Betulinic acid is a phytochemincal in the subclass of Triterpenoid, belonging to the group of Terpenes found abundantly in Ber tree, white birch, rosemary etc.
Health Benefits
1. Colorectal cancer
In the investigation of the enhancement of Betulinic acid (BA) cytotoxicity by α-mangostin, and the cytoprotection effect of α-mangostin and BA on cisplatin-induced cytotoxicity on HCT 116 human colorectal carcinoma cells, found that α-Mangostin and BA were more cytotoxic to the colon cancer cells than to the normal colonic cells, and both compounds showed a cytoprotective effect against cisplatin-induced cytotoxicity. On the other hand, α-mangostin enhanced the cytotoxic and apoptotic effects of BA. Combination therapy hits multiple targets, which may improve the overall response to the treatment, and may reduce the likelihood of developing drug resistance by the tumor cells, according to 'α-Mangostin Enhances Betulinic Acid Cytotoxicity and Inhibits Cisplatin Cytotoxicity on HCT 116 Colorectal Carcinoma Cells" by Aisha AF, Abu-Salah KM, Ismail Z, Majid AM.(1)
2. Anti cancers
In the identifitification of the agent as potently effective against a wide variety of cancer cells, also those derived from therapy-resistant and refractory tumors, found that In-vivo preclinically applied BetA showed some remarkable anticancer effects and a complete absence of systemic toxicity in rodents. BetA also cooperated with other therapies to induce tumor cell death and several potent derivatives have been discovered. Its antitumor activity has been related to its direct effects on mitochondria where it induces Bax/Bak-independent cytochrome-c release, according to 'Betulinic acid, a natural compound with potent anticancer effects" by Mullauer FB, Kessler JH, Medema JP.(2)
3. Anti inflammatory effects
In the investigation of the effect of betulinic acid (BA) on acute lung damage induced by bacterial endotoxin (lipopolysaccharide, LPS) in male Sprague-Dawley rats, found that Treatment with BA was found to significantly attenuate all these alterations. The present results suggest that BA is endowed with antiinflammatory and antioxidant properties that protect the lung against the deleterious actions of LPS, according to 'Effect of betulinic acid on neutrophil recruitment and inflammatory mediator expression in lipopolysaccharide-induced lung inflammation in rats" by Nader MA, Baraka HN.(3)
4. Ovarian Cancer
In elucidation of the effect of BH3-only proteins on cisplatin-resistant ovarian cancer cells,
indicate that Puma plays a critical role in the apoptosis of chemo-resistant ovarian cancer cells treated with betulinic acid (BetA). The reduction of Puma expression inhibits Bax activation and apoptosis, according to "JNK and Akt-mediated Puma Expression in the Apoptosis of Cisplatin-resistant Ovarian Cancer Cells" by Zhao Z, Wang J, Tang J, Liu X, Zhong Q, Wang F, Hu W, Yuan Z, Nie C, Wei Y.(4)
5. Anti-fibrotic effect
In the to investigation of the anti-fibrotic effect and the potential mechanisms of action of betulinic acid (BA) against hepatic fibrosis in vivo and in vitro, showed that BA effectively decreased the HSC-T6 cell viability induced by TNF-α and showed low toxicity in normal human chang liver cells. Moreover, BA significantly attenuated the expression of α-SMA and tissue inhibitor of metalloproteinase-1 (TIMP-1) and increased the levels of matrix metalloprotease (MMP)-13. BA also inhibited the expression of Toll-like receptor 4 (TLR4), myeloid differentiation factor 88 (MyD88) and the activation of nuclear factor-κB (NF-κB) in a time-dependent manner, according to 'The anti-fibrotic effect of betulinic acid is mediated through the inhibition of NF-κB nuclear protein translocation" by Wan Y, Wu YL, Lian LH, Xie WX, Li X, Ouyang BQ, Bai T, Li Q, Yang N, Nan JX.(5)
6. Antifungal metabolites
In the investigation of the Antifungal effects of two new natural compounds, 4-hydroxy-5,6-dimethoxynaphthalene-2-carbaldehyde (1) and 12,13-didehydro-20,29-dihydrobetulin (2) together with nine known compounds, including 7-methyljuglone (3), diospyrin (4), isodiospyrin (5), shinanolone (6), lupeol (7), betulin (8), betulinic acid (9), betulinaldehyde (10), and ursolic acid (11) from the acetone extract of the roots of Diospyros virginiana, found that All the isolated compounds were evaluated for their antifungal activities against Colletotrichum fragariae, C. gloeosporioides, C. acutatum, Botrytis cinerea, Fusarium oxysporum, Phomopsis obscurans, and P. viticola using in vitro micro-dilution broth assay, according to 'Antifungal metabolites from the roots of Diospyros virginiana by overpressure layer chromatography" by Wang X, Habib E, León F, Radwan MM, Tabanca N, Gao J, Wedge DE, Cutler SJ.(6)
7. Antileukemic activity
In an easy and efficient route to partial synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al (1), starting from betulinic acid (2), found that Compound 1 and the precursors (2, 3, 5, and 7) showed antiproliferative activities against human K562 leukemia, murine WEHI3 leukemia, and murine MEL erythroid progenitor, according to 'Synthesis of bioactive 28-hydroxy-3-oxolup-20(29)-en-30-al with antileukemic activity by Ghosh P, Mandal A, Ghosh J, Pal C, Nanda AK.(7)
8. HIV maturation inhibitor
In the study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3' dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class, may lead to led to the design and synthesis of compound 12 (EC(50): 0.0006 microM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor, according to " Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors" by Qian K, Kuo RY, Chen CH, Huang L, Morris-Natschke SL, Lee KH.(8)
9. Cytokine production and proliferation of CD4(+) T cells and CD19(+) B cells
In the examination of the effects of the triterpene acid mixture on the cytokine production and proliferation of CD4(+) T cells and CD19(+) B cells induced by a self-antigen, human thyroglobulin and by lipopolysaccharide in cultures of normal mononuclear cells, found that the mixture also inhibited CD4(+) T-cell and CD19(+) B-cell proliferation (IC(50) value 22 and 12 µg/mL, respectively). Together, these data demonstrate that oleanolic, ursolic and betulinic acid are active immunomodulatory constituents of the standardized rose hip powder, according to "Triterpene Acids from Rose Hip Powder Inhibit Self-antigen- and LPS-induced Cytokine Production and CD4(+) T-cell Proliferation in Human Mononuclear Cell Cultures" by Saaby L, Nielsen CH.(9)
10. Antiobesity effects
In the investigation of the antilipase function of betulinic acid, the ability of betulinic acid to inhibit pancreatic lipase activity in vitro and and prevention of the elevation of plasma triacylglycerol levels tested after oral administration of a lipid emulsion in rats, suggested that betulinic acid may exert antiobesity effects by directly inhibiting pancreatic lipase, which would prevent the absorption of lipid from the small intestine. In addition, it was found that betulinic acid may further accelerate fat mobilization by enhancing the levels of lipolysis in adipose tissues, according to "Betulinic Acid has an Inhibitory Effect on Pancreatic Lipase and Induces Adipocyte Lipolysis" by Kim J, Lee YS, Kim CS, Kim JS.(10)
11. Antimicrobial activity
In the investigation of the extract from of the isolation from leaves of Clusia burlemarxii, (3-O-α-L- rhamnopyranosylquercetin, 3-O-α-L-rhamnopyranosylkaempferol, 4-hydroxy-5,5-dimethyldihydrofuran-2-one, 2Z-δ-tocotrienoloic acid and friedelin) and from trunk (betulinic acid, protocatechuic acid, lyoniresinol, and a new biphenyl 2,2-dimethyl-3,5-dihydroxy-7-(4-hydroxyphenyl)chromane), found that the extracts and compounds showed significant activity against tested Gram-positive bacteria, none activity against tested Gram-negative bacteria and fungi, according to "A new biphenyl and antimicrobial activity of extracts and compounds from Clusia burlemarxii" by Ribeiro PR, Ferraz CG, Guedes ML, Martins D, Cruz FG.(11)
12. Etc.
8. HIV maturation inhibitor
In the study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3' dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class, may lead to led to the design and synthesis of compound 12 (EC(50): 0.0006 microM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor, according to " Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors" by Qian K, Kuo RY, Chen CH, Huang L, Morris-Natschke SL, Lee KH.(8)
9. Cytokine production and proliferation of CD4(+) T cells and CD19(+) B cells
In the examination of the effects of the triterpene acid mixture on the cytokine production and proliferation of CD4(+) T cells and CD19(+) B cells induced by a self-antigen, human thyroglobulin and by lipopolysaccharide in cultures of normal mononuclear cells, found that the mixture also inhibited CD4(+) T-cell and CD19(+) B-cell proliferation (IC(50) value 22 and 12 µg/mL, respectively). Together, these data demonstrate that oleanolic, ursolic and betulinic acid are active immunomodulatory constituents of the standardized rose hip powder, according to "Triterpene Acids from Rose Hip Powder Inhibit Self-antigen- and LPS-induced Cytokine Production and CD4(+) T-cell Proliferation in Human Mononuclear Cell Cultures" by Saaby L, Nielsen CH.(9)
10. Antiobesity effects
In the investigation of the antilipase function of betulinic acid, the ability of betulinic acid to inhibit pancreatic lipase activity in vitro and and prevention of the elevation of plasma triacylglycerol levels tested after oral administration of a lipid emulsion in rats, suggested that betulinic acid may exert antiobesity effects by directly inhibiting pancreatic lipase, which would prevent the absorption of lipid from the small intestine. In addition, it was found that betulinic acid may further accelerate fat mobilization by enhancing the levels of lipolysis in adipose tissues, according to "Betulinic Acid has an Inhibitory Effect on Pancreatic Lipase and Induces Adipocyte Lipolysis" by Kim J, Lee YS, Kim CS, Kim JS.(10)
11. Antimicrobial activity
In the investigation of the extract from of the isolation from leaves of Clusia burlemarxii, (3-O-α-L- rhamnopyranosylquercetin, 3-O-α-L-rhamnopyranosylkaempferol, 4-hydroxy-5,5-dimethyldihydrofuran-2-one, 2Z-δ-tocotrienoloic acid and friedelin) and from trunk (betulinic acid, protocatechuic acid, lyoniresinol, and a new biphenyl 2,2-dimethyl-3,5-dihydroxy-7-(4-hydroxyphenyl)chromane), found that the extracts and compounds showed significant activity against tested Gram-positive bacteria, none activity against tested Gram-negative bacteria and fungi, according to "A new biphenyl and antimicrobial activity of extracts and compounds from Clusia burlemarxii" by Ribeiro PR, Ferraz CG, Guedes ML, Martins D, Cruz FG.(11)
12. Etc.
Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/22402764(2) http://www.ncbi.nlm.nih.gov/pubmed/20075711
(3) http://www.ncbi.nlm.nih.gov/pubmed/22402186
(4) http://www.ncbi.nlm.nih.gov/pubmed/22394200
(5) http://www.ncbi.nlm.nih.gov/pubmed/22285267
(6) http://www.ncbi.nlm.nih.gov/pubmed/22162171
(7) http://www.ncbi.nlm.nih.gov/pubmed/22166062
(8) http://www.ncbi.nlm.nih.gov/pubmed/20329730
(9) http://www.ncbi.nlm.nih.gov/pubmed/22170858
(10) http://www.ncbi.nlm.nih.gov/pubmed/22114077
(11) http://www.ncbi.nlm.nih.gov/pubmed/21893172
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