Neoeriocitrin

CAS# 13241-32-2

Neoeriocitrin

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Quality Control of Neoeriocitrin

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Chemical structure

Neoeriocitrin

3D structure

Chemical Properties of Neoeriocitrin

Cas No. 13241-32-2 SDF Download SDF
PubChem ID 114627 Appearance White powder
Formula C27H32O15 M.Wt 596.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Eriodictyol 7-neohesperidoside; 3',4',5,7-Tetrahydroxyflavanone 7-neohesperidoside
Solubility Soluble in methanol; insoluble in water
Chemical Name (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-2,3-dihydrochromen-4-one
SMILES CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)O)O)O)CO)O)O)O)O)O
Standard InChIKey OBKKEZLIABHSGY-DOYQYKRZSA-N
Standard InChI InChI=1S/C27H32O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-6,9,16,18,20-31,33-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/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 Neoeriocitrin

1 Drynaria sp.

Biological Activity of Neoeriocitrin

DescriptionNeoeriocitrin has antioxidant capacity, it could rescue the inhibition effect of cell differentiation induced by PD98059 to some degree.Neoeriocitrin may be a new promising candidate drug for treatment of osteoporosis.
TargetsLDL | Runx2 | COLI | OCN
In vitro

Comparison of neoeriocitrin and naringin on proliferation and osteogenic differentiation in MC3T3-E1.[Pubmed: 21741227]

Phytomedicine. 2011 Aug 15;18(11):985-9.

Naringin is considered the main effective compound of Drynaria Rhizome, which is used commonly in the treatment of osteoporosis in traditional Chinese medicine. However, we found Neoeriocitrin, a new compound isolated from Drynaria Rhizome, showed a better activity than naringin on proliferation and osteogenic differentiation in MC3T3-E1.
METHODS AND RESULTS:
Both Neoeriocitrin and naringin exhibited the best effect on proliferation and osteogenic differentiation at concentration of 2μg/ml. Neoeriocitrin more significantly improved proliferation and alkaline phosphatase (ALP) activity as well as up-regulated Runx2, COLI and OCN expression by 56%, 37% and 14% respectively than naringin. Furthermore, Neoeriocitrin could rescue the inhibition effect of cell differentiation induced by PD98059 to some degree.
CONCLUSIONS:
Therefore, Neoeriocitrin may be a new promising candidate drug for treatment of osteoporosis.

Antioxidant activity of citrus limonoids, flavonoids, and coumarins.[Pubmed: 15769128 ]

J Agric Food Chem. 2005 Mar 23;53(6):2009-14.


METHODS AND RESULTS:
A variety of in vitro models such as beta-carotene-linoleic acid, 1,1-diphenyl-2-picryl hydrazyl (DPPH), superoxide, and hamster low-density lipoprotein (LDL) were used to measure the antioxidant activity of 11 citrus bioactive compounds. The compounds tested included two limonoids, limonin (Lim) and limonin 17-beta-D-glucopyranoside (LG); eight flavonoids, apigenin (Api), scutellarein (Scu), kaempferol (Kae), rutin trihydrate (Rut), neohesperidin (Neh), Neoeriocitrin (Nee), naringenin (Ngn), and naringin(Ng); and a coumarin (bergapten). The above compounds were tested at concentration of 10 microM in all four methods. It was found that Lim, LG, and Ber inhibited <7%, whereas Scu, Kae, and Rut inhibited 51.3%, 47.0%, and 44.4%, respectively, using the beta-carotene-linoleate model system. Lim, LG, Rut, Scu, Nee, and Kae showed 0.5% 0.25%, 32.2%, 18.3%, 17.2%, and 12.2%, respectively, free radical scavenging activity using the DPPH method. In the superoxide model, Lim, LG, and Ber inhibited the production of superoxide radicals by 2.5-10%, while the flavonoids such as Rut, Scu, Nee, and Neh inhibited superoxide formation by 64.1%, 52.1%, 48.3%, and 37.7%, respectively. However, LG did not inhibit LDL oxidation in the hamster LDL model. But, Lim and Ber offered some protection against LDL oxidation, increasing lag time to 345 min (3-fold) and 160 min (33% increase), respectively, while both Rut and Nee increased lag time to 2800 min (23-fold). Scu and Kae increased lag time to 2140 min (18-fold) and 1879 min (15.7-fold), respectively. In general, it seems that flavonoids, which contain a chromanol ring system, had stronger antioxidant activity as compared to limonoids and bergapten, which lack the hydroxy groups.
CONCLUSIONS:
The present study confirmed that several structural features were linked to the strong antioxidant activity of flavonoids. This is the first report on the antioxidant activity of limonin, limonin glucoside, and Neoeriocitrin.

Neoeriocitrin Dilution Calculator

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Preparing Stock Solutions of Neoeriocitrin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6764 mL 8.3822 mL 16.7645 mL 33.5289 mL 41.9111 mL
5 mM 0.3353 mL 1.6764 mL 3.3529 mL 6.7058 mL 8.3822 mL
10 mM 0.1676 mL 0.8382 mL 1.6764 mL 3.3529 mL 4.1911 mL
50 mM 0.0335 mL 0.1676 mL 0.3353 mL 0.6706 mL 0.8382 mL
100 mM 0.0168 mL 0.0838 mL 0.1676 mL 0.3353 mL 0.4191 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 Neoeriocitrin

Comparison of neoeriocitrin and naringin on proliferation and osteogenic differentiation in MC3T3-E1.[Pubmed:21741227]

Phytomedicine. 2011 Aug 15;18(11):985-9.

Naringin is considered the main effective compound of Drynaria Rhizome, which is used commonly in the treatment of osteoporosis in traditional Chinese medicine. However, we found Neoeriocitrin, a new compound isolated from Drynaria Rhizome, showed a better activity than naringin on proliferation and osteogenic differentiation in MC3T3-E1. Both Neoeriocitrin and naringin exhibited the best effect on proliferation and osteogenic differentiation at concentration of 2mug/ml. Neoeriocitrin more significantly improved proliferation and alkaline phosphatase (ALP) activity as well as up-regulated Runx2, COLI and OCN expression by 56%, 37% and 14% respectively than naringin. Furthermore, Neoeriocitrin could rescue the inhibition effect of cell differentiation induced by PD98059 to some degree. Therefore, Neoeriocitrin may be a new promising candidate drug for treatment of osteoporosis.

Antioxidant activity of citrus limonoids, flavonoids, and coumarins.[Pubmed:15769128]

J Agric Food Chem. 2005 Mar 23;53(6):2009-14.

A variety of in vitro models such as beta-carotene-linoleic acid, 1,1-diphenyl-2-picryl hydrazyl (DPPH), superoxide, and hamster low-density lipoprotein (LDL) were used to measure the antioxidant activity of 11 citrus bioactive compounds. The compounds tested included two limonoids, limonin (Lim) and limonin 17-beta-D-glucopyranoside (LG); eight flavonoids, apigenin (Api), scutellarein (Scu), kaempferol (Kae), rutin trihydrate (Rut), neohesperidin (Neh), Neoeriocitrin (Nee), naringenin (Ngn), and naringin(Ng); and a coumarin (bergapten). The above compounds were tested at concentration of 10 microM in all four methods. It was found that Lim, LG, and Ber inhibited <7%, whereas Scu, Kae, and Rut inhibited 51.3%, 47.0%, and 44.4%, respectively, using the beta-carotene-linoleate model system. Lim, LG, Rut, Scu, Nee, and Kae showed 0.5% 0.25%, 32.2%, 18.3%, 17.2%, and 12.2%, respectively, free radical scavenging activity using the DPPH method. In the superoxide model, Lim, LG, and Ber inhibited the production of superoxide radicals by 2.5-10%, while the flavonoids such as Rut, Scu, Nee, and Neh inhibited superoxide formation by 64.1%, 52.1%, 48.3%, and 37.7%, respectively. However, LG did not inhibit LDL oxidation in the hamster LDL model. But, Lim and Ber offered some protection against LDL oxidation, increasing lag time to 345 min (3-fold) and 160 min (33% increase), respectively, while both Rut and Nee increased lag time to 2800 min (23-fold). Scu and Kae increased lag time to 2140 min (18-fold) and 1879 min (15.7-fold), respectively. In general, it seems that flavonoids, which contain a chromanol ring system, had stronger antioxidant activity as compared to limonoids and bergapten, which lack the hydroxy groups. The present study confirmed that several structural features were linked to the strong antioxidant activity of flavonoids. This is the first report on the antioxidant activity of limonin, limonin glucoside, and Neoeriocitrin.

Description

Neoeriocitrin, isolated from Drynaria Rhizome, shows activity on proliferation and osteogenic differentiation in MC3T3-E1. Neoeriocitrin is a potent acetylcholinesterase (AChE) inhibitor.

Keywords:

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