2524-37-0Relevant articles and documents
THE INCORPORATION OF 3-HYDROXY-3-METHYLGLUTARIC ACID INTO THE LACTONE RING OF DIOSCORINE IN DIOSCOREA HISPIDA
Leete, Edward,Michelson, Robert H.
, p. 3325 - 3330 (1989)
- and -3-Hydroxy-3-methylglutaric acid were administered to Dioscorea hispida plants, resulting in formation of labelled dioscorine (0.2 percent absolute incorporation).A chemical degradation indicated that there was a non-random incorporation of (14)C into the lactone ring of the alkaloid, the major part of the radioactivity being at its C-10 position.This specific labelling was confirmed by examination of the 13C NMR spectrum of the enriched dioscorine derived from the (13)C2-labelled precursor.There was some scrambling of label, presumably due to catabolism of the 3-hydroxy-3-methylglutaric acid to acetyl-coenzyme A followed by recycling of this intermediate.However the most significant satellites in the 13C NMR spectrum were those arising from contiguous (13)C atoms at C-10 and C-13 of the dioscorine.Ethyl orcellinate failed to serve as a significant precursor of dioscorine.These results indicate that 3-hydroxy-3-methylglutaric acid, or more likely its mono coenzyme A ester, is an intermediate between acetate and the branched eight-carbon unit required for the biosynthesis of dioscorine.Key Word Index - Dioscorea hispida; Dioscoreaceae; dioscorine; alkaloid biosynthesis; 3-hydroxy-3-methylglutaric acid; 13C NMR spectroscopy.
Synthesis and biological evaluation of cajanonic acid A derivatives as potential PPARγ antagonists
Guo, Bing,Hu, Chu-Jiao,Peng, Jin-Gang,Tang, Lei,Wang, Jian-Ta,Xia, Jing,Zhang, Ji-Quan,Zhu, Gao-Feng
supporting information, (2021/10/22)
Four series of cajanonic acid A (CAA) derivatives have been designed and synthesized. The newly prepared compounds have been screened for glucose consumption activity in HepG2 cell lines and PPARγ antagonistic activity in HEK293 cell lines. Compound 26g bearing a tetrahydroisoquinolinone scaffold showed the most potent PPARγ antagonistic and hypoglycemic activities. An oral glucose tolerance test (OGTT) was performed and the results further confirmed that 26g was a potent hypoglycemic agent. In addition, the possible binding modes for compound 26g in the PPARγ protein have been investigated in this study.
Secondary Metabolites of Onygenales Fungi Exemplified by Aioliomyces pyridodomos
Lin, Zhenjian,Kakule, Thomas B.,Reilly, Christopher A.,Beyhan, Sinem,Schmidt, Eric W.
, p. 1616 - 1626 (2019/06/17)
Fungi from the order Onygenales include human pathogens. Although secondary metabolites are critical for pathogenic interactions, relatively little is known about Onygenales compounds. Here, we use chemical and genetic methods on Aioliomyces pyridodomos, the first representative of a candidate new family within Onygenales. We isolated 14 new bioactive metabolites, nine of which are first disclosed here. Thirty-two specialized metabolite biosynthetic gene clusters (BGCs) were identified. BGCs were correlated to some of the new compounds by heterologous expression of biosynthetic genes. Some of the compounds were found after one year of fermentation. By comparing BGCs from A. pyridodomos with those from 68 previously sequenced Onygenales fungi, we delineate a large biosynthetic potential. Most of these biosynthetic pathways are specific to Onygenales fungi and have not been found elsewhere. Family level specificity and conservation of biosynthetic gene content are evident within Onygenales. Identification of these compounds may be important to understanding pathogenic interactions.
First total synthesis of natural products cajanolactone A and cajanonic acid A
Chen, Wen-Zhang,Fan, Ling-Ling,Xiao, Hai-Tao,Zhou, Ying,Xiao, Wan,Wang, Jian-Ta,Tang, Lei
, p. 749 - 751 (2014/06/09)
First total synthesis of cajanolactone A and cajanonic acid A has been achieved through steps of anion-anion condensations, cyclization, Williams etherification, selective demethylation, 1,3-sigmatropic rearrangement and hydrolysis. This work provides an efficient method for future cajanonic acid A derivatives synthesis.
