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Daturaolone

From Wikipedia, the free encyclopedia
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 mass440.712 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Daturaolone is apentacyclic oleanane triterpenoid,[1] also known as 3-oxo-6-β-hydroxy-β-amyrin,[2] found inDatura species such asDatura stramonium[3] andDatura innoxia.[4]

History

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It was isolated for the first time fromSolanum arundo.[5]

Structure

[edit]

Daturaolone contains five rings with a ketone group and a hydroxyl group, which may be essential for its bioactivities. The structure was deduced throughmass spectroscopy and1H NMR spectroscopy.[6]

Functions

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Daturaolone isolated fromDatura metel Linnaeus has been found to haveanti-fungal andanti-bacterial activities. When tested against bacterial strains such asKlebsiella pneumoniae andS. aureus, daturaolone was shown to inhibit bacterial growth.[7]

See also

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References

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  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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