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
[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
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 |
|---|---|---|
| Bowdenol, a new 2,3-dihydrobenzofuran constituent from Bowdichia virgilioides. | 2001 |
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| Anti-inflammatory effect of Pimenta racemosa var. ozua and isolation of the triterpene lupeol. | 2001 Apr |
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| Lupeol esters from the twig bark of Japanese pear (Pyrus serotina Rehd.) cv. Shinko. | 2001 May |
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| New insights into the mechanism of action of the anti-inflammatory triterpene lupeol. | 2001 Nov |
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| Two new triterpene esters from the twigs of Brachylaena ramiflora from the Madagascar rainforest. | 2002 Aug |
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| A bis-bithiophene from Tridax procumbens L. (Asteraceae). | 2002 Aug |
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| [A review of the study on kudingcha]. | 2002 Feb |
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| Two novel long-chain alkanoic acid esters of lupeol from alecrim-propolis. | 2002 Mar |
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| [Studies on chemical constituents of Caesalpinia decapetala (Roth) Alston]. | 2002 Nov |
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| [Studies on chemical constituents of Salvia roborowskii Maxim]. | 2002 Nov |
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| Pentacyclic triterpenoids from Ilex macropoda. | 2002 Oct |
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| Antiangiogenic activity of lupeol from Bombax ceiba. | 2003 Apr |
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| A new pterocarpan, (-)-maackiain sulfate, from the roots of Sophora subprostrata. | 2003 Dec |
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| Triterpenoids from the stembark of Pyrus communis. | 2003 Dec |
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| Hypotensive activity and toxicology of constituents from Bombax ceiba stem bark. | 2003 Jan |
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| Dihydrobetulinic acid induces apoptosis in Leishmania donovani by targeting DNA topoisomerase I and II: implications in antileishmanial therapy. | 2003 Jan-Feb |
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| [Chemical constituents from the leaves of Dalbergia hainanensis]. | 2003 Jun |
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| Chemical composition of Tipuana tipu, a source for tropical honey bee products. | 2003 Mar-Apr |
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| Antiprotease effect of anti-inflammatory lupeol esters. | 2003 Oct |
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| [Studies on chemical constituents in leafs of Ilex kudingcha]. | 2003 Sep |
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| Cytotoxic lupane-type triterpenoids from Acacia mellifera. | 2004 Apr |
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| Potential anti-tumor promoting activity of lupane-type triterpenoids from the stem bark of Glochidion zeylanicum and Phyllanthus flexuosus. | 2004 Dec |
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| Glycosides from Grewia damine and Filicium decipiens. | 2004 Dec |
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| New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase beta. | 2004 Dec 1 |
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| Characterization of archaeological frankincense by gas chromatography-mass spectrometry. | 2004 Jan 16 |
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| Prolyl endopeptidase inhibitors from Syzygium samarangense (Blume) Merr. & L. M. Perry. | 2004 Jan-Feb |
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| Lignans from the roots of Echinops giganteus. | 2004 Jul |
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| A new 3,4-seco-lupane derivative from Lasianthus gardneri. | 2004 May |
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| New cytotoxic terpenoids from the wood of Vepris punctata from the Madagascar Rainforest. | 2004 May |
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| Furanolabdane diterpenes from Hypoestes purpurea. | 2004 Nov |
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| Antibacterial activity of naphthoquinones and triterpenoids from Euclea natalensis root bark. | 2004 Nov |
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| A new glucoceramide from the watermelon Begonia, Pellionia repens. | 2004 Oct |
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| A new lignan glycoside and phenylethanoid glycosides from Strobilanthes cusia BREMEK. | 2004 Oct |
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| A new sesquiterpene-coumarin ether and a new abietane diterpene and their effects as inhibitors of P-glycoprotein. | 2004 Sep |
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| Allanxanthone B, a polyisoprenylated xanthone from the stem bark of Allanblackia monticola Staner L.C. | 2004 Sep |
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| Caesaldecan, a cassane diterpenoid from the leaves of Caesalpinia decapetala. | 2005 Apr |
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| [Studies on chemical constituents from Salvia roborowskii Maxim]. | 2005 Feb |
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| A new and known cytotoxic aryltetralin-type lignans from stems of Bursera graveolens. | 2005 Feb |
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| Two diterpenes and three diterpene glucosides from Phlogacanthus curviflorus. | 2005 Jan |
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| Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L. | 2005 Jan |
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| A new triterpenoid ester from the fruits of Bruguiera parviflora. | 2005 Jan |
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| A new flavonol glycoside derivative from leaves of Moldenhawera nutans. | 2005 Jan-Feb |
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| Cardioprotective effect of pentacyclic triterpene, lupeol and its ester on cyclophosphamide-induced oxidative stress. | 2005 Jun |
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| Antimicrobial terpenoids from Pterocarpus indicus. | 2005 Jun |
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| Prenylated chalcones, flavone and other constituents of the twigs of Dorstenia angusticornis and Dorstenia barteri var. subtriangularis. | 2005 Mar |
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| Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis. | 2005 Mar |
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| An antibacterial biphenyl derivative from Garcinia bancana MIQ. | 2005 Mar |
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| New indolopyridoquinazoline, benzo[c]phenanthridines and cytotoxic constituents from Zanthoxylum integrifoliolum. | 2005 May |
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| Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis. | 2005 May |
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| Lupeol, a fruit and vegetable based triterpene, induces apoptotic death of human pancreatic adenocarcinoma cells via inhibition of Ras signaling pathway. | 2005 Nov |
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.
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| Code System | Code | Type | Description | ||
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LUPEOL
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6570
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7687
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C010480
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259846
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DTXSID901025006
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m6938
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90487
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208-889-9
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DB12622
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545-47-1
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O268W13H3O
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SUBSTANCE RECORD
