Betulinic acid

Papers

Limnophilaspiroketone, a highly oxygenated phenolic derivative from Limnophila geoffrayi. Dae Sik Jang et al J. Nat. Prod. 68, 1134-6, (2005)

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Diterpenoid, steroid, and triterpenoid agonists of liver X receptors from diversified terrestrial plants and marine sources. Hiranthi Jayasuriya et al J. Nat. Prod. 68, 1247-52, (2005)

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Three new triterpenes from Nerium oleander and biological activity of the isolated compounds. Liwei Fu et al J. Nat. Prod. 68, 198-206, (2005)

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Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A. Tadashi Honda et al Bioorg. Med. Chem. Lett. 16, 6306-9, (2006)

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Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines. Liqiong Fang et al J. Nat. Prod. 69, 332-7, (2006)

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Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. Chih-Chun Wen et al J. Med. Chem. 50, 4087-95, (2007)

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Synthesis and cytotoxic activity of 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives. Yi Bi et al Bioorg. Med. Chem. Lett. 17, 1475-8, (2007)

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Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds. Sara Hoet et al J. Nat. Prod. 70, 1360-3, (2007)

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Triterpenoid pyrazines and benzopyrazines with cytotoxic activity. Milan Urban et al J. Nat. Prod. 70, 526-32, (2007)

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Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies. Xiaoan Wen et al J. Med. Chem. 51, 3540-54, (2008)

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Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives. Vivek Kumar et al Bioorg. Med. Chem. Lett. 18, 5058-62, (2008)

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Inhibitors of DNA polymerase beta: activity and mechanism. Zhijie Gao et al Bioorg. Med. Chem. 16, 4331-40, (2008)

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Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana. Midori A Arai et al Bioorg. Med. Chem. 16, 9420-4, (2008)

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Isolation of cytotoxic metabolites from targeted peruvian amazonian medicinal plants. José C Aponte et al J. Nat. Prod. 71, 102-5, (2008)

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Lupane-type triterpenoids from Microtropis fokienensis and Perrottetia arisanensis and the apoptotic effect of 28-hydroxy-3-oxo-lup-20(29)-en-30-al. I-Hsiao Chen et al J. Nat. Prod. 71, 1352-7, (2008)

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Purity-activity relationships of natural products: the case of anti-TB active ursolic acid. Birgit U Jaki et al J. Nat. Prod. 71, 1742-8, (2008)

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Antiproliferative triterpenes from Melaleuca ericifolia. Fatma M Abdel Bar et al J. Nat. Prod. 71, 1787-90, (2008)

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alpha-Glucosidase inhibitory activity of triterpenoids from Cichorium intybus. Atta-ur-Rahman et al J. Nat. Prod. 71, 910-3, (2008)

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Hedgehog-Gli signaling pathway inhibitors as anticancer agents. Neeraj Mahindroo et al J. Med. Chem. 52, 3829-45, (2009)

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Betulinic acid derivatives as human immunodeficiency virus type 2 (HIV-2) inhibitors. Zhao Dang et al J. Med. Chem. 52, 7887-91, (2009)

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Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones. Ali Koohang et al Bioorg. Med. Chem. Lett. 19, 2168-71, (2009)

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Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products. Charles Gauthier et al Bioorg. Med. Chem. Lett. 19, 2310-4, (2009)

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Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents. Kyoko Nakagawa-Goto et al Bioorg. Med. Chem. Lett. 19, 3378-81, (2009)

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Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells. Malgorzata Drag-Zalesinska et al Bioorg. Med. Chem. Lett. 19, 4814-7, (2009)

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Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells. Do Thi Ha et al Bioorg. Med. Chem. Lett. 19, 5556-9, (2009)

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Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural lupane- and oleanane-type saponins. Charles Gauthier et al Bioorg. Med. Chem. 17, 2002-8, (2009)

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Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity. Rita C Santos et al Bioorg. Med. Chem. 17, 6241-50, (2009)

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Rational design and semisynthesis of betulinic acid analogues as potent topoisomerase inhibitors. Fatma M Abdel Bar et al J. Nat. Prod. 72, 1643-50, (2009)

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Betulin-derived compounds as inhibitors of alphavirus replication. Leena Pohjala et al J. Nat. Prod. 72, 1917-26, (2009)

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Bioactive constituents of the stem bark of Beilschmiedia zenkeri. Bruno Ndjakou Lenta et al J. Nat. Prod. 72, 2130-4, (2009)

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Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins. Charles Gauthier et al J. Nat. Prod. 72, 72-81, (2009)

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Structure-Activity Relationship Study of Betulinic Acid, A Novel and Selective TGR5 Agonist, and Its Synthetic Derivatives: Potential Impact in Diabetes. Genet, C., et al J. Med. Chem. 53, 178-190, (2010)

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Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana. Ki Hyun Kim et al Bioorg. Med. Chem. Lett. 20, 1944-7, (2010)

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Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity. Harish Kommera et al Bioorg. Med. Chem. Lett. 20, 3409-12, (2010)

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Synthesis, proapoptotic screening, and structure-activity relationships of novel aza-lupane triterpenoids. Aye Aye Mar et al Bioorg. Med. Chem. Lett. 20, 5389-93, (2010)

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Synthesis and biological evaluation of antitumour-active betulin derivatives. René Csuk et al Bioorg. Med. Chem. 18, 1344-55, (2010)

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Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives. Sami Alakurtti et al Bioorg. Med. Chem. 18, 1573-82, (2010)

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Synthesis and biological evaluation of antitumor-active gamma-butyrolactone substituted betulin derivatives. René Csuk et al Bioorg. Med. Chem. 18, 2549-58, (2010)

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Synthesis and structure-activity relationship study of novel cytotoxic carbamate and N-acylheterocyclic bearing derivatives of betulin and betulinic acid. Rita C Santos et al Bioorg. Med. Chem. 18, 4385-96, (2010)

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Synthesis, cytotoxicity and liposome preparation of 28-acetylenic betulin derivatives. René Csuk et al Bioorg. Med. Chem. 18, 7252-9, (2010)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties. Harish Kommera et al Eur. J. Med. Chem. 45, 3346-53, (2010)

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Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach. Kuo-Hsiung Lee et al J. Nat. Prod. 73, 500-16, (2010)

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Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida. Yulin Ren et al J. Nat. Prod. 73, 949-55, (2010)

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Synthesis and evaluation of library of betulin derivatives against the botulinum neurotoxin A protease. Peter Šilhár et al Bioorg. Med. Chem. Lett. 21, 2229-31, (2011)

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Identification of pentacyclic triterpenes derivatives as potent inhibitors against glycogen phosphorylase based on 3D-QSAR studies. Zhongjie Liang et al Eur. J. Med. Chem. 46, 2011-21, (2011)

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Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii. Teresa Mencherini et al J. Nat. Prod. 74, 2116-21, (2011)

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Novel triacsin C analogs as potential antivirals against rotavirus infections. Yunjeong Kim et al Eur. J. Med. Chem. 50, 311-8, (2012)

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Betulin induces mitochondrial cytochrome c release associated apoptosis in human cancer cells. Li Y, He K, Huang Y, Zheng D, Gao C, et al. Mol. Carcinog. 49, 630-640, (2010)

Betulinic acid prevention of d-galactosamine/lipopolysaccharide liver toxicity is triggered by activation of Bcl-2 and antioxidant mechanisms. Zheng ZW, Song SZ, Wu YL, Lian LH, et al. J. Pharm. Pharmacol. 63, 572-578, (2011)

Betulinic acid delivered in liposomes reduces growth of human lung and colon cancers in mice without causing systemic toxicity. Mullauer FB, van Bloois L, Daalhuisen JB, et al. Anticancer. Drugs 22, 223-233, (2011)

Betulinic acid induces Bax/Bak-independent cytochrome c release in human nasopharyngeal carcinoma cells. Liu Y, Luo W. Mol. Cell. 33, 517-524, (2012)

Betulinic acid ameliorates endothelium-dependent relaxation in L-NAME-induced hypertensive rats by reducing oxidative stress. Fu JY, Qian LB, Zhu LG, Liang HT, et al. Eur. J. Pharm. Sci. 44, 385-391, (2012)

Betulinic acid inhibits superoxide anion-mediated impairment of endothelium-dependent relaxation in rat aortas. Qian LB, Fu JY, Cai X, Xia ML. Indian J. Pharmacol. 44, 588-592, (2012)

Merck 14,1190

Beil. 10,III,1059

FT-IR 2 (3), 4240:C / FT-NMR 1 (3), 594:C / IR-Spectra (2), 1282:D / IR-Spectra (3), 1499:H / NMR-Reference 2 (2), 929:B / RegBook 1 (2), 2869:B / Structure Index 1, 459:B:6