Secoxyloganin

CAS# 58822-47-2

Secoxyloganin

Catalog No. BCN5800----Order now to get a substantial discount!

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Quality Control of Secoxyloganin

Number of papers citing our products

Chemical structure

Secoxyloganin

3D structure

Chemical Properties of Secoxyloganin

Cas No. 58822-47-2 SDF Download SDF
PubChem ID 162868 Appearance Colorless-beige crystals
Formula C17H24O11 M.Wt 404.4
Type of Compound Iridoids Storage Desiccate at -20°C
Synonyms Secologanoside 11-methyl ester
Solubility Soluble in methan
Chemical Name 2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid
SMILES COC(=O)C1=COC(C(C1CC(=O)O)C=C)OC2C(C(C(C(O2)CO)O)O)O
Standard InChIKey MQLSOVRLZHTATK-PEYNGXJCSA-N
Standard InChI InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/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 Secoxyloganin

1 Mentzelia sp.

Biological Activity of Secoxyloganin

DescriptionSecoxyloganin possesses hepato- protective, cytotoxic, and antibacterial activities, it has the perfect protective effect on PRRSV infected cell and with the minimum protection concentration of 6. 25 Âμg/mL.
TargetsAntifection
In vitro

Cytotoxic activity of Guettarda pohliana Müll. Arg. (Rubiaceae).[Pubmed: 23387288]

Nat Prod Res. 2013;27(18):1677-81.


METHODS AND RESULTS:
The cytotoxic activity of crude extracts and their fractions from leaves and roots of G. pohliana was assessed against nine human cancer cell lines: melanoma (UACC-62), breast (MCF-7), breast expressing the multidrug resistance phenotype (NCI-ADR), lung (NCI-460), prostate (PCO-3), kidney (786-0), ovarian (OVCAR), colon (HT-29) and leukaemia (K-562). The hexane fraction from leaves (HL) and ethyl acetate (EAR), chloroform (CR) and hydromethanolic (HMR) fractions from roots were the most active fractions against K-562 with GI₅₀ values being lower than 1 μg mL⁻1. Also, CR and HMR fractions were active against UACC-62 cell line in the same order of magnitude.
CONCLUSIONS:
The phytochemical study of the CR fraction allowed identifying the known iridoids Secoxyloganin, sweroside and loganin.

Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leaves.[Pubmed: 23265495]

Food Chem. 2013 May 1;138(1):327-33.

Our aim was to screen for antibacterial bioactive compounds from Lonicera japonica leaves. Staphylococcus aureus and Escherichia coli were used as the indicator bacteria. Bacteriostatic assay-guided extraction and stepwise partitioning of the samples yielded five compounds of interest.
METHODS AND RESULTS:
Antimicrobial activities of the compounds were determined using a disk diffusion assay. Extracts, fractions, and compounds from L. japonica leaves possessed considerable antibacterial activities against the tested bacterial strains and the most active fraction was attributed to J3B2, which primarily contained 3,5-di-O-caffeoylquinic acid and 4,5-di-O-caffeoylquinic acid. Meanwhile, five bacteriostatic constituents were isolated (3-O-caffeoylquinic acid, Secoxyloganin, luteoloside, 3,5-di-O-caffeoylquinic acid and 4,5-di-O-caffeoylquinic acid), among which, Secoxyloganin was isolated for the first time from leaves. The antibacterial activity of the compounds was in the order of 3,5-bis-O-caffeoyl quinic acid, 4,5-bis-O-caffeoylquinic acid, luteoloside>3-O-caffeoylquinic acid>Secoxyloganin.
CONCLUSIONS:
Our results suggested that the phenolic compounds might significantly contribute to antibacterial activity and were the most responsible for the bacteriostatic activity of L. japonica leaves.

CHEMICAL CONSTITUENTS IN FLOWER BUDS OF LONICERA JAPONICA THUNB.[Reference: WebLink]

Chemistry & Industry of Forest Products, 2005, 25(3):29-32.

Active constituents were isolated from the flower buds of Lonicera japonica Thunb. They were extracted with 70 % alcohol, then fractioned successively with petroleum ether, ethyl acetate and n-butanol.
METHODS AND RESULTS:
The ethyl acetate part was repeatedly chromatographed on silica gel column and purified with ODS column. Nine compounds, namely loganin(1),sweroside(2),7-epi-vogeloside(3),7-epi-loganin(4),Secoxyloganin(5),caffeic acid(6),p-hydroxybenzoic acid(7), β-sitosterol(8) and daucosterol (9) were obtained and their structures were deduced by comparison of their physico-chemical properties and spectral data with those of reference data.
CONCLUSIONS:
Compounds 4,5,6,7 were found for the first time in the flower buds of L. japonica Thunb., and compounds 1,4,5 were found to possess hepato- protective effect.

Protocol of Secoxyloganin

Cell Research

Isolation and identification of chemical constituents in effective fraction anti-PRRSV of the branches and leaves of the Lonicera japonica.[Reference: WebLink]

Journal of Huazhong Normal University, 2013,52(2):213.

The antiviral effect of the extracts of the Lonicera japonica leaves on PRRSV in vitro was evaluated by determining the minimum protection concentration on PRRSV infected Marc-145 cell and TCID50.
METHODS AND RESULTS:
The results showed that the 60% ethanol/water elution fraction possess the perfect protective effect on PRRSV infected cell and with the minimum protection concentration of 6. 25 Âμg/mL. The 6. 25 Âμg/mL 60% ethanol/water elution fractions decreased PRRSV titer from 105.8 TCID50 to 100.3 TCID50. That is to say, 60% ethanol/water elution fractions of Lonicera japonica is a potential antiviral drug owing to its perfect anti-PRRSV effect. To study the chemical constituents of the Lonicera japonica , the air-dried branches and leaves of this plant were extracted with 95% ethanol. The extracts were separated and purified by normal-phase, Sephadex LH-20 and RP-HPLC.
CONCLUSIONS:
Five compounds were obtained from the effective fractions anti-PRRSV of the branches and leaves of the Lonicera japonica and their structures were identified as Dihydrodehydrodiconiferyl alcohol 4'-O-Î2-D-glucoside (1), Apigenin 5-O-Î2-D-glucopyranoside (2) , Secoxyloganin (3) , Benzyl alcohol O-(6 -O-p-D-xylopyranosyl)-Î2-D-glucopyranoside (4) and Sweroside (5).

Structure Identification
Zhong Yao Cai. 2014 Aug;37(8):1383-5.

Chemical constituents from flower of Lonicera fragrantissima。[Pubmed: 25726645]

To study the chemical constituents from the flower of Lonicera fragrantissima.
METHODS AND RESULTS:
The chemical constituents were isolated and purified by means of several chromatographic techniques, and their structures were elucidated by spectroscopic methods. Nine compounds were isolated and identified as chlorogenic acid (1), caffeic acid (2), secologanoside (3), Secoxyloganin(4), loganin (5), sucrose (6), myo-inositol (7), rutin (8), and chrysoeriol-7-O-β-D-glucoside (9).
CONCLUSIONS:
Compounds 2-9 are obtained from this plant for the first time.

Secoxyloganin Dilution Calculator

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Secoxyloganin Molarity Calculator

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Preparing Stock Solutions of Secoxyloganin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4728 mL 12.364 mL 24.728 mL 49.456 mL 61.82 mL
5 mM 0.4946 mL 2.4728 mL 4.9456 mL 9.8912 mL 12.364 mL
10 mM 0.2473 mL 1.2364 mL 2.4728 mL 4.9456 mL 6.182 mL
50 mM 0.0495 mL 0.2473 mL 0.4946 mL 0.9891 mL 1.2364 mL
100 mM 0.0247 mL 0.1236 mL 0.2473 mL 0.4946 mL 0.6182 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 Secoxyloganin

Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leaves.[Pubmed:23265495]

Food Chem. 2013 May 1;138(1):327-33.

Our aim was to screen for antibacterial bioactive compounds from Lonicera japonica leaves. Staphylococcus aureus and Escherichia coli were used as the indicator bacteria. Bacteriostatic assay-guided extraction and stepwise partitioning of the samples yielded five compounds of interest. Antimicrobial activities of the compounds were determined using a disk diffusion assay. Extracts, fractions, and compounds from L. japonica leaves possessed considerable antibacterial activities against the tested bacterial strains and the most active fraction was attributed to J3B2, which primarily contained 3,5-di-O-caffeoylquinic acid and 4,5-di-O-caffeoylquinic acid. Meanwhile, five bacteriostatic constituents were isolated (3-O-caffeoylquinic acid, Secoxyloganin, luteoloside, 3,5-di-O-caffeoylquinic acid and 4,5-di-O-caffeoylquinic acid), among which, Secoxyloganin was isolated for the first time from leaves. The antibacterial activity of the compounds was in the order of 3,5-bis-O-caffeoyl quinic acid, 4,5-bis-O-caffeoylquinic acid, luteoloside>3-O-caffeoylquinic acid>Secoxyloganin. Our results suggested that the phenolic compounds might significantly contribute to antibacterial activity and were the most responsible for the bacteriostatic activity of L. japonica leaves.

Cytotoxic activity of Guettarda pohliana Mull. Arg. (Rubiaceae).[Pubmed:23387288]

Nat Prod Res. 2013;27(18):1677-81.

The cytotoxic activity of crude extracts and their fractions from leaves and roots of G. pohliana was assessed against nine human cancer cell lines: melanoma (UACC-62), breast (MCF-7), breast expressing the multidrug resistance phenotype (NCI-ADR), lung (NCI-460), prostate (PCO-3), kidney (786-0), ovarian (OVCAR), colon (HT-29) and leukaemia (K-562). The hexane fraction from leaves (HL) and ethyl acetate (EAR), chloroform (CR) and hydromethanolic (HMR) fractions from roots were the most active fractions against K-562 with GI(5)(0) values being lower than 1 mug mL(-)(1). Also, CR and HMR fractions were active against UACC-62 cell line in the same order of magnitude. The phytochemical study of the CR fraction allowed identifying the known iridoids Secoxyloganin, sweroside and loganin.

[Chemical constituents from flower of Lonicera fragrantissima].[Pubmed:25726645]

Zhong Yao Cai. 2014 Aug;37(8):1383-5.

OBJECTIVE: To study the chemical constituents from the flower of Lonicera fragrantissima. METHODS: The chemical constituents were isolated and purified by means of several chromatographic techniques, and their structures were elucidated by spectroscopic methods. RESULTS: Nine compounds were isolated and identified as chlorogenic acid (1), caffeic acid (2), secologanoside (3), Secoxyloganin(4), loganin (5), sucrose (6), myo-inositol (7), rutin (8), and chrysoeriol-7-O-beta-D-glucoside (9). CONCLUSION: Compounds 2-9 are obtained from this plant for the first time.

Description

Secoxyloganin, isolated from Lonicera japonica Thunb, inhibits the blood flow (BF) decrease. Secoxyloganin has allergy-preventive activity.

Keywords:

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