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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Piperlongumine
PubChem CID 637858
Molecular Weight 317.34g/mol
Synonyms

5,6-dihydro-1-(1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-2(1H)pyridinone, Piperlongumine, piplartine
Formula C₁₇H₁₉NO₅
SMILES COC1=CC(=CC(=C1OC)OC)C=CC(=O)N2CCC=CC2=O
InChI 1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChIKey VABYUUZNAVQNPG-BQYQJAHWSA-N
CAS Number 20069-09-4
ChEMBL ID CHEMBL465843
ChEBI ID CHEBI:8241
Herb ID HBIN040085
KEGG ID C10166
Structure 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
Piper longum Hot
Chineses Pinyin BiBa
Habitat YunNan, GuangDong
Flavor Pungent
Meridian Tropism Stomach; Large Intestine
Species
>Kingdom: Viridiplantae
　-->Phylum: Streptophyta
　　-->Class: Equisetopsida
　　　-->Order: Piperales
　　　　-->Family: Piperaceae
　　　　　-->Genus: Piper
　　　　　　-->Species: Piper longum
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: 9
Ref_1
Pair Name Piperlongumine, Doxorubicin
Partner Name Doxorubicin
Disease Info [ICD-11: 2B51] Osteosarcoma Investigative
Biological Phenomena Induction-->Blockade of cell cycle in G2/M phase
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Down-regulation Expression BIRC5 hsa332
Down-regulation Expression CDH2 hsa1000
Up-regulation Expression CDKN1A hsa1026
Down-regulation Expression CTNNB1 hsa1499
Down-regulation Expression FN1 hsa2335
Down-regulation Expression NFKB1 hsa4790
Up-regulation Expression ROS1 hsa6098
Up-regulation Expression SMAD4 hsa4089
Down-regulation Expression TNF hsa7124
Up-regulation Expression TP53 hsa7157
Down-regulation Expression TWIST1 hsa7291
In Vitro Model MG-63 Osteosarcoma Homo sapiens (Human) CVCL_0426
143B Osteosarcoma Homo sapiens (Human) CVCL_2270
KHOS/NP Osteosarcoma Homo sapiens (Human) CVCL_2546
Result Piperlongumine induces ROS mediated apoptosis by transcriptional regulation of SMAD4/P21/P53 genes and synergizes with doxorubicin in osteosarcoma cells
Combination Pair ID: 10
Ref_2
Pair Name Piperlongumine, Paclitaxel
Partner Name Paclitaxel
Disease Info [ICD-11: 2B90] Colon cancer Investigative
Biological Phenomena Induction-->ROS mediated cell death
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Down-regulation Expression BIRC5 hsa332
Down-regulation Expression CDH2 hsa1000
Up-regulation Expression CDKN1A hsa1026
Down-regulation Expression CTNNB1 hsa1499
Down-regulation Expression FN1 hsa2335
Up-regulation Expression ROS1 hsa6098
Up-regulation Expression SMAD4 hsa4089
Up-regulation Expression TP53 hsa7157
Down-regulation Expression TWIST1 hsa7291
In Vitro Model Intestine 407 Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_1907
HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
Result Piperlongumine induces ROS mediated cell death and synergizes paclitaxel in human intestinal cancer cells
Combination Pair ID: 11
Ref_3
Pair Name Piperlongumine, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C94] Bladder cancer Investigative
Biological Phenomena Induction-->ROS accumulation
Gene Regulation Up-regulation Phosphorylation DNM1L hsa10059
Up-regulation Phosphorylation MLKL hsa197259
Up-regulation Activity RIPK1 hsa8737
Up-regulation Phosphorylation RIPK3 hsa11035
In Vitro Model T24 Bladder carcinoma Homo sapiens (Human) CVCL_0554
Result Our results demonstrated the role of RIPK1 in cisplatin-resistant cells and the sensitization effect of the natural drug PL on bladder cancer. These may provide a new treatment strategy for overcoming cisplatin resistance in bladder cancer.
Combination Pair ID: 12
Ref_4
Pair Name Piperlongumine, Sorafenib
Partner Name Sorafenib
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Biological Phenomena Induction-->Blockade of cell cycle in G2/M phase
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Up-regulation Cleavage CASP3 hsa836
Down-regulation Expression CDK1 hsa983
Down-regulation Expression CPSF7 hsa79869
Down-regulation Expression MKI67 hsa4288
Up-regulation Cleavage PARP1 hsa142
Up-regulation Phosphorylation PRKAA1 hsa5562
In Vitro Model HCCLM3 Adult hepatocellular carcinoma Homo sapiens (Human) CVCL_6832
SMMC-7721 Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_0534
Result Piperlongumine synergistically enhances the antitumour activity of sorafenib by mediating ROS-AMPK activation and targeting CPSF7 in liver cancer
Combination Pair ID: 419
Ref_5
Pair Name Piperlongumine, Oxaliplatin
Partner Name Oxaliplatin
Disease Info [ICD-11: 2B72] Gastric cancer Investigative
Biological Phenomena Induction-->DNA damage
Gene Regulation Up-regulation Expression H2AX hsa3014
Up-regulation Phosphorylation MAPK14 hsa1432
Up-regulation Phosphorylation MAPK8 hsa5599
In Vitro Model SGC-7901 Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_0520
BGC-823 Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_3360
In Vivo Model HCT116 cells (5×10⁶ cells in 100 μl PBS) were harvested and injected subcutaneously into the right flanks of the mice. Next, the mice were divided into four experimental groups on randomization and blinding, with four mice in each group.
Result Piperlongumine significantly enhanced oxaliplatin-induced growth inhibition of these cells and that TrxR1 activity is involved in their synergistic effect both in vitro and in vivo. These data suggest that PL and oxaliplatin combination treatment of gastric cancer may be more effective than oxaliplatin alone.
Combination Pair ID: 618
Ref_6
Pair Name Piperlongumine, Oxaliplatin
Partner Name Oxaliplatin
Disease Info [ICD-11: 2B90] Colon cancer Investigative
Biological Phenomena Induction-->Oxidative Stress
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Up-regulation Activity CASP3 hsa836
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
LoVo Colon adenocarcinoma Homo sapiens (Human) CVCL_0399
In Vivo Model For a xenograft model, HCT-116 cells (1×10⁷ in 150 uL PBS) were subcutaneously injected into the right flank of five-week-old female athymic BALB/c nu/nu mice.
Result This study provides a novel combination therapy for colorectal cancer, and reveals that manipulating ROS production might constitute an effective tool for developing novel treatments in colorectal cancer.
Combination Pair ID: 969
Ref_7
Pair Name Piperlongumine, HSP90 inhibitors
Partner Name HSP90 inhibitors
Disease Info [ICD-11: 2B90] Colon cancer Investigative
Biological Phenomena Induction-->Endoplasmic reticulum stress
Gene Regulation Up-regulation Expression ATF4 hsa468
Up-regulation Expression DDIT3 hsa1649
Up-regulation Expression HSPA5 hsa3309
Up-regulation Phosphorylation MAPK8 hsa5599
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
RKO Colon carcinoma Homo sapiens (Human) CVCL_0504
HCT 15 Colon adenocarcinoma Homo sapiens (Human) CVCL_0292
In Vivo Model HCT 116 cells were injected subcutaneously into the flank of athymic BALB/c nude mice (female, five weeks old). The total number of nude mice is set to 24, based on our previous experience.
Result Combination therapy with HSP90 inhibitors and piperlongumine promotes ROS-mediated ER stress in colon cancer cells
Combination Pair ID: 970
Ref_8
Pair Name Piperlongumine, Bortezomib
Partner Name Bortezomib
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Biological Phenomena Induction-->Endoplasmic reticulum stress
Gene Regulation Up-regulation Expression ATF4 hsa468
Up-regulation Expression ATF6 hsa22926
Up-regulation Expression DDIT3 hsa1649
Up-regulation Cleavage PARP1 hsa142
Up-regulation Expression XBP1 hsa7494
In Vitro Model KKU-M055 Intrahepatic cholangiocarcinoma Homo sapiens (Human) CVCL_M258
KKU-213A Intrahepatic cholangiocarcinoma Homo sapiens (Human) CVCL_M261
Result Piperlongumine and bortezomib synergically inhibit cholangiocarcinoma via ER stress-induced cell death
04. Reference
No. Title Href
1 Piperlongumine induces ROS mediated apoptosis by transcriptional regulation of SMAD4/P21/P53 genes and synergizes with doxorubicin in osteosarcoma cells. Chem Biol Interact. 2022 Feb 25;354:109832. doi: 10.1016/j.cbi.2022.109832. Click
2 Piperlongumine induces ROS mediated cell death and synergizes paclitaxel in human intestinal cancer cells. Biomed Pharmacother. 2020 Aug;128:110243. doi: 10.1016/j.biopha.2020.110243. Click
3 Piperlongumine increases the sensitivity of bladder cancer to cisplatin by mitochondrial ROS. J Clin Lab Anal. 2022 Jun;36(6):e24452. doi: 10.1002/jcla.24452. Click
4 Piperlongumine synergistically enhances the antitumour activity of sorafenib by mediating ROS-AMPK activation and targeting CPSF7 in liver cancer. Pharmacol Res. 2022 Mar;177:106140. doi: 10.1016/j.phrs.2022.106140. Click
5 Piperlongumine potentiates the antitumor efficacy of oxaliplatin through ROS induction in gastric cancer cells. Cell Oncol (Dordr). 2019;42(6):847-860. doi:10.1007/s13402-019-00471-x Click
6 The synergistic effects of oxaliplatin and piperlongumine on colorectal cancer are mediated by oxidative stress. Cell Death Dis. 2019 Aug 8;10(8):600. doi: 10.1038/s41419-019-1824-6. Click
7 Combination therapy with HSP90 inhibitors and piperlongumine promotes ROS-mediated ER stress in colon cancer cells. Cell Death Discov. 2023 Oct 13;9(1):375. doi: 10.1038/s41420-023-01672-y. Click
8 Piperlongumine and bortezomib synergically inhibit cholangiocarcinoma via ER stress-induced cell death. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan;396(1):109-120. doi: 10.1007/s00210-022-02305-4. Click
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