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 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25620042	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells.	2012 Dec 1	22953882
Development of new reference material neohesperidin for quality control of dietary supplements.	2015 Jul	25170574
Hypoglycemic and hypolipidemic effects of neohesperidin derived from Citrus aurantium L. in diabetic KK-A(y) mice.	2015 Mar	25620042
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
Neohesperidin suppresses osteoclast differentiation, bone resorption and ovariectomised-induced osteoporosis in mice.	2017 Jan 5	27664516

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

Official Name

English

NEOHESPERIDIN [USP-RS]

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

NEOHESPERIDIN [INCI]

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