lariciresinol (Q6489358)

( )-lariciresinol metabolic process

part of

subject has role

participant

1 reference

Gene Ontology release 2019-11-16

( )-lariciresinol catabolic process

subject has role

reactant

1 reference

Gene Ontology release 2019-11-16

( )-lariciresinol biosynthetic process

subject has role

product

1 reference

Gene Ontology release 2019-11-16

chemical structure

Lariciresinol.svg
830 × 330; 16 KB

0 references

mass

360.157 dalton

1 reference

Lariciresinol (English)

7 October 2016

2 references

2alpha-(4-Hydroxy-3-methoxyphenyl)-4beta-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran-3alpha-methanol

inferred from InChI

2 references

inferred from InChI

chemical formula

C₂₀H₂₄O₆

1 reference

Lariciresinol (English)

20 November 2016

canonical SMILES

COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)O

1 reference

Lariciresinol (English)

20 November 2016

isomeric SMILES

COC1=C(C=CC(=C1)C[C@H]2CO[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O)OC)O

1 reference

Structural and spectroscopic characteristics of two lignans from Taxus baccata L.

Lariciresinol (English)

20 November 2016

2 references

Cytochrome P450 3A4 inhibitory constituents of the wood of Taxus yunnanensis

Magnolia denudata

1 reference

Lignan and Neolignan Derivatives from Magnolia denudata.

Hemerocallis fulva

2 references

Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves

Erratum to “Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves” [Life Sciences 75 (2004) 753–763]

Daphne feddei

1 reference

Phenylpropanoids from Daphne feddei and their inhibitory activities against NO production

Arum italicum

1 reference

Two New Lignan Glucosides from Arum italicum

Abies pinsapo

1 reference

Lignans from the wood of Abies pinsapo

Nierembergia aristata

1 reference

Cardenolides from Nierembergia aristata

Capsicum annuum

3 references

New sesquiterpenes from Capsicum annuum

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

New sesquiterpenes from Capsicum annuum

Enterococcus faecalis

1 reference

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of ( )-Pinoresinol to ( )-Lariciresinol

Rubia yunnanensis

6 references

Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis

Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis

Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis

Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis

Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis

Bioactive constituents from Chinese natural medicines. XI. inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone

Anastatica hierochuntica

5 references

Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells

(7R,8S) and (7S,8R) 8-5' Linked Neolignans from Egyptian Herbal Medicine Anastatica hierochuntica and Inhibitory Activities of Lignans on Nitric Oxide Production

Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells

Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells

(7R,8S) and (7S,8R) 8-5' Linked Neolignans from Egyptian Herbal Medicine Anastatica hierochuntica and Inhibitory Activities of Lignans on Nitric Oxide Production

Abies pinsapo subsp. marocana

1 reference

Two sesquilignans from the wood of Abies marocana

Araucaria angustifolia

2 references

Phenylpropanoid derivatives and biflavones at different stages of differentiation and development of Araucaria angustifolia.

Phenylpropanoid derivatives and biflavones at different stages of differentiation and development of Araucaria angustifolia.

Astragalus mongholicus

1 reference

New Constituents of Astragalus mongholicus

Daphne oleoides

2 references

A lignan from Daphne oleoides

A lignan from Daphne oleoides

Fagraea racemosa

2 references

Pharmacologically active components of Todopon Puok (Fagraea racemosa), a medicinal plant from Borneo

Pharmacologically active components of Todopon Puok (Fagraea racemosa), a medicinal plant from Borneo

Gliricidia sepium

1 reference

Saponins from Gliricidia sepium

Hibiscus cannabinus

1 reference

Lignanamides and other phenolic constituents from the bark of kenaf (Hibiscus cannabinus).

Justicia diffusa

2 references

Lignans from Justicia hyssopifolia

Justicia lignans VI--prostalidin D, a new arylnaphthalide lignan from Justicia diffusa var. prostrata C.B. Clarke

Justicia glauca

1 reference

Justiciresinol, a New Furanoid Lignan from Justicia glauca

Leitneria floridana

2 references

Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.

Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.

Linum album

2 references

Accumulation of podophyllotoxin and related lignans in cell suspension cultures of linum album

Accumulation of podophyllotoxin and related lignans in cell suspension cultures of linum album

Morina chinensis

1 reference

Morinols A-L, twelve novel sesquineolignans and neolignans with a new carbon skeleton from morina chinensis

Perovskia atriplicifolia

2 references

A new acylated steroid glucoside from Perovskia atriplicifolia

A new acylated steroid glucoside from Perovskia atriplicifolia

Korean Spruce

1 reference

Lignans from the wood of Picea koraiensis

Picea obovata

1 reference

Lignans from the wood of Picea koraiensis

Premna resinosa

1 reference

Lignans from the leaves of Premna recinosa (Verbenaceae)

Sambucus nigra

2 references

Potential allelochemicals from Sambucus nigra

Potential allelochemicals from Sambucus nigra

Saussurea medusa

1 reference

Immunosuppressive constituents from Saussurea medusa

Stellera chamaejasme

1 reference

Biflavanones, diterpenes, and coumarins from the roots of Stellera chamaejasme L.

Styrax camporum

2 references

Triterpenos de Styrax camporum (styracaceae)

Triterpenos de Styrax camporum (styracaceae)

Berberis koreana

2 references

Biological evaluation of phenolic constituents from the trunk of Berberis koreana

Biological evaluation of phenolic constituents from the trunk of Berberis koreana

Brassica fruticulosa

2 references

Lignans and Neolignans fromBrassicafruticulosa: Effects on Seed Germination and Plant Growth

Lignans and Neolignans fromBrassicafruticulosa: Effects on Seed Germination and Plant Growth

Vitex rotundifolia

1 reference

Anti-inflammatory constituents from the fruits of Vitex rotundifolia

Actinidia chinensis

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

garlic

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Cashew

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

peanut

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

asparagus

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Avena sativa

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Brassica oleracea var. botrytis

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

cabbage

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

broccoli

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Brassica oleracea var. viridis

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Camellia sinensis

2 references

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Camellisins A-C, three new triterpenoids from the roots of Camellia sinensis

Carya illinoinensis

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Castanea

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Cichorium intybus

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Coffea

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Corylus

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Cucumis melo var. dudaim

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Cucumis sativus

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Cucurbita pepo

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Daucus carota

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Fagopyrum esculentum

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Fragaria

3 references

Content, composition, and stereochemical characterisation of lignans in berries and seeds

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Glycine

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

common sunflower

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Bioactive lignans from a cultivar of Helianthus annuus

Hordeum vulgare

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Jugo

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

lettuce

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Linum usitatissimum

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Malus domestica

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Musa

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Olea europaea

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Papaver

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phaseolus vulgaris

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phoenix dactylifera

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Pistacia vera

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Prunus armeniaca

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Prunus domestica

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Prunus dulcis

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Prunus persica

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Pyrus communis

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Raphanus sativus var. sativus

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Ribes nigrum

2 references

Content, composition, and stereochemical characterisation of lignans in berries and seeds

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Rubus chamaemorus

1 reference

Content, composition, and stereochemical characterisation of lignans in berries and seeds

Secale cereale

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

sesame

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

New lignans from the perisperm of Sesamum indicum

Solanum melongena

1 reference

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

potato

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Spinacia oleracea

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Triticum aestivum

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Vaccinium myrtillus

1 reference

Content, composition, and stereochemical characterisation of lignans in berries and seeds

Vaccinium vitis-idaea

1 reference

Content, composition, and stereochemical characterisation of lignans in berries and seeds

Vitis vinifera

3 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Lignans in selected wines

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

maize

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Aquilaria sinensis

1 reference

Aquilarin A, a new benzenoid derivative from the fresh stem of Aquilaria sinensis.

Callicarpa furfuracea

1 reference

Lignanoids and Diterpenoids fromCallicarpa furfuraceae

Cedrus deodara

1 reference

A new neolignan and other phenolic constituents from Cedrus deodara

Cycas revoluta

1 reference

Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets: moderately active antibacterial biflavonoids

Daphne mezereum

1 reference

Triumbellin, A tricoumarin rhamnopyranoside from Daphne mezereum

Dirca occidentalis

1 reference

Plant anticancer agents XXVII: Antileukemic and cytotoxic constituents of Dirca occidentalis (Thymelaeaceae).

Ephedra viridis

1 reference

Isolation of lignans and biological activity studies of Ephedra viridis

Euterpe oleracea

1 reference

Lignans and other constituents of the fruits of Euterpe oleracea (Acai) with antioxidant and cytoprotective activities.

Gnetum montanum

1 reference

Lignans from Gnetum montanum Markgr. f. megalocarpua

Magnolia kachirachirai

1 reference

Secondary Metabolites from Magnolia kachirachirai

Rhodiola rosea

1 reference

Phenylpropanoids of a callus culture of Rhodiola rosea

Tsuga heterophylla

1 reference

Lignans causing photodiscoloration of Tsuga heterophylla: 8-hydroxy-oxomatairesinol from sapwood

tomato

3 references

Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Justicia tranquebariensis

1 reference

Justica tranquebariensis Linn. f.

Taxus baccata

1 reference

Antimicrobial activity of the heartwood of Taxus baccata

Cucumis melo

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Citrus × paradisi

2 references

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Polla

1 reference

Determination of lignans in edible and nonedible parts of pomegranate (Punica granatum L.) and products derived therefrom, particularly focusing on the quantitation of isolariciresinol using HPLC-DAD-ESI/MSn

Picea abies

1 reference

Lignans and Lipophilic Extractives in Norway Spruce Knots and Stemwood

Taiwania cryptomerioides

1 reference

The gene expression and enzymatic activity of pinoresinol-lariciresinol reductase during wood formation in Taiwania cryptomerioides Hayata

Malus pumila

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Taxus cuspidata

4 references

Phenolic constituents ofTaxus cuspidata I: lignans from the roots

Neutral taxoids from Taxus cuspidata as modulators of multidrug-resistant tumor cells.

Production of biologically active taxoids by a callus culture of Taxus cuspidata

Taxoids and abietanes from callus cultures of Taxus cuspidata

mandarin orange

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Prunus avium

1 reference

Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan

Tectona grandis

1 reference

Tectonoelins, new norlignans from a bioactive extract of Tectona grandis

Citrus × deliciosa

1 reference

Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol

Identifiers

InChI

InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20 /m0/s1

1 reference

Lariciresinol (English)

20 November 2016

2 references

Lariciresinol (English)

20 November 2016

ChEBI release 2020-09-01

CAS Registry Number

27003-73-2

2 references

Global Substance Registration System

UNII

73XCE5OZB0

lariciresinol (English)

20 November 2016

https://commonchemistry.cas.org/detail?cas_rn=27003-73-2

10 April 2021

1 reference

( )-lariciresinol (English)

20 November 2016

2 references

Lariciresinol (English)

20 November 2016

ChEBI ID

67246

mapping relation type

2 references

LARICIRESINOL (English)

20 November 2016

International Chemical Identifier

InChI

InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20 /m0/s1

1 reference

LARICIRESINOL (English)

20 November 2016

2 references

MSBNK-Washington_State_Univ-BML82415

1 reference

MassBank accession ID

0 references

MSBNK-Washington_State_Univ-BML82416

0 references

MSBNK-Washington_State_Univ-BML82417

0 references

MSBNK-Washington_State_Univ-BML82418

0 references

SPLASH

splash10-0a4i-0009100000-7cfc5cafbc79b8cb5e8d

0 references

splash10-03di-0009500000-5863e3dfa8d39ca0f267

0 references

splash10-0a4i-0009500000-88be09f969e7dad787f0

0 references

DSSTox substance ID

DTXSID30318362

2 references

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

DSSTOX compound identifier

0 references

0 references

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.222.965

27 December 2018

ECHA Substance Infocard ID

[No public or meaningful name is available] (English)

quotation

CAS no.: 27003-73-2 (English)

100.222.965

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.222.965

27 December 2018

Human Metabolome Database ID

[No public or meaningful name is available] (English)

quotation

CAS no.: 27003-73-2 (English)

1 reference

HMDB0303941

2 references

1 reference

Global Substance Registration System

( )-lariciresinol (English)

7 October 2016

2 references

UNII

73XCE5OZB0

lariciresinol (English)

20 November 2016

1 reference

( )-lariciresinol (English)