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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H50O
Molecular Weight 426.7174
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUPEOL

SMILES

[H][C@]12[C@@H](CC[C@]1(C)CC[C@]3(C)[C@]2([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(C)=C

InChI

InChIKey=MQYXUWHLBZFQQO-QGTGJCAVSA-N
InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H50O
Molecular Weight 426.7174
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Lupeol, a biologically active dietary triterpenoid, is found in many medicinal plants and different fruits such as olives, mangos, and strawberries. Lupeol exhibits a wide spectrum of pharmacological properties including anti-inflammatory, anti-cancer, anti-diabetic, anti-microbial, cardioprotective, and hepatoprotective activities. Lupeol inhibits LPS-induced microglial neuroinflammation via the P38-MAPK and JNK pathways and has therapeutic potential to treat various neuroinflammatory disorders. Lupeol possesses antiskin tumor-promoting effects in CD-1 mouse and inhibits conventional as well as novel biomarkers of tumor promotion. It strongly suppressed lipogenesis by modulating the IGF-1R/phosphatidylinositide 3 kinase (PI3K)/Akt/sterol response element-binding protein-1 (SREBP-1) signaling pathway in SEB-1 sebocytes, and reduced inflammation by suppressing the NF-κB pathway in SEB-1 sebocytes and HaCaT keratinocytes. Lupeol exhibited a marginal effect on cell viability and may have modulated dyskeratosis of the epidermis. These results demonstrate the clinical feasibility of applying lupeol for the treatment of acne.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
2% cream two times per day for 4 weeks
Route of Administration: Topical
In Vitro Use Guide
To examine whether lupeol modulates lipid synthesis in human SEB-1 sebocytes, intracellular neutral lipid content was analyzed by Nile Red staining after treating the cells with different concentrations of lupeol. Lupeol significantly decreased lipid by 58% in SEB-1 sebocytes treated with 20 uM lupeol.
Substance Class Chemical
Record UNII
O268W13H3O
Record Status Validated (UNII)
Record Version