71939-67-8Relevant academic research and scientific papers
(-)-Tarchonanthuslactone exerts a blood glucose-increasing effect in experimental type 2 diabetes mellitus
De Souza, Gabriela F. P.,Novaes, Luiz F. T.,Avila, Carolina M.,Nascimento, Lucas F. R.,Velloso, Licio A.,Pilli, Ronaldo A.
, p. 5038 - 5049 (2015/05/27)
A number of studies have proposed an anti-diabetic effect for tarchonanthuslactone based on its structural similarity with caffeic acid, a compound known for its blood glucose-reducing properties. However, the actual effect of tarchonanthuslactone on bloo
(-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies
Toneto Novaes, Luiz Fernando,Martins Avila, Carolina,Pelizzaro-Rocha, Karin Juliane,Vendramini-Costa, Débora Barbosa,Pereira Dias, Marina,Barbosa Trivella, Daniela Barreto,Ernesto De Carvalho, Jo?o,Ferreira-Halder, Carmen Veríssima,Pilli, Ronaldo Aloise
, p. 1687 - 1699 (2015/10/06)
Natural products containing the α,β-unsaturated δ-lactone skeleton have been shown to possess a variety of biological activities. The natural product (-)-tarchonanthuslactone (1) possessing this privileged scaffold is a popular synthetic target, but its biological activity remains underexplored. Herein, the total syntheses of dihydropyran-2-ones modeled on the structure of 1 were undertaken. These compounds were obtained in overall yields of 17-21 % based on the Keck asymmetric allylation reaction and were evaluated in vitro against eight different cultured human tumor cell lines. We further conducted initial investigation into the mechanism of action of selected analogues. Dihydropyran-2-one 8 [(S,E)-(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate], a simplified analogue of (-)-tarchonanthuslactone (1) bearing an additional electrophilic site and a catechol system, was the most cytotoxic and selective compound against six of the eight cancer cell lines analyzed, including the pancreatic cancer cell line. Preliminary studies on the mechanism of action of compound 8 on pancreatic cancer demonstrated that apoptotic cell death takes place mediated by an increase in the level of reactive oxygen species. It appears as though compound 8, possessing two Michael acceptors and a catechol system, may be a promising scaffold for the selective killing of cancer cells, and thus, it deserves further investigation to determine its potential for cancer therapy. Fighting the big C: We describe the synthesis of a new family of analogues based on the scaffold of the natural product (-)-tarchonanthuslactone; these compounds were evaluated in vitro against tumor cell lines. We further conducted an initial investigation into the mechanism of action, including the inhibition of phosphatases and glutathione-S-transferase and the production of reactive oxygen species.
A facile total synthesis of all stereoisomers of tarchonanthuslactone and euscapholide from chiral epichlorohydrin
Lee, Hee-Yoon,Sampath, Vasu,Yoon, Yeokwon
scheme or table, p. 249 - 252 (2009/06/25)
A versatile and facile synthetic route to all the stereoisomers of tarchonanthuslactone and euscapholide was developed using epichlorohydrin as the source of all the chiral centers. Georg Thieme Verlag Stuttgart.
Stereoselective synthesis of tarchonanthuslactone via the Prins cyclisation
Yadav,Kumar, N. Niranjan,Reddy, M. Sridhar,Prasad
, p. 2689 - 2694 (2007/10/03)
The stereoselective total synthesis of tarchonanthuslactone, a polyketide natural product, has been achieved. The synthesis exploits the high stereochemical control in the Prins cyclisation along with ring closing metathesis (RCM) as a key step.
Enantioselective synthesis of tarchonanthuslactone using proline-catalyzed asymmetric α-aminooxylation
George, Shyla,Sudalai, Arumugam
, p. 975 - 981 (2008/02/03)
A practical enantioselective synthesis of tarchonanthuslactone 1, an important natural product with a polyol unit, is described. The sequence of synthetic reactions involves proline-catalyzed α-aminooxylation and iodine-induced electrophilic cyclization as the chiral inducing steps.
Stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol
Yadav,Reddy, P. Murali Krishna,Gupta, Manoj K.,Chary, Ch. Janardhana
, p. 3639 - 3646 (2008/09/19)
A simple and efficient stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol is described using as the key steps Jacobsen's kinetic resolution and a Sharpless asymmetric epoxidation. The synthesis of tarchonanthus-la
Chelation-controlled reduction: An enantioselective synthesis of (-)-tarchonanthuslactone
Sabitha, Gowravaram,Sudhakar,Reddy, N. Mallikarjuna,Rajkumar,Yadav
, p. 6567 - 6570 (2007/10/03)
The total synthesis of tarchonanthuslactone (1) has been achieved by two different routes. In the first approach, LiAlH4-LiI reduction and RCM protocols, and in the second approach, Wacker oxidation and LiAlH 4-LiI reduction were use
Enantioselective synthesis of tarchonanthuslactone via iterative hydrolytic kinetic resolution
Gupta, Priti,Naidu, S. Vasudeva,Kumar, Pradeep
, p. 6571 - 6573 (2007/10/03)
A short and practical enantioselective synthesis of tarchonanthuslactone has been achieved in high diastereomeric excess using iterative Jacobsen's hydrolytic kinetic resolution and ring closing metathesis as the key steps.
Asymmetric synthesis of all the stereoisomers of tarchonanthuslactone
Baktharaman,Selvakumar,Singh, Vinod K.
, p. 7527 - 7529 (2007/10/03)
We describe herein an efficient synthesis of all the four stereoisomers of tarchonanthuslactone from (R)-3-hydroxy butanoate, easily prepared from l-threonine. The approach involves the use of a β,γ-unsaturated δ-lactone as an intermediate, obtained via a
A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements
Scott, Mark S.,Luckhurst, Chris A.,Dixon, Darren J.
, p. 5813 - 5816 (2007/10/03)
(Chemical Equation Presented) A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and su
