Balanophonin

CAS# 118916-57-7

Balanophonin

Catalog No. BCN6072----Order now to get a substantial discount!

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Chemical structure

Balanophonin

3D structure

Chemical Properties of Balanophonin

Cas No. 118916-57-7 SDF Download SDF
PubChem ID 23252258 Appearance Powder
Formula C20H20O6 M.Wt 356.4
Type of Compound Lignans Storage Desiccate at -20°C
Synonyms (+)-Balanophonin;215319-47-4
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-3-[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
SMILES COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)O)OC)C=CC=O
Standard InChIKey GWCSSLSMGCFIFR-LNFBDUAVSA-N
Standard InChI InChI=1S/C20H20O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-10,15,19,22-23H,11H2,1-2H3/b4-3+/t15-,19+/m0/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 Balanophonin

The herbs of Balanophora japonica Makino

Biological Activity of Balanophonin

DescriptionBalanophonin shows potent α-glucosidase inhibitory activity, it has antioxidant, and anti-cancer activities. (±)-Balanophonin shows significant antibacterial activity against cariogenic oral streptococci, Streptococcus mutans and S. sobrinus.
Targetsα-glucosidase
In vitro

Antioxidant phenolic compounds of cassava (Manihot esculenta) from Hainan.[Pubmed: 22157579]

Molecules. 2011 Dec 7;16(12):10157-67.


METHODS AND RESULTS:
An activity-directed fractionation and purification process was used to isolate antioxidant components from cassava stems produced in Hainan. The ethyl acetate and n-butanol fractions showed greater DPPH˙and ABTS·+ scavenging activities than other fractions. The ethyl acetate fraction was subjected to column chromatography, to yield ten phenolic compounds: Coniferaldehyde (1), isovanillin (2), 6-deoxyjacareubin (3), scopoletin (4), syringaldehyde (5), pinoresinol (6), p-coumaric acid (7), ficusol (8), Balanophonin (9) and ethamivan (10), which possess significant antioxidant activities. The relative order of DPPH· scavenging capacity for these compounds was ascorbic acid (reference) > 6 > 1 > 8 > 10 > 9 > 3 > 4 > 7 > 5 > 2, and that of ABTS·+ scavenging capacity was 5 > 7 > 1 > 10 > 4 > 6 > 8 > 2 > Trolox (reference compound) > 3 > 9.
CONCLUSIONS:
The results showed that these phenolic compounds contributed to the antioxidant activity of cassava.

Aquilarin A, a new benzenoid derivative from the fresh stem of Aquilaria sinensis.[Pubmed: 20657422 ]

Molecules. 2010 Jun 1;15(6):4011-6.


METHODS AND RESULTS:
Chemical investigation of the EtOH extract of the fresh stem of Aquilaria sinensis collected in Hainan Province of China resulted in the isolation of a new benzenoid, named aquilarin A (1), together with two known compounds Balanophonin (2) and (+)-lariciresinol (3). Their structures were elucidated by a study of their physical and spectral data. Compounds 2 and 3 exhibited cytotoxicity against SGC-7901 and SMMC-7721 cell lines.

Constituents of the seeds of Cornus officinalis with Inhibitory Activity on the Formation of Advanced Glycation End Products (AGEs)[Reference: WebLink]

J. Korean Soc. Appl.Biol.Chem., 2008, 51(4):316- 20.

Ten compounds, (+)-pinoresinol (1), (-)-Balanophonin (2), gallicin (3), vanillin (4), 4-hydroxybenzaldehyde (5), coniferaldehyde (6), betulinic acid (7), ursolic acid (8), 5-hydroxymethyl furfural (9), and malic acid (10), were isolated from a EtOAc-soluble fraction of the seeds of Cornus officinalis.
METHODS AND RESULTS:
The structures of these compounds were elucidated by spectroscopic methods as well as by comparison with reported values. Compounds 1, 2, and 4-7 were isolated from this species for the first time. All the isolates (1-10) were subjected to an in vitro bioassay to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation. Among these, compounds 2 and 3 showed the significant inhibitory activity on AGEs formation with values of 27.81 and 18.04, respectively.

Bioactive Phenolic constituents from the culms of Phyllostachys bambusoides[Reference: WebLink]

Natural Product Sciences, 2011, 17(4):267-72.


METHODS AND RESULTS:
Fractionation process of n-hexane and CHCl 3 extracts afforded four phenolic constituents, ferulic acid (1), vanillin (2), coniferaldehyde (3), and coniferyl alcohol (4) as guided by their DPPH free radical scavenging activities. Additionally, activity-guided fractionation of EtOAc extract with anti-cariogenic activity has resulted in the isolation of coniferaldehyde (3), 2,6-dimethoxy-p-benzoquinone (5), p-methoxycinnamic acid (6), (±)-Balanophonin (7), and 6-methoxychromanone (8). The structures of 1 - 8 were determined by spectroscopic data interpretation, and also by comparison of their data with the published values. Phenolic compounds 1 - 4 exhibited similar DPPH radical scavenging activities compared with the synthetic antioxidant, butylated hydroxytoluene (BHT), and compounds 3 and 5 - 8 showed significant antibacterial activity against cariogenic oral streptococci, Streptococcus mutans and S. sobrinus.

Protocol of Balanophonin

Kinase Assay

Screening of α-glucosidase inhibitory activity of Vietnamese medicinal plants: Isolation of Active Principles from Oroxylum indicum[Reference: WebLink]

Natural Product Sciences, 2014, 18(1):47-51.

Among 38 Vietnamese medicinal plant extracts investigated for their α-glucosidase inhibitory activity, 35 extracts showed IC 50 values below 250 µg/mL.
METHODS AND RESULTS:
The MeOH extracts of the heartwood of Oroxylum indicum, the seeds of Caesalpinia sappan, and the fruits of Xanthium strumarium exhibited strong α-glucosidase inhibitory activity with IC 50 values less than 50 µg/mL. Fractionation of the MeOH extract of the heartwood of O. indicum led to the isolation of oroxylin A (1), oroxyloside (2), hispidulin (3), apigenin (4), ficusal (5), Balanophonin (6), 2-(1-hydroxymethylethyl)-4H,9H-naphtho[2,3-b]furan-4,9-dione (7), salicylic acid (8), p-hydroxybenzoic acid (9), protocatechuic acid (10), isovanillin (11), and β-hydroxypropiovanillon (12). Compounds 1-3, 5, 6, 8, 10, and 12 showed more potent activities, with IC 50 values ranging from 2.13 to 133.51 µM, than a positive control acabose (IC 50 , 241.85 µM).
CONCLUSIONS:
The kinetic study indicated that oroxyloside (2) displayed mixed-type inhibition with inhibition constant (Ki) was 3.56 µM.

Structure Identification
J Chromatogr A. 2012 Nov 16;1264:143-7.

The role of harmonized, gas and liquid chromatography mass spectrometry in the discovery of the neolignan balanophonin in the fruit wall of Cirsium vulgare.[Pubmed: 23068765]

In order to identify and quantify fruit-lignans of Cirsium vulgare - authors introduced a special analysis system: with particular attention to the lignans enrichment/separation course.
METHODS AND RESULTS:
These synchronized, germination and enzymatic hydrolysis processes were followed by complementary gas and liquid chromatography, coupled with special mass selective detections (GC-MS, LC-MS/MS, LC-TOF/MS) and confirmed by nuclear magnetic resonance (NMR) spectroscopy. Mass fragmentations and NMR evidences, proved that the two main medicinal lignan constituents of the fruits of Cirsium vulgare are the neolignan-type, free Balanophonin and the butyrolactone-type tracheloside. As novelty to the field, these two lignans of different chemical structures could be quantitatively extracted, separately from each others, without impurities. Balanophonin and tracheloside do accumulate in the fruits of C. vulgare, separately: Balanophonin was found, in enormous high concentrations, in the fruit wall (23.2-24.9 mg/g), while in embryo part tracheloside was determined (20.3mg/g), exclusively.
CONCLUSIONS:
Consequently, the optimum source of Balanophonin proved to be the fruit wall, while tracheloside, - providing trachelogenin upon enzymatic hydrolysis, - could be obtained from the embryo parts of fruits. As further novelties of the study Balanophonin was identified and quantified at the first time with on-line chromatographic technique, in free form, without authentic standard compound.

Balanophonin Dilution Calculator

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Preparing Stock Solutions of Balanophonin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8058 mL 14.0292 mL 28.0584 mL 56.1167 mL 70.1459 mL
5 mM 0.5612 mL 2.8058 mL 5.6117 mL 11.2233 mL 14.0292 mL
10 mM 0.2806 mL 1.4029 mL 2.8058 mL 5.6117 mL 7.0146 mL
50 mM 0.0561 mL 0.2806 mL 0.5612 mL 1.1223 mL 1.4029 mL
100 mM 0.0281 mL 0.1403 mL 0.2806 mL 0.5612 mL 0.7015 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 Balanophonin

Aquilarin A, a new benzenoid derivative from the fresh stem of Aquilaria sinensis.[Pubmed:20657422]

Molecules. 2010 Jun 1;15(6):4011-6.

Chemical investigation of the EtOH extract of the fresh stem of Aquilaria sinensis collected in Hainan Province of China resulted in the isolation of a new benzenoid, named aquilarin A (1), together with two known compounds Balanophonin (2) and (+)-lariciresinol (3). Their structures were elucidated by a study of their physical and spectral data. Compounds 2 and 3 exhibited cytotoxicity against SGC-7901 and SMMC-7721 cell lines.

Isolation of cytotoxic compounds from the seeds of Crataegus pinnatifida.[Pubmed:23845552]

Chin J Nat Med. 2013 Jul;11(4):411-4.

AIM: To study the chemical constituents and bioactivity of the seeds of Crataegus pinnatifida. METHODS: The chemical constituents were isolated and purified by macroporous adsorptive resin D101, silica gel, and ODS column chromatography, and preparative HPLC. Their structures were elucidated on the basis of spectroscopic methods. In addition, the cytotoxic activities of compounds 1-4 were investigated on OPM2 and RPMI-8226 cells. RESULTS: Four compounds were obtained and their structures were identified as (7S, 8S)-4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3, 5-dimethoxybenzaldehyde (1), (+)-Balanophonin (2), erythro-guaiacylglycerol-beta-coniferyl aldehyde ether (3), buddlenol A (4). CONCLUSION: Compound 1 is a novel norlignan, while compounds 1-4 exhibited marginal inhibition on the proliferation of OPM2 and RPMI-8226 cells.

Antioxidant phenolic compounds of cassava (Manihot esculenta) from Hainan.[Pubmed:22157579]

Molecules. 2011 Dec 7;16(12):10157-67.

An activity-directed fractionation and purification process was used to isolate antioxidant components from cassava stems produced in Hainan. The ethyl acetate and n-butanol fractions showed greater DPPH and ABTS.+ scavenging activities than other fractions. The ethyl acetate fraction was subjected to column chromatography, to yield ten phenolic compounds: Coniferaldehyde (1), isovanillin (2), 6-deoxyjacareubin (3), scopoletin (4), syringaldehyde (5), pinoresinol (6), p-coumaric acid (7), ficusol (8), Balanophonin (9) and ethamivan (10), which possess significant antioxidant activities. The relative order of DPPH. scavenging capacity for these compounds was ascorbic acid (reference) > 6 > 1 > 8 > 10 > 9 > 3 > 4 > 7 > 5 > 2, and that of ABTS.+ scavenging capacity was 5 > 7 > 1 > 10 > 4 > 6 > 8 > 2 > Trolox (reference compound) > 3 > 9. The results showed that these phenolic compounds contributed to the antioxidant activity of cassava.

The role of harmonized, gas and liquid chromatography mass spectrometry in the discovery of the neolignan balanophonin in the fruit wall of Cirsium vulgare.[Pubmed:23068765]

J Chromatogr A. 2012 Nov 16;1264:143-7.

In order to identify and quantify fruit-lignans of Cirsium vulgare - authors introduced a special analysis system: with particular attention to the lignans enrichment/separation course. These synchronized, germination and enzymatic hydrolysis processes were followed by complementary gas and liquid chromatography, coupled with special mass selective detections (GC-MS, LC-MS/MS, LC-TOF/MS) and confirmed by nuclear magnetic resonance (NMR) spectroscopy. Mass fragmentations and NMR evidences, proved that the two main medicinal lignan constituents of the fruits of Cirsium vulgare are the neolignan-type, free Balanophonin and the butyrolactone-type tracheloside. As novelty to the field, these two lignans of different chemical structures could be quantitatively extracted, separately from each others, without impurities. Balanophonin and tracheloside do accumulate in the fruits of C. vulgare, separately: Balanophonin was found, in enormous high concentrations, in the fruit wall (23.2-24.9 mg/g), while in embryo part tracheloside was determined (20.3mg/g), exclusively. Consequently, the optimum source of Balanophonin proved to be the fruit wall, while tracheloside, - providing trachelogenin upon enzymatic hydrolysis, - could be obtained from the embryo parts of fruits. As further novelties of the study Balanophonin was identified and quantified at the first time with on-line chromatographic technique, in free form, without authentic standard compound.

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