NEOHESPERIDIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H34O15
Molecular Weight	610.5606
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=C(C=C1)[C@@H]2CC(=O)C3=C(O)C=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)C=C3O2

InChI

InChIKey=ARGKVCXINMKCAZ-UZRWAPQLSA-N

InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22953882

Neohesperidin is a biologically active natural flavanone glycoside unique to Citrus and specific citrus cultivars. It demonstrated hypoglycemic and hypolipidemic effects in vivo, in a preclinical model of diabetes. The drug also possesses neuroprotective activity and an anti-proliferative effect on human hepatoma cell lines.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25620042	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Neohesperidin suppresses osteoclast differentiation, bone resorption and ovariectomised-induced osteoporosis in mice.	2017-01-05	27664516
Neohesperidin Exerts Lipid-Regulating Effects in vitro and in vivo via Fibroblast Growth Factor 21 and AMP-Activated Protein Kinase/Sirtuin Type 1/Peroxisome Proliferator-Activated Receptor Gamma Coactivator 1α Signaling Axis.	2017	28554169
Development of new reference material neohesperidin for quality control of dietary supplements.	2015-07	25170574
Hypoglycemic and hypolipidemic effects of neohesperidin derived from Citrus aurantium L. in diabetic KK-A(y) mice.	2015-03	25620042
Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells.	2012-12-01	22953882

Patents

Sample Use Guides

In Vivo Use Guide

In a preclinical study, mice were fed with neohesperidin at a dose of 50 mg kg(-1) BW.

Route of Administration: Oral

In Vitro Use Guide

In a glucose consumption test, HepG2 cells were treated with neohesperidin for 24 h at concentrations 0.2, 1 and 5 ug/ml. Neohesperidin treatment increased the glucose consumption by 14.8%, 26.0%, and 31.4% at the three concentrations, respectively.

Name

Type

Language

NEOHESPERIDIN [USP-RS]

Preferred Name

English

NEOHESPERIDIN

Official Name

English

HESPERETIN 7-NEOHESPERIDOSIDE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (S)-

Common Name

English

(2S)-NEOHESPERIDIN

Common Name

English

FEMA NO. 4799

Code

English

NSC-31048

Code

English

4H-1-BENZOPYRAN-4-ONE, 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-, (2S)-

Common Name

English

FLAVANONE, 3',5,7-TRIHYDROXY-4'-METHOXY-, 7-(2-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE)

Common Name

English

Code System Code Type Description

FDA UNII

OA5C88H3L0