Lupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growth

Ngo

et al. 2021

Journal of Chemistry

Clinacanthus nutans Lindau has been traditionally used for healing of bone fragility, but the mechanism of actions has not been clarified yet. In this study, the bone regeneration activity of lupeol derived from C. nutans was assessed using an in vitro model of osteoblast cells MC3T3-E1. The finding revealed that the compound was not significantly toxic to osteoblast cells at concentration of ≤40 μg/mL. Lupeol demonstrated the osteogenic activity through enhancement of alkaline phosphatase (ALP) of osteoblast cells up to 31.2%, 21%, and 12% at concentrations of 5, 10, and 20 µg/mL, respectively ( p < 0.05). Besides, the mineralization activity was increased up to 170, 230, 185, and 117% at concentration of 5, 10, 20, and 40 μg/mL, respectively ( p < 0.05). The marker genes related to osteoblast differentiation evaluated on the expression level in the presence of lupeol, including collagen I (col 1), osteopontin (opn), osterix (osx), and runx2, showed upregulated expression in all the test genes ( p < 0.05). The Western blot analysis demonstrated a clear effect of lupeol on expression of p38/p-p38, and ERK/p-ERK proteins involved in the MAPK signaling pathway. Thus, lupeol isolated from C. nutans exhibited the osteogenic activity by enhancing expression of important markers of osteogenesis, as well as affected the MAPK signaling pathway relating to osteoblast differentiation. This is the first report on the detailed mechanism of action of lupeol on bone regeneration and also explains for the traditional use of this medicinal plant for bone healing.

Section: Isolation Of Lupeolmentioning

confidence: 71%

Osteogenic Activity of Lupeol Isolated from Clinacanthus nutans Lindau: Activity and Mode of Action

Ngo

et al. 2021

Journal of Chemistry

“…However, Soujanya et al (2017) reported a retention time of 27.16, 28.57, and 28.15. The NMR spectral 1 H NMR spectrum and 13 CNMR (Figures 1.B and 1.C) respectively, revealed that the isolated compound is lupeol with the chemical structure as depicted in Figure 2.E (Silva 2017;Beserra et al 2018, Gurupriya et al 2018Balde et al 2019). The NMR spectroscopic, structural analyses confirmed that the isolated compound (1) is lupeol (Figures 1.A, 1.B, and 2.A-D) and the chemical structure, as illustrated in Figure 2.E.…”

Section: Resultsmentioning

confidence: 94%

Isolation of lupeol from Grewia lasiocarpa stem bark: Antibacterial, antioxidant, and cytotoxicity activities

et al. 2020

Abstract. Akwu N, Naidoo Y, Singh M, Thimmegowda SC, Nundkumar N, Lin J. 2020. Isolation of lupeol from Grewia lasiocarpa stem bark: Antibacterial, antioxidant, and cytotoxicity activities. Biodiversitas 21: 5684-5691. Lupeol a pentacyclic triterpenoid, was extracted from the stem bark of Grewia lasiocarpa. Stem bark was macerated with chloroform (CHCl3) at 25 ± 2°C, and then purified using a silica gel column. The mobile phase was hexane (100%) and hexane: ethyl acetate (80:20) as the mobile phase. The structure of lupeol was identified by 1HNMR, and 13C NMR spectral data, compared with reported data. The antibacterial, antioxidant and cytotoxicity activities of lupeol were evaluated using agar-well diffusion against six clinic bacteria isolates, namely Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Klebsiella pneumoniae (ATCC 314588), and Salmonella typhimurium (ATCC 14026) Gram-positive bacteria: Staphylococcus aureus (ATCC 25923), methicillin-resistant Staphylococcus aureus (MRSA) (ATCC BAA-1683). The antioxidants assays were performed using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP). Cytotoxicity activity was carried out by MTT (3-(4,5-dimethylthiazol)-2,5-diphenyl tetrazolium bromide) assay was carried out against HEK293 (human embryonic kidney), HeLa (cervical carcinoma), and MCF-7 (breast adenocarcinoma) cell lines. The concentration range of lupeol was 240-15 µg/mL. Lupeol at the concentration of 240 and 120 µg/mL have no antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) (ATCC BAA-1683). The antioxidant activity was dose-dependent, while cytotoxic activities were observed in HEK293, HeLa, and MCF-7 cells. This study was the first report on the extraction, isolation, and biological activities of lupeol, from the stem bark of G. lasiocarpa.

“…Lupeol was isolated from Maytenus salicifolia Reissek (Celastraceae) hexanic extract as described in details by Magalhães et al (2011) and esteri cation with appropriate reagents gave rise to LS was performed as described in details by Silva et al (2017). The oral gastroprotective dose of LS of 1 mg/kg was chosen to be employed in this study based in ndings from Somensi et al (2021).…”

Section: Obtaining Lupeol Stearate (Ls) and Choice Of Dosementioning

confidence: 99%

Lupeol Stearate Accelerates Healing and Prevents Recurrence of Gastric Ulcer in Rodents

Somensi¹,

Costa²,

Boeing³

et al. 2021

Preprint

Self Cite

The gastric healing and gastric ulcer recurrence preventive effect of Lupeol Stearate (LS) was measured in this study. To evaluate the gastric healing effect, rats were submitted to the 80% acetic acid-induced ulcer model and treated with vehicle (1 ml/kg, p.o.), LS (1 mg/kg, p.o.) or omeprazole (20 mg/kg, p.o.) twice a day for seven days. The gastric injury was evaluated macroscopically, histologically and histochemical; and biochemical parameters were also quantified. To evaluate the effects of LS on gastric ulcer recurrence, mice were ulcerated by gastric instillation of 10% acetic acid and treated with vehicle (1 ml/kg, p.o.), LS (1 mg/kg, p.o.) or ranitidine (20 mg/kg, p.o.) twice a day for ten days. Then, the ulcer recurrence in these animals was induced by IL- 1β (1 µg/kg i.p) at five day after the end of the treatment period. The area of the lesion recurred were measured, as well as the activity of myeloperoxidase and TNF levels. Oral treatment with LS accelerated gastric healing by 63% compared to the group treated with vehicle, which was also evidenced by histological improvement and increased production of mucin in the gastric epithelium. LS elevated the activity of the glutathione S-transferase and reduced the activity of myeloperoxidase, but did not change the levels of reduced glutathione or the activity of superoxide dismutase and catalase at the ulcer site in rats. Regarding the recurrence, the LS treatment reduced the recurred lesions, reducing MPO activity but not TNF levels at ulcer site. It can be concluded that LS promotes the healing of gastric lesions by favoring the mucus production and reducing the migration of neutrophils and that it can reduce the severity of the ulcer recurrence.