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
CAS Number	41498-80-0
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2005473
ChemSpider	109521
PubChem CID	122859
CompTox Dashboard (EPA)	DTXSID70961770
InChI 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
SMILES CC1(CCC2(CCC3(C(=CCC4C3(CC(C5C4(CCC(=O)C5(C)C)C)O)C)C2C1)C)C)C
Properties
Chemical formula	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

• Scopine
• Daturadiol
• Withametelin