Daturaolone

Daturaolone is a pentacyclic oleanane triterpenoid,[1] also known as 3-oxo-6-β-hydroxy-β-amyrin,[2] found in Datura species such as Datura stramonium[3] and Datura innoxia.[4]

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.[5]

Structure

Daturaolone contains five rings with a ketone group and a hydroxyl group, which may be essential for its bioactivities. The structure was deduced through mass spectroscopy and 1H NMR spectroscopy.[6]

Functions

Daturaolone isolated from Datura metel Linnaeus has been found to have anti-fungal and anti-bacterial activities. When tested against bacterial strains such as Klebsiella pneumoniae and S. aureus, daturaolone was shown to inhibit bacterial growth.[7]

See also

References
  1. Baig, Muhammad Waleed; Fatima, Humaira; Akhtar, Nosheen; Hussain, Hidayat; Okla, Mohammad K.; Al-Hashimi, Abdulrahman; Al-Qahtani, Wahidah H.; AbdElgawad, Hamada; Haq, Ihsan-ul (2021-11-30). "Anti-Inflammatory Potential of Daturaolone from Datura innoxia Mill.: In Silico, In Vitro and In Vivo Studies". Pharmaceuticals. 14 (12): 1248. doi:10.3390/ph14121248. ISSN 1424-8247. PMC 8708807. PMID 34959649.
  2. Bawazeer, Saud; Rauf, Abdur; Bawazeer, Sami (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. ISSN 1663-9812. PMC 7546419. PMID 33101017.
  3. 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.
  4. 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.
  5. Grace MH, Saleh MM (August 1996). "Hepato-protective effect of daturaolone isolated from Solanum arundo". Die Pharmazie. 51 (8): 593–5. PMID 8794471.
  6. Grace, M. H.; Saleh, M. M. (August 1996). "Hepato-protective effect of daturaolone isolated from Solanum arundo". Die Pharmazie. 51 (8): 593–595. ISSN 0031-7144. PMID 8794471.
  7. Bawazeer, Sami; Rauf, Abdur (2021-09-18). "In Vitro Antibacterial and Antifungal Potential of Amyrin-Type Triterpenoid Isolated from Datura metel Linnaeus". BioMed Research International. 2021: 1543574. doi:10.1155/2021/1543574. ISSN 2314-6133. PMC 8476240. PMID 34589544.


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