limonin (Q2398745)

Gene Ontology release 2020-05-02

Rhea release 113

limonoid glucosyltransferase activity

1 reference

Gene Ontology release 2020-05-02

Rhea release 113

chemical structure

Limonin.svg
1,321 × 1,251; 23 KB

0 references

image of molecular model or crystal lattice model

Limonin molecule ball.png
2,000 × 1,902; 710 KB

depicts

ball-and-stick model

0 references

mass

470.194068 dalton

1 reference

(1R,2R,7S,10S,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione

Limonin (English)

5 October 2016

2 references

inferred from InChIKey

(1S,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione

inferred from InChI

1 reference

inferred from InChI

chemical formula

C₂₆H₃₀O₈

1 reference

Limonin (English)

5 October 2016

CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C

1 reference

Limonin (English)

5 October 2016

C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C

1 reference

Limonin (English)

5 October 2016

Spiranthera odoratissima

2 references

Activities of extracts and compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in leaf-cutting ants and their symbiotic fungus

New limonoids from Hortia oreadica and unexpected coumarin from H. superba using chromatography over cleaning Sephadex with sodium hypochlorite.

kabosu

1 reference

Ichangensin glucoside in Citrus junos, Citrus sudachi and Citrus sphaerocarpa

Citrus ×iyo

1 reference

Thin-layer and high-performance liquid chromatographic analyses of limonoids and limonoid glucosides in Citrus seeds

Citrus depressa

1 reference

Thin-layer and high-performance liquid chromatographic analyses of limonoids and limonoid glucosides in Citrus seeds

Citrus hanaju

1 reference

Limonoids in seeds of Citrus hanaju

Citrus grandis

5 references

Investigation of Limonoid in the Stem and the Leaf of Citrus Banpeiyu.

Stem bark coumarins of Citrus grandis

Chemical constituents from the peels of Citrus sudachi

Limonoids in Pummelos [Citrus grandis (L.) Osbeck]

"The isolation of limonoids of \"banpeiyu\" (C. grandis Osbeck)."

Phellodendron amurense

5 references

Limonoids in Phellodendron amurense (Kihada)

Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity

Two γ-Hydroxybutenolides from the Bark of Phellodendron amurense and Photooxidation of Limonoids

Several antifeedants from Phellodendron amurense against Reticulitermes speratus.

Isolation of limonin and obacunone from phellodendri cortex shorten the sleeping time induced in mice by alpha-chloralose-urethane

Citrus cavaleriei

2 references

Limonoids in seeds of three citrus hybrids related to citrus ichangensis

Limonoids in Citrus ichangensis

Skimmia japonica

1 reference

Limonoids in Miyamashikimi (Skimmia japonica Thunb.).

Citrus latipes

1 reference

Limonoid and flavonoid composition in varieties of Papeda and Papedocitrus

Citrus hystrix

1 reference

Limonoid and flavonoid composition in varieties of Papeda and Papedocitrus

Citrus macrophylla

1 reference

Limonoid and flavonoid composition in varieties of Papeda and Papedocitrus

Clausena anisata

1 reference

Limonoids from Clausena anisata

Euodia rutaecarpa

7 references

Limonoid glucosides in Tetradium rutaecarpa

Two 5-HT1AReceptor-Interactive Tryptamine Derivatives from the Unripe Fruit ofEvodiarutaecarpa

Antinociceptive activities of 70% methanol extract of evodiae fructus (fruit of Evodia rutaecarpa var. bodinieri) and its alkaloidal components

New 5.BETA.-H limonoids from Evodia rutaecarpa bentham.

Limonoids and quinolone alkaloids from Evodia rutaecarpa Bentham.

Studies on Constituents of Evodia rutaecarpa (Rutaceae). I. Constituents of the Leaves.

Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities

Dictamnus dasycarpus

4 references

Neuroprotective limonoids of root bark of Dictamnus dasycarpus

Vasorelaxing effect in rat thoracic aorta caused by fraxinellone and dictamine isolated from the Chinese herb Dictamnus dasycarpus Turcz: comparison with cromakalim and Ca2 channel blockers

Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus

Sesquiterpene glycosides from Dictamnus dasycarpus

Tetradium daniellii

1 reference

Constituents of the fruits and leaves of Euodia daniellii

Glycosmis parva

1 reference

Isolation of acridone alkaloids and N-[(4-monoterpenyloxy)phenylethyl]-substituted sulfur-containing propanamide derivatives from Glycosmis parva and their anti-herpes simplex virus activity

Vepris suaveolens

1 reference

Oxidative burst inhibitory and cytotoxic indoloquinazoline and furoquinoline alkaloids from Oricia suaveolens

Tetradium glabrifolium

5 references

The heartwood constituents of Tetradium glabrifolium

The Structure of Graucin A, a New Bitter Limonoid fromEvodia graucaMiq. (Rutaceae)

Glaucin B, a new bitter limonoid from Evodia glauca

The Biochemical of Tetradium, Euodia and Melicope and their significance in the Rutaceae

Limonoids, Alkaloids, and a Coumarin from the Root and Stem Barks of Tetradium glabrifolium

Murraya paniculata

1 reference

Coumarins from Murraya paniculata

Samadera bidwillii

1 reference

The secondary metabolites of aff. Samadera SAC-2825: An australian simaroubaceae with unusual chemistry

Dictamnus albus

1 reference

Limonoids and alkaloids of the root bark of Dictamnus angustifolius

Limonia acidissima

2 references

7-Phenylacetoxy coumarin from limonia crenulata

Three New Simple Indole Alkaloids from Limonia acidissima

Raulinoa echinata

1 reference

Limonoids from the endemic Brazilian species Raulinoa echinata

Luvunga sarmentosa

1 reference

Apotirucallane triterpenoids from Luvunga sarmentosa (Rutaceae).

Flacourtia jangomas

1 reference

Jangomolide, a novel limonoid from flacourtia jangomas

Euodia

1 reference

The Structure of Graucin A, a New Bitter Limonoid fromEvodia graucaMiq. (Rutaceae)

Citrus unshiu

4 references

Studies on the constituents of leaves of Citrus unshiu MARCOV.

Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines

Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis

Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer

Tetradium trichotomum

1 reference

Alkaloids and limonoids of Tetradium trichotomum: Chemotaxonomic significance

Fagaropsis glabra

1 reference

Limonoids of Fagaropsis glabra

Hyuganatsu

4 references

Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines

Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis

Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer

Isolation of cytochrome P450 3A (CYP3A) inhibitors from Hyuganatsu, Citrus tamurana Hort

Dictamnus

1 reference

Limonoids from the root of Dictamnus radicis cortex

Phellodendron amurense var. wilsonii

1 reference

Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity

Phellodendron chinense var. glabriusculum

1 reference

Constituents from the leaves of Phellodendron amurense var. wilsonii and their bioactivity

Citrus webberi

1 reference

Limonoid and flavonoid composition in varieties of Papeda and Papedocitrus

Vepris louisii

1 reference

Veprisilone, a prenylated 2-quinolone, and limonin from Vepris louisii

Phellodendron chinense

1 reference

Identification and analysis of alkaloids in cortex Phellodendron amurense by high-performance liquid chromatography with electrospray ionization mass spectrometry coupled with photodiode array detection

Mentha insularis

1 reference

Bioactive compounds from Mexican lime ( Citrus aurantifolia ) juice induce apoptosis in human pancreatic cells.

Citrus

1 reference

Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography

Citrus sudachi

2 references

Limonoids in Seeds of Sudachi (Citrus sudachi Hort. ex Shirai)

Mentha suaveolens

1 reference

Bioactive compounds from Mexican lime ( Citrus aurantifolia ) juice induce apoptosis in human pancreatic cells.

Citrus × paradisi

6 references

Quantitative Analysis of Limonin in Grapefruit Juice Using an Enzyme-Linked Immunoassay: Interlaboratory Study

Determination of Key Flavor Components in Methylene Chloride Extracts from Processed Grapefruit Juice

An improved method for the quantitation of limonin in citrus juice by high-pressure liquid chromatography

Improvements in the quantitation of limonin in citrus juice by reversed-phase high-performance liquid chromatography

Distribution of limonin during the growth and development of leaves and branches of Citrus paradisi

Changes in limonin and naringin levels in grapefruit albedo with maturity and the effects of gibberellic acid on these changes

Citrus tankan

1 reference

The Chemical Constituents of the Peel of Citrus Tankan Hayata

mandarin orange

9 references

The Chemical Constituents of the Peel of Citrus Tankan Hayata

Thin-layer and high-performance liquid chromatographic analyses of limonoids and limonoid glucosides in Citrus seeds

Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer

Studies on the constituents of leaves of Citrus unshiu MARCOV.

Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis

Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines

Limonoids in citrus seeds: origin and relative concentration

Limonoids from Citrus reticulata

Limonoids from Citrus reticulata and their moult inhibiting activity in mosquito Culex quinquefasciatus larvae.

Citrus × deliciosa

9 references

The Chemical Constituents of the Peel of Citrus Tankan Hayata

Thin-layer and high-performance liquid chromatographic analyses of limonoids and limonoid glucosides in Citrus seeds

Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer

Studies on the constituents of leaves of Citrus unshiu MARCOV.

Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis

Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines

Limonoids in citrus seeds: origin and relative concentration

Limonoids from Citrus reticulata

Limonoids from Citrus reticulata and their moult inhibiting activity in mosquito Culex quinquefasciatus larvae.

pomelo

5 references

Chemical constituents from the peels of Citrus sudachi

Stem bark coumarins of Citrus grandis

"The isolation of limonoids of \"banpeiyu\" (C. grandis Osbeck)."

Limonoids in Pummelos [Citrus grandis (L.) Osbeck]

Investigation of Limonoid in the Stem and the Leaf of Citrus Banpeiyu.

Citrus medica

2 references

Limonoids in Seeds of Sudachi (Citrus sudachi Hort. ex Shirai)

Trifoliate orange

2 references

Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata

Limonoids in Seeds of Karatachi. Poncirus trifoliata.

Kumquat

7 references

Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer

Limonoids in Seeds of Sudachi (Citrus sudachi Hort. ex Shirai)

Ichangensin glucoside in Citrus junos, Citrus sudachi and Citrus sphaerocarpa

Isolation of cytochrome P450 3A (CYP3A) inhibitors from Hyuganatsu, Citrus tamurana Hort

Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis

Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines

Citrus japonica

7 references

Limonoids in Seeds of Sudachi (Citrus sudachi Hort. ex Shirai)

Ichangensin glucoside in Citrus junos, Citrus sudachi and Citrus sphaerocarpa

Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer

Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis

Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines

Isolation of cytochrome P450 3A (CYP3A) inhibitors from Hyuganatsu, Citrus tamurana Hort

physically interacts with

taste receptor type 2

subject has role

agonist

1 reference

The Molecular Receptive Ranges of Human TAS2R Bitter Taste Receptors

1 reference

0 references

0 references

Limonin

0 references

Identifiers

InChI

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

1 reference

Limonin (English)

5 October 2016

2 references

Limonin (English)

5 October 2016

ChEBI release 2020-09-01

2 references

limonin (English)

5 October 2016

https://commonchemistry.cas.org/detail?cas_rn=1180-71-8

9 April 2021

1 reference

Limonin (English)

5 October 2016

2 references

English

title

Limonin (English)

retrieved

5 October 2016

ChEBI ID

16226

mapping relation type

2 references

English

title

limonin (English)

retrieved

5 October 2016

International Chemical Identifier

InChI

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

1 reference

LIMONIN (English)

5 October 2016

2 references

inferred from InChIKey

MSBNK-Univ_Toyama-TY000204

1 reference

MassBank accession ID

0 references

SPLASH

splash10-003r-0059100000-857f1c5c010069dae111

0 references

splash10-0f6x-0006950000-1ede4dd087750d4657e4

0 references

splash10-0006-0018950000-909e4fa09330fed06e89

0 references

splash10-057i-0179200000-6a4722683996591a97a2

0 references

splash10-0059-0189300000-6390dc4ce1d5fc60ac31

0 references

splash10-057i-0069500000-846eb7a9b89663df5e94

0 references

splash10-004i-0126950000-26de77f823a0a3750ffc

0 references

splash10-0w2a-0009950000-7e006d90d0af09885f74

0 references

splash10-01t9-1942300000-5d933507731b3c7da7c4

0 references

DSSTox substance ID

DTXSID8045985

2 references

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

0 references

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

27 December 2018

Limonin (English)

CAS no.: 1180-71-8 (English)

ECHA Substance Infocard ID

100.236.039

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

27 December 2018

Limonin (English)

CAS no.: 1180-71-8 (English)

Human Metabolome Database ID

HMDB0302538

2 references

inferred from InChIKey

1 reference

Global Substance Registration System

limonin (English)

5 October 2016

2 references

UNII

L0F260866S

English

title

LIMONIN (English)

retrieved

5 October 2016

reason for deprecated rank

0 references

incorrect identifier value

1 reference

limonin (English)

5 October 2016

1 reference