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
SMILES
CC(=C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12
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
| Molecular Formula | C30H50O |
| Molecular Weight | 426.7174 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lupeol, a fruit and vegetable based triterpene, induces apoptotic death of human pancreatic adenocarcinoma cells via inhibition of Ras signaling pathway. | 2005-11 |
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| Cardioprotective effect of pentacyclic triterpene, lupeol and its ester on cyclophosphamide-induced oxidative stress. | 2005-06 |
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| Antimicrobial terpenoids from Pterocarpus indicus. | 2005-06 |
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| New indolopyridoquinazoline, benzo[c]phenanthridines and cytotoxic constituents from Zanthoxylum integrifoliolum. | 2005-05 |
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| Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis. | 2005-05 |
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| Caesaldecan, a cassane diterpenoid from the leaves of Caesalpinia decapetala. | 2005-04 |
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| A new flavonol glycoside derivative from leaves of Moldenhawera nutans. | 2005-03-25 |
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| Prenylated chalcones, flavone and other constituents of the twigs of Dorstenia angusticornis and Dorstenia barteri var. subtriangularis. | 2005-03 |
|
| Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis. | 2005-03 |
|
| An antibacterial biphenyl derivative from Garcinia bancana MIQ. | 2005-03 |
|
| [Studies on chemical constituents from Salvia roborowskii Maxim]. | 2005-02 |
|
| A new and known cytotoxic aryltetralin-type lignans from stems of Bursera graveolens. | 2005-02 |
|
| Two diterpenes and three diterpene glucosides from Phlogacanthus curviflorus. | 2005-01 |
|
| Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L. | 2005-01 |
|
| A new triterpenoid ester from the fruits of Bruguiera parviflora. | 2005-01 |
|
| New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta. | 2004-12-01 |
|
| Potential anti-tumor promoting activity of lupane-type triterpenoids from the stem bark of Glochidion zeylanicum and Phyllanthus flexuosus. | 2004-12 |
|
| Glycosides from Grewia damine and Filicium decipiens. | 2004-12 |
|
| Furanolabdane diterpenes from Hypoestes purpurea. | 2004-11 |
|
| Antibacterial activity of naphthoquinones and triterpenoids from Euclea natalensis root bark. | 2004-11 |
|
| A new glucoceramide from the watermelon Begonia, Pellionia repens. | 2004-10 |
|
| A new lignan glycoside and phenylethanoid glycosides from Strobilanthes cusia BREMEK. | 2004-10 |
|
| Apoptotic activity of betulinic acid derivatives on murine melanoma B16 cell line. | 2004-09-13 |
|
| A new sesquiterpene-coumarin ether and a new abietane diterpene and their effects as inhibitors of P-glycoprotein. | 2004-09 |
|
| Allanxanthone B, a polyisoprenylated xanthone from the stem bark of Allanblackia monticola Staner L.C. | 2004-09 |
|
| New cycloartenol esters from Ixora coccinea. | 2004-08 |
|
| Anti-inflammatory constituents of Mortonia greggii Gray. | 2004-07-10 |
|
| Lupeol modulates NF-kappaB and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice. | 2004-07-01 |
|
| Effect of lupeol isolated from Crataeva nurvala Buch.-Ham. stem bark extract against free radical induced nephrotoxicity in rats. | 2004-07 |
|
| Lignans from the roots of Echinops giganteus. | 2004-07 |
|
| A new 3,4-seco-lupane derivative from Lasianthus gardneri. | 2004-05 |
|
| New cytotoxic terpenoids from the wood of Vepris punctata from the Madagascar Rainforest. | 2004-05 |
|
| Cytotoxic lupane-type triterpenoids from Acacia mellifera. | 2004-04 |
|
| Prolyl endopeptidase inhibitors from Syzygium samarangense (Blume) Merr. & L. M. Perry. | 2004-03-17 |
|
| Lipoxygenase inhibition by anadanthoflavone, a new flavonoid from the aerial parts of Anadenanthera colubrina. | 2004-03 |
|
| Cytotoxic activity of five compounds isolated from Colombian plants. | 2004-03 |
|
| Induction of apoptosis by lupeol isolated from mokumen (Gossampinus malabarica L. Merr) in human promyelotic leukemia HL-60 cells. | 2004-02 |
|
| Characterization of archaeological frankincense by gas chromatography-mass spectrometry. | 2004-01-16 |
|
| Erythrocyte membrane modifying agents and the inhibition of Plasmodium falciparum growth: structure-activity relationships for betulinic acid analogues. | 2004-01-02 |
|
| A new pterocarpan, (-)-maackiain sulfate, from the roots of Sophora subprostrata. | 2003-12 |
|
| Antimicrobial and cytotoxicity evaluation of Buchholzia coriacea stem bark. | 2003-12 |
|
| Triterpenoids from the stembark of Pyrus communis. | 2003-12 |
|
| Antiprotease effect of anti-inflammatory lupeol esters. | 2003-10 |
|
| [Studies on chemical constituents in leafs of Ilex kudingcha]. | 2003-09 |
|
| [Studies on the chemical constituents of Ampelopsis humulifolia var. heterophylla (Thunb.) K. Koch]. | 2003-09 |
|
| Lupeol, a triterpene, prevents free radical mediated macromolecular damage and alleviates benzoyl peroxide induced biochemical alterations in murine skin. | 2003-08 |
|
| [Chemical constituents from the leaves of Dalbergia hainanensis]. | 2003-06 |
|
| [Studies on chemical constituents of Caesalpinia decapetala (Roth) Alston]. | 2002-11 |
|
| [Studies on chemical constituents of Salvia roborowskii Maxim]. | 2002-11 |
|
| [A review of the study on kudingcha]. | 2002-02 |
Patents
Sample Use Guides
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
Created
by
admin
on
Edited
Mon Mar 31 20:06:22 GMT 2025
by
admin
on
Mon Mar 31 20:06:22 GMT 2025
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| Record UNII |
O268W13H3O
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| Record Status |
Validated (UNII)
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| Record Version |
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LUPEOL
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m6938
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208-889-9
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O268W13H3O
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
CALENDULA OFFICINALIS FLOWER terpenoid
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