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Secologanoside

CAS# 59472-23-0

Secologanoside

Catalog No. BCN8698----Order now to get a substantial discount!

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Quality Control of Secologanoside

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Chemical structure

Secologanoside

3D structure

Chemical Properties of Secologanoside

Cas No. 59472-23-0 SDF Download SDF
PubChem ID 14136854 Appearance White powder
Formula C16H22O11 M.Wt 390.34
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in methan
Chemical Name (2~{S},3~{R},4~{S})-4-(carboxymethyl)-3-ethenyl-2-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2~{H}-pyran-5-carboxylic acid
SMILES C=CC1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)CC(=O)O
Standard InChIKey RGTONEMDTVVDMY-GRTPNEQMSA-N
Standard InChI InChI=1S/C16H22O11/c1-2-6-7(3-10(18)19)8(14(23)24)5-25-15(6)27-16-13(22)12(21)11(20)9(4-17)26-16/h2,5-7,9,11-13,15-17,20-22H,1,3-4H2,(H,18,19)(H,23,24)/t6-,7+,9-,11-,12+,13-,15+,16+/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 Secologanoside

1 Ligustrum sp. 2 Lonicera sp. 3 Olea sp.

Biological Activity of Secologanoside

DescriptionSecologanoside shows anti-complementary, allelopathic, and anti-elastase activities.
In vitro

Biological activities of triterpenoids from Poraqueiba sericea stems.[Pubmed: 27736194 ]

Nat Prod Res. 2017 Jun;31(11):1333-1338.


METHODS AND RESULTS:
Eleven compounds were isolated from Poraqueiba sericea stems and identified as niga-ichigoside-F1 (1), trachelosperoside B1 (2), 4-epi-niga-ichigoside (7), 19α-hydroxyasiatic acid (3), myrianthic acid (4), hyptatic acid (5), trachelosperogenin B (6), arjunolic acid (8), and trachelosperogenin E (9), Secologanoside (10) and secoxyloganin (11). Compounds 1-11 were tested for their antileishmanial activities against Leishmania infantum promastigotes, 1-6 and 8-11 were tested for their cytotoxic activities on fibroblasts, 1-3, 5-6, 8-11 were evaluated for their anti-elastase and anti-acetylcholinesterase assays activities by a spectrophotometric method and 1-2, 5 and 7-10 were tested using bioautography for their β-glucosidase.
CONCLUSIONS:
No antileishmanial activity was detected; compounds 1, 2 and 11 showed a moderate cytotoxic activity with IC50 17.7, 20.5 and 10.9 μg/mL, respectively; compounds 2, 8, 9 and 10 gave a percentage of inhibition ranging from 13 to 16% (at 50 μg/mL) and compounds 1 and 2 showed an inhibition zone on β-glucosidase and anti-acetylcholinesterase assays.

Anti-complementary phenolic acids from Lonicera japonica.[Pubmed: 26080557]

Zhongguo Zhong Yao Za Zhi. 2015 Jan;40(2):269-74.

To study the anti-complementary phenolic acids from Lonicera japonica.
METHODS AND RESULTS:
The anti-complementary activity-directed isolation was carried out with the hemolysis test as guide. All isolation was evaluated for their in vitro anti-complementary activities. The structures were identified by various spectroscopic data including ESI-MS, 1H-NMR, 13C-NMR data. Fourteen compounds were isolated from the EtOAc fraction of L. japonica extracts, including 8 phenolic acids: 5-O-caffeoylquinic acid (1), chlorogenic (2), 4-O-caffeoylquinic acid (3), 3,5-di-O-caffeoylquinic acid (4), 4,5-di-O-caffeoylquinic acid (5), 3,4-di-O-caffeoylquinic acid (6), caffeic acid (7) and methyl caffeate acid (8); 3 iridoids: Secologanoside (9), sweroside (10) and secoxyloganin (11); and 3 flavonoids: luteolin (12), quercetin (13) and kaempferol (14). Compounds 1-9 and 11-14 showed anti-complementary activity in different extents and 3,5-di-O-caffeoylquinic acid (4) exhibited the most significant activity against the classical pathway.
CONCLUSIONS:
Compound 14 is obtained from this plant for the first time, phenolic acids are the main anti-complementary constituents of L. japonica and 3,5-di-O-caffeoylquinic acid(4) is a potential complement inhibitor with strong activity, which worthy to be studied further in the future.

Protocol of Secologanoside

Structure Identification
Planta Med. 1996 Aug;62(4):365-8.

Secoiridoids and xanthones from Gentianella nitida.[Pubmed: 17252473]


METHODS AND RESULTS:
From GENTIANELLA NITIDA twelve known metabolites were isolated and identified by HPLC-UV and/or by spectroscopic methods as Secologanoside, amaroswerin, amarogentin (secoiridoids), isoorientin (C-glucosylflavone), mangiferin, demethylbellidifolin 8-O-glucoside, norswertianine 1-O-glucoside, swertianine 1-O-primeveroside, swertianine 8-O-glucoside, norswertianine, demethylbellidifolin, and swertianine (xanthone glycosides and aglycones).
CONCLUSIONS:
Secologanoside is reported here for the first time in Gentianaceae species; the antioxidant mangiferin was obtained as the major compound in good yield.

Phytochemistry (Oxford), 2000, 55(2):131-140.

Allelochemicals of the tropical weed Sphenoclea zeylanica.[Reference: WebLink]

Nine plant growth inhibitors were isolated from the tropical weed Sphenoclea zeylanica, which shows allelopathic properties.
METHODS AND RESULTS:
Those compounds hitherto not reported from any plant source were the isomers of cyclic thiosulfinate, (1S,3R,4R)-(+)- and (1R,3R,4R)-(+)-4-hydroxy-3-hydroxymethyl-1,2-dithiolane-1-oxides, and (2R,3R,4R)-(-)- and (2S,3R,4R)-(+)-4-hydroxy-3-hydroxymethyl-1,2-dithiolane-2-oxides. These were named zeylanoxide A, epi-zeylanoxide A, zeylanoxide B and epi-zeylanoxide B, respectively. The absolute configurations at C-3 and C-4 were elucidated by chemical synthesis of both enantiomers from L- and D-glucose. Two of the inhibitors were secologanic acid and Secologanoside. and three other inhibitors were by known secoiridoid glucosides formed as artifacts during extraction with methanol.
CONCLUSIONS:
The cyclic thiosulfinates and secoiridoid glucosides completely inhibit the root growth of rice seedlings at 3.0 mM. While the specific activity of the inhibitors was not high, since they accumulated to circa 0.61% S. zelanica by dry weight, this suggests that the inhibitors are nervertheless potent allelochemicals in this weed.

Secologanoside Dilution Calculator

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Secologanoside Molarity Calculator

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Preparing Stock Solutions of Secologanoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5619 mL 12.8093 mL 25.6187 mL 51.2374 mL 64.0467 mL
5 mM 0.5124 mL 2.5619 mL 5.1237 mL 10.2475 mL 12.8093 mL
10 mM 0.2562 mL 1.2809 mL 2.5619 mL 5.1237 mL 6.4047 mL
50 mM 0.0512 mL 0.2562 mL 0.5124 mL 1.0247 mL 1.2809 mL
100 mM 0.0256 mL 0.1281 mL 0.2562 mL 0.5124 mL 0.6405 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 Secologanoside

Secoiridoids and xanthones from Gentianella nitida.[Pubmed:17252473]

Planta Med. 1996 Aug;62(4):365-8.

From Gentianella nitida twelve known metabolites were isolated and identified by HPLC-UV and/or by spectroscopic methods as Secologanoside, amaroswerin, amarogentin (secoiridoids), isoorientin (C-glucosylflavone), mangiferin, demethylbellidifolin 8-O-glucoside, norswertianine 1-O-glucoside, swertianine 1-O-primeveroside, swertianine 8-O-glucoside, norswertianine, demethylbellidifolin, and swertianine (xanthone glycosides and aglycones). Secologanoside is reported here for the first time in Gentianaceae species; the antioxidant mangiferin was obtained as the major compound in good yield.

Description

Secologanoside is a triterpenoid isolated from Poraqueiba sericea, weakly inhibits elastase with an IC50 of 164 μg/mL. Secologanoside is moderate cytotoxic to fibroblasts.

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