Lupeol

Names

[ CAS No. ]:
545-47-1

[ Name ]:
Lupeol

[Synonym ]:
Lup-20(29)-en-3-ol, (3β)-
Cautchicol
Fagarsterol
MFCD00017351
Fagarasterol
monogynolb
Clerodol
Lup-20(29)-en-3β-ol (8CI)
Lupeol
b-viscol
MONOGYNOL
(3b)-Lup-20(29)-en-3-ol
Monogynol B
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethylicosahydro-1H-cyclopenta[a]chrysen-9-ol
Lup-20(29)-en-3b-ol
(3β)-Lup-20(29)-en-3-ol
β-Viscol
Lupenol
EINECS 208-889-9
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexaméthyl-1-(1-propèn-2-yl)icosahydro-1H-cyclopenta[a]chrysén-9-ol
Lup-20(29)-en-3-β-ol (8CI)

Biological Activity

[Description]:

Lupeol is a novel androgen receptor inhibitor.

[Related Catalog]:

Signaling Pathways >> Others >> Androgen Receptor

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

[Target]

Androgen receptor[1]

[In Vitro]

Lupeol, an effective AR inhibitor, can be developed as a potential agent to treat human prostate cancer (CaP). Lupeol (10–50 μM) treatment for 48 h results in a dose-dependent growth inhibition of androgen-dependent phenotype (ADPC) cells viz., LAPC4 and LNCaP cells with an IC50 of 15.9 and 17.3 μM, respectively. Lupeol also inhibits the growth of 22Rν_1 with an IC50 of 19.1 μM. Further, Lupeol inhibits the growth of C4-2b cells with an IC50 of 25 μM. Lupeol has the potential to inhibit the growth of CaP cells of both ADPC and CRPC phenotype. Androgens by activating AR are known to drive the growth of CaP cells[1].

[In Vivo]

Lupeol is an effective agent that has the potential to inhibit the tumorigenicity of CaP cells in vivo. At the conclusion of the study on day 56, the total circulating serum-PSA levels (secreted by the implanted tumor cells) are measured. At 56thday post-implantation, PSA levels are observed between 11.95-12.79 ng/mL in control animals with LNCaP-tumors and C4-2b-tumors, respectively. However, Lupeol-treated counterpart animals exhibits reduced serum-PSA levels in a range of 4.25-7.09 ng/mL. Tumor tissues of animals receiving Lupeol treatment exhibits reduced serum-PSA levels as compared to control[1].

[Cell Assay]

LAPC4 (wild-functional AR/ADPC); LNCaP (mutant-functional AR/ADPC); 22Rν1 (mutant-functional AR/androgen-independent but responsive); C4-2b cells (mutant-functional AR/CRPC) and PC-3 and DU-145 (lack of endogenous AR) are grown under standard cell culture conditions at 37°C and 5% CO2 environment. The cells (60-70% confluent) are treated with Lupeol (10-50 μM) for 48 h in complete growth medium. For combination set of experiments, cells are treated with either agonistic androgen-analogue R1881 (1 nM), or antagonist Bicalutamide (10 μM), and/or combination (R1881+Lupeol) for 48 h. After incubation for specified times at 37°C, MTT assay is performed. For sensitization studies, hormone refractory C4-2b cells are treated with Lupeol for 24 h. After 24 h, cells are incubated with Bicalutamide (10 μM) for further 24 h. Cells are assessed for viability[1].

[Animal admin]

Mice[1] Tumor studies are conducted in athymic nude mice and two cohorts of animals are created. 3×106 of cells are injected subcutaneously in the right flanks of each mouse. Each cohort receive a specific cell type either LNCaP or C4-2b. One week post-implantation, twenty mice (with visible tumors) in each cohort are randomly divided into two groups, with 10 animals in each group. The first group of animals receive intraperitoneal (i.p.) administration of corn oil (100 μL) and served as control. The second group of animals receive i.p. administration of Lupeol (40 mg/kg in 100 μL of corn oil) three times/week. Body weights and tumor volumes are recorded. All animals of group 1 and group 2 are sacrificed when tumors cross a pre-set endpoint volume of 1,000 mm3.

[References]

[1]. Siddique HR, et al. Lupeol, a novel androgen receptor inhibitor: implications in prostate cancer therapy. Clin Cancer Res. 2011 Aug 15;17(16):5379-91.

[Related Small Molecules]

ARN-509 | Dehydroepiandrosterone | Flutamide | ODM-201 | Danazol | 3,3'-Diindolylmethane | AZD3514 | RAD140 | BMS-564929 | GLPG0492 | Cyproterone acetate | LGD-4033 | Andarine | MK-0773 | ORM-15341

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
488.1±14.0 °C at 760 mmHg

[ Melting Point ]:
215-216ºC

[ Molecular Formula ]:
C₃₀H₅₀O

[ Molecular Weight ]:
426.717

[ Flash Point ]:
216.9±12.4 °C

[ Exact Mass ]:
426.386169

[ PSA ]:
20.23000

[ LogP ]:
10.98

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.516

[ Storage condition ]:
2-8°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
OK5763000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Analysis of triterpenoids and phytosterols in vegetables by thin-layer chromatography coupled to tandem mass spectrometry.

J. Chromatogr. A. 1381 , 229-38, (2015)

Three TLC methods were used for an initial screening of some common plant triterpenoids and phytosterols in cuticular wax extracts of different vegetables (zucchini, eggplant, tomato, red pepper, mang...

Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.

Bioorg. Med. Chem. 18 , 2225-31, (2010)

There are many of pathogen parasite species with different susceptibility profile to antiparasitic drugs. Unfortunately, almost QSAR models predict the biological activity of drugs against only one pa...

Negative regulation of signal transducer and activator of transcription-3 signalling cascade by lupeol inhibits growth and induces apoptosis in hepatocellular carcinoma cells.

Br. J. Cancer 111(7) , 1327-37, (2014)

Constitutive activation of signal transducer and activator of transcription signalling 3 (STAT3) has been linked with survival, proliferation and angiogenesis in a wide variety of malignancies includi...