Jolkinolide A

CAS# 37905-07-0

Jolkinolide A

Catalog No. BCN3771----Order now to get a substantial discount!

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Jolkinolide A: 5mg $903 In Stock
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Quality Control of Jolkinolide A

Number of papers citing our products

Chemical structure

Jolkinolide A

3D structure

Chemical Properties of Jolkinolide A

Cas No. 37905-07-0 SDF Download SDF
PubChem ID 161953 Appearance Cryst.
Formula C20H26O3 M.Wt 314.4
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1=C2C3C4(O3)CCC5C(CCCC5(C4C=C2OC1=O)C)(C)C
Standard InChIKey OYXDHOVYZKWSRM-PHJMNMFVSA-N
Standard InChI InChI=1S/C20H26O3/c1-11-15-12(22-17(11)21)10-14-19(4)8-5-7-18(2,3)13(19)6-9-20(14)16(15)23-20/h10,13-14,16H,5-9H2,1-4H3/t13-,14+,16-,19-,20+/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 Jolkinolide A

The herbs of Stellera chamaejasme Linn.

Biological Activity of Jolkinolide A

DescriptionJolkinolide A has anti-tumor activity. It inhibited VEGF expression in A549 cells through the inhibition of the Akt-STAT3-mTOR signaling pathway, and directly inhibited the proliferation and migration of HUVECs.
TargetsVEGF | Akt | Akt | STAT | mTOR
In vitro

Jolkinolide A and Jolkinolide B Inhibit Proliferation of A549 Cells and Activity of Human Umbilical Vein Endothelial Cells.[Pubmed: 28087861]

Medical Science Monitor, 2017, 23:223-237.

Jolkinolide A (JA) and Jolkinolide B (JB) are diterpenoids extracted from the roots of Euphorbia fischeriana Steud and have been shown to have anti-tumor activity. However, their effects on the ability of tumor cells to invade blood vessels and metastasize remain largely unknown. Investigations into the effects of JA and JB on the angiogenesis of tumor tissues may facilitate the identification of new natural drugs with anti-tumor growth and metastasis activities.
METHODS AND RESULTS:
We used different concentrations of JA and JB (20 μg/ml, 40 μg/ml, 60 μg/ml, 80 μg/ml, and 100 μg/ml) to stimulate A549 cells and then studied the effects on the growth and metastasis of lung cancers. In addition, we used conditional media from A549 cells (A549-CM) stimulated by either JA or JB in different concentrations to culture human umbilical vein endothelial cells (HUVECs). We found that both JA and JB significantly inhibited the Akt-STAT3-mTOR signaling pathway and reduced the expression of VEGF in A549 cells, but JB exhibited more significant inhibitory effects than JA. The JB-stimulated A549 cell conditional media had a greater inhibitory effect on the proliferation and migration of HUVECs than did the conditional media of JA-stimulated A549 cells. This effect gradually increased with increasing concentrations of either type of Jolkinolide.
CONCLUSIONS:
Our results suggest that JA and JB inhibited VEGF expression in A549 cells through the inhibition of the Akt-STAT3-mTOR signaling pathway, and directly inhibited the proliferation and migration of HUVECs. These findings are of great significance for the development of new plant-derived chemotherapy agents for the treatment of cancer.

Cytotoxic diterpenoids from the roots of Euphorbia ebracteolata.[Pubmed: 15856412]

Planta Medica, 2005, 71(4):349-354.


METHODS AND RESULTS:
Three new diterpenoids, yuexiandajisu D (1), E (2) and F were isolated from the roots of Euphorbia ebracteolata, along with eight known diterpenoids, jolkinolide B (4), Jolkinolide A, ent-11alpha-hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide (6), ent-(13S)-hydroxyatis-16-ene-3,14-dione, ent-3beta,(13S)-dihydroxyatis-16-en-14-one, ent-3-oxokaurane-16alpha,17-diol, ent-16alpha,17-dihydroxyatisan-3-one and ent-atisane-3beta,16alpha,17-triol. The structures of all compounds were deduced using spectroscopic methods and confirmed for 1 and 2 by single-crystal X-ray diffraction. A biogenetic pathway for the formation of 1 and 2 is proposed briefly. Cytotoxic activities were evaluated against ANA-1, B 16 and Jurkat tumor cells.
CONCLUSIONS:
Jolkinolide B (4) displayed modest activity on ANA-1, B 16 and Jurkat tumor cells with IC50 values 4.46 x 10(-2), 4.48 x 10(-2), 6.47 x 10(-2) microM, and ent-11alpha-hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide (6) showed significant activity against ANA-1 and Jurkat cells with IC50 values 7.12 x 10(-3) and 1.79 x 10(-2) microM. Compound 1 was found to be slightly active against ANA-1 cells with an IC50 value 2.88 x 10(-1)microM. Structure-activity relationships of isolated compounds are also discussed.

Protocol of Jolkinolide A

Structure Identification
Chinese Journal of Pharmaceutical Analysis (2006) 26(9) 1204-1206.

HPLC determination of jolkinolide A and jolkinolide B in Chinese herb medicine" Lang- du"[Reference: WebLink]

To establish a method for the determination of two diterpenoide lactones, Jolkinolide A and jolkinolide B in Chinese herbal medicine "Lang -du" by HPLC.
METHODS AND RESULTS:
: C18 column(4.6 mm *250 mm,5 mum) was used with acetonitrile -water(75:25 )as the mobile phase. The flow rate was 1.0 mL· min^-1 ,and the detection wavelength was 250 nm. By using the established HPLC method, nine samples of "Lang - du" were analyzed to determine the contents of Jolkinolide A and B. It was showed that the contents of Jolkinolide A and B ranged from 0. 007% to 0. 043% and 0. 012% to 0. 204% , respectively. Among the samples, the two diterpenoids were found in most of the samples of Euphorbia fischeriana and E. ebracteolata, but Stellera chamaejasme and Alocasia macrorrhiza contained neither Jolkinolide A nor jolkinolide B.
CONCLUSIONS:
A simple, effective and feasible HPLC method with good accuracy, precision and reproducibility to determine the contents of two diterpenoids in" Lang - du" was established which could be applied for the quality control of this herb.

Jolkinolide A Dilution Calculator

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Jolkinolide A Molarity Calculator

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Preparing Stock Solutions of Jolkinolide A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1807 mL 15.9033 mL 31.8066 mL 63.6132 mL 79.5165 mL
5 mM 0.6361 mL 3.1807 mL 6.3613 mL 12.7226 mL 15.9033 mL
10 mM 0.3181 mL 1.5903 mL 3.1807 mL 6.3613 mL 7.9517 mL
50 mM 0.0636 mL 0.3181 mL 0.6361 mL 1.2723 mL 1.5903 mL
100 mM 0.0318 mL 0.159 mL 0.3181 mL 0.6361 mL 0.7952 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 Jolkinolide A

Jolkinolide A and Jolkinolide B Inhibit Proliferation of A549 Cells and Activity of Human Umbilical Vein Endothelial Cells.[Pubmed:28087861]

Med Sci Monit. 2017 Jan 14;23:223-237.

BACKGROUND Jolkinolide A (JA) and Jolkinolide B (JB) are diterpenoids extracted from the roots of Euphorbia fischeriana Steud and have been shown to have anti-tumor activity. However, their effects on the ability of tumor cells to invade blood vessels and metastasize remain largely unknown. Investigations into the effects of JA and JB on the angiogenesis of tumor tissues may facilitate the identification of new natural drugs with anti-tumor growth and metastasis activities. MATERIAL AND METHODS We used different concentrations of JA and JB (20 mug/ml, 40 mug/ml, 60 mug/ml, 80 mug/ml, and 100 mug/ml) to stimulate A549 cells and then studied the effects on the growth and metastasis of lung cancers. In addition, we used conditional media from A549 cells (A549-CM) stimulated by either JA or JB in different concentrations to culture human umbilical vein endothelial cells (HUVECs). RESULTS We found that both JA and JB significantly inhibited the Akt-STAT3-mTOR signaling pathway and reduced the expression of VEGF in A549 cells, but JB exhibited more significant inhibitory effects than JA. The JB-stimulated A549 cell conditional media had a greater inhibitory effect on the proliferation and migration of HUVECs than did the conditional media of JA-stimulated A549 cells. This effect gradually increased with increasing concentrations of either type of Jolkinolide. CONCLUSIONS Our results suggest that JA and JB inhibited VEGF expression in A549 cells through the inhibition of the Akt-STAT3-mTOR signaling pathway, and directly inhibited the proliferation and migration of HUVECs. These findings are of great significance for the development of new plant-derived chemotherapy agents for the treatment of cancer.

ent-Abietane Lactones from Euphorbia.[Pubmed:27670580]

Mini Rev Med Chem. 2017;17(4):380-397.

Extracted from Euphorbia, ent-Abietane lactones can be classified into several categories, such as Jolkinolides and Helioscopinolides, according to their structural features. The study of ent- Abietane lactones could date back to 1972, when Jolkinolide A and B were first isolated from Euphorbia jolkini Boiss. Since then, many other ent-Abietane lactones have been extracted from different species of Euphorbia. Their bio-activities include anti-tumor activity, anti-inflammatory activity as well as anti-bacterial activity. Among them, derivatives of Jolkinolide B draw the most attention for their high anti-tumor activity. There are many studies focus on the syntheses of Jolkinolides. In 1989, the first and efficient synthesis of Jolkinolides was accomplished by Katsumura et al. Their strategy to construct the last ring of Jolkinolides contributes a lot to the following studies. In the following thirty years, there are also other semi-syntheses of Jolkinolides conducted, basing on different starting materials. In this review, we will give a brief clarification of ent-Abietane lactones, as well as their bio-activities and syntheses.

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