Ajugol

CAS# 52949-83-4

Ajugol

Catalog No. BCN2883----Order now to get a substantial discount!

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Quality Control of Ajugol

Number of papers citing our products

Chemical structure

Ajugol

3D structure

Chemical Properties of Ajugol

Cas No. 52949-83-4 SDF Download SDF
PubChem ID 6325127 Appearance White powder
Formula C15H24O9 M.Wt 348.4
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility DMSO : ≥ 3.7 mg/mL (10.62 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7S,7aS)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O
Standard InChIKey VELYAQRXBJLJAK-XKKWFBPMSA-N
Standard InChI InChI=1S/C15H24O9/c1-15(21)4-7(17)6-2-3-22-13(9(6)15)24-14-12(20)11(19)10(18)8(5-16)23-14/h2-3,6-14,16-21H,4-5H2,1H3/t6-,7+,8+,9+,10+,11-,12+,13-,14-,15-/m0/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 Ajugol

1 Cistanche sp. 2 Leonurus sp. 3 Rehmannia sp. 4 Scrophularia sp. 5 Verbascum sp.

Biological Activity of Ajugol

DescriptionAjugol shows some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3–73.0 ug/ml).
TargetsAntifection
In vitro

Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.[Pubmed: 15680992 ]

Phytochemistry, 2005, 66(3):355-62.

The ethanolic root extract of Scrophularia lepidota, an endemic plant of the Turkish flora, has been investigated for its anti-protozoal and inhibitory effect towards plasmodial enoyl-ACP reductase (FabI), a key enzyme of fatty acid biosynthesis in Plasmodium falciparum.
METHODS AND RESULTS:
Chromatographic separation of the extract yielded 10 iridoids (1-10), two of which are new, and a known phenylethanoid glycoside (11). The structures of the new compounds were determined as 3,4-dihydro-methylcatalpol (8) and 6-O-[4''-O-trans-(3,4-dimethoxycinnamoyl)-alpha-L-rhamnopyranosyl]aucubin (scrolepidoside, 9) by spectroscopic means. The remaining metabolites were characterized as catalpol (1), 6-O-methylcatalpol (2), aucubin (3), 6-O-alpha-L-rhamnopyranosyl-aucubin (sinuatol, 4), 6-O-beta-D-xylopyranosylaucubin (5), Ajugol (6), ajugoside (7), an iridoid-related aglycone (10) and angoroside C (11). Nine isolates were active against Leishmania donovani, with the new compound 9 being most potent (IC50 6.1 microg/ml). Except for 4, all pure compounds revealed some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3-73.0 microg/ml). Only compound 10 showed moderate anti-plasmodial (IC50 40.6 microg/ml) and FabI enzyme inhibitory activity (IC50 100 microg/ml). 10 is the second natural product inhibiting the fatty acid biosynthesis of Plasmodium falciparum.

Protocol of Ajugol

Structure Identification
Volume 23, Issue 11, 1982, Pages 1215-1216

Structural revision of ajugol and myoporoside[Reference: WebLink]


METHODS AND RESULTS:
An analysis of existing 13C NMR data shows that the structures reported for the iridoid glucosides Ajugol and myoporoside should be interchanged.
CONCLUSIONS:
Consequently, the structures of ajugoside and laterioside, both acyl-derivatives of Ajugol, as well as that of 8-O-acetyl-myoporoside need revision.

Ajugol Dilution Calculator

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Ajugol Molarity Calculator

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Preparing Stock Solutions of Ajugol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8703 mL 14.3513 mL 28.7026 mL 57.4053 mL 71.7566 mL
5 mM 0.5741 mL 2.8703 mL 5.7405 mL 11.4811 mL 14.3513 mL
10 mM 0.287 mL 1.4351 mL 2.8703 mL 5.7405 mL 7.1757 mL
50 mM 0.0574 mL 0.287 mL 0.5741 mL 1.1481 mL 1.4351 mL
100 mM 0.0287 mL 0.1435 mL 0.287 mL 0.5741 mL 0.7176 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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Background on Ajugol

Ajugol is an iridiod glucoside.

References:
[1]. Elusiyan CA, et al. Distribution of iridiod glucosides and anti-oxidant compounds in Spathodea campanulata parts. Afr J Tradit Complement Altern Med. 2011;8(1):27-33.

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References on Ajugol

Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.[Pubmed:15680992]

Phytochemistry. 2005 Feb;66(3):355-62.

The ethanolic root extract of Scrophularia lepidota, an endemic plant of the Turkish flora, has been investigated for its anti-protozoal and inhibitory effect towards plasmodial enoyl-ACP reductase (FabI), a key enzyme of fatty acid biosynthesis in Plasmodium falciparum. Chromatographic separation of the extract yielded 10 iridoids (1-10), two of which are new, and a known phenylethanoid glycoside (11). The structures of the new compounds were determined as 3,4-dihydro-methylcatalpol (8) and 6-O-[4''-O-trans-(3,4-dimethoxycinnamoyl)-alpha-L-rhamnopyranosyl]aucubin (scrolepidoside, 9) by spectroscopic means. The remaining metabolites were characterized as catalpol (1), 6-O-methylcatalpol (2), aucubin (3), 6-O-alpha-L-rhamnopyranosyl-aucubin (sinuatol, 4), 6-O-beta-D-xylopyranosylaucubin (5), Ajugol (6), ajugoside (7), an iridoid-related aglycone (10) and angoroside C (11). Nine isolates were active against Leishmania donovani, with the new compound 9 being most potent (IC50 6.1 microg/ml). Except for 4, all pure compounds revealed some trypanocidal potential against Trypanosoma brucei rhodesiense (IC50 values 29.3-73.0 microg/ml). Only compound 10 showed moderate anti-plasmodial (IC50 40.6 microg/ml) and FabI enzyme inhibitory activity (IC50 100 microg/ml). 10 is the second natural product inhibiting the fatty acid biosynthesis of Plasmodium falciparum.

Description

Ajugol is an iridiod glucoside.

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