64181-07-3Relevant articles and documents
Synthesis of lupeol derivatives and their antileishmanial and antitrypanosomal activities
Machado, Vanessa R.,Sandjo, Louis P.,Pinheiro, Giovanni L.,Moraes, Milene H.,Steindel, Mario,Pizzolatti, Moacir G.,Biavatti, Maique W.
, p. 275 - 281 (2017/10/06)
The natural product lupeol 1 was isolated from aerial parts of Vernonia scorpioides with satisfactory yield, which made it viable to be used as starting material in semisynthetic approach. Ten lupeol derivatives 2–11 were prepared by classical procedures. Including, five new esters derivatives 7–11, which were obtained by structural modifications in the isopropylidene fragment. All semisynthetic compounds and lupeol 1–11 were confirmed by 1H NMR, 13C NMR and HRMS. Their antiprotozoal activity was evaluated in vitro against L. amazonensis and T. cruzi. Derivative 6 showed the best antitrypanosomal activity (IC50?=?12.48?μg/mL) and the lowest cytotoxic derivative (CC50?=?161.50?μg/mL). The mechanism of action of the most active derivatives (4, 6 and 11) is not dependent from the enzyme trypanothione reductase.
Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors
Bhandari, Pamita,Patel, Neeraj Kumar,Bhutani, Kamlesh Kumar
, p. 3596 - 3599 (2014/07/22)
A series of heterocyclic derivatives including indoles, pyrazines along with oximes and esters were synthesized from lupeol and evaluated for anti-inflammatory activity through inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW 264.7 and J774A.1 cells. All the synthesized molecules of lupeol were found to be more active in inhibiting NO production with an IC50 of 18.4-48.7 μM in both the cell lines when compared to the specific nitric oxide synthase (NOS) inhibitor, L-NAME (IC50 = 69.21 and 73.18 μM on RAW 264.7 and J774A.1 cells, respectively). The halogen substitution at phenyl ring of indole moiety leads to potent inhibition of NO production with half maximal concentration ranging from 18.4 to 41.7 μM. Furthermore, alkyl (11, 12) and p-bromo/iodo (15, 16) substituted compounds at a concentration of 20 μg/mL exhibited mild inhibition (29-42%) of LPS-induced tumor necrosis factor alpha (TNF-α) and weak inhibition (10-22%) towards interleukin 1-beta (IL-1β) production in both the cell lines. All the derivatives were found to be non-cytotoxic when tested at their IC50 (μM). These findings suggest that the derivatives of lupeol could be a lead to potent inhibitors of NO.
Novel class of hybrid natural products derived from lupeol (Part-Iii) pharmacomodulation on lupeol skeleton: Design, synthesis and biological evaluation of novel lupeol derivatives as antimalarial agents
Mishra, Namita,Kumar, Satish,Khare, Pritibha,Raj, Kanwal
, p. 97 - 110 (2019/01/21)
Novel hybrid lupeol heterocyclics (quinoline, pyrimidine and pyrazole) were prepared. Triterpene lupeol 1 isolated from plant Crataeva nurvala was chemically modified and hybrid natural products 2a, 3a-p, 4a-p, 5a-b, 6e, 7a-b, 8a-c, 9 and 10 were evaluated for antimalarial activity in vitro. Compounds 3g, 3e, 3i, 4e, 4f, 5e, 7b and 8c showed MIC against chloroquine sensitive 3D7 strain of P. falciparum at 10 μg/ml.
