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Natural Product (NP) Details

General Information of the NP (ID: NP6882)
Name
Arctigenin
Synonyms
Arctigenin; (-)-Arctigenin; 7770-78-7; UNII-U76MR9VS6M; C21H24O6; CHEBI:79; U76MR9VS6M; (3R,4R)-4-(3,4-dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one; (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone; (+/-)-Arctigenin; Arctigenin, (+/-)-; Arctigenen; Arctigenin, trans-((+/-)-; 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-; Tocris-1777; SCHEMBL381820; CHEMBL435734; MEGxp0_001799; ACon1_000416; DTXSID60998919; HMS3268E18; HMS3412H04; HMS3676H04; HY-N0035; ZINC1615344; BDBM50375656; MFCD00870597; s3897; STL565840; AKOS015897121; CCG-268327; MCULE-1275881531; MCULE-5621583813; NCGC00025291-01; NCGC00025291-02; NCGC00025291-04; 144901-91-7; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-rel-; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, trans-; AS-56162; AB0019692; (-)-Arctigenin, >=95% (LC/MS-ELSD); N2399; C10545; 770A787; SR-01000597504; Q-100825; Q4787603; SR-01000597504-1; BRD-K53523901-001-01-0; UNII-2FD8L150E7 component NQWVSMVXKMHKTF-JKSUJKDBSA-N; 4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-oxidanyl-phenyl)methyl]oxolan-2-one; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one; (3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy- 3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one; 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-Furanone; 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-Furanone; EQC
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Species Origin Arctium lappa ...     Click to Show/Hide
Arctium lappa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Arctium
Species: Arctium lappa
Disease Depression [ICD-11: 6A70-6A71] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C21H24O6
PubChem CID
64981
Canonical SMILES
COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC
InChI
1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
InChIKey
NQWVSMVXKMHKTF-JKSUJKDBSA-N
CAS Number
CAS 7770-78-7
ChEBI ID
CHEBI:79
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)
Arctigenin has a therapeutic potential in combination with chemotherapeutic agents for NSLC.
          Ultraviolet A irradiation      Systemic sclerosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression PRKAA2  Molecule Info 
Pathway MAP
                    In-vitro Model Human mesenchymal stem cells derived from adipose tissue Healthy Homo sapiens
                    Experimental
                    Result(s)
Arctigenin protects against ultraviolet-A-induced damage to stemness through inhibition of the NF-KappaB/MAPK pathway.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)
ATG might alleviate the side effects and improve the therapeutic efficacy of DOX.
References
Reference 1 Arctigenin protects against depression by inhibiting microglial activation and neuroinflammation via HMGB1/TLR4/NF-KappaB and TNF-Alpha/TNFR1/NF-KappaB pathways. Br J Pharmacol. 2020 Nov;177(22):5224-5245.
Reference 2 Arctigenin enhances chemosensitivity to cisplatin in human nonsmall lung cancer H460 cells through downregulation of survivin expression. J Biochem Mol Toxicol. 2014 Jan;28(1):39-45.
Reference 3 Arctigenin protects against ultraviolet-A-induced damage to stemness through inhibition of the NF-KappaB/MAPK pathway. Chem Biol Interact. 2018 Feb 25;282:63-68.
Reference 4 Arctigenin Enhances the Cytotoxic Effect of Doxorubicin in MDA-MB-231 Breast Cancer Cells. Int J Mol Sci. 2020 Apr 23;21(8):2997.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China