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dc.contributor.authorShao, Chang-Lun
dc.contributor.authorFeng Mou, Xiao
dc.contributor.authorCao, Fei
dc.contributor.authorSpadafora, Carmenza
dc.contributor.authorGlukhov, Evgenia
dc.contributor.authorGerwick, Lena
dc.contributor.authorYun Wang, Chang
dc.contributor.authorGerwick, William H.
dc.date.accessioned2020-06-26T04:51:12Z
dc.date.available2020-06-26T04:51:12Z
dc.date.issued2018-01-12
dc.identifier.otherDOI: 10.1021/acs.jnatprod.7b00917
dc.identifier.urihttp://repositorio-indicasat.org.pa/handle/123456789/119
dc.descriptionWe reported previously the discovery of the potent antimalarial 40-membered macrolide bastimolide A (1) from the tropical marine cyanobacterium Okeania hirsute. Continued investigation has led to the discovery of a new analogue, bastimolide B (2), a 24-membered polyhydroxy macrolide with a long aliphatic chain and unique terminal tertbutyl group. Its complete structure was determined by a combination of extensive spectroscopic methods and comparative analysis of its methanolysis products with those of bastimolide A. A methanolysis mechanism for bastimolide A is proposed, and one unexpected isomerization product of the C2−C3 double bond, 2-(E)-bastimolide A (3), was obtained. Bastimolide B (2) showed strong antimalarial activity against chloroquine-sensitive Plasmodium falciparum strain HB3. A preliminary investigation of the structure−activity relationship based on six analogues revealed the importance of the double bond as well as the 1,3-diol and 1,3,5-triol functionalities.en_US
dc.description.abstractWe reported previously the discovery of the potent antimalarial 40-membered macrolide bastimolide A (1) from the tropical marine cyanobacterium Okeania hirsute. Continued investigation has led to the discovery of a new analogue, bastimolide B (2), a 24-membered polyhydroxy macrolide with a long aliphatic chain and unique terminal tertbutyl group. Its complete structure was determined by a combination of extensive spectroscopic methods and comparative analysis of its methanolysis products with those of bastimolide A. A methanolysis mechanism for bastimolide A is proposed, and one unexpected isomerization product of the C2−C3 double bond, 2-(E)-bastimolide A (3), was obtained. Bastimolide B (2) showed strong antimalarial activity against chloroquine-sensitive Plasmodium falciparum strain HB3. A preliminary investigation of the structure−activity relationship based on six analogues revealed the importance of the double bond as well as the 1,3-diol and 1,3,5-triol functionalities.en_US
dc.formatApplication/pdf
dc.language.isoengen_US
dc.rightshttps://creativecommons.org/licenses/by/4.0/
dc.subjectAntimalarial 24-Membereden_US
dc.subjectMarine Macrolideen_US
dc.subjectPossessing a tert-Butyl Groupen_US
dc.titleBastimolide B, an Antimalarial 24-Membered Marine Macrolide Possessing a tert-Butyl Groupen_US
dc.typeinfo:eu-repo/semantics/articleen_US
dc.typeInfo:eu-repo/semantics/publishedversion


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