U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H30O8
Molecular Weight 470.5116
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIMONIN

SMILES

[H][C@@]12CC(=O)[C@]3(C)[C@]([H])(CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C6=COC=C6)[C@]17COC(=O)C[C@@H]7OC2(C)C

InChI

InChIKey=KBDSLGBFQAGHBE-MSGMIQHVSA-N
InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H30O8
Molecular Weight 470.5116
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. In vitro experiments shows that limonin possess anti-HIV-1, and anti-cancer properties.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Effect of compound sequence on bitterness enhancement.
2001 May
Electron ionization mass spectrometry of citrus limonoids.
2003
Bioavailability of citrus limonoids in humans.
2003 Jul 2
Limonoids from Citrus reticulata.
2003 Mar-Apr
Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells.
2003 Oct
Determination of limonin D-ring lactone hydrolase activity by solid phase extraction with indirect fluorescence detection.
2004 Jun 16
Quantitative analysis of 23-hydroxybetulinic acid in mouse plasma using electrospray liquid chromatography/mass spectrometry.
2005
Antioxidant activity of citrus limonoids, flavonoids, and coumarins.
2005 Mar 23
Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells.
2006
A new limonoid from the fruits of Evodia rutaecarpa (Juss.) Benth.
2006 Dec
Modulation of P-glycoprotein activity by acridones and coumarins from Citrus sinensis.
2007 Apr
Molecular analysis of post-harvest withering in grape by AFLP transcriptional profiling.
2008
Citrus genomics.
2008
Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
2008 Dec 14
Neuroprotective limonoids of root bark of Dictamnus dasycarpus.
2008 Feb
Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy.
2008 Mar-Apr
[Studies on ethyl acetate soluble constituents of Huanglian Jiedutang].
2008 Sep
Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata.
2010 Jul
Antiviral activity of seed extract from Citrus bergamia towards human retroviruses.
2011 Mar 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Viability of SW480 colon cancer cells after treatment with limonoids was measured by the MTT method. Approximately 10*10^3 cells/well were plated into a 96-well. After 24 h of growth, media was replaced along with compounds at concentrations ranging from 6.25 to 100 uM. After 24, 48, and 72 h, MTT solutionwas added to each well and incubated at 37 C for 2 h.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:07:20 GMT 2023
Edited
by admin
on Sat Dec 16 10:07:20 GMT 2023
Record UNII
L0F260866S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIMONIN
MI  
Common Name English
NSC-36508
Code English
OBACULACTONE
Common Name English
DICTAMNOLACTONE
Brand Name English
EVODIN
Common Name English
11H,13H-OXIRENO(D)PYRANO(4',3':3,3A)ISOBENZOFURO(5,4-F)(2)BENZOPYRAN-4,6,13(2H,5AH)-TRIONE, 8-(3-FURYL)DECAHYDRO-2,2,4A,8A-TETRAMETHYL-
Systematic Name English
LIMONOIC ACID, DI-.DELTA.-LACTONE
Common Name English
CITROLIMONIN
Common Name English
11H,13H-OXIRENO(D)PYRANO(4',3':3,3A)ISOBENZOFURO(5,4-F)(2)BENZOPYRAN-4,6,13(2H,5AH)-TRIONE, 8-(3-FURANYL)DECAHYDRO-2,2,4A,8A-TETRAMETHYL-, (2AR,4AR,4BR,5AS,8S,8AS,10AR,10BR,14AS)-
Systematic Name English
LIMONINE
Common Name English
LIMONIN [MI]
Common Name English
Code System Code Type Description
NSC
36508
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY
PUBCHEM
179651
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID8045985
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY
MERCK INDEX
m6817
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY Merck Index
FDA UNII
L0F260866S
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY
CHEBI
16226
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY
CAS
1180-71-8
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY
WIKIPEDIA
Limonin
Created by admin on Sat Dec 16 10:07:20 GMT 2023 , Edited by admin on Sat Dec 16 10:07:20 GMT 2023
PRIMARY