Aglain C

CAS# 177468-85-8

Aglain C

2D Structure

Catalog No. BCN6604----Order now to get a substantial discount!

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Aglain C

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Chemical Properties of Aglain C

Cas No. 177468-85-8 SDF Download SDF
PubChem ID 131637770 Appearance Powder
Formula C36H42N2O8 M.Wt 630.7
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-N-[(2S)-1-[(1S,9S,10S,11R,12R)-1,12-dihydroxy-3,5-dimethoxy-9-(4-methoxyphenyl)-10-phenyl-8-oxatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-11-carbonyl]pyrrolidin-2-yl]-2-methylbutanamide
SMILES CCC(C)C(=O)NC1CCCN1C(=O)C2C(C3(C(C2(C4=C(C=C(C=C4O3)OC)OC)O)O)C5=CC=C(C=C5)OC)C6=CC=CC=C6
Standard InChIKey KPCVKSYNYMIDEN-JQCYSCQSSA-N
Standard InChI InChI=1S/C36H42N2O8/c1-6-21(2)32(39)37-28-13-10-18-38(28)33(40)31-29(22-11-8-7-9-12-22)36(23-14-16-24(43-3)17-15-23)34(41)35(31,42)30-26(45-5)19-25(44-4)20-27(30)46-36/h7-9,11-12,14-17,19-21,28-29,31,34,41-42H,6,10,13,18H2,1-5H3,(H,37,39)/t21-,28-,29+,31-,34+,35+,36+/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 Aglain C

The seeds and leaves of Aglaia argentea.

Protocol of Aglain C

Structure Identification
Tetrahedron, 1996, 52(20):6931-6942.

New nitrogenous and aromatic derivatives from Aglaia argentea and A. forbesii.[Reference: WebLink]

Seeds and leaves of Aglaia argentea and bark of A. forbesii were extracted.
METHODS AND RESULTS:
The known cyclopentatetrahydrobenzofuran derivative rocaglaol (1) and the aminopyrrolidine odorine (5), were isolated together with nine new compounds: didesmethylrocaglamide (6), aglain A (7), aglain B (8) and Aglain C (9), aglaforbesins A (10) and B (11), ethylrocaglaol (12) and forbaglins A (13) and B (14). Compounds 7–11 and 13,14 possess a new cyclopentatetrahydrobenzopyran and benzoxepine skeleton, respectively, linked to an odorine type moiety. All the structures were elucidated notably by 2D NMR spectroscopy. In addition, the structure of forbaglin A was established by X-Ray crystallographic analysis.
CONCLUSIONS:
Didesmethylrocaglamide revealed strong cytotoxic activity against KB cells (IC50 0.006 μg/ml).

Aglain C Dilution Calculator

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Preparing Stock Solutions of Aglain C

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 Aglain C

1H-cyclopenta[b]benzofuran lignans from Aglaia species inhibit cell proliferation and alter cell cycle distribution in human monocytic leukemia cell lines.[Pubmed:10685499]

Z Naturforsch C. 1999 Dec;54(12):1075-83.

Thirteen naturally occurring 1H-cyclopenta[b]benzofuran lignans of the rocaglamide type as well as one naturally occurring Aglain Congener all of them isolated from three Aglaia species (Aglaia duperreana, A. oligophylla and A. spectabilis) collected in Vietnam were studied for their antiproliferative effects using the human monocytic leukemia cell lines MONO-MAC-1 and MONO-MAC-6. Only rocaglamide type compounds showed significant inhibition of [3H-]thymidine incorporation and the most active compound didesmethylrocaglamide inhibited cell growth in a similar concentration range as the well-known anticancer drug vinblastine sulfate. Detailed structure-activity analysis indicated that the OH-group at C-8b which is a common structural feature of most naturally occurring rocaglamide compounds is essential for the described antiproliferative activity since replacement of this group by methylation led to a complete loss of the inhibitory activity for the resulting derivative. Rocaglamide derivatives rapidly inhibited DNA as well as protein biosynthesis of MONO-MAC-6 cells at concentrations well below those of actinomycin D or cycloheximide which were used as positive controls in the respective experiments. Didesmethylrocaglamide was furthermore able to induce growth arrest of MONO-MAC-1 cells in the G2/M and probably G0/G1-phase of the cell cycle with no morphological indication of cellular damage. Our data suggests that 1H-cyclopenta[b]benzofuran lignans of the rocaglamide type act primarily by a cytostatic mechanism.

Structure activity relationships of antiproliferative rocaglamide derivatives from Aglaia species (Meliaceae).[Pubmed:10223787]

Z Naturforsch C. 1999 Jan-Feb;54(1-2):55-60.

Eleven rocaglamide derivatives (cyclopentatetrahydrobenzofurans) and one structurally related Aglain Congener all isolated from different Aglaia species (Meliaceae) were tested for growth inhibiting properties using the human cancer cell lines MONO-MAC-6 and MEL-JUSO. Proliferation of both cell lines was efficiently inhibited in a dose and compound dependent manner. Applying MTT-Assay, the IC50 of the most active compound didesmethyl-rocaglamide (1) was observed at 0.002 and 0.006 micrograms/ml (0.004 and 0.013 microM) depending on the cell line investigated. Bulky aminoacyl substituents at C-2, acetylation of the OH substituent at C-1 or insertion of a OH or OMe substituent at C-3 of the rocaglamide skeleton all diminished the activity of the compounds investigated. The aglain derivative 12 was inactive up to a concentration of 3 micrograms/ml (4.6 microM). This loss of activity is assumed to be mainly due to the presence of a pyran ring in the aglains vs. a furan ring as found in rocaglamide derivatives. Rocaglamide derivatives may act primarily by inhibition of cell proliferation as evidenced by the absence of a significant cytotoxic effect in long-term cultures of MONO-MAC-6 cells treated with high doses of didesmethylrocaglamide. Our data suggest that rocaglamide derivatives could exert a potential role in the treatment of malignant diseases and are worth to be investigated in further studies of experimental medicine and pharmacology.

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