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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Fisetin
PubChem CID 5281614
Molecular Weight 286.24g/mol
Synonyms

2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-1-benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one, 3,3',4',7-Tetrahydroxy-flavone, 3,3',4',7-Tetrahydroxyflavone, 5-Desoxy-quercetin, fisetin, fisetinidin

Formula C₁₅H₁₀O₆
SMILES C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
InChI 1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
InChIKey XHEFDIBZLJXQHF-UHFFFAOYSA-N
CAS Number 528-48-3
ChEMBL ID CHEMBL31574
ChEBI ID CHEBI:42567
Herb ID HBIN026506
Drug Bank ID DB07795
KEGG ID C10041
Toxicity Organism Test Type Route(Dose)
rat LD50 intraperitoneal(165 mg/kg)
mouse LD50 intraperitoneal(254 mg/kg)
rat LD50 oral(322 mg/kg)
Structure 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
(1) Acacia catechu Cold
Chineses Pinyin ErCha
Use Part Peeled Branches And Trunks
Habitat YunNan, GuangDong, GuangXi, FuJian
Flavor Bitter, Astringent
Meridian Tropism Lung, Heart
(2) Dalbergia odorifera Warm
Chineses Pinyin JiangXiang
Use Part Dried Heartwood Of Tree Trunk And Root
Habitat HaiNan, GuangDong, GuangXi, YunNan
Flavor Pungent
Meridian Tropism Liver, Spleen
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Fabales
    -->Family: Fabaceae
     -->Genus: Dalbergia
      -->Species: Dalbergia odorifera
(3) Gleditsia sinensis Warm
Chineses Pinyin ZaoJiaoCi
Use Part Thorn
Habitat JiangSu, HuBei, HeBei, ShanXi, HeNan, ShanDong, GuangDong, GuangXi, SiChuan, AnHui, ZheJiang, GuiZhou, Shaanxi, JiangXi, GanSu
Flavor Pungent
Meridian Tropism Liver, Stomach
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Fabales
    -->Family: Fabaceae
     -->Genus: Gleditsia
      -->Species: Gleditsia sinensis
(4) Selaginella tamariscina Even
Chineses Pinyin JuanBai
Use Part Dried Whole Herb
Habitat China
Flavor Pungent
Meridian Tropism Liver, Heart
(5) Mangifera indica Even
Chineses Pinyin MangGuoYe
Use Part Leaf
Habitat FuJian, TaiWan, GuangDong, HaiNan, GuangXi, YunNan
Flavor Mildly sour
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Sapindales
    -->Family: Anacardiaceae
     -->Genus: Mangifera
      -->Species: Mangifera indica
(6) Rhus succedanea Cold
Chineses Pinyin LinBeiZi
Use Part Root, Root Cortex
Habitat SiChuan, GuiZhou, YunNan, XiZang, ChongQing, JiangSu, ZheJiang, AnHui, FuJian, JiangXi, ShanDong, ShangHai, HeBei, HeNan
Flavor Bitter
Meridian Tropism Heart, Liver, Spleen
(7) Toxicodendron succedaneum Warm
Chineses Pinyin YeQiShuYe
Use Part Leaf
Habitat JiangSu, ZheJiang, AnHui, FuJian, TaiWan, JiangXi, HuBei, HuNan, GuiZhou, SiChuan
Flavor Pungent
Meridian Tropism Lung, Liver, Spleen, Large intestine
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Sapindales
    -->Family: Anacardiaceae
     -->Genus: Toxicodendron
      -->Species: Toxicodendron succedaneum
(8) Fragaria × ananassa Cool
Chineses Pinyin CaoMei
Use Part Fruit
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Rosales
    -->Family: Rosaceae
     -->Genus: Fragaria
      -->Species: Fragaria × ananassa
03. Combinatorial Therapeutic Effect(s)
Synergistic Effect
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Drug(s) whose efficacy can be enhanced by this phytochemical
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Combination Pair ID: 73
Pair Name Fisetin, Fluorouracil
Partner Name Fluorouracil
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Phosphorylation AKT1 hsa207
Down-regulation Phosphorylation AKT1S1 hsa84335
Down-regulation Phosphorylation EIF4E KEGG ID N.A.
Down-regulation Phosphorylation EIF4EBP1 hsa1978
Down-regulation Expression MLST8 KEGG ID N.A.
Down-regulation Phosphorylation MTOR hsa2475
Down-regulation Expression PIK3CA hsa5290
Up-regulation Phosphorylation PRKAA1 hsa5562
Down-regulation Expression RICTOR hsa253260
Down-regulation Phosphorylation RPS6KB1 hsa6198
Down-regulation Expression RPTOR hsa57521
In Vitro Model SW480 Colon adenocarcinoma Homo sapiens (Human) CVCL_0546
HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
HT-29 Colon adenocarcinoma Homo sapiens (Human) CVCL_0320
In Vivo Model Since FC13K1ApcMin/+ mice develop adenomas around 1 month of age, the treatment with fisetin and 5-FU by intraperitoneal injection was started between 26 and 30 days.
Result Fisetin and 5-fluorouracil: Effective combination for PIK3CA-mutant colorectal cancer
Combination Pair ID: 632
Pair Name Fisetin, Sorafenib
Partner Name Sorafenib
Disease Info [ICD-11: 2C30] Melanoma Investigative
Biological Phenomena Inhibition-->Epithelial-mesenchymal transition
Gene Regulation Up-regulation Expression CDH1 hsa999
Down-regulation Expression CDH2 hsa1000
Down-regulation Expression FN1 hsa2335
Down-regulation Expression MMP2 hsa4313
Down-regulation Expression MMP9 hsa4318
Down-regulation Expression SNAI1 hsa6615
Down-regulation Expression SNAI2 hsa6591
Down-regulation Expression TWIST1 hsa7291
Down-regulation Expression VIM hsa7431
Down-regulation Expression ZEB1 hsa6935
In Vitro Model A-375 Amelanotic melanoma Homo sapiens (Human) CVCL_0132
SK-MEL-28 Cutaneous melanoma Homo sapiens (Human) CVCL_0526
In Vivo Model Female athymic nude mice of five weeks age were subcutaneously transplanted with A375 or SK-MEL-28 cells (2.5×10⁶ A375 cells in 50 ul DMEM + 50 ul matrigel or 5×10⁶ SK-MEL-28 cells in 50 ul RPMI + 50 ul matrigel) in each flank
Result Our findings demonstrate that fisetin potentiates the anti-invasive and anti-metastatic effects of sorafenib. Our data suggest that fisetin may be a worthy adjuvant chemotherapy for the management of melanoma.
Combination Pair ID: 633
Pair Name Fisetin, Sorafenib
Partner Name Sorafenib
Disease Info [ICD-11: 2C77] Cervical cancer Investigative
Biological Phenomena Induction-->Mitochondria-mediated apoptosis
Gene Regulation Up-regulation Expression BAX hsa581
Up-regulation Expression BCL2 hsa596
Up-regulation Expression CASP3 hsa836
Up-regulation Expression CASP8 hsa841
Up-regulation Expression PARP1 hsa142
Up-regulation Expression TNFRSF10B hsa8795
In Vitro Model HeLa Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_0030
In Vivo Model For the in vivo experiments, 1×10⁶ HeLa cells (diluted in Matrigel) were established by subcutaneous injec tion into the animal's right flank.
Result The combination of fisetin and sorafenib exerted better synergistic effects in vitro and in vivo than either agent used alone against human cervical cancer, and this synergism was based on apoptotic potential through a mitochondrial- and DR5-dependent caspase-8/caspase-3 signaling pathway
Combination Pair ID: 634
Pair Name Fisetin, Sorafenib
Partner Name Sorafenib
Disease Info [ICD-11: 2C30] Melanoma Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression AKT1 hsa207
Up-regulation Expression BAK1 hsa578
Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Up-regulation Expression CASP3 hsa836
Down-regulation Phosphorylation MAP2K2 hsa5605
Down-regulation Expression MAPK3 hsa5595
Down-regulation Expression MCL1 hsa4170
Down-regulation Phosphorylation MEK1 hsa5604
Down-regulation Expression MTOR hsa2475
Up-regulation Expression PARP1 hsa142
Down-regulation Expression PIK3CA hsa5290
In Vitro Model RPMI-7951 Melanoma Homo sapiens (Human) CVCL_1666
A-375 Amelanotic melanoma Homo sapiens (Human) CVCL_0132
In Vivo Model Mice were subcutaneously inoculated with 0.1ml of 2.5×10⁶ A375 cells or 5×10*6 SK-MEL-28 cells (prepared in a 50ul media + 50ul matrigel) in each flank to initiate tumor growth.
Result Fisetin potentiates sorafenib-induced apoptosis and abrogates tumor growth in athymic nude mice implanted with BRAF-mutated melanoma cells.
Drug(s) whose resistance can be reversed by this phytochemical
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Combination Pair ID: 985
Pair Name Fisetin, Paclitaxel
Partner Name Paclitaxel
Disease Info [ICD-11: 2C73] Ovarian cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression ABCG2 hsa9429
Up-regulation Expression BAK1 hsa578
Down-regulation Expression BCL-xL hsa598
Up-regulation Activity CASP3 hsa836
In Vitro Model OVCAR-3 High grade ovarian serous adenocarcinoma Homo sapiens (Human) CVCL_0465
Caov-3 High grade ovarian serous adenocarcinoma Homo sapiens (Human) CVCL_0201
TOV-112D Ovarian endometrioid adenocarcinoma Homo sapiens (Human) CVCL_3612
SW626 Colon adenocarcinoma Homo sapiens (Human) CVCL_1725
Result Our study shows that PTX-FA and Fis-FA PBM NPs directly target platinum-resistant OvCa cells, induce cytotoxic/apoptotic effects, and reverse multi-drug resistance (MDR). These findings allow us to create new clinical applications using PTX-FA and Fis-FA combination nanoparticles to treat drug-resistant cancers.
Drug(s) whose toxicity can be decreased by this phytochemical
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Combination Pair ID: 984
Pair Name Fisetin, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C25] Lung cancer Investigative
In Vitro Model LL/2 (LLC1) Malignant tumors of the mouse pulmonary system Mus musculus (Mouse) CVCL_4358
In Vivo Model Female 6-weeks old C57BL/6J mice were used for anti-tumor evaluation. Lewis lung tumor fragments (about 30 mm3) were injected subcutaneously (s.c.) bilaterally into the flanks of the mice (day 1).
Result The combination index between liposomal fisetin and liposomal cisplatin on 3LL cell line after 24 h of exposure showed a clear synergism: CI = 0.7 for the co loaded liposomes and CI = 0.9 for the mixture of cisplatin loaded and fisetin loaded liposomes. The co-encapsulating formulation showed in vivo efficacy against an ectopic murine model of Lewis Lung carcinoma with a probable reduction in the toxicity of cisplatin through co-encapsulation with fisetin.
04. Reference
No. Title Href
1 Co-encapsulation of fisetin and cisplatin into liposomes: Stability considerations and in vivo efficacy on lung cancer animal model. Int J Pharm. 2024 Feb 15;651:123744. doi: 10.1016/j.ijpharm.2023.123744. Click
2 Fisetin and 5-fluorouracil: Effective combination for PIK3CA-mutant colorectal cancer. Int J Cancer. 2019 Dec 1;145(11):3022-3032. doi: 10.1002/ijc.32367. Click
3 Fisetin, a dietary flavonoid, augments the anti-invasive and anti-metastatic potential of sorafenib in melanoma. Oncotarget. 2016 Jan 12;7(2):1227-41. doi: 10.18632/oncotarget.6237. Click
4 Synergistic effect of fisetin combined with sorafenib in human cervical cancer HeLa cells through activation of death receptor-5 mediated caspase-8/caspase-3 and the mitochondria-dependent apoptotic pathway. Tumour Biol. 2016 May;37(5):6987-96. doi: 10.1007/s13277-015-4526-4. Click
5 Fisetin, a phytochemical, potentiates sorafenib-induced apoptosis and abrogates tumor growth in athymic nude mice implanted with BRAF-mutated melanoma cells. Oncotarget. 2015 Sep 29;6(29):28296-311. doi: 10.18632/oncotarget.5064. Click
6 The effect of paclitaxel- and fisetin-loaded PBM nanoparticles on apoptosis and reversal of drug resistance gene ABCG2 in ovarian cancer. J Ovarian Res. 2023 Nov 21;16(1):220. doi: 10.1186/s13048-023-01308-w. Click
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