Literature DB >> 12141860

Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su".

Yoshiaki Kamano1, Toshihiko Nogawa, Ayano Yamashita, Masahiko Hayashi, Masuo Inoue, Pavel Drasar, George R Pettit.   

Abstract

Steroid bufenolides resulting from epoxidation of the 17beta-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line.

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Year:  2002        PMID： 12141860     DOI： 10.1021/np0200360

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  8 in total

1.  Configurational reassignment and improved preparation of the competitive IL-6 receptor antagonist 20R,21R-epoxyresibufogenin-3-formate.

Authors:  Terrence L Boos; Kejun Cheng; Elisabeth Greiner; Jeffrey R Deschamps; Arthur E Jacobson; Kenner C Rice
Journal:  J Nat Prod       Date:  2012-02-23       Impact factor: 4.050

2.  The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).

Authors:  George R Pettit; Bryan R Moser; Ricardo F Mendonça; John C Knight; Fiona Hogan
Journal:  J Nat Prod       Date:  2012-05-18       Impact factor: 4.050

3.  Anti-leukemic effect of 2-pyrone derivatives via MAPK and PI3 kinase pathways.

Authors:  Jin Sun Yoon; Young Woong Won; Seo Ju Kim; Suk Joong Oh; Eun Shil Kim; Byoung Kook Kim; Cheon Gyu Cho; Jung Hye Choi; Byeong Bae Park; Min Ho Lee; Young Yiul Lee
Journal:  Invest New Drugs       Date:  2012-04-19       Impact factor: 3.850

4.  Pilot study of huachansu in patients with hepatocellular carcinoma, nonsmall-cell lung cancer, or pancreatic cancer.

Authors:  Zhiqiang Meng; Peiying Yang; Yehua Shen; Wenying Bei; Ying Zhang; Yongqian Ge; Robert A Newman; Lorenzo Cohen; Luming Liu; Bob Thornton; David Z Chang; Zongxing Liao; Razelle Kurzrock
Journal:  Cancer       Date:  2009-11-15       Impact factor: 6.860

Review 5.  New therapeutic aspects of steroidal cardiac glycosides: the anticancer properties of Huachansu and its main active constituent Bufalin.

Authors:  Chien-Shan Cheng; Jiaqiang Wang; Jie Chen; Kuei Ting Kuo; Jian Tang; Huifeng Gao; Lianyu Chen; Zhen Chen; Zhiqiang Meng
Journal:  Cancer Cell Int       Date:  2019-04-11       Impact factor: 5.722

6.  Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones.

Authors:  Matam Parameshwar; Manda Rajesh; Sridhar Balasubramanian; Maddi Sridhar Reddy
Journal:  ACS Omega       Date:  2019-10-30

Review 7.  Biosynthesis of α-pyrones.

Authors:  Till F Schäberle
Journal:  Beilstein J Org Chem       Date:  2016-03-24       Impact factor: 2.883

Review 8.  Interleukin-6: Molecule in the Intersection of Cancer, Ageing and COVID-19.

Authors:  Jan Brábek; Milan Jakubek; Fréderic Vellieux; Jiří Novotný; Michal Kolář; Lukáš Lacina; Pavol Szabo; Karolína Strnadová; Daniel Rösel; Barbora Dvořánková; Karel Smetana
Journal:  Int J Mol Sci       Date:  2020-10-26       Impact factor: 5.923
  8 in total

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