Ajugatakasins A

CAS# 197723-20-9

Ajugatakasins A

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Quality Control of Ajugatakasins A

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Chemical structure

Ajugatakasins A

3D structure

Chemical Properties of Ajugatakasins A

Cas No. 197723-20-9 SDF Download SDF
PubChem ID 56658114 Appearance Powder
Formula C34H46O11 M.Wt 630.7
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-7,8-dimethyl-8-[(2S)-2-[(E)-2-methylbut-2-enoyl]oxy-2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (E)-2-methylbut-2-enoate
SMILES CC=C(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)CC(C4=CC(=O)OC4)OC(=O)C(=CC)C)COC(=O)C
Standard InChIKey BGAZAIQJEALJJF-NFWHYXGOSA-N
Standard InChI InChI=1S/C34H46O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h9-10,14,21,25-27,29H,11-13,15-18H2,1-8H3/b19-9+,20-10+/t21-,25-,26+,27+,29-,32+,33+,34-/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 Ajugatakasins A

The herbs of Ajuga ciliata Bunge.

Biological Activity of Ajugatakasins A

DescriptionAjugatakasin A is a natural product from Ajuga ciliata Bunge.
In vitro

Ajugatakasins A and B, New Diterpenoids from Ajuga decumbens, and Feeding Stimulative Activity of Related Neoclerodane Analogs toward the Turnip Sawfly[Reference: WebLink]

Bioscience Biotechnology & Biochemistry , 1997 , 61 (9) :1518-1522.

Adults of the turnip sawfly, Athalia rosae ruficornis, are strongly attracted to the leaves of Ajuga decumhens (Labiatae).
METHODS AND RESULTS:
Specific feeding stimulants of the sawfly were examined in the leaf surface extracts of A. decumbens. Among seven neoclerodane diterpenoids isolated from the extracts, two new analogs, Ajugatakasin A and ajugatakasin B, were characterized as 6α,18-diacetoxy-1β,12-ditigloyloxy-4α,17-epoxyneoclerod-13-en-15,16-olide and its 1β,12-di-(2-methylbutanoyl)-oxy analog, respectively.
CONCLUSIONS:
Among these analogs, clerodendrin D, a very minor constituent which possesses a tetrahydrofurofuran moiety, was identified as the feeding stimulant for A. rosae ruficornis, while the other analogs with an α,β-unsaturated γ-lactone moiety were found to be completely inactive in the sawfly feeding test.

Protocol of Ajugatakasins A

Structure Identification
Natural Product Communications , 2006 , 1 (3) :183-189.

Isolation and identification of neo-clerodane diterpenes from Ajuga nipponensis Makino[Reference: WebLink]

An extract of the aerial parts of Ajuga nipponensis Makino was examined by HPLC for neo-clerodane diterpenes.
METHODS AND RESULTS:
The suitability of reversed-phase HPLC for the semi-preparative fractionation of this extract was explored, resulting in the isolation of two new neo-clerodane diterpenes, which we have named ajuganipponin A, (12S)-1β,6α,19-triacetoxy-4α,18-epoxy-12- tigloyl-neo-clerod-13-en-15,16-olide (AJNP A, 1), and ajuganipponin B, (12S)-6α,19-diacetoxy-4α,18-epoxy-12-tigloyl-neoclerod-13-en-15, 16-olide (AJNP B, 6). In addition, ajugamarins A2 and F4, ajugamacrin B, ajugacumbin A and Ajugatakasin A, were newly isolated compounds from A. nipponensis, along with the previously reported ajugamarins A1, B2 and L2 (ajugacumbin B).
CONCLUSIONS:
The structures of all the isolated compounds were unambiguously elucidated based on extensive NMR spectral studies (one and two-dimensional experiments) and their reversed-phase chromatographic behavior was established. The antifeedant activity of the isolated diterpenes against Spodoptera littoralis is also reported here.

Ajugatakasins A Dilution Calculator

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Ajugatakasins A Molarity Calculator

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Preparing Stock Solutions of Ajugatakasins A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5855 mL 7.9277 mL 15.8554 mL 31.7108 mL 39.6385 mL
5 mM 0.3171 mL 1.5855 mL 3.1711 mL 6.3422 mL 7.9277 mL
10 mM 0.1586 mL 0.7928 mL 1.5855 mL 3.1711 mL 3.9638 mL
50 mM 0.0317 mL 0.1586 mL 0.3171 mL 0.6342 mL 0.7928 mL
100 mM 0.0159 mL 0.0793 mL 0.1586 mL 0.3171 mL 0.3964 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 Ajugatakasins A

Ajugatakasins A and B, New Diterpenoids from Ajuga decumbens, and Feeding Stimulative Activity of Related Neoclerodane Analogs toward the Turnip Sawfly

Bioscience Biotechnology & Biochemistry , 1997 , 61 (9) :1518-1522.

Adults of the turnip sawfly, Athalia rosae ruficornis, are strongly attracted to the leaves of Ajuga decumhens (Labiatae). Specific feeding stimulants of the sawfly were examined in the leaf surface extracts of A. decumbens. Among seven neoclerodane diterpenoids isolated from the extracts, two new analogs, Ajugatakasin A and ajugatakasin B, were characterized as 6α,18-diacetoxy-1β,12-ditigloyloxy-4α,17-epoxyneoclerod-13-en-15,16-olide and its 1β,12-di-(2-methylbutanoyl)-oxy analog, respectively. Among these analogs, clerodendrin D, a very minor constituent which possesses a tetrahydrofurofuran moiety, was identified as the feeding stimulant for A. rosae ruficornis, while the other analogs with an α,β-unsaturated γ-lactone moiety were found to be completely inactive in the sawfly feeding test.

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