Betulonic acid

Chemical name: 3-Oxolup-20(29)-en-28-oic acid // Synonyms: 3-Oxobetulinic acid, Liquidambaric acid, Liquidambronic acid, (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid

Art-No.:LSB5009
Cas-no.:4481-62-3
Formula:C30H46O3
Molecular weight:454,68 g/mol
Grouped product items
Product variant
1 g
$263.25
LSB5009.0001
2,5 g
$398.25
LSB5009.2500
5 g
$540.00
LSB5009.0005
10 g
$810.00
LSB5009.0010
description
Betulin and derivatives are pentacyclic lupane-type triterpenoids and are widely distributed throughout the plant kingdom. They exhibit a variety of biological and medicinal properties such as inhibition of human immunodeficiency virus (HIV), anti-bacterial, anti-malarial, anti-inflammatory anthelmintic, immunomo dulatory, anti-fibrotic, antinociceptive, anti HSV 1, and anticancer activities. The growth of cancer cells is inhibited, without affecting normal cells and its lack of cytotoxic activity has been demonstrated in human astrocytes, human dermal fibroblasts, peripheral blood lymp fibroblasts, peripheral blood lymphoblasts and animal studies. The cytotoxicity and mode of cell death were determined using the MTT assay and DNA fragmentation analysis, respectively. Cells treated with high concentrations exhibited features characteristic of apoptosis such as blebbing and shrinking. Combined treatment with Betulin derivatives and anticancer drugs acted in concert to induce loss of mitochondrial membrane potential and the release of cytochrome C and Smac from mitocho ndria, resulting in activation of Caspases and apoptosis.Compounds with lupane structure typically exhibit limited solubility in organic solvents such as methanol and ethanol, chloroform, and ether and has low solubility in water, petroleum ether, dimethyl formamide, dimethyl sulfoxide, and benzene. However, they are normally highly soluble in pyridine and acetic acid.

references
Anti-AIDS Agents 38. Anti-HIV Activity of 3-O-Acyl Ursolic Acid Derivatives; Yoshiki Kashiwada, Tsuneatsu Nagao, Ayumi Hashimoto, Yasumasa Ikeshiro, Hikaru Okabe, L. Mark Cosentino, Kuo-Hsiung Lee; J. Nat. Prod. 2000; 63(12): 1619-1622. DOI: org/10.1021/np990633v.

Design, Synthesis, and Evaluation of Novel 1,2,3-Triazole-Tethered Glycolipids as Vaccine Adjuvants; Debabrata Bhunia, Preethi M. C. Pallavi, Srinivasa Reddy Bonam, Sandeep A. Reddy, Yogesh Verma, and M. Sampath Kumar Halmuthur; Arch. Pharm. Chem. Life Sci. 2015; 348: 689703. DOI: 10.1002/ardp.201500143.

Betulin and its derivatives as novel compounds with different pharmacological effects; Shayan Amiri, Sanaz Dastghaib, Mazaher Ahmadi, Parvaneh Mehrbod, Forough Khadem, Hamid Behrouj, Mohamad-Reza Aghanoori, Filip Machaj, Mahdi Ghamsari, Jakub Rosik, Andrzej Hudecki, Abbas Afkhami, Mohammad Hashemi, Marek J. Losj, Pooneh Mokarram, Tayyebeh Madrakian, Saeid Ghavami; Biotechnology Advances 2019: DOI: org/10.1016/j.biotechadv.2019.06.008.

Structural modifications of 2,3-indolobetulinic acid: design and synthesis of highly potent -glucosidase inhibitors; Elmira F. Khusnutdinova, Anastasiya V. Petrova, Ha Nguyen Thi Thu, Anh Le Thi Tu, Tra Nguyen Thanh, Cham Ba Thi, Denis A. Babkov, Oxana B. Kazakova; Bioorganic Chemistry 2019; 88: 102957. DOI: org/10.1016/j.bioorg.2019.102957.

Synthesis and cytotoxic activity of heterocyclic ring-substituted betulinic acid derivatives; Vivek Kumar, Nidhi Rani, Pawan Aggarwal, Vinod K. Sanna, Anu T. Singh, Manu Jaggi, Narendra Joshi, Pramod K. Sharma, Raghuveer Irchhaiya, Anand C. Burman; Bioorg. Med. Chem. Lett. 2008; 18: 50585062. DOI: 10.1016/j.bmcl.2008.08.003.

Synthesis and cytotoxic evaluation of novel amide-triazole-linked triterpenoid-AZT conjugates; Tuyet Anh Dang Thi, Nguyen Thi Kim Tuyet, Chinh Pham The, Ha Thanh Nguyen, Cham Ba Thi, Hoang Thi Phuong, Luu Van Boi, Tuyen Van Nguyen, Matthias Dhooghe; Tet. Lett. 2015; 56(1): 218-224. DOI: org/10.1016/j.tetlet.2014.11.069.

Synthesis and cytotoxicity of Baylis-Hillman template derived betulinic acid-triazole conjugates; Pathi Suman, Amardeep Patel, Lucas Solano, Gayathri Jampana, Zachary S. Gardner, Crystal M. Holt, Subash C. Jonnalagadda; Tetrahedron 2017; 73: 4214-4226. DOI: org/10.1016/j.tet.2016.11.056.

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