DEHYDROCOSTUS LACTONE, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H18O2
Molecular Weight	230.3022
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DEHYDROCOSTUS LACTONE, (-)-

Structure Search

SMILES

[H][C@@]12CCC(=C)[C@]1([H])[C@@]3([H])OC(=O)C(=C)[C@]3([H])CCC2=C

InChI

InChIKey=NETSQGRTUNRXEO-XUXIUFHCSA-N

InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H18O2
Molecular Weight	230.3022
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27545438
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25625870

Dehydrocostus lactone (DHL) is a sesquiterpene lactone originally found in species of Saussurea lappa C.B. Clarke (Compositae). DHL exhibits antibiotic, antioxidative, anti-angiogenic, anticancer chemotherapeutic, and chemopreventive activities. DHL inhibited cancer cell lines throughout PI3K/Akt Signaling Pathway, through inhibiting Wnt/β-catenin pathway. One of the latest investigation showed, that DHL inhibited the activity of cytosolic thioredoxin reductase (TrxR1) in HeLa cells, which elicited an accumulation of reactive oxygen species (ROS) in cells and a collapse of the intracellular redox equilibrium and eventually induced apoptosis of HeLa cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26017248	Inhibitor 8297
Thioredoxin reductase 1 2 Target ID: CHEMBL1927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27545438	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27545438	Primary	Basic research	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25850883	Primary	Basic research	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18848968	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Dehydrocostus Lactone Inhibits Proliferation, Antiapoptosis, and Invasion of Cervical Cancer Cells Through PI3K/Akt Signaling Pathway.	2015 Sep	26017248
Bioassay-guided isolation of dehydrocostus lactone from Saussurea lappa: A new targeted cytosolic thioredoxin reductase anticancer agent.	2016 Oct 1	27545438

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Dehydrocostus lactone (DHC) inhibited human cervical carcinoma HeLa cells with an IC50 of ∼12.00 μM but displayed less cytotoxicity to human immortalized normal liver cells L02. DHC killed HeLa cells through induction of apoptosis. DHC inhibited the activity of TrxR1 in HeLa cells, which elicited an accumulation of reactive oxygen species (ROS) in cells and a collapse of the intracellular redox equilibrium and eventually induced apoptosis of HeLa cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:05:26 UTC 2023` Edited by `admin` on `Fri Dec 15 20:05:26 UTC 2023`
Record UNII	71TRF5K040
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEHYDROCOSTUS LACTONE, (-)-

Common Name

English

COSTUS LACTONE, DEHYDRO-

Common Name

English

DEHYDROCOSTUS LACTONE

Common Name

English

EPILIGULYL OXIDE

Common Name

English

(-)-DEHYDROCOSTUS LACTONE

Common Name

English

AZULENO(4,5-B)FURAN-2(3H)-ONE, DECAHYDRO-3,6,9-TRIS(METHYLENE)-, (3AS-(3A.ALPHA.,6A.ALPHA.,9A.ALPHA.,9B.BETA.))-

Common Name

English

AZULENO(4,5-B)FURAN-2(3H)-ONE, DECAHYDRO-3,6,9-TRIS(METHYLENE)-, (3AS,6AR,9AR,9BS)-

Common Name

English

GUAIA-4(15),10(14),11(13)-TRIEN-12-OIC ACID, 6.ALPHA.-HYDROXY-, .GAMMA.-LACTONE

Common Name

English

Code System Code Type Description

FDA UNII

71TRF5K040