Chemistry:Betulin

From HandWiki

Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees, hence its name, from betula. It forms up to 30% of the dry weight of silver birch bark.[1] It is also found in birch sap.[2] Inonotus obliquus contains betulin.[3]

The compound in the bark gives the tree its white color which appears to protect the tree from mid-winter overheating by the sun. As a result, birches are some of the northernmost occurring deciduous trees.

History

Betulin was discovered in 1788 by German-Russian chemist Johann Tobias Lowitz.[4][5]

Chemistry

Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28.

See also

References

  1. Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. (2007-12-01). "Isolation of Betulin and Rearrangement to Allobetulin. A Biomimetic Natural Product Synthesis" (in EN). Journal of Chemical Education 84 (12): 1985. doi:10.1021/ed084p1985. Bibcode2007JChEd..84.1985G. 
  2. Alakurtti, Sami; Mäkelä, Taru; Koskimies, Salme; Yli-Kauhaluoma, Jari (2006-09-01). "Pharmacological properties of the ubiquitous natural product betulin". European Journal of Pharmaceutical Sciences 29 (1): 1–13. doi:10.1016/j.ejps.2006.04.006. ISSN 0928-0987. PMID 16716572. https://www.sciencedirect.com/science/article/abs/pii/S0928098706001102. 
  3. Gao, Yuan; Xu, Hongyu; Lu, Zhenming; Xu, Zhenghong (November 2009). "Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of Inonotus obliquus". Se Pu 27 (6): 745–749. ISSN 1000-8713. PMID 20352924. 
  4. Lowitz, J. T. (1788). "Űber eine neue, fast benzoeartige substanz der briken". Crell's Chem. Ann. 1: 312–317. 
  5. Król, Sylwia Katarzyna; Kiełbus, Michał; Rivero-Müller, Adolfo; Stepulak, Andrzej (2015). "Comprehensive Review on Betulin as a Potent Anticancer Agent". BioMed Research International 2015. doi:10.1155/2015/584189. PMID 25866796.