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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H16O5
Molecular Weight 276.2845
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROMETHYSTICIN

SMILES

COC1=CC(=O)O[C@@H](CCC2=CC=C3OCOC3=C2)C1

InChI

InChIKey=RSIWXFIBHXYNFM-NSHDSACASA-N
InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1

HIDE SMILES / InChI

Description

Dihydromethysticin is one of the six major kavalactones found in the roots of kava plant. Dihydromethysticin was found to be very effective in producing analgesia in the tail immersion test. Dihydromethysticin kavalactone induces apoptosis in osteosarcoma cells through modulation of PI3K/Akt pathway, disruption of mitochondrial membrane potential and inducing cell cycle arrest. Dihydromethysticin was identified as a promising lung cancer chemopreventive agent. Low concentrations of the kavalactone (+)-dihydromethysticin enhanced the binding of ligands to the GABAA receptors on freeze-dried rat cortex preparations.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.5 µM [IC50]
0.43 µM [IC50]
13.35 µM [IC50]
14.8 µM [IC50]
37.03 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 1 mg/g of diet
Route of Administration: Oral
In Vitro Use Guide
Dihydromethysticin induced dose-dependent as well as time-dependent antiproliferative effects against MG-63 cell growth. Cell death and apoptotic body formation was noticed followed dihydromethysticin treatment at various doses. The percentage of apoptotic cells (early apoptosis+late apoptosis) increased from 6.63% in untreated control to 23.92%, 23.81% and 93.9% in 25uM, 75uM and 100uM dihydromethysticin-treated cells respectively.