Vitexilactone

CAS# 61263-49-8

Vitexilactone

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Chemical structure

Vitexilactone

3D structure

Chemical Properties of Vitexilactone

Cas No. 61263-49-8 SDF Download SDF
PubChem ID 21636178 Appearance Powder
Formula C22H34O5 M.Wt 378.5
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1R,3R,4R,4aS,8aS)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-3-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
SMILES CC1CC(C2C(CCCC2(C1(CCC3=CC(=O)OC3)O)C)(C)C)OC(=O)C
Standard InChIKey FBWWXAGANVJTLU-HEXLTJKYSA-N
Standard InChI InChI=1S/C22H34O5/c1-14-11-17(27-15(2)23)19-20(3,4)8-6-9-21(19,5)22(14,25)10-7-16-12-18(24)26-13-16/h12,14,17,19,25H,6-11,13H2,1-5H3/t14-,17-,19+,21+,22-/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 Vitexilactone

The seeds of Vitex trifolia L.

Biological Activity of Vitexilactone

Description1. Vitexilactone dramatically induces apoptosis both on tsFT210 and K562 cells at higher concentrations while at lower concentrations it inhibits the cell cycle progression of both tsFT210 and K562 cells at the G0/G1 phase; it is one anticancer component of Vitex trifolia L., which exerts its anti-proliferative effect on cancer cells through inducing apoptosis and inhibiting the cell cycle. 2. Vitexilactone has trypanocidal activity, the minimum lethal concentration against epimastigotes of Trypanosoma cruzi is 66 microM . 3. Vitexilactone is a HIV-1 reverse transcriptase inhibitor in virtual screening against Indonesian Herbal Database using AutoDock4 performed on HIV-1 reverse transcriptase.
TargetsHIV | NADPH-oxidase | Antifection

Vitexilactone Dilution Calculator

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Vitexilactone Molarity Calculator

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Preparing Stock Solutions of Vitexilactone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.642 mL 13.21 mL 26.4201 mL 52.8402 mL 66.0502 mL
5 mM 0.5284 mL 2.642 mL 5.284 mL 10.568 mL 13.21 mL
10 mM 0.2642 mL 1.321 mL 2.642 mL 5.284 mL 6.605 mL
50 mM 0.0528 mL 0.2642 mL 0.5284 mL 1.0568 mL 1.321 mL
100 mM 0.0264 mL 0.1321 mL 0.2642 mL 0.5284 mL 0.6605 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 Vitexilactone

New norditerpenoids with trypanocidal activity from Vitex trifolia.[Pubmed:15577254]

Chem Pharm Bull (Tokyo). 2004 Dec;52(12):1492-4.

Trypanocidal constituents of the fruits of Vitex trifolia were investigated. Activity-guided isolation of the acetone extract resulted in the isolation of two new norditerpene aldehydes, 1 and 2, together with five known diterpenes: vitexifolin E (3), vitexifolin F (4), Vitexilactone (5), 6-acetoxy-9-hydroxy-13(14)-labden-16,15-olide (6), and preVitexilactone (7). In vitro minimum lethal concentrations of the isolated compounds against epimastigotes of Trypanosoma cruzi were 11 microM (1), 36 microM (2), 34 microM (3), 34 microM (4), 66 microM (5), 66 microM (6), and >265 microM (7).

Labdane-type diterpenes as new cell cycle inhibitors and apoptosis inducers from Vitex trifolia L.[Pubmed:15621610]

J Asian Nat Prod Res. 2005 Apr;7(2):95-105.

Five labdane-type diterpenes, Vitexilactone (1), (rel 5S,6R,8R,9R,10S)-6-acetoxy-9-hydroxy-13(14)-labden-16,15-olide (2), rotundifuran (3), vitetrifolin D (4), and vitetrifolin E (5), have been isolated from Vitex trifolia L., a Chinese folk medicine used to treat cancers, as new cell cycle inhibitors and apoptosis inducers through a bioassay-guided separation procedure and were identified by spectroscopic methods. Compounds 1-5 dramatically induced apoptosis both on tsFT210 and K562 cells at higher concentrations while at lower concentrations they inhibited the cell cycle progression of both tsFT210 and K562 cells at the G0/G1 phase. MIC values for 1-5 for inducing apoptosis and concentration regions for 1-5 for inhibiting cell cycle both on tsFT210 and K562 cells have also been determined. Furthermore, the inhibitory effects of 1-5 on the proliferation of tsFT210 and K562 cells have been evaluated by MTT assay to obtain IC50 values to confirm that 1-5 are anticancer components of Vitex trifolia L., which exert their anti-proliferative effect on cancer cells through inducing apoptosis and inhibiting the cell cycle. The present results provide labdane-type diterpenes, 1-5, as a new class of cell cycle inhibitors and compounds 1, 2, 4, and 5 as new apoptosis inducers, which also explains, for the first time, the usage of Vitex trifolia L. by Chinese people to treat cancers.

Virtual screening of Indonesian herbal database as HIV-1 reverse transcriptase inhibitor.[Pubmed:23275721]

Bioinformation. 2012;8(24):1206-10.

HIV-1 (Human immunodeficiency virus type 1) is a member of retrovirus family that could infect human and causing AIDS disease. AIDS epidemic is one of most destructive diseases in modern era. There were more than 33 million people infected by HIV until 2010. Various studies have been widely employed to design drugs that target the essential enzymes of HIV-1 that is, reverse transcriptase, protease and integrase. In this study, in silico virtual screening approach is used to find lead molecules from the library or database of natural compounds as HIV-1 reverse transcriptase inhibitor. Virtual screening against Indonesian Herbal Database using AutoDock4 performed on HIV-1 reverse transcriptase. From the virtual screening, top ten compounds were mulberrin, plucheoside A, Vitexilactone, brucine N-oxide, cyanidin 3-arabinoside, alpha-mangostin, guaijaverin, erycristagallin, morusin and sanggenol N.

Development and validation of a rapid ultra-high performance liquid chromatography diode array detector method for Vitex agnus-castus.[Pubmed:23522912]

J Chromatogr B Analyt Technol Biomed Life Sci. 2013 May 15;927:181-90.

A rapid ultra-high performance liquid chromatography diode array detector (UHPLC-DAD) method was developed and validated for the simultaneous determination of all classes of non-volatile phytochemicals (iridoids, flavonoids and diterpenes) in Vitex agnus-castus (Lamiaceae) fruits, a traditional medicinal plant used against premenstrual symptoms (PMS) and other disorders. Seven marker compounds, 3,4-dihydroxybenzoic acid, p-hydroxybenzoic acid, agnuside, 5-hydroxykaempferol-3,6,7,4'-tetramethylether, 1,2-dibenzoic acid glucose, methoxy-Vitexilactone, and vitetrifolin D were isolated from the methanol extract of V. agnus-castus to be used as reference substances. Chromatographic separation was performed on a Zorbax Eclipse XDB-C18 (50mmx2.1mm) UHPLC column with 1.8mum particle size, within 20min. A solvent gradient from 0.5% acetic acid to acetonitrile at a flow rate of 0.6mL/min was used as mobile phase. Analyte detection and quantification was realized at 210nm and 260nm. The UHPLC-DAD assay was validated for the quantitative analysis of agnuside, isovitexin, casticin, 5-hydroxykaempferol-3,6,7,4'-tetramethylether and vitetrifolin D. It was found to be specific, accurate, precise, and reproducible for the quantification of these compound within a concentration range of 0.7-500.0mug/mL for casticin and 5-hydroxykaempferol-3,6,7,4'-tetramethylether, 1.4-1000.0mug/mL for isovitexin and agnuside, and 12.4-1000.0mug/mL for vitetrifolin D. Intra- and inter-day variations showed relative standard deviations (RSD) of less than 3.9% and 6.4%, respectively. Tentatively assignment of 62 chromatographic features found in the UHPLC-DAD assay was carried out by coupling the UHPLC instrument to a quadrupole time-of-flight mass spectrometer via an electrospray ionization interface (ESI-QTOF-MS) operated in positive and negative ion mode. By using the established quantitative UHPLC-DAD assay to asses agnuside, isovitexin, casticin, 5-hydroxykaempferol-3,6,7,4'-tetramethylether and vitetrifolin D in V. agnus-castus derived preparations as extracts, tinctures and tablets, the applicability of the developed assay to phytopharmaceuticals was successfully proven.

Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.[Pubmed:23662135]

Evid Based Complement Alternat Med. 2013;2013:432829.

As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits of Vitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing an alpha , beta -unsaturated gamma -lactam moiety. Structurally, they were elucidated to be 9 alpha -hydroxy-13(14)-labden-16,15-amide (2) and 6 beta -acetoxy-9 alpha -hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as Vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8), cis-dihydro-dehydro-diconiferylalcohol-9-O- beta -D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4'-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), beta -sitosterol (16), p-hydroxybenzoic acid (17), and p-hydroxybenzoic acid glucose ester (18). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds 6, 8, 9, and 18 were reported from a Vitex spieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound 7 demonstrated promising QR1 induction effect, while the new compound vitexlactam (3) was only slightly active.

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