Terretonin N: A New Meroterpenoid from Nocardiopsis sp.

Hamed A, Abdel-Razek AS, Frese M, Stammler H-G, El-Haddad AF, Ibrahim TMA, Sewald N, Shaaban M (2018)
Molecules 23(2): 299.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Hamed, Abdelaaty; Abdel-Razek, Ahmed S.; Frese, MarcelUniBi ; Stammler, Hans-GeorgUniBi; El-Haddad, Atef F.; Ibrahim, Tarek M. A.; Sewald, NorbertUniBi ; Shaaban, Mohamed
Abstract / Bemerkung
Terretonin N (1), a new highly oxygenated and unique tetracyclic 6-hydroxymeroterpenoid, was isolated together with seven known compounds from the ethyl acetate extract of a solid-state fermented culture of Nocardiopsis sp. Their structures were elucidated by spectroscopic analysis. The structure and absolute configuration of 1 were unambiguously determined by X-ray crystallography. The isolation and taxonomic characterization of Nocardiopsis sp. is reported. The antimicrobial activity and cytotoxicity of the strain extract and compound 1 were studied using different microorganisms and a cervix carcinoma cell line, respectively.
Nocardiopsis sp LGO5; terretonin N; 6-hydroxymeroterpenoid; antimicrobial activity; cytotoxicity
Page URI


Hamed A, Abdel-Razek AS, Frese M, et al. Terretonin N: A New Meroterpenoid from Nocardiopsis sp. Molecules. 2018;23(2): 299.
Hamed, A., Abdel-Razek, A. S., Frese, M., Stammler, H. - G., El-Haddad, A. F., Ibrahim, T. M. A., Sewald, N., et al. (2018). Terretonin N: A New Meroterpenoid from Nocardiopsis sp. Molecules, 23(2), 299. doi:10.3390/molecules23020299
Hamed, Abdelaaty, Abdel-Razek, Ahmed S., Frese, Marcel, Stammler, Hans-Georg, El-Haddad, Atef F., Ibrahim, Tarek M. A., Sewald, Norbert, and Shaaban, Mohamed. 2018. “Terretonin N: A New Meroterpenoid from Nocardiopsis sp.”. Molecules 23 (2): 299.
Hamed, A., Abdel-Razek, A. S., Frese, M., Stammler, H. - G., El-Haddad, A. F., Ibrahim, T. M. A., Sewald, N., and Shaaban, M. (2018). Terretonin N: A New Meroterpenoid from Nocardiopsis sp. Molecules 23:299.
Hamed, A., et al., 2018. Terretonin N: A New Meroterpenoid from Nocardiopsis sp. Molecules, 23(2): 299.
A. Hamed, et al., “Terretonin N: A New Meroterpenoid from Nocardiopsis sp.”, Molecules, vol. 23, 2018, : 299.
Hamed, A., Abdel-Razek, A.S., Frese, M., Stammler, H.-G., El-Haddad, A.F., Ibrahim, T.M.A., Sewald, N., Shaaban, M.: Terretonin N: A New Meroterpenoid from Nocardiopsis sp. Molecules. 23, : 299 (2018).
Hamed, Abdelaaty, Abdel-Razek, Ahmed S., Frese, Marcel, Stammler, Hans-Georg, El-Haddad, Atef F., Ibrahim, Tarek M. A., Sewald, Norbert, and Shaaban, Mohamed. “Terretonin N: A New Meroterpenoid from Nocardiopsis sp.”. Molecules 23.2 (2018): 299.

1 Zitation in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Natural Product Potential of the Genus Nocardiopsis.
Ibrahim AH, Desoukey SY, Fouad MA, Kamel MS, Gulder TAM, Abdelmohsen UR., Mar Drugs 16(5), 2018
PMID: 29710816

45 References

Daten bereitgestellt von Europe PubMed Central.

Laatsch H., AntiBase A.., 0
The role of natural product chemistry in drug discovery.
Butler MS., J. Nat. Prod. 67(12), 2004
PMID: 15620274
New bioactive compounds from the marine-derived actinomycete Nocardiopsis lucentensis sp. ASMR2
Eliwa E.M., Abdel-Razek A.S., Frese M., Halawa A.H., El-Agrody A.M., Bedair A.H., Sewald N., Shaaban M.., 2017
Isolation, structure and HIV-1 integrase inhibitory activity of xanthoviridicatin E and F, two novel fungal metabolites produced by penicillium chrysogenum
Singh S.B., Zink D.L., Guan Z., Collado J., Pelaez F., Felock P.J., Hazuda D.J.., 2003
Biology and chemistry of endophytes.
Zhang HW, Song YC, Tan RX., Nat Prod Rep 23(5), 2006
PMID: 17003908
Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths.
Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX., FEMS Microbiol. Lett. 241(1), 2004
PMID: 15556711
New Oxaphenalene Derivative from marine-derived Streptomyces griseorubens sp. ASMR4
Hamed A., Abdel-Razek A.S., Frese M., Wibberg D., El-Haddad A.F., Ibrahim T.M.A., Kalinowski J., Sewald N., Shaaban M.., 2017
Natural bioactive compounds and biotechnological potential of marine bacteria.
Debnath M, Paul AK, Bisen PS., Curr Pharm Biotechnol 8(5), 2007
PMID: 17979723
Marine natural products.
Blunt JW, Copp BR, Hu WP, Munro MH, Northcote PT, Prinsep MR., Nat Prod Rep 24(1), 2007
PMID: 17268607
Terretonin, ophiobolin, and drimane terpenes with absolute configurations from an algicolous Aspergillus ustus
Liu X.-H., Miao F.-P., Qiao M.-F., Cichewicz R.H., Ji N.-Y.., 2013
Terpene synthases are widely distributed in bacteria.
Yamada Y, Kuzuyama T, Komatsu M, Shin-Ya K, Omura S, Cane DE, Ikeda H., Proc. Natl. Acad. Sci. U.S.A. 112(3), 2014
PMID: 25535391
Terpenoids produced by actinomycetes: isolation, structural elucidation and biosynthesis of new diterpenes, gifhornenolones A and B from Verrucosispora gifhornensis YM28-088.
Shirai M, Okuda M, Motohashi K, Imoto M, Furihata K, Matsuo Y, Katsuta A, Shizuri Y, Seto H., J. Antibiot. 63(5), 2010
PMID: 20379218
Bendigoles A approximately C, new steroids from Gordonia australis Acta 2299.
Schneider K, Graf E, Irran E, Nicholson G, Stainsby FM, Goodfellow M, Borden SA, Keller S, Sussmuth RD, Fiedler HP., J. Antibiot. 61(6), 2008
PMID: 18667783
Terretonin, a toxic compound from aspergillus terreus
Springer J.P., Dorner J.W., Cole R.J., Cox R.H.., 1979
Sesterterpenoids, terretonins A-D, and an alkaloid, asterrelenin, from Aspergillus terreus.
Li GY, Li BG, Yang T, Yin JH, Qi HY, Liu GY, Zhang GL., J. Nat. Prod. 68(8), 2005
PMID: 16124769
Ophiobolin sesterterpenoids and pyrrolidine alkaloids from the sponge-derived fungus Aspergillus ustus
Liu H.B., Drada-Ebel R., Ebel E.R., Schulz W.B., Draeger S., Mueller W.E.G., Wary V., Lin W.H., Proksch P.., 2011
Drimane sesquiterpenoids from the fungus Aspergillus ustus isolated from the marine sponge Suberites domuncula.
Liu H, Edrada-Ebel R, Ebel R, Wang Y, Schulz B, Draeger S, Muller WE, Wray V, Lin W, Proksch P., J. Nat. Prod. 72(9), 2009
PMID: 19778087
Marine Natural Products. XI. An Antiinflammatory Scalarane-type Bishomosesterterpene, Foliaspongin, from the Okinawan Marine Sponge Phyllospongia foliascens (PALLAS)
Kikuchi H., Tsukitani Y., Kobayshi M., Kitagawa I.., 1983
Thorectandrols C, D, and E, new sesterterpenes from the marine sponge Thorectandra sp.
Charan RD, McKee TC, Boyd MR., J. Nat. Prod. 65(4), 2002
PMID: 11975486
Scalaradical derivatives from the nurdibranch chromodoris youngbleuthi and the sponge Spongia Oceania
Terem B., Scheuer P.J.., 1986
Five new C tetracyclic terpenes from a sponge (Lendenfeldia sp.)
Kazlauskas R., Murphy P.T., Wells R.J.., 1982
New cytotoxic scalarane sesterterpenes from the Dictyoceratid sponge Strepsichordaia lendenfeldi.
Bowden BF, Coll JC, Li H, Cambie RC, Kernan MR, Bergquist PR., J. Nat. Prod. 55(9), 1992
PMID: 1431942
Two new meroterpenoids, penisimplicin A and B, isolated from Penicillium simplicissimum.
Komai S, Hosoe T, Itabashi T, Nozawa K, Okada K, Campos Takaki GM, Yaguchi T, Takizawa K, Fukushima K, Kawai K., Chem. Pharm. Bull. 53(9), 2005
PMID: 16141578
Bioactive Secondary Metabolites from Marine and Terrestrial Bacteria: Isoquinolinequinones, Bacterial Compounds with a Novel Pharmacophor
Shaaban M.., 2004
Steroids and Glycosides from Astragalus turczaninowii
Agzamova M.A., Isaev I.M., Rakhmatov K.A.., 2017
Bisamides and rhamnosides from mangrove actinomycete Streptomyces sp. SZ-A15.
Ma Q, Ding W, Chen Z, Ma Z., Nat. Prod. Res. 32(7), 2017
PMID: 28438038
Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination.
Nagia MM, El-Metwally MM, Shaaban M, El-Zalabani SM, Hanna AG., Org Med Chem Lett 2(1), 2012
PMID: 22380482
MEGA7: Molecular Evolutionary Genetics Analysis Version 7.0 for Bigger Datasets.
Kumar S, Stecher G, Tamura K., Mol. Biol. Evol. 33(7), 2016
PMID: 27004904
Dendrophen, a Novel Glycyrrhetyl Amino Acid from Dendronephthya hemprichi
Shaaban M., Shaaban K.A., Abd-Alla H.I., Hanna A.G., Laatsch H.., 2011
Aroma of Basil, Scent of Pine. Bacteria Could Be Rich Source for Making Terpenes. 22 December 2014 Media Contact: Kevin Stacey 401-863-3766
Novel terpenes generated by heterologous expression of bacterial terpene synthase genes in an engineered Streptomyces host.
Yamada Y, Arima S, Nagamitsu T, Johmoto K, Uekusa H, Eguchi T, Shin-ya K, Cane DE, Ikeda H., J. Antibiot. 68(6), 2015
PMID: 25605043
Exploration and mining of the bacterial terpenome.
Cane DE, Ikeda H., Acc. Chem. Res. 45(3), 2011
PMID: 22039990
Two distinct mechanisms for TIM barrel prenyltransferases in bacteria.
Doud EH, Perlstein DL, Wolpert M, Cane DE, Walker S., J. Am. Chem. Soc. 133(5), 2011
PMID: 21214173
Terretonin biosynthesis requires methylation as essential step for cyclization.
Matsuda Y, Awakawa T, Itoh T, Wakimoto T, Kushiro T, Fujii I, Ebizuka Y, Abe I., Chembiochem 13(12), 2012
PMID: 22782788
Bacterial terpene cyclases.
Dickschat JS., Nat Prod Rep 33(1), 2016
PMID: 26563452
Novel bacterial metabolite merochlorin A demonstrates in vitro activity against multi-drug resistant methicillin-resistant Staphylococcus aureus.
Sakoulas G, Nam SJ, Loesgen S, Fenical W, Jensen PR, Nizet V, Hensler M., PLoS ONE 7(1), 2012
PMID: 22279537
Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid terretonin.
Guo CJ, Knox BP, Chiang YM, Lo HC, Sanchez JF, Lee KH, Oakley BR, Bruno KS, Wang CC., Org. Lett. 14(22), 2012
PMID: 23116177
An improved method for isolation of genomic DNA from filamentous actinomycetes
Kumar V., Bharti A., Gusain O., Bisht G.S.., 2010
Differential tolerance of streptomycetes to sodium chloride as a taxonomic aid.
Tresner HD, Hayes JA, Backus EJ., Appl Microbiol 16(8), 1968
PMID: 5675504
Antibiotic susceptibility testing by a standardized single disk method.
Bauer AW, Kirby WM, Sherris JC, Turck M., Am. J. Clin. Pathol. 45(4), 1966
PMID: 5325707

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

PMID: 29385078
PubMed | Europe PMC

Suchen in

Google Scholar