(Q3629783)

Auraptene (English)

14 October 2016

C₁₉H₂₂O₃

1 reference

Auraptene (English)

14 October 2016

CC(=CCCC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)C)C

1 reference

Auraptene (English)

14 October 2016

CC(=CCC/C(=C/COC1=CC2=C(C=C1)C=CC(=O)O2)/C)C

1 reference

Chemical Constituents of Three Rutaceae Species from Sri Lanka

Auraptene (English)

14 October 2016

2 references

Coumarins from the roots of Feronia limonia

Ferula penninervis

1 reference

Grilactone fromFerula penninervis

Zanthoxylum ailanthoides

2 references

Studies on the Chemical Constituents of Rutaceous Plants. XLVIII. The Chemical Constituents of Xanthoxylum ailanthoides SIEB. et ZUCC. [Fagara ailanthoides (SIEB. et ZUCC.) ENGL.]. (3) Isolation of the Chemical Constituents of the Bark

Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides

Zanthoxylum coco

2 references

Fagara coco Gill. (Zanthoxylum coco Gill.)

Aurapten and Flindersine From Zanthoxylum coco

Ferula microloba

1 reference

Microlobin — A new coumarin fromFerula microloba

Phebalium squamulosum

2 references

Coumarins and their taxonomic value in the genus Phebalium

Phebaloparvilactone: A new protolimonoid from the leaves of phebulium souamulosum ssp. Parvifolium

Citrus hassaku

7 references

Coumarin Constituents of the Juice Oil fromCitrus hassakuand Their Spasmolytic Activity

7-Hydroxycoumarin derivatives from the juice oil of Citrus hassaku

7-Geranyloxycoumarin from juice oil of hassaku(citrus hassaku) and antimicrobial effects of related coumarins.

Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes

Epoxyaurapten and marmin from juice oil in hassaku (Citrus hassaku) and the spasmolytic activity of 7-geranyloxycoumarin-related compounds.

7-Geranyloxycoumarin from Juice Oil of Hassaku(Citrus hassaku) and Antimicrobial Effects of Related Coumarins

Epoxyaurapten and Marmin from Juice Oil in Hassaku (Citrus hassaku) and the Spasmolytic Activity of 7-Geranyloxycoumarin-related Compounds

Zanthoxylum rhoifolium

1 reference

Chemistry of Zanthoxylum rhoifolium: A new secofuroquinoline alkaloid

Phebalium filifolium

2 references

Coumarins and their taxonomic value in the genus Phebalium

Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium

Phebalium tuberculosum

2 references

Coumarins and their taxonomic value in the genus Phebalium

Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium

Phebalium stenophyllum

1 reference

Coumarins and their taxonomic value in the genus Phebalium

Pilocarpus riedelianus

2 references

3-Methoxyfurocoumarins from Pilocarpus riedelianus

Alcaloides β-indolopiridoquinazolínicos de Esenbeckia grandiflora mart. (Rutaceae)

Metrodorea nigra

1 reference

Dihydrochalcones, coumarins and alkaloids from Metrodorea nigra

Atalantia monophylla

22 references

Immunomodulatory action of citrus auraptene on macrophage functions and cytokine production of lymphocytes in female BALB/c mice

Evaluation of auraptene content in citrus fruits and their products

In vitro absorption and metabolism of a citrus chemopreventive agent, auraptene, and its modifying effects on xenobiotic enzyme activities in mouse livers

Suppression by citrus auraptene of phorbol ester-and endotoxin-induced inflammatory responses: role of attenuation of leukocyte activation.

Dietary supplementation of the citrus antioxidant auraptene inhibits N,N-diethylnitrosamine-induced rat hepatocarcinogenesis

Zingiberaceous and citrus constituents, 1'-acetoxychavicol acetate, zerumbone, auraptene, and nobiletin, suppress lipopolysaccharide-induced cyclooxygenase-2 expression in RAW264.7 murine macrophages through different modes of action

Citrus auraptene targets translation of MMP-7 (matrilysin) via ERK1/2-dependent and mTOR-independent mechanism

Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells.

Citrus auraptene suppresses azoxymethane-induced colonic preneoplastic lesions in C57BL/KsJ-db/db mice.

Citrus auraptene reduces Helicobacter pylori colonization of glandular stomach lesions in Mongolian gerbils

Citrus auraptene acts as an agonist for PPARs and enhances adiponectin production and MCP-1 reduction in 3T3-L1 adipocytes

Auraptene, a citrus fruit compound, regulates gene expression as a PPARalpha agonist in HepG2 hepatocytes.

Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats

Effects of citrus auraptene (7-geranyloxycoumarin) on hepatic lipid metabolism in vitro and in vivo

Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells

Quantitative evaluation of auraptene and umbelliferone, chemopreventive coumarins in citrus fruits, by HPLC-UV-FL-MS.

Anti-inflammatory and neuroprotective effects of auraptene, a citrus coumarin, following cerebral global ischemia in mice

Hypotensive activity of auraptene, a monoterpene coumarin from Citrus spp.

Anti-inflammatory and wound healing potential of citrus auraptene

Auraptene in the Peels of Citrus kawachiensis (Kawachi Bankan) Ameliorates Lipopolysaccharide-Induced Inflammation in the Mouse Brain.

Auraptene, a Major Compound of Supercritical Fluid Extract of Phalsak (Citrus Hassaku Hort ex Tanaka), Induces Apoptosis through the Suppression of mTOR Pathways in Human Gastric Cancer SNU-1 Cells

Potential anti-allergic acridone alkaloids from the roots of Atalantia monophylla

Dictamnus albus

2 references

Constituents of the root of Dictamnus albus L.

Note on the presence of aurapten in Dictamnus albus

Aegle marmelos

3 references

Effects of constituents of Beli (Aegle marmelos) on spontaneous beating and calcium-paradox of myocardial cells

Semisynthetic studies identify mitochondria poisons from botanical dietary supplements--geranyloxycoumarins from Aegle marmelos.

Chemical constituents from Aegle marmelos

Baccharis darwinii

2 references

Diterpene glycosides and other constituents from argentinian baccharis species

Antifungal activity of extracts and prenylated coumarins isolated from Baccharis darwinii Hook & Arn. (Asteraceae)

Baccharis eggersii

1 reference

Clerodane and labdane diterpenoids from Baccharis species

mandarin orange

1 reference

Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes

Citrus unshiu

1 reference

Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes

Diplotaenia damavandica

1 reference

Antifungal Activity of <I>Diplotaenia damavandica</I>

Esenbeckia conspecta

1 reference

Alkaloids, coumarins and sesquiterpenes from Esenbeckia conspecta Kunt (Rutaceae)

Ferulago brachyloba

1 reference

Coumarins from Ferulago capillaris and F. brachyloba

Murraya paniculata

2 references

The isolation of a prenylcoumarin of chemotaxonomic significance from Murraya paniculata var. omphalocarpa

Prenylcoumarin Derivatives from the Leaves of An Indonesian Medicinal Plant Murraya paniculata(Rutaceae).

Pleiospermium alatum

1 reference

Coumarins from Pleiospermium alatum

Polygala paniculata

1 reference

Coumarins from Polygala paniculata

Skimmia reevesiana

1 reference

Alkaloids and coumarins of Skimmia reevesiana

Solidago drummondii

1 reference

Alicyclic diterpenes from solidago species.

Spiranthera odoratissima

1 reference

Coumarins, furoquinoline alkaloids and terpenes from Spiranthera odoratissima (Rutaceae)

Triphasia trifolia

1 reference

Coumarins from the leaves of Murraya paniculata

Zanthoxylum schinifolium

4 references

Peroxycoumarins from the Root Bark of Zanthoxylum schinifolium

Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium

Coumarins and antiplatelet constituents from the root bark of Zanthoxylum schinifolium

Cytotoxic Constituents from the Leaves of Zanthoxylum schinifolium

Afraegle paniculata

1 reference

Coumarins and other components of Afraegle paniculata

Krubera peregrina

1 reference

Natürlich vorkommende Cumarin-Derivate, VI. Über die Inhaltsstoffe vonCapnophyllum-Arten

Citrus canaliculata

1 reference

Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer

Citrus grandis

1 reference

Biochemical Studies on “Natsumikan, ” Citrus Aurantium, L

pomelo

1 reference

Biochemical Studies on “Natsumikan, ” Citrus Aurantium, L

Clausena anisum-olens

1 reference

Coumarins from Clausena anisum-olens Merr

Geijera parviflora

1 reference

Extractives of Geijera parviflora

Sinacalia tangutica

1 reference

Four New Compounds fromSinacalia tangutica

Toddalia asiatica

1 reference

Alkaloids from Toddalia aculeata

Citrus medica

7 references

Coumarin Constituents of the Juice Oil fromCitrus hassakuand Their Spasmolytic Activity

Epoxyaurapten and Marmin from Juice Oil in Hassaku (Citrus hassaku) and the Spasmolytic Activity of 7-Geranyloxycoumarin-related Compounds

Epoxyaurapten and marmin from juice oil in hassaku (Citrus hassaku) and the spasmolytic activity of 7-geranyloxycoumarin-related compounds.

7-Hydroxycoumarin derivatives from the juice oil of Citrus hassaku

7-Geranyloxycoumarin from Juice Oil of Hassaku(Citrus hassaku) and Antimicrobial Effects of Related Coumarins

7-Geranyloxycoumarin from juice oil of hassaku(citrus hassaku) and antimicrobial effects of related coumarins.

Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes

Boronia koniambiensis

1 reference

Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis

Citrus × deliciosa

1 reference

Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes

Zanthoxylum asiaticum

1 reference

Alkaloids from Toddalia aculeata

Citrus × paradisi

4 references

Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes

Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi

Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4.

Synthesis and inhibitory activity of 7-geranoxycoumarin against Penicillium species in Citrus fruit

Arivela viscosa

1 reference

Coumarins from the roots of Cleme Viscosa (L.) antimicrobial and cytotoxic studies

Ferula szowitziana

1 reference

Microlobin — A new coumarin fromFerula microloba

Atalantia buxifolia

3 references

Severibuxine, a new quinolin-2,4-dione and other constituents from Severinia buxifolia

Constituents of the root bark of Severinia buxifolia collected in Hainan

A New Sesquiterpene, α-Santalane-11,12,13-Triol from the Root Bark ofSeverinia Buxifoliain Hainan

Trifoliate orange

24 references

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

Terpenoids and coumarins isolated from the fruits of Poncirus trifoliata

Dietary supplementation of the citrus antioxidant auraptene inhibits N,N-diethylnitrosamine-induced rat hepatocarcinogenesis

In vitro absorption and metabolism of a citrus chemopreventive agent, auraptene, and its modifying effects on xenobiotic enzyme activities in mouse livers

Auraptene, a Major Compound of Supercritical Fluid Extract of Phalsak (Citrus Hassaku Hort ex Tanaka), Induces Apoptosis through the Suppression of mTOR Pathways in Human Gastric Cancer SNU-1 Cells

Effects of citrus auraptene (7-geranyloxycoumarin) on hepatic lipid metabolism in vitro and in vivo

Evaluation of auraptene content in citrus fruits and their products

Citrus auraptene targets translation of MMP-7 (matrilysin) via ERK1/2-dependent and mTOR-independent mechanism

Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats

Immunomodulatory action of citrus auraptene on macrophage functions and cytokine production of lymphocytes in female BALB/c mice

Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells.

Anti-inflammatory and neuroprotective effects of auraptene, a citrus coumarin, following cerebral global ischemia in mice

Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells

Citrus auraptene acts as an agonist for PPARs and enhances adiponectin production and MCP-1 reduction in 3T3-L1 adipocytes

Quantitative evaluation of auraptene and umbelliferone, chemopreventive coumarins in citrus fruits, by HPLC-UV-FL-MS.

Auraptene in the Peels of Citrus kawachiensis (Kawachi Bankan) Ameliorates Lipopolysaccharide-Induced Inflammation in the Mouse Brain.

Suppression by citrus auraptene of phorbol ester-and endotoxin-induced inflammatory responses: role of attenuation of leukocyte activation.

Zingiberaceous and citrus constituents, 1'-acetoxychavicol acetate, zerumbone, auraptene, and nobiletin, suppress lipopolysaccharide-induced cyclooxygenase-2 expression in RAW264.7 murine macrophages through different modes of action

Hypotensive activity of auraptene, a monoterpene coumarin from Citrus spp.

Citrus auraptene suppresses azoxymethane-induced colonic preneoplastic lesions in C57BL/KsJ-db/db mice.

Auraptene, a citrus fruit compound, regulates gene expression as a PPARalpha agonist in HepG2 hepatocytes.

Anti-inflammatory and wound healing potential of citrus auraptene

Citrus auraptene reduces Helicobacter pylori colonization of glandular stomach lesions in Mongolian gerbils

Anti-inflammatory effect of auraptene extracted from trifoliate orange (Poncirus trifoliate) on LPS-stimulated RAW 264.7 cells

Identifiers

InChI

InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

1 reference

Auraptene (English)

14 October 2016

2 references

Auraptene (English)

14 October 2016

ChEBI release 2020-09-01

CAS Registry Number

495-02-3

2 references

Global Substance Registration System

UNII

F79I1ZEL2E

https://commonchemistry.cas.org/detail?cas_rn=495-02-3

auraptene (English)

14 October 2016

3 April 2021

1 reference

Auraptene (English)

14 October 2016

2 references

English

title

Auraptene (English)

14 October 2016

ChEBI ID

134355

mapping relation type

exact match

2 references

ChEBI release 2019-10-02

International Chemical Identifier

InChI

InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

1 reference

MSBNK-RIKEN_NPDepo-CB000250

AURAPTENE (English)

14 October 2016

1 reference

MassBank accession ID

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-RIKEN_NPDepo-NGA01953

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-RIKEN_NPDepo-NGA01954

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-RIKEN_NPDepo-NGA01955

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

MSBNK-RIKEN_NPDepo-NGA01956

1 reference

MassBank/MassBank-data: release version 2022.06 to wikidata

4 September 2022

splash10-08fr-1900000000-b149439e3218a537d0ac

0 references

DSSTox substance ID

DTXSID80897576

1 reference

DSSTOX compound identifier

DTXCID501326923

0 references

Human Metabolome Database ID

HMDB0034054

2 references

inferred from InChIKey

KNApSAcK ID

C00029763

2 references

inferred from InChIKey

UNII

F79I1ZEL2E

2 references

Global Substance Registration System

UNII

F79I1ZEL2E

English

title

auraptene (English)

14 October 2016