Paniculoside I

CAS# 60129-63-7

Paniculoside I

2D Structure

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Quality Control of Paniculoside I

3D structure

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Paniculoside I

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Chemical Properties of Paniculoside I

Cas No. 60129-63-7 SDF Download SDF
PubChem ID 14396747 Appearance Powder
Formula C26H40O8 M.Wt 480.6
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC12CCCC(C1CCC34C2CCC(C3)C(=C)C4O)(C)C(=O)OC5C(C(C(C(O5)CO)O)O)O
Standard InChIKey RSQGPCRWQCUQBR-HLTNFVLASA-N
Standard InChI InChI=1S/C26H40O8/c1-13-14-5-6-17-24(2)8-4-9-25(3,16(24)7-10-26(17,11-14)21(13)31)23(32)34-22-20(30)19(29)18(28)15(12-27)33-22/h14-22,27-31H,1,4-12H2,2-3H3/t14-,15-,16+,17+,18-,19+,20-,21-,22+,24-,25-,26-/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 Paniculoside I

The herbs of Stevia rebaudiana

Biological Activity of Paniculoside I

DescriptionPaniculoside I is a natural product from Stevia rebaudiana.

Protocol of Paniculoside I

Structure Identification
Chemical & Pharmaceutical Bulletin , 2008 , 25 (11) :2895-2899.

Application of ^<13>C Nuclear Magnetic Resonance Spectroscopy to Chemistry of Glycosides : Structures of Paniculosides-I, -II, -III, -IV, and -V, Diterpene Glucosides of Stevia paniculata LAG.[Reference: WebLink]

From the aerial part of Stevia paniculata (Compositae), five new diterpene glucosides, named Paniculoside I, Paniculoside II, Paniculoside III, Paniculoside IV, and Paniculoside V(5-9) were isolated.
METHODS AND RESULTS:
On comparison of ^<13>C nuclear magnetic resonance spectra of these glucosides with those of the aglycones, ent-15α-hydroxykaur-16-en-19-oic acid (1) [as methyl ester (17)], ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid (2), ent-11α, 15α-dihydroxykaur-16-en-19-oic acid (3), and ent-16β, 17-dihydroxykauran-19-oic acid (4) as well as some model glucosides, paniculosides I-IV (5-8) can be formulated as β-glucopyranosyl ester of 1,3,2,and 4,respectively and paniculoside-V (9) can be represented by 15-O-β-glucopyranoside of 5.

Paniculoside I Dilution Calculator

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Paniculoside I Molarity Calculator

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Preparing Stock Solutions of Paniculoside I

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0807 mL 10.4037 mL 20.8073 mL 41.6146 mL 52.0183 mL
5 mM 0.4161 mL 2.0807 mL 4.1615 mL 8.3229 mL 10.4037 mL
10 mM 0.2081 mL 1.0404 mL 2.0807 mL 4.1615 mL 5.2018 mL
50 mM 0.0416 mL 0.2081 mL 0.4161 mL 0.8323 mL 1.0404 mL
100 mM 0.0208 mL 0.104 mL 0.2081 mL 0.4161 mL 0.5202 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 Paniculoside I

Phytochemical, antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1beta,2alpha,3beta,19alpha,23-pentahydroxy-urs-12-en-28-oic acid.[Pubmed:30422011]

Nat Prod Res. 2018 Nov 13:1-6.

Phytochemical study of the aerial part of Pulicaria undulata L. led to the isolation of nine compounds. The structure of 1beta,2alpha,3beta,19alpha,23-pentahydroxy-urs-12-en-28-oic acid (4) was revised and confirmation of the stereochemical configuration of the hydroxyl groups was established using NOESY and selective decoupling experiments. The other compounds were identified as 1,2-dehydro-1,10alpha-dihydropseudoivalin (1), axillarin (2), grandifloric acid-15-beta-glucoside (3), myrianthic acid (5), caffeic acid (6), quercetin (7), Paniculoside IV (8) and caffeic anhydride (9). The structures were characterized by 1 D, 2 D NMR spectroscopy and confirmed with HRMS. Antimicrobial and antiquorum-sensing activities of the different extracts and isolated compounds of the plant were investigated. Generally, the phenolic rather than the terpenoidal compounds exhibited remarkable antimicrobial and antiquorum-sensing activity. [Formula: see text].

New ent-kauranes from the fruits of Annona glabra and their inhibitory nitric oxide production in LPS-stimulated RAW264.7 macrophages.[Pubmed:25499882]

Bioorg Med Chem Lett. 2015 Jan 15;25(2):254-8.

Three new ent-kaurane diterpenoids, 7beta,16alpha,17-trihydroxy-ent-kauran-19-oic acid (1), 7beta,17-dihydroxy-16alpha-ent-kauran-19-oic acid 19-O-beta-d-glucopyranoside ester (2), 7beta,17-dihydroxy-ent-kaur-15-en-19-oic acid 19-O-beta-d-glucopyranoside ester (3) along with five known compounds, Paniculoside IV (4), 16alpha,17-dihydroxy-ent-kaurane (5), 16beta,17-dihydroxy-ent-kaurane (6), 16beta,17-dihydroxy-ent-kauran-19-al (7), and 16beta,17-dihydroxy-ent-kauran-19-oic acid (8) were isolated from the fruits of Annona glabra. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for inhibitory activity against nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages. As the results, compound 3 showed potent inhibitory LPS-stimulated NO production in RAW 264.7 macrophages with the IC50 value of 0.01+/-0.01muM; compounds 1 and 7 showed significant inhibitory NO production with the IC50 values of 0.39+/-0.12muM and 0.32+/-0.04muM, respectively.

Helikauranoside a, a new bioactive diterpene.[Pubmed:18071822]

J Chem Ecol. 2008 Jan;34(1):65-9.

A new ent-kaurane glucoside, named helikauranoside A (4), was isolated from the aerial parts of Helianthus annuus L. together with three known ent-kaurane-type diterpenoids: (-)-kaur-16-en-19-oic acid (1), grandifloric acid (2), and Paniculoside IV (3). The structure of 4 was determined by using a combination of 1D (1H-NMR and 13C-NMR) and 2D (COSY, HSQC, and HMBC) NMR techniques. Bioactivity spectra of isolated compounds were tested by using the etiolated wheat coleoptile bioassay in aqueous solutions at concentrations ranging from 10(-3) to 10(-6)M. Helikauranoside A (4) was the most active (-84%, 10(-3)M; -56%, 10(-4)M). These results suggest that this new compound may be involved in defense mechanisms of H. annuus.

A new ent-kaurane diterpenoid glycoside from the leaves of Cussonia bojeri, a Malagasy endemic plant.[Pubmed:12192150]

Chem Pharm Bull (Tokyo). 2002 Aug;50(8):1122-3.

A new ent-kaurane diterpene glycoside, beta-D-glucopyranosyl 17-hydroxy-ent-kauran-19-oate-16-O-beta-D-glucopyranoside (4) was isolated from the dried leaves of Cussonia bojeri SEEM., together with four known compounds identified as 16beta,17-dihydroxy-kauran-19-oic acid (1), beta-D-glucopyranosyl 16beta,17-dihydroxy-(-)-kauran-19-oate (2), Paniculoside IV (3), and rutin (5). The structure of 4 was deduced on the basis of chemical and spectroscopic evidence.

Ent-kaurane diterpenoid glycosides from the leaves of Cussonia racemosa, a Malagasy endemic plant.[Pubmed:11848221]

Chem Pharm Bull (Tokyo). 2002 Feb;50(2):268-71.

Six new ent-kaurane diterpenoid glycosides, cussoracosides A (3), B (4), C (5), D (6), E (7), and F (8) were isolated from the dried leaves of Cussonia racemosa, along with two known compounds identified as beta-D-glucopyranosyl ent-16beta,17-dihydroxykauran-19-oate (1) and Paniculoside IV (2). The structures of these new compounds were deduced on the basis of chemical and spectroscopic evidence.

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