Ocotillone

CAS# 22549-21-9

Ocotillone

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Chemical structure

Ocotillone

3D structure

Chemical Properties of Ocotillone

Cas No. 22549-21-9 SDF Download SDF
PubChem ID 25567101 Appearance Cryst.
Formula C30H50O3 M.Wt 458.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5R,8R,9R,10R,13R,14R,17S)-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
SMILES CC1(C2CCC3(C(C2(CCC1=O)C)CCC4C3(CCC4C5(CCC(O5)C(C)(C)O)C)C)C)C
Standard InChIKey XSQYWMLMQVUWSF-FEDWKDCGSA-N
Standard InChI InChI=1S/C30H50O3/c1-25(2)21-12-17-29(7)22(27(21,5)15-13-23(25)31)10-9-19-20(11-16-28(19,29)6)30(8)18-14-24(33-30)26(3,4)32/h19-22,24,32H,9-18H2,1-8H3/t19-,20+,21+,22-,24+,27+,28-,29-,30-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Ocotillone

The barks of Ailanthus altissima

Biological Activity of Ocotillone

DescriptionOcotillone has potent antibacterial activity against Gram-negative bacteria, P. aeruginosa and S. typhimurium, that are without hemolytic activity, whereas it has weak antimicrobial activity against Gram-positive bacteria and fungi. Ocotillone shows only weak inhibitory activity against MCF-7 and NCI-H460 cells but moderate activity against A375-C5 cells.
TargetsAntifection
In vitro

Effect of triterpenoids and limonoids isolated from Cabralea canjerana and Carapa guianensis (Meliaceae) against Spodoptera frugiperda (J. E. Smith).[Pubmed: 21812341]

Z Naturforsch C. 2011 May-Jun;66(5-6):245-50.


METHODS AND RESULTS:
The activities of two triterpenoids, Ocotillone and cabraleadiol, and four limonoids, methyl angolensate, 3-beta-deacetylfissinolide, 7-deacetoxy-7-oxogedunin, and beta-photogedunin, isolated from arillus of Carapa guianensis and fruits and seeds of Cabralea canjerana (Meliaceae), were evaluated against the fall armyworm Spodoptera frugiperda. Gedunin was used as a positive control.
CONCLUSIONS:
7-Deacetoxy-7-oxogedunin and beta-photogedunin reduced the pupal weight as occurred with gedunin. Cabraleadiol, 3-beta-deacetylfissinolide, and 7-deacetoxy-7-oxogedunin prolonged the larval phase similar to the control (gedunin) of approximately 1.2 days at 50.0 mg kg(-1). The highest insecticidal activity was obtained for beta-photogedunin.

Antimicrobial effects of ocotillone isolated from stem bark of Ailanthus altisshima.[Reference: WebLink]

J. Microbial. Biotechnol.,2002,12(5):854-7.


METHODS AND RESULTS:
Bioassay-directed chromatographic fractionation of a methylene chloride extract of Ailanthus altisshima indicated the presence of 20(S), 24(R), epoxy-25-hydroxydammarane-3-one (compound 1, Ocotillone) which was isolated from this plant, for the first time. Antimicrobial activity of compound 1 was measured by inhibition of bacterial and fungal cells growth and by a hemolytic assay with human erythrocytes, respectively. The results revealed that compound 1 had potent antibacterial activity against Gram-negative bacteria, P. aeruginosa and S. typhimurium, that were without hemolytic activity, whereas it had weak antimicrobial activity against Gram-positive bacteria and fungi.
CONCLUSIONS:
These results demonstrated that the compound 1 has more antibacterial activity against Gram-negative bacteria, which have no hemolytic activity, than Gram-positive bacteria and fungi. This is the first report on the biological activities of the compound 1.

Protocol of Ocotillone

Structure Identification
Chem Biodivers. 2006 Aug;3(8):930-4.

Two new tetracyclic triterpenes from the heartwood of Ailanthus excelsa Roxb.[Pubmed: 17193324]


METHODS AND RESULTS:
Two new dammarane-type triterpenes, ailexcelone and ailexcelol, together with Ocotillone, malabaricol, epoxymalabaricol, lupeol, and sitosterol-3-O-beta-D-glucoside were isolated from the heartwood of Ailanthus excelsa. The structures of the new compounds were established on the basis of 1D- and 2D-NMR data.
CONCLUSIONS:
Ocotillone, malabaricol and epoxymalabaricol were isolated for the first time from A. excelsa. All of the isolates were tested for their antifungal activity.

Ocotillone Dilution Calculator

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Ocotillone Molarity Calculator

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Preparing Stock Solutions of Ocotillone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1801 mL 10.9004 mL 21.8007 mL 43.6015 mL 54.5019 mL
5 mM 0.436 mL 2.1801 mL 4.3601 mL 8.7203 mL 10.9004 mL
10 mM 0.218 mL 1.09 mL 2.1801 mL 4.3601 mL 5.4502 mL
50 mM 0.0436 mL 0.218 mL 0.436 mL 0.872 mL 1.09 mL
100 mM 0.0218 mL 0.109 mL 0.218 mL 0.436 mL 0.545 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Ocotillone

Two new tetracyclic triterpenes from the heartwood of Ailanthus excelsa Roxb.[Pubmed:17193324]

Chem Biodivers. 2006 Aug;3(8):930-4.

Two new dammarane-type triterpenes, ailexcelone and ailexcelol, together with Ocotillone, malabaricol, epoxymalabaricol, lupeol, and sitosterol-3-O-beta-D-glucoside were isolated from the heartwood of Ailanthus excelsa. The structures of the new compounds were established on the basis of 1D- and 2D-NMR data. Ocotillone, malabaricol and epoxymalabaricol were isolated for the first time from A. excelsa. All of the isolates were tested for their antifungal activity.

Effect of triterpenoids and limonoids isolated from Cabralea canjerana and Carapa guianensis (Meliaceae) against Spodoptera frugiperda (J. E. Smith).[Pubmed:21812341]

Z Naturforsch C. 2011 May-Jun;66(5-6):245-50.

The activities of two triterpenoids, Ocotillone and cabraleadiol, and four limonoids, methyl angolensate, 3-beta-deacetylfissinolide, 7-deacetoxy-7-oxogedunin, and beta-photogedunin, isolated from arillus of Carapa guianensis and fruits and seeds of Cabralea canjerana (Meliaceae), were evaluated against the fall armyworm Spodoptera frugiperda. Gedunin was used as a positive control. 7-Deacetoxy-7-oxogedunin and beta-photogedunin reduced the pupal weight as occurred with gedunin. Cabraleadiol, 3-beta-deacetylfissinolide, and 7-deacetoxy-7-oxogedunin prolonged the larval phase similar to the control (gedunin) of approximately 1.2 days at 50.0 mg kg(-1). The highest insecticidal activity was obtained for beta-photogedunin.

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