Literature DB >> 19481937

Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.

Kyoko Nakagawa-Goto1, Koji Yamada, Masahiko Taniguchi, Harukuni Tokuda, Kuo-Hsiung Lee.   

Abstract

C-3 esterifications of betulinic acid (BA, 1) and its A-ring homolog, ceanothic acid (CA, 2), were carried out to provide sixteen terpenoids, 4-19, including nine new compounds (4-12). All synthesized compounds were evaluated in an in vitro antitumor-promoting assay using the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Among them, compounds 4-6, 11-14, 16, and 17 displayed remarkable inhibitory effects of EBV-EA activation. BA analog 6, which contains a prenyl-like group, showed the most potent inhibitory effect (100%, 76%, 37%, and 11% inhibition of EBA activation at 1000, 500, 100, and 10mol ratio/TPA, respectively, with IC(50) value of 285mol ratio/32pmol TPA). Compound 6 merits further development as a cancer preventive agent.

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Year:  2009        PMID： 19481937      PMCID： PMC2747314          DOI： 10.1016/j.bmcl.2009.05.050

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  22 in total

1.  Betulinic acid: isolation from Triphyophyllum peltatum and Ancistrocladus heyneanus, antimalarial activity, and crystal structure of the benzyl ester.

Authors:  G Bringmann; W Saeb; L A Assi; G François; A S Sankara Narayanan; K Peters; E M Peters
Journal:  Planta Med       Date:  1997-06       Impact factor: 3.352

2.  Studies on the anti-inflammatory activity of rhizomes of Nelumbo nucifera.

Authors:  P K Mukherjee; K Saha; J Das; M Pal; B P Saha
Journal:  Planta Med       Date:  1997-08       Impact factor: 3.352

3.  New triterpenoids with antibacterial activity from Zizyphus joazeiro.

Authors:  W Schühly; J Heilmann; I Calis; O Sticher
Journal:  Planta Med       Date:  1999-12       Impact factor: 3.352

4.  Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents.

Authors:  Y Kashiwada; F Hashimoto; L M Cosentino; C H Chen; P E Garrett; K H Lee
Journal:  J Med Chem       Date:  1996-03-01       Impact factor: 7.446

5.  Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids.

Authors:  T Fujioka; Y Kashiwada; R E Kilkuskie; L M Cosentino; L M Ballas; J B Jiang; W P Janzen; I S Chen; K H Lee
Journal:  J Nat Prod       Date:  1994-02       Impact factor: 4.050

Review 6.  Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection.

Authors:  Robert H Cichewicz; Samir A Kouzi
Journal:  Med Res Rev       Date:  2004-01       Impact factor: 12.944

7.  Anti-tumor-promoting activities of euglobals from Eucalyptus plants.

Authors:  M Takasaki; T Konoshima; M Kozuka; H Tokuda
Journal:  Biol Pharm Bull       Date:  1995-03       Impact factor: 2.233

8.  PA-457: a potent HIV inhibitor that disrupts core condensation by targeting a late step in Gag processing.

Authors:  F Li; R Goila-Gaur; K Salzwedel; N R Kilgore; M Reddick; C Matallana; A Castillo; D Zoumplis; D E Martin; J M Orenstein; G P Allaway; E O Freed; C T Wild
Journal:  Proc Natl Acad Sci U S A       Date:  2003-10-22       Impact factor: 11.205

9.  Cancer chemopreventive activity of phenylpropanoids and phytoquinoids from Illicium plants.

Authors:  Masataka Itoigawa; Chihiro Ito; Harukuni Tokuda; Fumio Enjo; Hoyoku Nishino; Hiroshi Furukawa
Journal:  Cancer Lett       Date:  2004-10-28       Impact factor: 8.679

10.  Anti-AIDS agents 73: structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives.

Authors:  Keduo Qian; Kyoko Nakagawa-Goto; Donglei Yu; Susan L Morris-Natschke; Theodore J Nitz; Nicole Kilgore; Graham P Allaway; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem Lett       Date:  2007-12-01       Impact factor: 2.823
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  9 in total

1.  Antiproliferative cardenolides from Pentopetia androsaemifolia Decne. from the Madagascar rain forest.

Authors:  Eba Adou; James S Miller; Fidisoa Ratovoson; Chris Birkinshaw; Rabodo Andriantsiferana; Vincent E Rasamison; David G I Kingston
Journal:  Indian J Exp Biol       Date:  2010-03       Impact factor: 0.818

2.  Design, synthesis and experimental validation of novel potential chemopreventive agents using random forest and support vector machine binary classifiers.

Authors:  Brienne Sprague; Qian Shi; Marlene T Kim; Liying Zhang; Alexander Sedykh; Eiichiro Ichiishi; Harukuni Tokuda; Kuo-Hsiung Lee; Hao Zhu
Journal:  J Comput Aided Mol Des       Date:  2014-05-20       Impact factor: 3.686

3.  A-ring modified betulinic acid derivatives as potent cancer preventive agents.

Authors:  Hsin-Yi Hung; Kyoko Nakagawa-Goto; Harukuni Tokuda; Akira Iida; Nobutaka Suzuki; Ibrahim D Bori; Keduo Qian; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem Lett       Date:  2013-12-16       Impact factor: 2.823

4.  Efficient synthesis and biological evaluation of epiceanothic acid and related compounds.

Authors:  Pu Zhang; Li Xu; Keduo Qian; Jun Liu; Luyong Zhang; Kuo-Hsiung Lee; Hongbin Sun
Journal:  Bioorg Med Chem Lett       Date:  2010-11-05       Impact factor: 2.823

5.  Distribution and expression characteristics of triterpenoids and OSC genes in white birch (Betula platyphylla suk.).

Authors:  Jing Yin; Chun-Lin Ren; Ya-Guang Zhan; Chun-Xiao Li; Jia-Lei Xiao; Wei Qiu; Xin-Yu Li; Hong-Mei Peng
Journal:  Mol Biol Rep       Date:  2011-06-07       Impact factor: 2.316

6.  Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata.

Authors:  Chihiro Morita; Yukiko Kobayashi; Yohei Saito; Katsunori Miyake; Harukuni Tokuda; Nobutaka Suzuki; Eiichiro Ichiishi; Kuo-Hsiung Lee; Kyoko Nakagawa-Goto
Journal:  J Nat Prod       Date:  2016-11-07       Impact factor: 4.050

7.  Screening of filamentous fungi to identify biocatalysts for lupeol biotransformation.

Authors:  Tatiane C de Carvalho; Aline M Polizeli; Izabel C C Turatti; Marcela E Severiano; Carlos E de Carvalho; Sérgio R Ambrósio; Antônio E M Crotti; Uir S de Figueiredo; Paulo C Vieira; Niege A J C Furtado
Journal:  Molecules       Date:  2010-09-01       Impact factor: 4.411

8.  Betulinic acid reduces the complications of autoimmune diabetes on the body and kidney through effecting on inflammatory cytokines in C57BL/6 mice.

Authors:  Yaser Jafari Khataylou; Somayyeh Ahmadi Afshar; Navideh Mirzakhani
Journal:  Vet Res Forum       Date:  2021-06-15       Impact factor: 1.054

Review 9.  Dianthi herba: a comprehensive review of its botany, traditional use, phytochemistry, and pharmacology.

Authors:  Qian Liu; Er-Huan Zang; Cong-Cong Wang; Yu-Chao Liu; Hui Niu; Yuan Gao; Min-Hui Li
Journal:  Chin Med       Date:  2022-01-21       Impact factor: 5.455
  9 in total

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