Sesquiterpenes from the Saudi Red Sea: Litophyton arboreum with their cytotoxic and antimicrobial activities
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Lamia T. Abou El-Kassem
,
Samy K. El-Desouky
Abstract
A new pseudoguaiane-type sesquiterpene named litopharbol (1) was isolated from the methanolic extract of the Red Sea soft coral Litophyton arboreum, along with known sesquiterpenoids alismol (2), alismorientol B (3), teuhetenone A (4), and calamusin I (5); steroid, 24-methyl-cholesta-5,24(28)-diene-3β-ol (6), alkyl glyceryl ether, chimyl alcohol (7); sphingolipid, erythro-N-dodecanoyl-docosasphinga-(4E,8E)-dienine (8); and nitrogenous bases, thymine (9) and thymidine (10). The structures were determined on the basis of nuclear magnetic resonance (NMR) spectroscopic (1D and 2D NMR data including heteronuclear single quantum coherence spectroscopy, heteronuclear multiple-bond correlation spectroscopy, and nuclear Overhauser effect spectroscopy) and mass spectrometric analyses. Compounds 1–5 were explored for antimicrobial activity and cancer cell line sensitivity tests. Compound 1 exhibited antibacterial activity against Bacillus cereus with a minimum inhibition concentration of 1.8 μg/mL, whereas compound 3 showed significant potent cytotoxic effect against MCF-7 (breast cancer cells) with IC50 4.32 μM.
Acknowledgement
The project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, Kingdom of Saudi Arabia, under grant no. (254/150/1434). The authors, therefore, acknowledge with thanks (DSR) technical and financial support.
References
1. Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR. Marine natural products. Nat Prod Rep 2016;33:382–431.10.1039/C5NP00156KSearch in Google Scholar PubMed
2. Li R, Wang S, Tan G, Long K. Two polyhydroxylated steroids from the Chinese soft coral Litophyton arboretum. Steroids 1994;59:503–5.10.1016/0039-128X(94)90066-3Search in Google Scholar
3. Shaker KH, Müller M, Ghani MA, Dahse HM, Seifert K. Terpenes from the soft corals Litophyton arboreum and Sarcophyton ehrenbergi. Chem Biodivers 2010;7:2007–15.10.1002/cbdv.201000016Search in Google Scholar PubMed
4. Grote D, Dahse HM, Seifert K. Furanocembranoids from the soft corals Sinularia asterolobata and Litophyton arboretum. Chem Biodivers 2008;5:2449–56.10.1002/cbdv.200890210Search in Google Scholar
5. Ellithey MS, Lall N, Hussein AA, Meyerb D. Cytotoxic, cytostatic and HIV-1 PR inhibitory activities of the soft coral Litophyton arboreum. Mar Drugs 2013;11:4917–36.10.3390/md11124917Search in Google Scholar PubMed
6. Ghandourah MA, Alarif WM, Abdel-Lateff A, Al-Lihaibi SS, Ayyad SN, Basaif SA, et al. Two new terpenoidal derivatives: a himachalene-type sesquiterpene and 13,14-secosteroid from the soft coral Litophyton arboretum. Med Chem Res 2015;24:4070–7.10.1007/s00044-015-1456-zSearch in Google Scholar
7. Rezanka T, Dembitsky VM. γ-Lactones from the soft corals Sarcophyton trocheliophorum and Lithophyton arboreum. Tetrahedron 2001;57:8743–9.10.1016/S0040-4020(01)00853-5Search in Google Scholar
8. Jiang Z-Y, Zhang X-M, Zhou J, Zhang F-X, Chen J-J, Lu Y, et al. Two new sesquiterpenes from Alisma orientalis. Chem Pharm Bull 2007;55:905–7.10.1248/cpb.55.905Search in Google Scholar PubMed
9. Fraga BM, Hernandez MG, Mestres T, Terrero D, Arteaga JM. Nor-sesquiterpenes from Tecrium heterophyllum. Phytochemistry 1995;39:617–9.10.1016/0031-9422(94)00947-RSearch in Google Scholar
10. Hao Z-Y, Liang D, Luo H, Liu Y-F, Ni G, Zhang Q-J, et al. Bioactive sesquiterpenoids from the rhizomes of Acorus calamus. J Nat Prod 2012;75:1083–9.10.1021/np300095cSearch in Google Scholar PubMed
11. Newton RP, Kingston EE, Overton A. Identification of novel nucleotides found in the red seaweed Porphyra umbilicalis. Rapid Commun Mass Spectrom 1995;9:305–11.10.1002/rcm.1290090409Search in Google Scholar PubMed
12. Morikawa T, Abdel-Halim OB, Matsuda H, Ando S, Muraoka O, Yoshikawa M. Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia. Tetrahedron 2006;62:6435–42.10.1016/j.tet.2006.03.091Search in Google Scholar
13. Egorov NS. Antibiotics: a scientific approach (translated from the Russian by Alexander Poshinkin). Moscow: Mir Publishers, 1985:170–7.Search in Google Scholar
14. Messmer UK, Reed UK, Brüne B. Bcl-2 protects macrophages from nitric oxide-induced apoptosis. J Biol Chem 1998;271:20192–7.10.1074/jbc.271.33.20192Search in Google Scholar
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Articles in the same Issue
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- Three new coumarin types from aerial parts of Ammi majus L. and their cytotoxic activity
- Sesquiterpenes from the Saudi Red Sea: Litophyton arboreum with their cytotoxic and antimicrobial activities
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Articles in the same Issue
- Frontmatter
- Three new coumarin types from aerial parts of Ammi majus L. and their cytotoxic activity
- Sesquiterpenes from the Saudi Red Sea: Litophyton arboreum with their cytotoxic and antimicrobial activities
- Biotechnology for bioenergy dedicated trees: meeting future energy demands
- Malusides, novel glucosylceramides isolated from apple pomace (Malus domestica)
- GC-MS characterization of n-hexane soluble fraction from dandelion (Taraxacum officinale Weber ex F.H. Wigg.) aerial parts and its antioxidant and antimicrobial properties
- N-Acetylborrelidin B: a new bioactive metabolite from Streptomyces mutabilis sp. MII
- Synthesis of methyl 4-dihydrotrisporate B and methyl trisporate B, morphogenetic factors of Zygomycetes fungi
- Volatiles from Cinnamomum cassia buds
- A new method for fast extraction and determination of chlorophylls in natural water
- Synthesis and biological evaluation of acyl derivatives of hydroxyflavones as potent antiproliferative agents against drug resistance cell lines
