Gardenin B

CAS# 2798-20-1

Gardenin B

Catalog No. BCN3816----Order now to get a substantial discount!

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Quality Control of Gardenin B

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Chemical structure

Gardenin B

3D structure

Chemical Properties of Gardenin B

Cas No. 2798-20-1 SDF Download SDF
PubChem ID 96539 Appearance Yellow powder
Formula C19H18O7 M.Wt 358.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 5-Demethyltangeretin; 5-Hydroxy 4',6,7,8-tetramethoxyflavone
Solubility Soluble in methan
Chemical Name 5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
SMILES COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3O)OC)OC)OC
Standard InChIKey LXEVSYZNYDZSOB-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3
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 Gardenin B

The fruits of Gardenia jasminoides Ellis

Biological Activity of Gardenin B

DescriptionGardenin B exhibits superior antiproliferative activity against lung, breast, colon, hepatic and leukaemia cell lines as well as in keratinocytes .Gardenin B-induced cell death in human leukemia cells involves multiple caspases but is independent of the generation of reactive oxygen species. Gardenin B can strongly inhibit biochemical production of nitric oxide (IC50=10.59±0.4 ug/mL).
TargetsNO | ROS | Caspase | PARP
In vitro

Gardenin B-induced cell death in human leukemia cells involves multiple caspases but is independent of the generation of reactive oxygen species.[Pubmed: 27423764 ]

Chem Biol Interact. 2016 Aug 25;256:220-7.

Flavonoids have attracted great interest due to their possible anticancer activities.
METHODS AND RESULTS:
Here we investigated the antiproliferative activity of the flavonoids isolated from Baccharis scandens against human leukemia cell lines and found that the methoxyflavonoid Gardenin B was the most cytotoxic compound against HL-60 and U-937 cells, showing IC50 values between 1.6 and 3.0 μM, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. These effects on viability were accompanied by the concentration- and time-dependent appearance of apoptosis as evidenced by DNA fragmentation, formation of apoptotic bodies and a sub-G1 ratio increase. Comparative studies with the best-studied bioflavonoid quercetin indicate that Gardenin B is a more cytotoxic and more apoptotic inducer than quercetin. Cell death induced by Gardenin B was associated with: (i) a significant induction of caspase-2, -3, -8 and -9 activities; (ii) cleavage of the initiator caspases (caspase-2, -8 and -9), of the executioner caspase-3, and of poly(ADP-ribose) polymerase; and (iii) a concentration-dependent reactive oxygen species generation.
CONCLUSIONS:
In conclusion, apoptosis induced by Gardenin B is associated with activation of both the extrinsic and the intrinsic apoptotic pathways of cell death and occurs through a mechanism that is independent of the generation of reactive oxygen species.

Characterization of bioactive constituents from the gum resin of Gardenia lucida and its pharmacological potential.[Pubmed: 27899258 ]

Biomed Pharmacother. 2017 Jan;85:444-456.


METHODS AND RESULTS:
In the present study we mined the information on Gardenia lucida (Dikamali) and identified seven polymethoxyflavones from its gum resin. We also investigated its antiproliferative and antioxidant potential. Xanthomicrol (8) found as potent DPPH scavenger (85.86±1.3%) along with strong ferric plummeting ability (53.60±2.0 FSE) and reducing potential (1.07±0.01) as compared to ascorbic acid. Gardenin B (5) strongly inhibit biochemical production of nitric oxide (IC50 10.59±0.4μg/mL) followed by 5-Desmethylnobiletin (7) and Gardenin E (10, IC5011.01±0.7-34.53±2.7μg/mL). Methanol extract, chloroform fraction and Acerosin (11), Gardenin D (9) and Gardenin B (5) exhibited superior antiproliferative activity against lung, breast, colon, hepatic and leukaemia cell lines as well as in keratinocytes (IC50 12.82±0.67-94.63±1.27μg/mL) whereas other fractions and isolated compounds moderately affect the cell proliferation (21.40±0.12-48.12±0.47%) with least and non-specific interaction against succinate dehydrogenase. Except compound 2, 3, 6, 8 and 11, others were found as a significant inhibitor of ODC (IC50 2.36±0.7-8.53±0.32μg/mL) with respect to DFMO (IC50 10.85±0.28μg/mL). In silico analysis also revealed enervated binding energy (-4.30 to -5.02kcal/mol) and inhibition constant (704.18-210.26μM) wherein 5, 7, 8, 9 and 10 showed specific interaction with the receptor while rest were non-specific. Except butanol fraction and Gardenin E, others were potently inhibited the cathepsin D activity with non-specific interaction and better binding energy (-5.78 to -7.24kcal/mol) and inhibition constant (57.87-4.90μM).
CONCLUSIONS:
In conclusion, it can be interpreted that isolated polymethoxyflavones (Gardenin B, 5-Desmethylnobiletin, Gardenin E) could be taken up as a lead for target specific studies. Methanol extract and chloroform fraction prevails in all the tested activity therefore cumulative and composite intervention of polymethoxyflavones present in it reveals its pharmacological attributes and traditional value.

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Preparing Stock Solutions of Gardenin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7902 mL 13.9509 mL 27.9018 mL 55.8036 mL 69.7545 mL
5 mM 0.558 mL 2.7902 mL 5.5804 mL 11.1607 mL 13.9509 mL
10 mM 0.279 mL 1.3951 mL 2.7902 mL 5.5804 mL 6.9754 mL
50 mM 0.0558 mL 0.279 mL 0.558 mL 1.1161 mL 1.3951 mL
100 mM 0.0279 mL 0.1395 mL 0.279 mL 0.558 mL 0.6975 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 Gardenin B

Characterization of bioactive constituents from the gum resin of Gardenia lucida and its pharmacological potential.[Pubmed:27899258]

Biomed Pharmacother. 2017 Jan;85:444-456.

In the present study we mined the information on Gardenia lucida (Dikamali) and identified seven polymethoxyflavones from its gum resin. We also investigated its antiproliferative and antioxidant potential. Xanthomicrol (8) found as potent DPPH scavenger (85.86+/-1.3%) along with strong ferric plummeting ability (53.60+/-2.0 FSE) and reducing potential (1.07+/-0.01) as compared to ascorbic acid. Gardenin B (5) strongly inhibit biochemical production of nitric oxide (IC50 10.59+/-0.4mug/mL) followed by 5-Desmethylnobiletin (7) and Gardenin E (10, IC5011.01+/-0.7-34.53+/-2.7mug/mL). Methanol extract, chloroform fraction and Acerosin (11), Gardenin D (9) and Gardenin B (5) exhibited superior antiproliferative activity against lung, breast, colon, hepatic and leukaemia cell lines as well as in keratinocytes (IC50 12.82+/-0.67-94.63+/-1.27mug/mL) whereas other fractions and isolated compounds moderately affect the cell proliferation (21.40+/-0.12-48.12+/-0.47%) with least and non-specific interaction against succinate dehydrogenase. Except compound 2, 3, 6, 8 and 11, others were found as a significant inhibitor of ODC (IC50 2.36+/-0.7-8.53+/-0.32mug/mL) with respect to DFMO (IC50 10.85+/-0.28mug/mL). In silico analysis also revealed enervated binding energy (-4.30 to -5.02kcal/mol) and inhibition constant (704.18-210.26muM) wherein 5, 7, 8, 9 and 10 showed specific interaction with the receptor while rest were non-specific. Except butanol fraction and Gardenin E, others were potently inhibited the cathepsin D activity with non-specific interaction and better binding energy (-5.78 to -7.24kcal/mol) and inhibition constant (57.87-4.90muM). In conclusion, it can be interpreted that isolated polymethoxyflavones (Gardenin B, 5-Desmethylnobiletin, Gardenin E) could be taken up as a lead for target specific studies. Methanol extract and chloroform fraction prevails in all the tested activity therefore cumulative and composite intervention of polymethoxyflavones present in it reveals its pharmacological attributes and traditional value.

Gardenin B-induced cell death in human leukemia cells involves multiple caspases but is independent of the generation of reactive oxygen species.[Pubmed:27423764]

Chem Biol Interact. 2016 Aug 25;256:220-7.

Flavonoids have attracted great interest due to their possible anticancer activities. Here we investigated the antiproliferative activity of the flavonoids isolated from Baccharis scandens against human leukemia cell lines and found that the methoxyflavonoid Gardenin B was the most cytotoxic compound against HL-60 and U-937 cells, showing IC50 values between 1.6 and 3.0 muM, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. These effects on viability were accompanied by the concentration- and time-dependent appearance of apoptosis as evidenced by DNA fragmentation, formation of apoptotic bodies and a sub-G1 ratio increase. Comparative studies with the best-studied bioflavonoid quercetin indicate that Gardenin B is a more cytotoxic and more apoptotic inducer than quercetin. Cell death induced by Gardenin B was associated with: (i) a significant induction of caspase-2, -3, -8 and -9 activities; (ii) cleavage of the initiator caspases (caspase-2, -8 and -9), of the executioner caspase-3, and of poly(ADP-ribose) polymerase; and (iii) a concentration-dependent reactive oxygen species generation. In conclusion, apoptosis induced by Gardenin B is associated with activation of both the extrinsic and the intrinsic apoptotic pathways of cell death and occurs through a mechanism that is independent of the generation of reactive oxygen species.

Description

Gardenin B is a flavonoid isolated from Baccharis scandens. Gardenin B induces cell death in human leukemia cells involves multiple caspases.

Keywords:

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