Ajugol - CAS 52949-83-4
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Ajugol
Catalog Number:
52949-83-4
Synonyms:
(2S,3S,4R,5R,6S)-6-[[(4aS,7S,7aR)-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-2-(hydroxymethyl)oxane-2,3,4,5-tetrol;
CAS Number:
52949-83-4
Description:
Ajugol is an iridiod glucoside isolated from the roots of Rehmannia glutinosa.
Molecular Weight:
348.35
Molecular Formula:
C15H24O9
Quantity:
Milligrams-Grams
Quality Standard:
Enterprise Standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC1(CCC2C1C(OC=C2)OC3C(C(C(C(O3)(CO)O)O)O)O)O
InChI:
1S/C15H24O9/c1-14(20)4-2-7-3-5-22-12(8(7)14)23-13-10(18)9(17)11(19)15(21,6-16)24-13/h3,5,7-13,16-21H,2,4,6H2,1H3/t7-,8-,9+,10+,11-,12?,13-,14-,15-/m0/s1
InChIKey:
OUJVIWOUXFHELC-ZDSSIQEISA-N
Targets:
Others
Chemical Structure
CAS 52949-83-4 Ajugol

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Reference Reading


1.Pharmacokinetics and tissue distribution of Aucubin, Ajugol and Catalpol in rats using a validated simultaneous LC-ESI-MS/MS assay.
Xue B1, Ma B2, Zhang Q3, Li X4, Zhu J2, Liu M2, Wu X2, Wang C2, Wu Z5. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:245-53. doi: 10.1016/j.jchromb.2015.08.026. Epub 2015 Aug 28.
To enable an investigation of pharmacokinetics and tissue distribution of Aucubin, Ajugol and Catalpol in rats, a high-performance liquid chromatography-electro spray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) method was developed for the simultaneous quantitative determination of the three compounds. Biological samples were prepared by a simple protein precipitation with methanol (containing 0.05% formic acid). The analytes were separated by a C18 reversed phase column and detected with a triple quadrupole tandem mass spectrometer in the multiple-reaction monitoring (MRM) mode to monitor the precursor-to-product ion transitions of m/z 364.3→149.0 for Aucubin, m/z 366.5→151.1 for Ajugol, m/z 380.0→183.3 for Catalpol and m/z 530.3→183.1 for Picroside-II (IS) in positive ionization. Good linearity of each calibration curve was produced over the concentration range of 1-1000ng/mL. The lower limit of quantification (LLOQ) was 1ng/mL for the three analytes.
2.Chiroptical properties of ajugol investigated by quantum chemical calculation using time-dependent density functional theory.
Li L1, Liu YF, Si YK, Yu DQ. J Asian Nat Prod Res. 2013;15(6):670-9. doi: 10.1080/10286020.2013.802691.
The chiroptical properties of an iridoid glycoside ajugol were fully investigated by quantum chemical calculations of specific optical rotation at the sodium D line ([α]D value), optical rotatory dispersion (ORD), and electronic circular dichroism (ECD) using time-dependent density functional theory (TDDFT). TDDFT calculations of the [α]D value and ORD of ajugol over the range of 365-633 nm were in good agreement with the experimental data. The predicted ECD spectrum of ajugol was also consistent with the experiment, showing a strong negative Cotton effect (CE) at around 190 nm and a weak positive CE at around 220 nm. Our results unambiguously determined the absolute configuration (AC) of the aglycone part of ajugol as (1S, 5R, 6R, 8S, 9S) and supported the generally accepted AC assignments of iridoid glycosides. Semi-empirical rule for the enol ether chromophore, basis set selection, and effect of glucose group on ECD spectra were also discussed in the case of ajugol.