Lupeol

426.72

426.72

208-889-9

O268W13H3O

90487

Needles from alcohol, acetone

29061990

20.23000

10.98

white powder

0.9457 g/cm³ @ Temp: 18 °C

216 °C

482.1°C (rough estimate)

216.9±12.4 °C

1.516

Very soluble in ethanol, acetone, chloroform

2-8°C

5.03X10-11 mm Hg at 25 °C (est)

D20 +27.2° (c = 4.8 in chloroform)

Henry's Law constant = 1.46X10-4 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 9.11X10-11 cu cm/molec-sec at 25 °C (est)|Ozone radical reaction rate constant = 1.2X10-17 cu cm/molec-sec at 25 °C (est)

426.72

NONH for all modes of transport

2

24/25

OK5763000

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 4 companies from 2 notifications to the ECHA C&L Inventory.

In in vivo studies, using an orthotopic metastatic nude mouse model of oral tongue squamous cell carcinoma, lupeol at a dose of 2 mg/animal dramatically decreased tumor volume and suppressed local metastasis, which was more effective than cisplatin alone. Lupeol exerted a significant synergistic cytotoxic effect when combined with low-dose cisplatin without side effects....|... The present study ... investigated the effects of lupeol on 7,12-dimethylbenz[a]anthracene (DMBA), induced DNA strand breaks in mouse skin, using an alkaline unwinding assay. Increasing doses of lupeol (50-200 ug/mouse) were given topically, prior or after the single topical application of DMBA (100 ug/mouse) with the sampling time of 24, 48, 72 and 96 hr, respectively. Both pre and post treatment of lupeol showed significant (p<0.001) preventive effects in DMBA induced DNA strand breaks in dose and time dependent manner. The pre-treatment of lupeol at the dose of 200 ug/mouse showed 56.05% prevention, and post-treatment at the same dose showed 43.26% prevention, at 96 hr time interval, against DMBA induced DNA strand breakage...|... The antigenotoxic potential of lupeol, a triterpene, and mango pulp extract (MPE) was evaluated in Swiss albino mice. Benzo[a]pyrene (B[a]P), a well-known mutagen, was given at a single dose of 100 mg/kg body weight intraperitoneally. Pretreatment with lupeol (1 mg/animal) and MPE (1 mL, 20%) was given through oral intubation for 7 days prior to B[a]P administration. Animals from all the groups were killed at sampling time of 24 hr and their bone marrow tissue was analyzed for chromosomal damage and micronuclei induction. In B[a]P-treated animals a significant induction of chromosomal aberration and micronuclei was recorded, with a decrease in mitotic index. In lupeol- or MPE-supplemented groups, a significant decrease in B[a]P-induced clastogenicity was recorded. The incidence of aberrant cells and micronuclei was found to be reduced by both lupeol and MPE when compared to the B[a]P-treated group. The anti-cytotoxic effects of lupeol or MPE were also evident, as observed by significant increase in mitotic index. Thus, results of the present investigation revealed that lupeol and MPE have protective effects against B[a]P-induced clastogenic changes in Swiss albino mice.|To investigate antioxidant potential of lupeol/mango pulp extract (MPE) in testosterone induced oxidative stress in prostate of male Swiss albino mice. .... lupeol (1 mg/animal) and MPE (1 mL [20% w/v]/animal) was given /orally/ to animals along with subcutaneous injection of testosterone (5 mg/kg body weight) consecutively for 15 days. At the end of the study period, the prostate was dissected out for the determination of reactive oxygen species (ROS) levels, lipid peroxidation and antioxidant enzymes status (catalase, superoxide dismutase, glutathione reductase, glutathione-S-transferase). RESULTS: In testosterone treated animals, increased ROS resulted in depletion of antioxidant enzymes and increase in lipid peroxidation in mouse prostate. However, lupeol/MPE treatment resulted in a decrease in ROS levels with restoration in the levels of lipid peroxidation and antioxidant enzymes. ... The results of the present study demonstrate that lupeol/MPE are effective in combating oxidative stress-induced cellular injury of mouse prostate...|For more Interactions (Complete) data for LUPEOL (14 total), please visit the HSDB record page.

LD50 Rat oral >2 g/kg /from table/|LD50 Mouse oral >2 g/kg /from table/

Abundant plant triterpene. Occurs in the skin of lupin seeds, in chicle, in the latex of fir trees and of rubber plants. Was detected in cocoons of Bombyx mori

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

Lupeol, a triterpene found in fruits and vegetables, selectively induced substantial head and neck squamous cell carcinoma (HNSCC) cell death but exhibited only a minimal effect on a normal tongue fibroblast cell line in vitro. Down-regulation of NF-kappaB was identified as the major mechanism of the anticancer properties of lupeol against HNSCC. Lupeol alone was not only found to suppress tumor growth but also to impair HNSCC cell invasion by reversal of the NF-kappaB-dependent epithelial-to-mesenchymal transition. Lupeol exerted a synergistic effect with cisplatin, resulting in chemosensitization of HNSCC cell lines with high NF-kappaB activity in vitro.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/ALTERNATIVE and IN VITRO TESTS/ ... Human pancreatic adenocarcinoma cells AsPC-1 were used to investigate the effect of Lupeol on cell growth and its effects on the modulation of multiple Ras-induced signaling pathways. Lupeol caused a dose-dependent inhibition of cell growth as assessed by MTT assay and induction of apoptosis as assessed by flow cytometry, fluorescence microscopy and western blotting. Lupeol treatment to cells was found to significantly reduce the expression of Ras oncoprotein and modulate the protein expression of various signaling molecules involved in PKCalpha/ODC, PI3K/Akt and MAPKs pathways along with a significant reduction in the activation of NFkappaB signaling pathway. ...|/OTHER TOXICITY INFORMATION/ DNA topoisomerases (Topos) are enzymes that play a crucial role in DNA metabolism events such as replication, transcription, recombination, and chromosome segregation at mitosis. Thus, Topo inhibitors could be expected to have antitumor effects. Naturally occurring lupane- and oleanane-type triterpenoids isolated from the bark of Phyllanthus flexuosus were screened for human Topos I and II inhibitory activities. Olean-12-en-3 beta,15 alpha-diol (1), olean-12-en-3 beta,15 alpha,24-triol (3), lupeol (4), and betulin (6) were found to be selective catalytic inhibitors of human Topo II activity with IC(50) values in the range of 10-39 uM.

lup-20(29)-en-3-ol

Abundant plant triterpene. Occurs in the skin of lupin seeds, in chicle, in the latex of fir trees and of rubber plants. Was detected in cocoons of Bombyx mori

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]