Natural Product (NP) Details

General Information of the NP (ID: NP3545)
Name
Schisandrol B
Synonyms
Schisandrol B; Gomisin A; 58546-54-6; Schizandrol B; (+)-Gomisin A; Wuweizi alcohol B; Wuweizichun B; Gomisin-A;TJN-101;Wuweizi alcohol-B; Schisantherinol B; NCGC00183134-01; SCHEMBL2109595; TJN 101; MFCD01941645; 3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-9-ol; LS-15009; AB0109732; W1799; 546S546; Q-100673; (+)-(6S,7S, Biar-R)-5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl benzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-6-ol; (6S,7S,13aR)- 5,6,7,8-Tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-benzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-6-ol; 1,2,3,13-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxol-6-ol; 1,2,3,13-Tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-6-ol, (6S,7S,13aR)-; Benzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-6-ol, 5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, (6S,7S,13aR)-
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Species Origin Schisandra chinensis ...     Click to Show/Hide
Schisandra chinensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Austrobaileyales
Family: Schisandraceae
Genus: Schisandra
Species: Schisandra chinensis
Disease Cholestatic liver disease [ICD-11: EC90] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.726
 
MDCK Permeability
 -4.667
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 0.145
 
PPB
 90.7%
 
BBB
 +
 
Metabolism
CYP1A2 inhibitor
 +
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 ++
CYP2D6 inhibitor
 - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 ++
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 ++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - - -
 
Excretion
CLplasma
 4.543
 
T1/2
 1.274
Toxicity
DILI
 +
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 ++
 
Respiratory
 +
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 +
 
Drug-induced Neurotoxicity
 +
 
Hematotoxicity
 +
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C23H28O7
PubChem CID
634470
Canonical SMILES
CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4CC1(C)O)OC)OC)OC)OC)OCO3
InChI
1S/C23H28O7/c1-12-7-13-8-16-20(30-11-29-16)22(28-6)17(13)18-14(10-23(12,2)24)9-15(25-3)19(26-4)21(18)27-5/h8-9,12,24H,7,10-11H2,1-6H3
InChIKey
ZWRRJEICIPUPHZ-UHFFFAOYSA-N
CAS Number
CAS 58546-54-6
Herb ID
HBIN043331
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Apatinib      Breast 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		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
                    In-vitro Model SGC-7901 CVCL_0520 Human gastric cancer Homo sapiens
                    Experimental
                    Result(s)		 Low-toxicity Sch.B combined with low dosage apatinib has a more potent anti-cancer effect that apatinib alone.
          Docetaxel      Solid tumour/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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
                    In-vitro Model Ca Ski CVCL_1100 Cervical squamous cell carcinoma Homo sapiens
                    In-vivo Model Mice were subcutaneously implanted with cell suspension holding 1*106 Caski cells in the right flank.
                    Experimental
                    Result(s)		 Sch B enhanced the anti-tumor effects of DTX in vitro and in vivo via growth, invasion, and apoptosis regulating.
          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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model The experiments were carried out on male Balb/c mice (8 - 10 weeks old).
                    Experimental
                    Result(s)		 Schisandrin B, attenuates cisplatin-induced oxidative stress, genotoxicity and neurotoxicity through modulating NF-KappaB pathway in mice.
          Dexrazoxane      Breast 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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model A total of 150 healthy New Zealand white rabbits, weight 1.98 + 0.15 kg, male and female in equal numbers were used in this study.
                    Experimental
                    Result(s)		 Schisandrin B had dose-dependent effects in decreasing the magnitude of doxorubicin-induced indicators of cardiomyopathy to a degree that approximated the decrease produced by dexrazoxane treatment.
          Albendazole      Parasitic worm infestation     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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Third-stage larvae (L3) were used to infect Sprague-Dawley (SD) rats.
                    Experimental
                    Result(s)		 Albendazole-schisandrin B co-treatment significantly inhibited inflammasome activation, pyroptosis, and apoptosis.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Cyclosporin      Psoriasis vulgaris     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 [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression LDHA  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Increase ATP generation
Induction ROS generation
                    In-vitro Model HK2 CVCL_0302 Healthy Homo sapiens
                    Experimental
                    Result(s)		 Sch B appears to protect against CsA-induced nephrotoxicity by decreasing oxidative stress and cell death.
          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 [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Down-regulation Expression MSH3  Molecule Info 
Pathway MAP
                    In-vivo Model Male ICR mice (18-22 g) and male Sprague-Dawley rats (300-350 g) were used in this study.
                    Experimental
                    Result(s)		 Schisandrin B prevents doxorubicin-induced cardiotoxicity via enhancing glutathione redox cycling.
          Tacrine      Alzheimer disease     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 [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model In the Sch B pretreatment group in the hepatotoxicity study, mice (Adult male ICR mice) were treated intragastrically with Sch B at daily doses of 0.125 and 0.5 mmol/kg for 3 days.
                    Experimental
                    Result(s)		 Sch B may be useful for reducing the potential hepatotoxicity of THA/bis(7)-THA in anti-Alzheimer's therapy.
          Bis(7)-tacrine      Glaucoma     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 [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model In the Sch B pretreatment group in the hepatotoxicity study, mice (Adult male ICR mice) were treated intragastrically with Sch B at daily doses of 0.125 and 0.5 mmol/kg for 3 days.
                    Experimental
                    Result(s)		 Sch B may be useful for reducing the potential hepatotoxicity of THA/bis(7)-THA in anti-Alzheimer's therapy.
References
Reference 1 Schisandrol B protects against cholestatic liver injury through pregnane X receptors. Br J Pharmacol. 2017 Apr;174(8):672-688.
Reference 2 The synergistic anti-tumor effect of schisandrin B and apatinib. J Asian Nat Prod Res. 2020 Sep;22(9):839-849.
Reference 3 Schisandrin B synergizes docetaxel-induced restriction of growth and invasion of cervical cancer cells in vitro and in vivo. Ann Transl Med. 2020 Sep;8(18):1157.
Reference 4 Schisandrin B, attenuates cisplatin-induced oxidative stress, genotoxicity and neurotoxicity through modulating NF-KappaB pathway in mice. Free Radic Res. 2012 Jan;46(1):50-60.
Reference 5 Prevention and treatment of doxorubicin-induced cardiotoxicity by dexrazoxane and schisandrin B in rabbits. Int J Toxicol. 2011 Dec;30(6):681-9.
Reference 6 Albendazole-Schisandrin B Co-Therapy on Angiostrongylus cantonensis-Induced Meningoencephalitis in Mice. Biomolecules. 2020 Jul 5;10(7):1001.
Reference 7 Protective effect of schisandrin B against cyclosporine A-induced nephrotoxicity in vitro and in vivo. Am J Chin Med. 2012;40(3):551-66.
Reference 8 Schisandrin B prevents doxorubicin-induced cardiotoxicity via enhancing glutathione redox cycling. Clin Cancer Res. 2007 Nov 15;13(22 Pt 1):6753-60.
Reference 9 Schisandrin B protects against tacrine- and bis(7)-tacrine-induced hepatotoxicity and enhances cognitive function in mice. Planta Med. 2002 Mar;68(3):217-20.
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