Literature DB >> 20622928

Chemical modifications of natural triterpenes - glycyrrhetinic and boswellic acids: evaluation of their biological activity.

G S R Subba Rao1, Paturu Kondaiah, Sanjay K Singh, Palaniyandi Ravanan, Michael B Sporn.   

Abstract

Synthetic analogues of naturally occurring triterpenoids; glycyrrhetinic acid, arjunolic acid and boswellic acids, by modification of A-ring with a cyano- and enone- functionalities, have been reported. A novel method of synthesis of α-cyanoenones from isoxazoles is reported. Bio-assays using primary mouse macrophages and tumor cell lines indicate potent anti-inflammatory and cytotoxic activities associated with cyanoenones of boswellic acid and glycyrrhetinic acid.

Entities:  

Year:  2008        PMID： 20622928      PMCID： PMC2900779          DOI： 10.1016/j.tet.2008.10.035

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  13 in total

1.  Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A.

Authors:  Tadashi Honda; Karen T Liby; Xiaobo Su; Chitra Sundararajan; Yukiko Honda; Nanjoo Suh; Renee Risingsong; Charlotte R Williams; Darlene B Royce; Michael B Sporn; Gordon W Gribble
Journal:  Bioorg Med Chem Lett       Date:  2006-09-25       Impact factor: 2.823

2.  Novel triterpenoid CDDO-Me is a potent inducer of apoptosis and differentiation in acute myelogenous leukemia.

Authors:  Marina Konopleva; Twee Tsao; Peter Ruvolo; Irina Stiouf; Zeev Estrov; Clinton E Leysath; Shourong Zhao; David Harris; Shirong Chang; C Ellen Jackson; Mark Munsell; Nanjoo Suh; Gordon Gribble; Tadashi Honda; W Stratford May; Michael B Sporn; Michael Andreeff
Journal:  Blood       Date:  2002-01-01       Impact factor: 22.113

3.  The synthetic triterpenoid CDDO-imidazolide induces monocytic differentiation by activating the Smad and ERK signaling pathways in HL60 leukemia cells.

Authors:  Yan Ji; Hong Jin Lee; Catherine Goodman; Milan Uskokovic; Karen Liby; Michael Sporn; Nanjoo Suh
Journal:  Mol Cancer Ther       Date:  2006-06       Impact factor: 6.261

4.  Novel synthetic oleanane triterpenoids: a series of highly active inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; B V Rounds; L Bore; F G Favaloro; G W Gribble; N Suh; Y Wang; M B Spor
Journal:  Bioorg Med Chem Lett       Date:  1999-12-20       Impact factor: 2.823

5.  Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; G W Gribble; N Suh; H J Finlay; B V Rounds; L Bore; F G Favaloro; Y Wang; M B Sporn
Journal:  J Med Chem       Date:  2000-05-04       Impact factor: 7.446

6.  A synthetic triterpenoid, 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), is a ligand for the peroxisome proliferator-activated receptor gamma.

Authors:  Y Wang; W W Porter; N Suh; T Honda; G W Gribble; L M Leesnitzer; K D Plunket; D J Mangelsdorf; S G Blanchard; T M Willson; M B Sporn
Journal:  Mol Endocrinol       Date:  2000-10

7.  Synthetic oleanane and ursane triterpenoids with modified rings A and C: a series of highly active inhibitors of nitric oxide production in mouse macrophages.

Authors:  T Honda; B V Rounds; L Bore; H J Finlay; F G Favaloro; N Suh; Y Wang; M B Sporn; G W Gribble
Journal:  J Med Chem       Date:  2000-11-02       Impact factor: 7.446

8.  The bortezomib/proteasome inhibitor PS-341 and triterpenoid CDDO-Im induce synergistic anti-multiple myeloma (MM) activity and overcome bortezomib resistance.

Authors:  Dharminder Chauhan; Guilan Li; Klaus Podar; Teru Hideshima; Reshma Shringarpure; Laurence Catley; Constantine Mitsiades; Nikhil Munshi; Yu Tzu Tai; Nanjoo Suh; Gordon W Gribble; Tadashi Honda; Robert Schlossman; Paul Richardson; Michael B Sporn; Kenneth C Anderson
Journal:  Blood       Date:  2003-12-11       Impact factor: 22.113

9.  The novel synthetic triterpenoid, CDDO-imidazolide, inhibits inflammatory response and tumor growth in vivo.

Authors:  Andrew E Place; Nanjoo Suh; Charlotte R Williams; Renee Risingsong; Tadashi Honda; Yukiko Honda; Gordon W Gribble; Lisa M Leesnitzer; Julie B Stimmel; Timothy M Willson; Evan Rosen; Michael B Sporn
Journal:  Clin Cancer Res       Date:  2003-07       Impact factor: 12.531

10.  A novel synthetic oleanane triterpenoid, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity.

Authors:  N Suh; Y Wang; T Honda; G W Gribble; E Dmitrovsky; W F Hickey; R A Maue; A E Place; D M Porter; M J Spinella; C R Williams; G Wu; A J Dannenberg; K C Flanders; J J Letterio; D J Mangelsdorf; C F Nathan; L Nguyen; W W Porter; R F Ren; A B Roberts; N S Roche; K Subbaramaiah; M B Sporn
Journal:  Cancer Res       Date:  1999-01-15       Impact factor: 12.701
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  10 in total

1.  Synthetic triterpenoid cyano enone of methyl boswellate activates intrinsic, extrinsic, and endoplasmic reticulum stress cell death pathways in tumor cell lines.

Authors:  Palaniyandi Ravanan; Renata Sano; Priti Talwar; Satoshi Ogasawara; Shu-ichi Matsuzawa; Michael Cuddy; Sanjay K Singh; G S R Subba Rao; Paturu Kondaiah; John C Reed
Journal:  Mol Cancer Ther       Date:  2011-07-11       Impact factor: 6.261

2.  Growth inhibitory, apoptotic and anti-inflammatory activities displayed by a novel modified triterpenoid, cyano enone of methyl boswellates.

Authors:  Palaniyandi Ravanan; Sanjay K Singh; Gsr Subba Rao; Paturu Kondaiah
Journal:  J Biosci       Date:  2011-06       Impact factor: 1.826

Review 3.  Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents.

Authors:  Reen-Yen Kuo; Keduo Qian; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  Nat Prod Rep       Date:  2009-08-13       Impact factor: 13.423

4.  The synthesis of glycyrrhetinic acid derivatives containing a nitrogen heterocycle and their antiproliferative effects in human leukemia cells.

Authors:  Yuan Gao; Xin Guo; Xiaojing Li; Dan Liu; Dandan Song; Ye Xu; Ming Sun; Yongkui Jing; Linxiang Zhao
Journal:  Molecules       Date:  2010-06-21       Impact factor: 4.411

5.  Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives.

Authors:  Daniela P S Alho; Jorge A R Salvador; Marta Cascante; Silvia Marin
Journal:  Molecules       Date:  2019-08-14       Impact factor: 4.411

6.  Trioxolone Methyl, a Novel Cyano Enone-Bearing 18βH-Glycyrrhetinic Acid Derivative, Ameliorates Dextran Sulphate Sodium-Induced Colitis in Mice.

Authors:  Andrey V Markov; Aleksandra V Sen'kova; Oksana V Salomatina; Evgeniya B Logashenko; Dina V Korchagina; Nariman F Salakhutdinov; Marina A Zenkova
Journal:  Molecules       Date:  2020-05-21       Impact factor: 4.411

7.  An investigation of the antileishmanial properties of semi-synthetic saponins.

Authors:  Orlagh Anderson; Joseph Beckett; Carla C Briggs; Liam A Natrass; Charles F Cranston; Elizabeth J Wilkinson; Jack H Owen; Rhodri Mir Williams; Angelos Loukaidis; Marc E Bouillon; Deiniol Pritchard; Martina Lahmann; Mark S Baird; Paul W Denny
Journal:  RSC Med Chem       Date:  2020-06-09

8.  Anti-Obesity Effects of Matoa (Pometia pinnata) Fruit Peel Powder in High-Fat Diet-Fed Rats.

Authors:  Toshikazu Suzuki; Mayumi Nagata; Natsuko Kagawa; Shiori Takano; Jun Nomura
Journal:  Molecules       Date:  2021-11-07       Impact factor: 4.411

Review 9.  An Overview of Structurally Modified Glycyrrhetinic Acid Derivatives as Antitumor Agents.

Authors:  Bing Xu; Gao-Rong Wu; Xin-Yu Zhang; Meng-Meng Yan; Rui Zhao; Nan-Nan Xue; Kang Fang; Hui Wang; Meng Chen; Wen-Bo Guo; Peng-Long Wang; Hai-Min Lei
Journal:  Molecules       Date:  2017-06-02       Impact factor: 4.411

10.  Tirucallane Triterpenoids from the Stems and Stem Bark of Cornus walteri that Control Adipocyte and Osteoblast Differentiations.

Authors:  Seoung Rak Lee; Eunyong Choi; Se Hun Jeon; Xue Yan Zhi; Jae Sik Yu; Seon-Hee Kim; Jeongmi Lee; Ki-Moon Park; Ki Hyun Kim
Journal:  Molecules       Date:  2018-10-23       Impact factor: 4.411
  10 in total

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