Physalin G

CAS# 76045-38-0

Physalin G

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Chemical structure

Physalin G

3D structure

Chemical Properties of Physalin G

Cas No. 76045-38-0 SDF Download SDF
PubChem ID 42620981 Appearance Powder
Formula C28H30O10 M.Wt 526.5
Type of Compound Steroids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,15-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.118,27.01,5.02,24.08,17.09,14.021,26]nonacosa-11,13-diene-4,10,22,29-tetrone
SMILES CC12CC3C4(C56C1C(=O)C(O5)(C7CC(C8=CC=CC(=O)C8(C7CCC6(C(=O)O4)O)C)O)OCC2C(=O)O3)C
Standard InChIKey CGVBSJOSWAZUIF-UHFFFAOYSA-N
Standard InChI InChI=1S/C28H30O10/c1-23-10-18-25(3)28-19(23)20(31)27(38-28,35-11-15(23)21(32)36-18)14-9-16(29)13-5-4-6-17(30)24(13,2)12(14)7-8-26(28,34)22(33)37-25/h4-6,12,14-16,18-19,29,34H,7-11H2,1-3H3
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 Physalin G

The herbs of Physalis alkekengi

Biological Activity of Physalin G

DescriptionPhysalin G has antinociceptive property.
In vitro

Chemopreventive Agents from Physalis minima Function as Michael Reaction Acceptors.[Pubmed: 27279713]

Pharmacogn Mag. 2016 May;12(Suppl 2):S231-6.

The fruits of some varieties of genus Physalis have been used as delicious fruits and functional food in the Northeast of China.
METHODS AND RESULTS:
To reveal the functional material basis, we performed bioactivity-guided phytochemical research and chemopreventive effect assay of the constituents from Physalis minima. It was demonstrated that the ethyl acetate extract of P. minima L. (EEPM) had potential quinone reductase (QR) inducing activity with induction ratio (IR, QR induction activity) value of 1.47 ± 0.24, and glutathione binding property as potential Michael reaction acceptors (with an α, β-unsaturated ketone moiety). Furthermore, bioactivity-guided phytochemical research led eight compounds (1-8), which were elucidated as 3-isopropyl-5-acetoxycyclohexene-2-one-1 (1), isophysalin B (2), Physalin G (3), physalin D (4), physalin I (5), physordinose B (6), stigmasterol-3-O-β-D-glucopyranoside (7) and 5α-6β-dihydroxyphysalin R (8) on the basis of nuclear magnetic resonance spectroscopy analyses and HRESIMS. Then, isophysalin B (2) and physordinose B (6) showed significant QR inducing activity with IR value of 2.80 ± 0.19 and 2.38 ± 0.46, respectively. An ultra-performance liquid chromatographic method with glutathione as the substrate was used to detect the Michael reaction acceptors in extracts of Physalis minima (EPM).We investigated the chemical constituents of EPM guided by biological activity methodIsophysalin B (1) and physordinose B (6) showed strong quinone reductase inducing activity with induction ratio values of 2.80 ± 0.19 and 2.38 ± 0.46.
CONCLUSIONS:
This study generated useful information for consumers and many encourage researchers to utilize edible fruits from Physalis as a source of phytochemicals.

In vivo

Antinociceptive properties of physalins from Physalis angulata.[Pubmed: 25396337]

J Nat Prod. 2014 Nov 26;77(11):2397-403.

Pain is the most common reason a patient sees a physician. Nevertheless, the use of typical painkillers is not completely effective in controlling all pain syndromes; therefore further attempts have been made to develop improved analgesic drugs. The present study was undertaken to evaluate the antinociceptive properties of physalin B (1), physalin D (2), physalin F (3), and Physalin G (4) isolated from Physalis angulata in inflammatory and centrally mediated pain tests in mice.
METHODS AND RESULTS:
Systemic pretreatment with 1-4 produced dose-related antinociceptive effects on the writhing and formalin tests, traditional screening tools for the assessment of analgesic drugs. On the other hand, only 3 inhibited inflammatory parameters such as hyperalgesia, edema, and local production of TNF-α following induction with complete Freund's adjuvant. Treatment with 1, 3, and 4 produced an antinociceptive effect on the tail flick test, suggesting a centrally mediated antinociception. Reinforcing this idea, 2-4 enhanced the mice latency reaction time during the hot plate test. Mice treated with physalins did not demonstrate motor performance alterations.
CONCLUSIONS:
These results suggest that 1-4 present antinociceptive properties associated with central, but not anti-inflammatory, events and indicate a new pharmacological property of physalins.

Physalin G Dilution Calculator

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Preparing Stock Solutions of Physalin G

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8993 mL 9.4967 mL 18.9934 mL 37.9867 mL 47.4834 mL
5 mM 0.3799 mL 1.8993 mL 3.7987 mL 7.5973 mL 9.4967 mL
10 mM 0.1899 mL 0.9497 mL 1.8993 mL 3.7987 mL 4.7483 mL
50 mM 0.038 mL 0.1899 mL 0.3799 mL 0.7597 mL 0.9497 mL
100 mM 0.019 mL 0.095 mL 0.1899 mL 0.3799 mL 0.4748 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 Physalin G

Simultaneous pharmacokinetics and stability studies of physalins in rat plasma and intestinal bacteria culture media using liquid chromatography with mass spectrometry.[Pubmed:29331063]

J Sep Sci. 2018 Apr;41(8):1781-1790.

Physalins are the major steroidal constituent of Physalis plants and display a range of biological activities. For this study, a rapid and sensitive high-performance liquid chromatography with triple quadrupole mass spectrometry method was developed for the simultaneous quantification of six physalins. Specifically, it was for the quantification of physalin A, physalin B, physalin D, Physalin G, 4,7-didehydroneophysalin B, and isophysalin B in rat plasma and rat intestinal bacteria. After a solid-phase extraction, analytes and internal standards (prednisolone) were separated on a Shield reverse-phase C18 column (measuring 3 mm x 150 mm with an internal diameter of 3.5 mum) and determined using multiple reactions in a monitoring mode with a positive-ion electrospray ionization source. The mobile phase was a mixture of 0.1% formic acid in water (A) and acetonitrile (B) and was used at a flow rate of 0.6 mL/min. The intra- and interday precisions were within 15% with accuracies ranging from 86.2 to 114%. The method was validated and successfully applied to pharmacokinetics and stability studies of six physalins in rat plasma and rat intestinal bacteria, respectively. The results showed that physalin B and isophysalin B could not be absorbed by rats, and rat intestinal bacteria could quickly transform physalins.

Chemopreventive Agents from Physalis minima Function as Michael Reaction Acceptors.[Pubmed:27279713]

Pharmacogn Mag. 2016 May;12(Suppl 2):S231-6.

BACKGROUND: The fruits of some varieties of genus Physalis have been used as delicious fruits and functional food in the Northeast of China. MATERIALS AND METHODS: To reveal the functional material basis, we performed bioactivity-guided phytochemical research and chemopreventive effect assay of the constituents from Physalis minima. RESULTS: It was demonstrated that the ethyl acetate extract of P. minima L. (EEPM) had potential quinone reductase (QR) inducing activity with induction ratio (IR, QR induction activity) value of 1.47 +/- 0.24, and glutathione binding property as potential Michael reaction acceptors (with an alpha, beta-unsaturated ketone moiety). Furthermore, bioactivity-guided phytochemical research led eight compounds (1-8), which were elucidated as 3-isopropyl-5-acetoxycyclohexene-2-one-1 (1), isophysalin B (2), Physalin G (3), physalin D (4), physalin I (5), physordinose B (6), stigmasterol-3-O-beta-D-glucopyranoside (7) and 5alpha-6beta-dihydroxyphysalin R (8) on the basis of nuclear magnetic resonance spectroscopy analyses and HRESIMS. Then, isophysalin B (2) and physordinose B (6) showed significant QR inducing activity with IR value of 2.80 +/- 0.19 and 2.38 +/- 0.46, respectively. SUMMARY: An ultra-performance liquid chromatographic method with glutathione as the substrate was used to detect the Michael reaction acceptors in extracts of Physalis minima (EPM)We investigated the chemical constituents of EPM guided by biological activity methodIsophysalin B (1) and physordinose B (6) showed strong quinone reductase inducing activity with induction ratio values of 2.80 +/- 0.19 and 2.38 +/- 0.46This study generated useful information for consumers and many encourage researchers to utilize edible fruits from Physalis as a source of phytochemicals Abbreviations used: EPM: Extracts of Physalis minima, EEPM: Ethyl acetate extract of Physalis minima L., GSH: Glutathione, MRAs: Michael reaction acceptors, QR: Quinone reductase.

Physalin H from Solanum nigrum as an Hh signaling inhibitor blocks GLI1-DNA-complex formation.[Pubmed:24454566]

Beilstein J Org Chem. 2014 Jan 13;10:134-40.

Hedgehog (Hh) signaling plays an important role in embryonic development, cell maintenance and cell proliferation. Moreover, Hh signaling contributes to the growth of cancer cells. Physalins are highly oxidized natural products with a complex structure. Physalins (1-7) were isolated from Solanum nigrum (Solanaceae) collected in Bangladesh by using our cell-based assay. The isolated physalins included the previously reported Hh inhibitors 5 and 6. Compounds 1 and 4 showed strong inhibition of GLI1 transcriptional activity, and exhibited cytotoxicity against cancer cell lines with an aberrant activation of Hh signaling. Compound 1 inhibited the production of the Hh-related proteins patched (PTCH) and BCL2. Analysis of the structures of different physalins showed that the left part of the physalins was important for Hh inhibitory activity. Interestingly, physalin H (1) disrupted GLI1 binding to its DNA binding domain, while the weak inhibitor Physalin G (2) did not show inhibition of GLI1-DNA complex formation.

Physalins with anti-inflammatory activity are present in Physalis alkekengi var. franchetii and can function as Michael reaction acceptors.[Pubmed:22197662]

Steroids. 2012 Apr;77(5):441-7.

Michael reaction acceptors (MRAs) are a class of active molecules that are directly or indirectly involved in various cellular processes, including the regulation of many signaling pathways. In this study, the inducible nitric oxide synthase (iNOS) assay was used to demonstrate that the dichloromethane extract of Physalis alkekengi var. franchetii (DCEP) possesses anti-inflammatory activity that might be attributed to the modification of key cysteine residues in IKKbeta by the MRAs in DCEP. To isolate these MRAs, glutathione (GSH) was employed, and a simple ultra-performance liquid chromatography/tandem mass spectrometry (UPLC-MS/MS) screening method was developed to investigate the GSH conjugates with potential MRAs. Five physalins, including one new compound isophysalin A (2), together with four known steroidal compounds, physalin A (1), physalin O (3), physalin L (4) and Physalin G (5), were isolated to evaluate the GSH conjugating abilities, and it was indicated that compounds 1, 2 and 3, which had a common alpha,beta-unsaturated ketone moiety, exhibited conjugating abilities with GSH and also showed significant nitric oxide (NO) production inhibiting activities. The anti-inflammatory activities of compounds 1, 2 and 3 might be attributed to their targeting multiple cysteine residues on IKKbeta; therefore, the alkylation of IKKbeta by compound 1 was further studied by micrOTOF-MS. The result showed that six cysteine residues (C(59), C(179), C(299), C(370), C(412), and C(618)) were alkylated, which indicated that IKKbeta is a potential target for the anti-inflammatory activity of physalin A.

An ultra-pressure liquid chromatography-tandem mass spectrometry method for the simultaneous determination of three physalins in rat plasma and its application to pharmacokinetic study of Physalis alkekengi var. franchetii (Chinese lantern) in rats.[Pubmed:21996065]

J Pharm Biomed Anal. 2012 Jan 25;58:94-101.

An ultra-high pressure liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed for the quantification of three major ingredients in Chinese lantern preparations (CLP) in rat plasma. Following extraction by ethyl acetate, the analytes were separated on an Acquity UPLC BEH Shield RP C(18) column using a gradient mobile phase system of acetonitrile-water. Electrospray ionization (ESI) tandem interface was employed prior to mass spectrometric detection. The calibration curves were linear over the range of 5.0-500.0 ng/ml for physalin D, 2.3-230.0 ng/ml for Physalin G and 0.71-71.0 ng/ml for 4,7-didehydroneophysalin B. The average extraction recoveries, examined at four concentration levels, carried from 57.1% to 76.9%, and the accuracies ranged from 94.0% to 113.3% with precision (RSD) <15%. The validated method was successfully applied to the determination of the three physalins in rat plasma after intragastric administration of CLP suspension.

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