SCOPOLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18O9
Molecular Weight	354.3087
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(OC(=O)C=C2)C=C1O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O

InChI

InChIKey=SGTCGCCQZOUMJJ-YMILTQATSA-N

InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Method development and validation for the simultaneous determination of four coumarins in Saussurea superba by capillary zone electrophoresis.	2010-12-15	21140650
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.	2010-12-13	21144003
Cassava: an appraisal of its phytochemistry and its biotechnological prospects.	2010-12	20943239
[Chemical constituents from Hydrangea paniculata].	2010-11	21355271
The differential spatial distribution of secondary metabolites in Arabidopsis leaves reacting hypersensitively to Pseudomonas syringae pv. tomato is dependent on the oxidative burst.	2010-07	20530195
Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots.	2010-04	20137795
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.	2010-03-02	20479987
Coumarins from the leaves of Bambusa pervariabilis McClure.	2010-03	20390773
Scopolin-hydrolyzing beta-glucosidases in roots of Arabidopsis.	2010-01	19965874
Diterpene esters and phenolic compounds from Sapium insigne (ROYLE) BENTH. ex HOOK. fil.	2009-11	19881284
[Non-alkaloid constituents of Gelsemium elegans].	2009-09	20030082
[Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense].	2009-09	19943487
Protein and metabolite analysis reveals permanent induction of stress defense and cell regeneration processes in a tobacco cell suspension culture.	2009-07-06	19742122
Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis.	2009-07	19327410
[Effects of chemical constituents of Crossostephium chinense on insulin secretion in rat islets in vitro].	2009-06	19771872
Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense.	2009	19177244
Investigation of biosynthetic pathways to hydroxycoumarins during post-harvest physiological deterioration in Cassava roots by using stable isotope labelling.	2008-12-15	19035613
Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: the E-Z-isomerisation stage.	2008-12	19004461
A high-performance liquid chromatographic method for determination of scopolin in rat plasma: application to pharmacokinetic studies.	2008-10	18506740
Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana.	2008-09	18547395
Evaluation of natural substances from Evolvulus alsinoides L. with the purpose of determining their antioxidant potency.	2008-08	18666003
On the extent and origins of genic novelty in the phylum Nematoda.	2008-07-02	18596977
[Studies on chemical constituents of Saussurea laniceps].	2008-05	18652351
Antifungal activity of a new phenolic compound from capitulum of a head rot-resistant sunflower genotype.	2007-12	18034282
A new C9 nor-isoprenoid glucoside from Rantherium suaveolens.	2007-08	17680498
Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.	2007-08	17599369
Regulation of arbuscular mycorrhization by apoplastic invertases: enhanced invertase activity in the leaf apoplast affects the symbiotic interaction.	2007-08	17521407
Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia.	2007-07	17570448
Identification and determination of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry.	2007-02	17396585
Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the Fungus Phellinus igniarius.	2007-02	17279797
[Studies on the chemical constituents from Inula cappa (II)].	2007-01	17539299
Accumulation of coumarins in Arabidopsis thaliana.	2006-02	16405932
Growth at elevated CO2 concentrations leads to modified profiles of secondary metabolites in tobacco cv. SamsunNN and to increased resistance against infection with potato virus Y.	2006-01	17086759
A new bisabolane sesquiterpenoid from Euphorbia chrysocoma.	2005-12	16308205
Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum.	2005-03-25	15787250
Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products.	2004-12-02	15566295
Molecular phenotyping of the pal1 and pal2 mutants of Arabidopsis thaliana reveals far-reaching consequences on phenylpropanoid, amino acid, and carbohydrate metabolism.	2004-10	15377757
Ectopic expression of a UDP-glucose:phenylpropanoid glucosyltransferase leads to increased resistance of transgenic tobacco plants against infection with Potato Virus Y.	2004-09	15509841
Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves.	2004-07	15145789
Cytotoxic activity of five compounds isolated from Colombian plants.	2004-03	15030931
Over-expression of a scopoletin glucosyltransferase in Nicotiana tabacum leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance.	2004-01	15159640
Phytochemical constituents from Diodia teres.	2004-01	14969336
Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity.	2004-01	14750192
Agrobacterium tumefaciens AK-6b gene modulates phenolic compound metabolism in tobacco.	2004-01	14732276
Scaphopetalone and scaphopetalumate, a lignan and a triterpene ester from Scaphopetalum thonneri.	2003-02	12560041
Study on the determination of polyphenols in tobacco by HPLC coupled with ESI-MS after solid-phase extraction.	2003-01	12597595
Resistance of transgenic tobacco seedlings expressing the Agrobacterium tumefaciens C58-6b gene, to growth-inhibitory levels of cytokinin is associated with elevated IAA levels and activation of phenylpropanoid metabolism.	2002-08	12198197
Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance.	2002-05	12034899
[Determination of polyphenols in tobacco by solid phase extraction and high performance liquid chromatography].	2001-11	12545477
[Nonpolar components of the leaves of Philadelphus coronarius L].	2001-11	11797195

Patents

Name

Type

Language

SCOPOLIN

Common Name

English

NSC-404560

Preferred Name

English

6-METHOXYCOUMARIN 7-O-.BETA.-D-GLUCOSIDE

Common Name

English

SCOPOLETIN 7-GLUCOSIDE

Common Name

English

SCOPOLETIN 7-O-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

SCOPOLOSIDE

Common Name

English

SCOPOLETIN 7-O-GLUCOSIDE

Common Name

English

2H-1-BENZOPYRAN-2-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXY-

Systematic Name

English

7-O-.BETA.-GLUCOPYRANOSYLSCOPOLETIN

Common Name

English

7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXYCOUMARIN

Common Name

English

6-METHOXY-7-(.BETA.-D-GLUCOPYRANOSYLOXY)COUMARIN

Common Name

English

SCOPOLIN [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

439514