ring at C-5 and C-6, while 2 has a keto-hydroxy sterol structure. The known DNA primary metabolites uracil, thymine, adenine, uridine, 2 -deoxyuridine, and thymidine were also isolated and identified. Structures of the new sterols 1 and 2 were confirmed by NMR ( 1 H, 13 C, 1 H-1 H COSY, HMQC, HMBC, and NOESY) spectroscopy, mass spectrometry (EI, ESI, and HRMS), and by comparison with related structures. The antimicrobial and cytotoxic activities of compounds 1 and 2 along with that of the coral extract were also determined. Zahramycin B (2) showed high (15 mm) and moderate (12 mm) antibacterial activity against Staphylococcus aureus and Bacillus subtilis, and fungus Pythium ultimum (12 mm), while zahramycin A (1) and the crude extract of Sarcophyton trocheliophorum were inactive. Both steroids and the crude extract of Sarcophyton trocheliophorum showed no cytotoxicity.

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

Cited by 37 publications

References 31 publications

Marine Natural Products as Models to Circumvent Multidrug Resistance

Marine Natural Products as Models to Circumvent Multidrug Resistance

Metabolites from marine invertebrates and their symbiotic microorganisms: molecular diversity discovery, mining, and application

Zahramycins A-B, Two New Steroids from the Coral Sarcophyton trocheliophorum

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