Distribution of betulinic acid in plant kingdom
DOI:
https://doi.org/10.14719/pst.2014.1.3.58Keywords:
Betulinic acid, TriterpenoidsAbstract
Betulinic acid (3ß-hydroxy-lup-20(29)-en-28-oic acid) is a ubiquitous pentacyclic triterpenoid found in the plants. It is highly valued for its role in wide array of ailments viz. anti-HIV, anti-malarial, anti-cancerous, hepatoprotective, and many more. In lights of tremendous interest in recent years on chemistry and pharmacological properties of betulinic acid (BA), comprehensive data have been collected in this review to present its distribution in plant kingdom.
Downloads
References
Abyshev, A. Z., Agaev, É. M., & Guseinov, A. B. (2007). Studies of the chemical composition of birch bark Extracts (Cortex betula) from the Betulaceae family. Pharmaceutical Chemistry Journal, 41(8), 22–26. http://dx.doi.org/10.1007/s11094-007-0091-5
Abyshev, A. Z., Zhurkovich, I. K., Agaev, É. M., Abdulla-zade, A. A., & Guseinov, A. B. (2006). Methods of standardization of the quality of betulenol parent substance and its ready-to-use medicinal forms. Pharmaceutical Chemistry Journal, 40(1). http://dx.doi.org/10.1007/s11094-006-0056-0
Atta-ur-Rahman, Zareen S., Choudhary, M. I., Akhtar, M. N., & Khan, S. N. (2008). A-glucosidase inhibitory activity of triterpenoids from Cichorium intybus. Journal of Natural Products, 71, 910-913, 2008. http://dx.doi.org/10.1021/np800001v PMid:18341288
Begum, S., Sultana, I., Siddiqui, B. S., Shaheen, F., & Gilani, A. H. (2002). Structure and spasmolytic activity of eucalyptanoic acid from Eucalyptus camaldulensis var. obtusa and synthesis of its active derivative from oleanolic acid. Journal of Natural Products, 65, 1939-1941. http://dx.doi.org/10.1021/np020127x PMid:12502346
Bringmann, G., Saeb, W., Aké Assi, L., Francois, G., Sankara Narayanan, A. S., Peters, K., & Peters, E. M. (1997). Betulinic acid: Isolation from Triphyophyllum peltatum and Ancistrocladus heyneanus, antimalarial activity, and crystal structure of the benzyl ester. Planta Medica, 63, 255 – 257. http://dx.doi.org/10.1055/s-2006-957666 PMid:9225608
Calderon, A. I., Terreaux, C., Schenk, K., Pattison, P., Burdette, J. E., Pezzuto, J. M., Gupta, M. P., & Hostettmann, K. (2002). Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis. Journal of Natural Products, 65(12), 1749-1753. http://dx.doi.org/10.1021/np0201164 PMid:12502307
Chang, C., Wu, T., Hsieh, Y., Kuo, S., & Lee Chao, P. (1999). Terpenoids of Syzygium formosanum. Journal of Natural Products, 62, 327-328. http://dx.doi.org/10.1021/np980313w PMid:10075776
Chaturvedula, V. S. P., Schilling, J. K., Johnson, R. K., & Kingston, D. G. I. (2003). New cytotoxic lupane triterpenoids from the twigs of Coussarea paniculata. Journal of Natural Products, 66, 419-422. http://dx.doi.org/10.1021/np0204848 PMid:12662105
Chien, N. Q., Hung, N. V., Santarsiero, B. D., Mesecar, A. D., Cuong, N. M., Soejarto, D. D., Pezzuto, J. M., Fong, H. H. S., & Tan, G. T. (2004). New 3-O-acyl betulinic acids from Strychnos vanprukii Craib. Journal of Natural Product, 67, 994-998. http://dx.doi.org/10.1021/np030469i PMid:15217281
De Carvalho, M. G., de Oliveira Cândido, L. F., da Costa, P. M., do Nascimento, I. A., & Braz-Filho, R. (2008). Triterpenes acids and saponins isolated from Licania arianeae Prance (Chrysobalanaceae). Journal of Natural Medicine, 62, 122–123. http://dx.doi.org/10.1007/s11418-008-0241-4
De Oliveira, B. H., Santos, C. A. M., & Espindola, A. P. D. M. (2002). Determination of the triterpenoid, betulinic acid, in Doliocarpus schottianus by HPLC. Phytochemical Analysis, 13: 95–98. http://dx.doi.org/10.1002/pca.628 PMid:12018029
Fang, L., Ito, A., Chai, H., Mi, Q., Jones, W. P., Madulid, D. R., Oliveros, M. B., Gao, Q., Orjala, J., Farnsworth, N. R., Soejarto, D. D., Cordell, G. A., Swanson, S. M., Pezzuto, J. M., & Kinghorn, A. D. (2006). Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines. Journal of Natural Product, 69, 332-337. http://dx.doi.org/10.1021/np058083q PMid:16562829 PMCid:PMC2543135
Fu, L., Zhang, S., Li, N., Wang, J., Zhao, M., Sakai, J., Hasegawa, T., Mitsui, T., Kataoka, T., Oka, S., Kiuchi, M., Hirose, K., & Ando, M. (2005). Three new triterpenes from Nerium oleander and biological activity of the isolated compounds. Journal of Natural Products, 68, 198-206.
Fujioka, T., Kashiwada, Y., Kilkuskie, R. E., Cosentino, L. M., Ballas, L. M., Jiang, J. B., Janzen, W. P., Chen, I. S., & Lee, K. H. (1994). 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. Journal of Natural Products, 57(2), 243-247. http://dx.doi.org/10.1021/np50104a008 PMid:8176401
Galgon, T., Hoke, D. & Drager, B. (1999). Identification and quantification of betulinic acid. Phytochemical Analysis, 10(4), 187 – 190. http://dx.doi.org/10.1002/(SICI)1099-1565(199907/08)10:4<187::AID-PCA443>3.0.CO;2-K
Goity, L.E., Queupil, M. J., Jara, D., Alegría, S. E., Pe-a, M., Barriga, A., Aguirre, M. C., & Delporte, C. (2013). An HPLC-UV and HPLC-ESI-MS based method for identification of anti-inflammatory triterpenoids from the extracts of Ugni molinae. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, 12(1), 108 – 116.
Guo, S., Duan, J., Tang, Y., Su, S., Shang, E., Ni, S., & Qian, D. (2009). High-performance liquid chromatography-two wavelength detection of triterpenoid acids from the fruits of Ziziphus jujuba containing various cultivars in different regions and classification using chemometric analysis. Journal of Pharmaceutical and Biomedical Analysis, 49(5), 1296-1302. http://dx.doi.org/10.1016/j.jpba.2009.03.006 PMid:19359121
Hamburger, M., Riese, U., Graf, H., Melzig, M. F., Ciesielski, S., Baumann, D., Dittmann, K., & Wegner, C. (2002). Constituents in evening primrose oil with radical scavenging, cyclooxygenase, and neutrophil elastase inhibitory activities. Journal of Agriculture and Food Chemistry, 50, 5533-5538.
Holonec, L., Ranga, F., Crainic, D., Truta, A., & Socaciu, C. (2012). Evaluation of betulin and betulinic acid content in birch bark from different forestry areas of Western Carpathians. Notulae Botanicae Horti Agrobotanici, 40(2), 99-105.
How, F. C., Wu, T. L., Ko, W. C., & Chen, T. C. (1982). In: A dictrionary of the families and genera of Chienese seed plants. Beijing: Science Press. pp 483, http://dx.doi.org/10.1039/b606816b PMid:17119640
Jagadeesh, S. G., David Krupadanam, G. L., & Srimannarayana, G. (1998). Tobacco caterpillar antifeedent from the gotti stem wood triterpene betulinic acid. Journal of Agriculture and Food Chemistry, 46, 2797-2799. http://dx.doi.org/10.1021/jf970768b
Jäger, S., Winkler, K., Pfüller, U., & Scheffler, A. (2007). Solubility studies of oleanolic acid and betulinic acid in aqueous solutions and plant extracts of Viscum album L. Planta Medica, 73, 157-162. http://dx.doi.org/10.1055/s-2007-967106 PMid:17415876
Kantamreddi, V. S. S., & Wright, C. W. (2007). Investigation of Indian Diospyros species for antiplasmodial properties. eCAM, 1- 4.
Ko, H, Yu, S., Ko, F., Teng, C., & Lin, C. (1997). Bioactive constituents of Morus australis and Broussonetia papyrifera. Journal of Natural Product, 60, 1008-1011. http://dx.doi.org/10.1021/np970186o PMid:9358644
Kokdil, G., Yalçin, S. M., & Topçu, G. (1999). Nepetalactones and other constituents of Nepeta nuda ssp. Albiflora. Turkish Journal of Chemistry, 23, 99-104.
Krasutsky, P. A. (2006). Birch bark research and development. Natural Product Reports, 23(6), 919-942.
Lee, C. (1998). A new norlupene from the leaves of Melaleuca leucadendron. Journal of Natural Product, 61, 375-376. http://dx.doi.org/10.1021/np9606052 PMid:9548878
Lin, H., Ding, H., & Wu, Y. (1998). Two novel compounds from Paeonia suffruticosa. Journal of Natural Product, 61(3), 343-346. http://dx.doi.org/10.1021/np9704258 PMid:9548873
Nattapong, S., & Omboon, L. (2008). A new source of whitening agent from a Thai Mulberry plant and its betulinic acid quantitation. Natural Product Research, 22(9), 727–734. http://dx.doi.org/10.1080/14786410601130794 PMid:18569714
Nick, A., Wright, A. D., Rali, T., & Sticher, O. (1995). Antibacterial triterpenoids from Dillenia papuana and their structure activity relationship. Phytochemistry, 40, 1691–1695. http://dx.doi.org/10.1016/0031-9422(95)00491-O
Pai, S. R. Nimbalkar, M. S., Pawar, N. V., & Dixit, G. B. (2011). Optimization of extraction techniques and quantification of betulinic acid (BA) by RP-HPLC method from Ancistrocladus heyneanus Wall. Ex Grah. Industrial Crops and Products, 34, 1458-1464. http://dx.doi.org/10.1016/j.indcrop.2011.05.006
Pai, S. R., Upadhya, V., Hegde, H. V., Joshi, R. K., & Kholkute, S. D. (2014). New report of triterpenoid betulinic acid (BA) along with oleanolic acid (OA) from Achyranthes aspera by RP-UFLC analysis and confirmation using HPTLC and FTIR techniques. Journal of Planar Chromatography – Modern TLC, 27(1), 38–41.
Pan, P., Jia, L. Y., & Sun, Q. S. (2008). RP-HPLC determination of betulinic acid in Callicarpa macrophylla. Zhongguo Zhong Yao Za Zhi, 33(7), 753-755. PMid:18589770
Pereira, P. S., França, S. de C., de Oliveira, P. V. A., de Souza Breves, C. M., e Vaz Pereira, S. I., e Auro Nomizo, S. V. S., & Dias, D. A. (2008). Chemical constituents from Tabernaemontana catharinensis root bark: a brief NMR review of indole alkaloids and in vitro cytotoxicity. Quimica Nova, 31(1), 20-24. http://dx.doi.org/10.1590/S0100-40422008000100004
Pisha, E., Chai, H., Lee, I. S., Chagwedera, T. E., Farnsworth, N. R., Cordell, G. A., Beecher, C. W., Fong, H. H., Kinghorn, A. D., Brown, D. M., Wani, M. C., Wall, M. E., Hieken, T. J., Das Gupta, T. K., & Pezzuto, J. M. (1995). Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nature Medicine, 1, 1046–1051. http://dx.doi.org/10.1038/nm1095-1046 PMid:7489361
Raskin, I., & Ripoll, C. (2004). Can an apple a day keep the doctor away? Current Pharmaceutical Design, 10, 3419-3429. http://dx.doi.org/10.2174/1381612043383070 PMid:15544525
Razborek, M. I., Voncina, D. B., Dolecek, V., & Voncina, E. (2007). Determination of major phenolic acids, phenolic diterpenes and triterpenes in Rosemary (Rosmarinus officinalis L.) by gas chromatography and mass spectrometry. Acta Chimica Slovenica, 54, 60–67.
Razborek, M. I., Voncina, D. B., Dolecek, V., & Voncina, E. (2008). Determination of oleanolic, betulinic and ursolic acid in Lamiaceae and mass spectral fragmentation of their trimethylsilylated derivatives. Chromatographia, 67, 433-440. http://dx.doi.org/10.1365/s10337-008-0533-6
Recio, M. C., Giner, R. M., Manez, S., Gueho, J., Julien, H. R., Hostettmann, K., & Rios, J. L. (1995). Investigations on the steroidal anti-inflammatory activity of triterpenoids from Diospyros leucomelas. Planta Medica, 61, 9-12. http://dx.doi.org/10.1055/s-2006-957988 PMid:7701004
Rosas, L. V., Cordeiro, M. S. C., Campos, F. R., Nascimento, S. K. R., Januário, A. H., França, S. C., Nomizo, A., Toldo, M. P. A., Albuquerque, S., & Pereira, P. S. (2007). In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae). Brazilian Journal of Medical and Biological Research, 40, 663-670. http://dx.doi.org/10.1590/S0100-879X2007000500009 PMid:17464428
Saklani, A., & Kutty, S. K. (2008). Plant derived compounds in clinical trials. Drug Discovery Today, 13(3-4), 161-171. http://dx.doi.org/10.1016/j.drudis.2007.10.010 PMid:18275914
Sousa, A. F., Pinto, P. C. R. O., Silvestre, A. J. D., & Neto, C. P. (2006). Triterpenic and other lipophilic components from industrial cork byproducts. Journal of Agriculture and Food Chemistry, 54, 6888-6893. http://dx.doi.org/10.1021/jf060987 PMid:16939354
Takeoka, G., Dao, L., Teranishi, R., Wong, R., Flessa, S., Harden, L., & Edwards, R. (2000). Identification of three triterpenoids in Almond Hulls. Journal of Agriculture and Food Chemistry, 48, 3437-3439. http://dx.doi.org/10.1021/jf9908289 PMid:10956130
Taralkar, S. V, & Chattopadhyay, S. (2012). A HPLC Method for determination of ursolic acid and betulinic acids from their methanolic extracts of Vitex Negundo Linn. Journal of Analytical and Bioanalytical Techniques, 3, 134. http://dx.doi.org/10.4172/2155-9872.1000134
Woldemichael, G. M., Singh, M. P., Maiese, W. M., & Timmermann, B. N. (2003). Constituents of antibacterial extract of Caesalpinia paraguariensis Burk. Zeitschrift fur Naturforschung, 58, 70–75. PMid:12622230
Yogeeswari, P. & Sriram, D. (2005). Betulinic acid & its derivatives: A review on their biological properties. Current Medicinal Chemistry, 12, 657-666. http://dx.doi.org/10.2174/0929867053202214 PMid:15790304
Zhang, Y., Yu, T., & Wang, Y. (2003). Extraction of betulin from bark of Betula platyphylla by supercritical carbon dioxide extraction. Journal of Forestry Research, 14(3), 202-204. http://dx.doi.org/10.1007/BF02856830
Zhu, M., Phillipson, J. D., Greengrass, P. M., & Bowery, N. G. (1996). Chemical and biological investigation of the root bark of Clerodendrum mandarinorum. Planta Medica, 62(5), 393-396. http://dx.doi.org/10.1055/s-2006-957923 PMid:9005449
Downloads
Published
How to Cite
Issue
Section
License
Copyright and Licence details of published articles
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
Open Access Policy
Plant Science Today is an open access journal. There is no registration required to read any article. All published articles are distributed under the terms of the Creative Commons Attribution License (CC Attribution 4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited (https://creativecommons.org/licenses/by/4.0/). Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
