Isolation, biological significance, synthesis, and cytotoxic evaluation of new natural parathiosteroids A-C and analogues from the soft coral Paragorgia sp.
作者： Javier Jesús Poza , Rogelio Fernández , Fernando Reyes , Jaime Rodríguez , Carlos Jiménez
DOI: 10.1021/JO801198U
关键词:
摘要: Three unusual new steroid thioesters, parathiosteroids A−C (1a−3a), were isolated from the 2-propanol extract of soft coral Paragorgia sp. collected in Madagascar. Their structures, determined by detailed spectroscopic analysis, confirmed synthesis and represent first isolation natural steroids bearing a C22 thioester their side chain. These compounds displayed cytotoxicity against panel three human tumor cell lines at micromolar level. The preparation several analogues revealed structure/activity relationships this type steroids, for example, that XCH2CH2NHCOCH3 moiety (X = S, O, NH) chain is essential antiproliferative activity, low degree oxidation A-ring results higher bioactivity. products could be biosynthetic intermediates degradation pathway involving activation with CoA β-oxidations.
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sci-hub.se 参考文章(21)
Takao Kurosawa, Masato Fujiwara, Hiroyuki Nakano, Masahiro Sato, Teruki Yoshimura, Tsuyoshi Murai, Synthesis of coenzyme A esters of 3α,7α,12α-trihydroxy- and 3α,7α-dihydroxy-24-oxo-5β-cholestan-26-oic acids for the study of β-oxidation in bile acid biosynthesis Steroids. ,vol. 66, pp. 499- 504 ,(2001) , 10.1016/S0039-128X(00)00209-9
Noemı́ González, Miguel A Barral, Jaime Rodrı́guez, Carlos Jiménez, New cytotoxic steroids from the gorgonian Isis hippuris. Structure–activity studies Tetrahedron. ,vol. 57, pp. 3487- 3497 ,(2001) , 10.1016/S0040-4020(01)00223-X
P Fernandes, A Cruz, B Angelova, H.M Pinheiro, J.M.S Cabral, Microbial conversion of steroid compounds: recent developments Enzyme and Microbial Technology. ,vol. 32, pp. 688- 705 ,(2003) , 10.1016/S0141-0229(03)00029-2
Antoinette Birkenmaier, Johannes Holert, Henrike Erdbrink, Heiko M. Moeller, Anke Friemel, René Schoenenberger, Marc J.-F. Suter, Janosch Klebensberger, Bodo Philipp, Biochemical and Genetic Investigation of Initial Reactions in Aerobic Degradation of the Bile Acid Cholate in Pseudomonas sp. Strain Chol1 Journal of Bacteriology. ,vol. 189, pp. 7165- 7173 ,(2007) , 10.1128/JB.00665-07
Patrizia Ferraboschi, Diego Colombo, Paolo Prestileo, A convenient synthesis of oxandrolone through a regioselective Candida antarctica lipase-catalyzed transformation Tetrahedron-asymmetry. ,vol. 14, pp. 2781- 2785 ,(2003) , 10.1016/S0957-4166(03)00593-7
Sarah C. Lievens, Håkon Hope, Tadeusz F. Molinski, New 3-oxo-chol-4-en-24-oic acids from the marine soft coral Eleutherobia sp. Journal of Natural Products. ,vol. 67, pp. 2130- 2132 ,(2004) , 10.1021/NP049766T
Gui-Yang-Sheng Wang, Phil Crews, Geodisterol, a novel polyoxygenated sterol with an aromatic A ring from the tropical marine sponge Geodia sp. Tetrahedron Letters. ,vol. 37, pp. 8145- 8146 ,(1996) , 10.1016/0040-4039(96)01894-1
Gonzalo G. Mellado, Eva Zubía, María J. Ortega, Pablo J. López-González, Steroids from the Antarctic octocoral Anthomastus bathyproctus. Journal of Natural Products. ,vol. 68, pp. 1111- 1115 ,(2005) , 10.1021/NP050080Q
Tomoo Murohisa, Mitsugi Iida, Microbial degradation of 19-hydroxy-sterol side chains Journal of Fermentation and Bioengineering. ,vol. 75, pp. 13- 17 ,(1993) , 10.1016/0922-338X(93)90170-D
Jaime Rodríguez, Lucia Nuñez, Solange Peixinho, Carlos Jiménez, Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one- steroids from the sponges Cinachyrella spp Tetrahedron Letters. ,vol. 38, pp. 1833- 1836 ,(1997) , 10.1016/S0040-4039(97)00163-9