Daturaolone

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

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

History[]

It was isolated for the first time from .^[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]

References[]

^ Li J, Lin B, Wang G, Gao H, Qin M (February 2012). "[Chemical constituents of Datura stramonium seeds]". (in Chinese). 37 (3): 319–22. PMID 22568232.
^ 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.
^ Grace MH, Saleh MM (August 1996). "Hepato-protective effect of daturaolone isolated from Solanum arundo". Die Pharmazie. 51 (8): 593–5. PMID 8794471.
^ 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.
^ 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.
^ 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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[pmid22568232-1] Li J, Lin B, Wang G, Gao H, Qin M (February 2012). "[Chemical constituents of Datura stramonium seeds]". (in Chinese). 37 (3): 319–22. PMID 22568232.

[pmid4745874-2] 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.

[pmid8794471-3] Grace MH, Saleh MM (August 1996). "Hepato-protective effect of daturaolone isolated from Solanum arundo". Die Pharmazie. 51 (8): 593–5. PMID 8794471.

[BawazeerRauf2020-4] 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.

[pmid27042189-5] 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.

[pmid33101017-6] 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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Daturaolone

Contents

History[]

Research[]

See also[]

References[]