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Hederins, Oleanane Triterpenes, Oleanol, Oleanolic Acid, Triterpenes, Oleanane

No.	Title	Href
1	Oleanolic acid increases the anticancer potency of doxorubicin in pancreatic cancer cells. J Biochem Mol Toxicol. 2023 Oct;37(10):e23426. doi: 10.1002/jbt.23426.	`Click`
2	A Synergistic Combination of Oleanolic Acid and Apatinib to Enhance Antitumor Effect on Liver Cancer Cells and Protect against Hepatic Injury. Recent Pat Anticancer Drug Discov. 2024;19(2):199-208. doi: 10.2174/1574892818666230417093208.	`Click`
3	Enhancement of gemcitabine efficacy by K73-03 via epigenetically regulation of miR-421/SPINK1 in gemcitabine resistant pancreatic cancer cells. Phytomedicine. 2021 Oct;91:153711. doi: 10.1016/j.phymed.2021.153711.	`Click`
4	Identification of a novel oxidative stress induced cell death by Sorafenib and oleanolic acid in human hepatocellular carcinoma cells. Biochem Pharmacol. 2016 Oct 15;118:9-17. doi: 10.1016/j.bcp.2016.08.011.	`Click`
5	Olean-28,13b-olide 2 plays a role in cisplatin-mediated apoptosis and reverses cisplatin resistance in human lung cancer through multiple signaling pathways. Biochem Pharmacol. 2019;170:113642. doi:10.1016/j.bcp.2019.113642	`Click`

No.

Title

Href

Oleanolic acid increases the anticancer potency of doxorubicin in pancreatic cancer cells. J Biochem Mol Toxicol. 2023 Oct;37(10):e23426. doi: 10.1002/jbt.23426.

Click

A Synergistic Combination of Oleanolic Acid and Apatinib to Enhance Antitumor Effect on Liver Cancer Cells and Protect against Hepatic Injury. Recent Pat Anticancer Drug Discov. 2024;19(2):199-208. doi: 10.2174/1574892818666230417093208.

Click

Enhancement of gemcitabine efficacy by K73-03 via epigenetically regulation of miR-421/SPINK1 in gemcitabine resistant pancreatic cancer cells. Phytomedicine. 2021 Oct;91:153711. doi: 10.1016/j.phymed.2021.153711.

Click

Identification of a novel oxidative stress induced cell death by Sorafenib and oleanolic acid in human hepatocellular carcinoma cells. Biochem Pharmacol. 2016 Oct 15;118:9-17. doi: 10.1016/j.bcp.2016.08.011.

Click

Olean-28,13b-olide 2 plays a role in cisplatin-mediated apoptosis and reverses cisplatin resistance in human lung cancer through multiple signaling pathways. Biochem Pharmacol. 2019;170:113642. doi:10.1016/j.bcp.2019.113642

Click

Name	Oleanolic Acid
PubChem CID	10494
Molecular Weight	456.7g/mol
Synonyms	Hederins, Oleanane Triterpenes, Oleanol, Oleanolic Acid, Triterpenes, Oleanane
Formula	C₃₀H₄₈O₃
SMILES	CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C
InChI	1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1
InChIKey	MIJYXULNPSFWEK-GTOFXWBISA-N
CAS Number	508-02-1
ChEMBL ID	CHEMBL168
ChEBI ID	CHEBI:37659
KEGG ID	C17148
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			Download 2D MOL 3D MOL

Chineses Pinyin	GuangHuoXiang
Use Part	Aerial Parts
Habitat	GuangDong, HaiNan
Flavor	Pungent
Meridian Tropism	Spleen, Stomach, Lung
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Lamiales 　　　　-->Family: Lamiaceae 　　　　　-->Genus: Pogostemon 　　　　　　-->Species: Pogostemon cablin

Chineses Pinyin	HuoXiang
Use Part	Aerial Parts
Habitat	GuangDong, HaiNan
Flavor	Pungent
Meridian Tropism	Spleen, Stomach
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Lamiales 　　　　-->Family: Lamiaceae 　　　　　-->Genus: Pogostemon 　　　　　　-->Species: Pogostemon cablin

Chineses Pinyin	DiFuZi
Use Part	Fruit
Habitat	China
Flavor	Pungent, Bitter
Meridian Tropism	Kidney, Bladder
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Caryophyllales 　　　　-->Family: Amaranthaceae 　　　　　-->Genus: Kochia 　　　　　　-->Species: Kochia scoparia

Chineses Pinyin	AiDiCha
Use Part	Whole Herb
Habitat	HuNan, JiangXi, ZheJiang, FuJian, GuangDong, GuiZhou, YunNan, HaiNan, XiZang, TaiWan
Flavor	Pungent, Mildly bitter

Chineses Pinyin	HeiRenDong
Use Part	Flower Bud
Habitat	JiLin
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Dipsacales 　　　　-->Family: Caprifoliaceae 　　　　　-->Genus: Lonicera 　　　　　　-->Species: Lonicera nigra

Chineses Pinyin	HuangHuaBaiJiang
Use Part	Whole Herb
Habitat	China
Flavor	Pungent, Bitter
Meridian Tropism	Stomach

Chineses Pinyin	QiDunGuo
Use Part	Pulp oil
Flavor	Slightly Bitter
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Lamiales 　　　　-->Family: Oleaceae 　　　　　-->Genus: Olea 　　　　　　-->Species: Olea europaea

Pair Name	Oleanolic Acid, Gemcitabine
Partner Name	Gemcitabine
Disease Info	[ICD-11: 2C10]	Pancreatic cancer		Investigative
Biological Phenomena	Induction-->Mitochondrial damage
Gene Regulation	Down-regulation	Expression	EGFR	hsa1956
	Down-regulation	Expression	EZH2	hsa2146
	Down-regulation	Expression	MAP2K7	hsa5609
	Down-regulation	Expression	MAPK1	hsa5594
	Down-regulation	Expression	SPINK1	hsa6690
In Vitro Model	AsPC-1	Pancreatic ductal adenocarcinoma	Homo sapiens (Human)	CVCL_0152
In Vitro Model	MIA PaCa-2	Pancreatic ductal adenocarcinoma	Homo sapiens (Human)	CVCL_0428
Result	We found an interesting finding that the 73-03 in combination with GCB can improve GCB efficacy and decrease PCa resistance, which induced apoptosis and mitochondrial damage through epigenetic inhibition of SPINK1 transcription by miR-421 up-regulation. This was the first study that used OA derivatives on GCB-resistant PCa cells, so this combined strategy warrants further investigation.

Pair Name	Oleanolic Acid, Sorafenib
Partner Name	Sorafenib
Disease Info	[ICD-11: 2C12]	Hepatocellular carcinoma		Investigative
Biological Phenomena	Induction-->Oxidative Stress
Gene Regulation	Up-regulation	Cleavage	CASP3	hsa836
	Up-regulation	Cleavage	CASP7	hsa840
	Up-regulation	Expression	ROS1	hsa6098
In Vitro Model	Huh-7	Adult hepatocellular carcinoma	Homo sapiens (Human)	CVCL_0336
In Vitro Model	Hep-G2	Hepatoblastoma	Homo sapiens (Human)	CVCL_0027
Result	OA represents a novel approach to increase the sensitivity of HCC cells to Sorafenib via oxidative stress.

Pair Name	Oleanolic Acid, Cisplatin
Partner Name	Cisplatin
Disease Info	[ICD-11: 2C25]	Lung cancer		Investigative
Biological Phenomena	Induction-->DNA damage
Gene Regulation	Down-regulation	Expression	ABCB1	hsa5243
	Down-regulation	Expression	AKT1	hsa207
	Down-regulation	Phosphorylation	AKT1	hsa207
	Up-regulation	Cleavage	CASP3	hsa836
	Down-regulation	Expression	ERCC1	hsa2067
	Down-regulation	Phosphorylation	MAPK1	hsa5594
	Down-regulation	Phosphorylation	NFKB1	hsa4790
	Up-regulation	Cleavage	PARP1	hsa142
	Down-regulation	Phosphorylation	STAT3	hsa6774
	Down-regulation	Expression	TXNRD1	hsa7296
In Vitro Model	Hep-G2	Hepatoblastoma	Homo sapiens (Human)	CVCL_0027
In Vitro Model	Huh-7	Adult hepatocellular carcinoma	Homo sapiens (Human)	CVCL_0336
Result	OLO-2 treatment also exhibited up to 4.6-fold selectivity against human lung adenocarcinoma cells. Taken together, the results of the present study shed light on the drug resistance-reversing effects of OLO-2 in lung cancer cells.

Pair Name	Oleanolic Acid, Doxorubicin
Partner Name	Doxorubicin
Disease Info	[ICD-11: 2C10]	Pancreatic cancer		Investigative
Biological Phenomena	Induction-->Apoptosis
Gene Regulation	Up-regulation	Expression	BAX	hsa581
	Down-regulation	Expression	BCL2	hsa596
	Down-regulation	Expression	BIRC5	hsa332
	Up-regulation	Expression	CASP3	hsa836
	Up-regulation	Expression	CASP8	hsa841
	Up-regulation	Expression	CASP9	hsa842
	Up-regulation	Expression	DIABLO	hsa56616
	Up-regulation	Expression	TP53	hsa7157
In Vitro Model	PANC-1	Pancreatic ductal adenocarcinoma	Homo sapiens (Human)	CVCL_0480
In Vitro Model	MRC-5	Healthy	Homo sapiens (Human)	CVCL_0440
Result	This approach may increase the efficiency of chemotherapy and reduce unintended side effects by lowering the prescribed dose of DOX.

Pair Name	Oleanolic Acid, Apatinib
Partner Name	Apatinib
Disease Info	[ICD-11: 2C12]	Hepatocellular carcinoma		Investigative
Biological Phenomena	Induction-->Oxidative Stress
In Vitro Model	H22	Hepatocellular carcinoma	Mus musculus (Mouse)	CVCL_H613
In Vivo Model	H22 tumor-burdened mice model was established in vivo.
Result	OA can treat apatinib induced liver injury in H22 Tumor-burdened mice by enhancing the suppresssive effect of apatinib on the growth of tumor.