10140-70-2Relevant articles and documents
A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7
Ye, Xuewei,Anjum, Komal,Song, Tengfei,Wang, Wenling,Yu, Siran,Huang, Haocai,Lian, Xiao-Yuan,Zhang, Zhizhen
, p. 1156 - 1161 (2016)
Five curvularin macrolides (1-5) were isolated from the cultured broth of marine actinomycete Pseudonocardia sp. HS7 that was obtained from the cloacal aperture of sea cucumber Holothuria moebii. The structures of these isolates were characterized as (11S,15R)-11-hydroxycurvularin (1), (11R,15R)-11-hydroxycurvularin (2), curvularin-7-O-α-D-glucopyranoside (3), trans-dehydrocurvularin (4) and curvularin (5) based on their NMR and HRESIMS data as well as chemical degradation. Compound 3 is a new macrolide with a rare α-D-glucopyranose substituent. Compounds 1-4, 5a and 5c (the acyl products of 5), suppressed the proliferation of all six tested cancer cell lines and 4 is the most active compound with IC50 values ranging from 0.59 to 3.39 M. The 11-hydroxycurvularins 1 and 2 also showed antibacterial activity inhibiting the growth of Escherichia coli.
Microbial transformation of curvularin
Zhan, Jixun,Gunatilaka, A. A. Leslie
, p. 1271 - 1273 (2005)
The microbiological transformation of curvularin (1) with Beauveria bassiana ATCC 7159 afforded three new metabolites identified as curvularin-7-O-β-D-glucopyranoside (2), curvularin-4′-O-methyl-7-O- β-D-glucopyranoside (3), and 6-hydroxycurvularin-4′-O-methyl-6-O- β-D-glucopyranoside (4) resulting from hydroxylation, glucosidation, and methylglucosidation of the substrate. Isolation of 6-methyl-2,4-dihydroxyphenyl- 4′-O-methyl-1-O-β-D-glucopyranoside (5) from the fermentation broth of B. bassiana ATCC 7159 without any added substrate suggested that hydroxylase, glucosyl transferase, and methylase are constitutive enzymes of this organism.
Stereoselective total synthesis of (-)-curvularin
Radha Krishna, Muniganti,Sridhar, Gattu,Syed, Tasqeeruddin,Jayaprakash
, p. 37 - 42 (2021/12/22)
A concise total synthesis of (-)-Curvularin have been synthesized from commercially available (S)-(?)-propylene epoxide and (3,5-Dimethoxyphenyl)acetic acid. The key steps involved in the synthesis are Vilsmeier-Haack formylation, Grignard reaction, alkyl
A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites
Allu, Srinivasa Rao,Banne, Sreenivas,Jiang, Jia,Qi, Na,Guo, Jian,He, Yun
, p. 7227 - 7237 (2019/06/07)
A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A-D were synthesized for the first time. The key steps in this approach inclu
Umpolung Pd-Catalyzed α-arylation reactions in natural product synthesis: Syntheses of (+)-xestodecalactone A, (-)-curvularin, (+)-12-oxocurvularin and (-)-citreofuran
De Joarder, Dripta,Jennings, Michael P.
, p. 3303 - 3313 (2015/05/20)
The syntheses (total and formal) of four phenylacetic acid lactone (PAL) natural products have been accomplished by utilizing a unified strategy of an umpolung Pd-catalyzed α-arylation of complex α-bromo esters and boronic acids under mild reaction conditions. As part of the synthetic approaches to these natural products, it was observed that the mild coupling reaction conditions readily tolerated terminal alkenes, other labile ester functionalities, an α,β-unsaturated ester moiety, and a protected allylic alcohol, while chemoselectively engaging the α-bromo ester. The completion of (+)-xestodecalactone A and (-)-curvularin coupled with the formal syntheses of (+)-12-oxocurvularin and (-)-citreofuran highlight the umpolung Pd-catalyzed α-arylation strategy as a key convergent tactic in complex natural product synthesis.
Aryne acyl-alkylation in the general and convergent synthesis of benzannulated macrolactone natural products: An enantioselective synthesis of (-)-curvularin
Tadross, Pamela M.,Virgil, Scott C.,Stoltz, Brian M.
supporting information; experimental part, p. 1612 - 1614 (2010/06/17)
(Figure Presented) A general approach for the synthesis of benzannulated macrolactone natural products utilizing an ary ne acyl-alkylation reaction is described. Toward this end, the total syntheses of the natural products (-)-curvularin, curvulin, and (-
Total synthesis of (S)-(-)-curvularin: A ring-closing-metathesis-based construction of the macrocyclic framework
Mohapatra, Debendra K.,Rahaman, Hasibur,Pal, Rita,Gurjar, Mukund K.
scheme or table, p. 1801 - 1804 (2009/04/08)
A convergent, flexible, and efficient approach to the synthesis of curvularin is described. Key step is the high-yielding macrocyclic ring formation by ring-closing metathesis (RCM) using the Grubbs second-generation catalyst. Georg Thieme Verlag Stuttgar
Biosynthetic incorporation of advanced precursors into dehydrocurvularin, a polyketide phytotoxin from Alternaria cinerariae
Liu, Yaoquan,Li, Zhe,Vederas, John C.
, p. 15937 - 15958 (2007/10/03)
Biosynthesis of the polyketide, dehydrocurvularin 1, by Alternaria cinerariae was examined by incorporation experiments with N-acetylcysteamine (NAC) thiolesters of potential labeled di-, tri-, tetra-, and pentaketide assembly intermediates, 5-10. The results show that diketide and α,β- unsaturated tetraketide precursors can be utilized intact, whereas a saturated tetraketide can not, thereby suggesting that 1 is the initial PKS product. Curvularin 2 and 1 could not be interconverted by A. cinerariae, but 8-hydroxycurvularin 3 and 1 are transformed into each other by component(s) in the fermentation media.
Biosyntheses of Antibiotic A26771B by Penicillium turbatum and Dehydrocurvularin by Alternaria cinerariae: Comparison of Stereochemistry of Polyketide and Fatty Acid Enoyl Thiol Ester Reductases
Arai, Kunizo,Rawlings, Bernard J.,Yoshizawa, Yuko,Vederas, John C.
, p. 3391 - 3399 (2007/10/02)
The biosyntheses of reduced polyketides and fatty acids were compared by use of stable isotope labeling and NMR spectroscopy.Incorporations of sodium -, -, -, -, -, and acetates i
