Pentacyclic hemiacetal sterol with antifouling and cytotoxic activities from the soft coral Nephthea sp.

Zhang, Jun; Li, Liang‐Chun; Wang, Kai-Ling; Liao, Xiaojian; Deng, Zhou J.; Xu, Shi‐Hai

doi:10.1016/j.bmcl.2012.12.012

Cited by 30 publications

(21 citation statements)

References 22 publications

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“…On the other hand, compound 1 showed the highest in vitro cytotoxic activity against the human cervical cancer cell lines (HeLa) by the MTT assay, followed by compounds 33 and 2, with IC 50 values of 10.1, 12.3 and 19.6 μg/mL, respectively. [12] Seven 4α-methylated steroids (3, 13-17 and 56) were obtained from the methylene chloride/methanol extract of the gorgonian Litophyton mollis MACFADYAN collected from Hurghada in the Red Sea coastline of Egypt. Compound 3 showed significant cytotoxic activity against K562 human chronic myelogenous leukemia cell lines with IC 50 of 5.6 � 1.2 μM, followed by compounds 15 and 13, with IC 50 values of 7.7 � 0.8 and 8.9 � 0.9 μM, respectively.…”

Section: Steroidsmentioning

confidence: 99%

“…Nevertheless, analysis of the reviewed data has revealed some considerable gaps in studying Nephtheidae family. Firstly, some genera like Capnella, Gersemia and Umbellulifera have received less attention regarding investigating their phytoconstituents [12] 2 (18R)-18-O-Acetylnephthoacetal N. sp. [12] 3 23ζ-Acetoxy-4α,24-dimethyl-5α-cholest-24(28)-ene-3β,8β,11β-triol Litophyton mollis [16] 4 (12β,22R)-12-Acetoxy-22-hydroxycholesta-1,4-dien-3-one N. sp.…”

Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

“…[11] Among the metabolic diversity of the Nephtheidae, steroids, sesquiterpenes and diterpenes were found to prevail (Figure 1). Moreover, biological investigations carried out on these compounds demonstrated their varied potential as anticancer, [12] antimicrobial, [13] and anti-inflammatory [14] agents. In a previous literature survey on the family Nephtheidae, Hu et al reported the isolation of 329 compounds together with their biological activities before 2011.…”

Section: Introductionmentioning

confidence: 99%

“…[17] 23 3β-Methoxypregna-5,20-diene Scleronephthya flexilis [21] 24 24-methylenecholesta-1,4,22-trien-3-one D. studeri RIDLEY [19] 25 (22E,24S)-24-methyl-19-norcholesta-1,3,5(10),22-tetraen-3-ol D. studeri RIDLEY [19] 26 24-methylene-19-norcholesta-1,3,5(10),22-tetraen-3-ol D. studeri RIDLEY [19] 27 4α-methylergosta-22E,24(28)-dien-3-β-ol N. columnaris [52] 28 Nebrosteroid Q N. chabrolii [22] 29 Nebrosteroid R N. chabrolii [22] 30 Nebrosteroid S N. chabrolii [22] 31 Nephtheasteroid A N. erecta [23] 32 Nephtheasteroid B N. erecta [23] 33 Nephthoacetal N. sp. [12] 34 (22E)-19-Norcholesta-1,3,5(10),22-tetraen-3-ol D. studeri RIDLEY [19] 35 13,14-Seco-22-norergosta-4,24(28)-dien-19-hydroperoxide-3-one L. arboreum [24] 36 3-Oxocholesta-1,4-dien-12β-ol D. gigantea [25] 37 3-Oxocholesta-1,4-dien-20β-ol D. gigantea [25] 38 3-Oxocholesta-1,22-dien-12β-ol D. gigantea [25] 39…”

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confidence: 99%

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Recent Updates on Corals from Nephtheidae

Abdelhafez

Fahim

Desoukey

et al. 2019

Chemistry & Biodiversity

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Marine natural products display a wide range of biological activities, which play a vital role in the innovation of lead compounds for the drug development. Soft corals have been ranked at the top in regard to the discovery of bioactive metabolites with potential pharmaceutical applications. Many of the isolated cembranoids revealed diverse biological activities, such as anticancer, antidiabetic and anti‐osteoporosis. Likewise, sterols from soft corals exhibited interesting biological potential as anti‐inflammatory, antituberculosis and anticancer. Consequently, investigating marine soft corals will definitely lead to the discovery of a large number of chemically varied secondary metabolites with countless bioactivities for possible applications in medicine and pharmaceutical industry. This review provides a complete survey of all metabolites isolated from the family Nephtheidae, from 2011 until November 2018, along with their natural sources and biological potential whenever possible.

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Section: Steroidsmentioning

confidence: 99%

Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Recent Updates on Corals from Nephtheidae

Abdelhafez

Fahim

Desoukey

et al. 2019

Chemistry & Biodiversity

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“…Steroids are considered as major natural compounds in soft corals [1]. A multitude of studies mentioned a wide range of pharmacological activity for these compounds such as anti-inflammatory [2], antifouling [3], and anticancer [2,4,5]. In our previous work, the soft coral Litophyton arboreum total extract has been found to show promising anticancer activity in the ovarian (Hela) and leukemia (U937) cell lines, these findings supported the isolation, and the purification of the most active compounds that showed promising cytotoxic activity and high safety margins reported in our previous study [6].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Marine-Derived Compounds as Potential Anticancer Candidates

Ellithey

Ahmed

2018

Asian J Pharm Clin Res

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Objective: The objective of this research was to evaluate for the 1st time the anticancer activities of sarcophytol M (1), alismol (2), alismoxide (5), 7β-acetoxy-24-methylcholesta-5-24(28)-diene-3,19-diol (7), erythro-N-dodecanoyl-docosasphinga-(4E,8E)-dienine (8), and 24 methylcholesta- 5,24(28)-diene-3β,7β,19-triol (9). Compounds were isolated from the soft coral Lithophyton arboreum and tested in liver (HepG2), lung (A549), and breast (MDA) cancer cell line.Methods: Anticancer activities of the compounds were tested using (XTT) 2,3-bis-(2-methoxy-4-nitro- 5-sulfophenyl)-2H-tetrazolium-5-carboxanilide, Na2) in vitro assay in order to estimate the cytotoxicity and to determine the IC50s. The free radical scavenging activity of the compounds were measured by 1,1-diphenyl-2-picryl-hydrazil (DPPH•). All compounds were screened at 100 μg/ml while the most potent active compounds were assayed at lower concentrations.Results: Compounds (7) and (9) showed a strong cytotoxic effect with IC50 of 6.07, 8.5 μg/ml in HepG2, 6.3, 5.5 μg/ml in MDA cells, and 5.2, 9.3 μg/ml in A549 cancer cell lines, respectively. In addition, moderate cytotoxicity was shown by compound (2) (IC50 16.5, 15, and 13 μg/mL) in HepG2, MDA, and A549 cancer cell lines, respectively.Conclusion: The results obtained in this research work indicated a promising potential cytotoxicity of compounds (7) and (9) compared to its safety margins in Vero cells, and the expected cytostatic effect of compound (2) can be used in drug cocktails for the treatment of the major cancer types’ lung, breast, and liver cancer.

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New Cytotoxic Monoalkyl Glycerol Ether from the Red Sea Soft Coral Nephthea mollis

Eissa,

Abdel‐Tawab,

Hamed

et al. 2023

Chemistry & Biodiversity

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A new monoalkyl glycerol ether, 3‐(n‐henicosyloxy) propane‐1,2‐diol (1), was isolated from the CH2Cl2/MeOH crude extract of the Red Sea soft coral Nephthea mollis. Additionally, three known related analogues were identified: chimyl alcohol (2), batyl alcohol (3), and 3‐(icosyloxy) propane‐1,2‐diol (4). The chemical structure of 3‐(n‐henicosyloxy) propane‐1,2‐diol was determined using advanced spectroscopic analyses, including 1D, 2D Nuclear Magnetic Resonance (NMR), Electron Ionization mass spectra (EI‐MS), and High‐Resolution Electron Spray Ionization mass spectra (HRESIMS) analyses. Furthermore, the identification of chimyl alcohol, batyl alcohol and 3‐(icosyloxy) propane‐1,2‐diol was achieved by studying their EI mass fragmentation analyses and comparing their mass data with those previously reported in the literature. The cytotoxic activity of the Nephthea mollis crude extract and 3‐(n‐henicosyloxy) propane‐1,2‐diol was evaluated against five human cancer cell lines: HepG2 (hepatocellular carcinoma), MCF‐7 (breast carcinoma), NCI‐1299 (lung carcinoma), HeLa (cervical cancer cell), and HT‐29 (colon adenocarcinoma). Moreover, 3‐(n‐henicosyloxy) propane‐1,2‐diol revealed moderate cytotoxicity against the HeLa cell line with an IC50 value of 24.1 μM, while showing inactivity against the remaining cell lines (IC50 >100 μM).

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Pentacyclic hemiacetal sterol with antifouling and cytotoxic activities from the soft coral Nephthea sp.

Cited by 30 publications

References 22 publications

Recent Updates on Corals from Nephtheidae

Recent Updates on Corals from Nephtheidae

Bioactive Marine-Derived Compounds as Potential Anticancer Candidates

New Cytotoxic Monoalkyl Glycerol Ether from the Red Sea Soft Coral Nephthea mollis

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