Daturaolone

Daturaolone is a triterpene found in Datura species such as Datura stramonium[1] and Datura innoxia.[2]

Daturaolone
Names
Preferred IUPAC name
(4aR,5R,6aR,6bS,8aR,12aR,14aR,14bR)-5-Hydroxy-4,4,6a,6b,8a,14b-hexamethyl-1,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicen-3(2H)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C30H48O2/c1-25(2)13-14-27(5)15-16-29(7)19(20(27)17-25)9-10-22-28(6)12-11-23(32)26(3,4)24(28)21(31)18-30(22,29)8/h9,20-22,24,31H,10-18H2,1-8H3/t20-,21+,22+,24-,27+,28+,29+,30+/m0/s1
    Key: YCTXVPCDHZMBHX-QCDSSADQSA-N
  • CC1(CCC2(CCC3(C(=CCC4C3(CC(C5C4(CCC(=O)C5(C)C)C)O)C)C2C1)C)C)C
Properties
C30H48O2
Molar mass 440.712 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

History

It was isolated for the first time from Solanum arundo.[3]

Research

It has shown to exhibit dose-dependent anti-inflammatory results in in-vivo models of inflammation by inhibiting COX-1 as well as having potent α-glucosidase and β-secretase inhibitory activity[4] however further studies are needed to better clarify its effect on humans.[5]

It may have antipyretic, muscle relaxant properties and decrease gastrointestinal motility although it is only evaluated in animals. [6]

See also

References
  1. Li J, Lin B, Wang G, Gao H, Qin M (February 2012). "[Chemical constituents of Datura stramonium seeds]". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica (in Chinese). 37 (3): 319–22. PMID 22568232.
  2. Kocór M, Pyrek JS, Atal CK, Bedi KL, Sharma BR (October 1973). "Triterpenes of Datura innoxia Mill. Structure of daturadiol and daturaolone". The Journal of Organic Chemistry. 38 (21): 3685–8. doi:10.1021/jo00961a005. PMID 4745874.
  3. Grace MH, Saleh MM (August 1996). "Hepato-protective effect of daturaolone isolated from Solanum arundo". Die Pharmazie. 51 (8): 593–5. PMID 8794471.
  4. Bawazeer, Saud; Rauf, Abdur; Bawazeer, Sami (2020). "Potent In Vitro α-Glucosidase and β-Secretase Inhibition of Amyrin-Type Triterpenoid Isolated from Datura metel Linnaeus (Angel's Trumpet) Fruits". BioMed Research International. 2020: 1–5. doi:10.1155/2020/8530165. ISSN 2314-6133. PMC 7468596.
  5. Rauf A, Maione F, Uddin G, Raza M, Siddiqui BS, Muhammad N, Shah SU, Khan H, De Feo V, Mascolo N (2016). "Biological Evaluation and Docking Analysis of Daturaolone as Potential Cyclooxygenase Inhibitor". Evidence-Based Complementary and Alternative Medicine. 2016: 4098686. doi:10.1155/2016/4098686. PMC 4793090. PMID 27042189.
  6. Bawazeer S, Rauf A, Bawazeer S (2020). "Gastrointestinal Motility, Muscle Relaxation, Antipyretic and Acute Toxicity Screening of Amyrin Type Triterpenoid (Daturaolone) Isolated From Datura metel Linnaeus (Angel's Trumpet) Fruits". Frontiers in Pharmacology. 11: 544794. doi:10.3389/fphar.2020.544794. PMC 7546419. PMID 33101017.


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