1617-68-1Relevant articles and documents
Design and synthesis of new lupeol derivatives and their α-glucosidase inhibitory and cytotoxic activities
Phan, Hoang-Vinh-Truong,Duong, Thuc-Huy,Pham, Duc-Dung,Pham, Hoang-Anh,Nguyen, Van-Kieu,Nguyen, Thi-Phuong,Nguyen, Huu-Hung,Nguyen, Ngoc-Hong,Sam-ang, Pornpat,Phontree, Kiettipum,Sichaem, Jirapast
, p. 1 - 7 (2020/05/13)
A series of lupeol derivatives 2, 2a-2f, 2a-2h, 3a-3e, and 4a-4b were designed, synthesised and evaluated for their α-glucosidase inhibitory and cytotoxic activities. Among synthetic derivatives, lupeol analogues 2b and 2e containing a benzylidene chain exhibited the best activity against α-glucosidase and superior to the positive agent with the IC50 values of 29.4 ± 1.33 and 20.1 ± 0.91 μM, respectively. Lupeol analogues 2d and 3a showed weak cytotoxicity against K562 cell line with the IC50 values of 76.6 ± 2.40 and 94.4 ± 1.51 μM, respectively.
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.
Improved isolation of betulin and lupeol from birch bark and oxidation of their acetylated derivatives with chromyl chloride
Luká?, Milo?,Horváth, Branislav,Pisár?ik, Martin,Devínsky, Ferdinand,Horáková, Renáta
, p. 947 - 952 (2018/02/14)
Abstract: An improved method of isolation of betulin and lupeol from birch bark is developed and reported. The method afforded triterpenes with purity of 98.2% (betulin) and 96.3% (lupeol), respectively. Chromyl chloride was also investigated as an oxidating agent of O-acetylated betulin and lupeol. The transformation of isopropenyl moiety to aldehyde group was observed.
Solvent-induced Gel Formation Hypothesis for Natural Product Gelators with Polycyclic Structures
Zhi, Kangkang,Zhao, Haitian,Yang, Xin,Zhang, Hua,Wang, Jing,Wang, Zhenyu
, p. 797 - 803 (2018/09/11)
Natural products have long been used as pharmaceutical actives for the treatment of diseases. More recently, natural products with the ability to self-assemble to form soft material-gels, i.e. natural product gelators (NPGs), were discovered. This subverts our traditional insight into natural products as drugs and drives us to elucidate how NPGs form gels. Here, we interpret “why gel” from the perspective of solvents based on the basic theory of thermodynamics for liquids, and then propose the hypothesis of solvent-induced gel formation in combination with the NPGs with polycyclic structures. This hypothesis provides a complete explanation of how the gelator and solvent play a role in the overall gel formation and helps us to more easily understand the gelation.
Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase
Chen, Dongyin,Xu, Fengguo,Zhang, Pu,Deng, Jie,Sun, Hongbin,Wen, Xiaoan,Liu, Jun
, (2017/10/20)
A practical synthesis of α-amyrin (1), β-amyrin (2), and lupeol (3) was accomplished in total yields of 32, 42, and 40% starting from easily available ursolic acid (4), oleanolic acid (5), and betulin (6), respectively. Remarkably, these three natural pentacyclic triterpenes exhibited potential inhibitory activity against human oxidosqualene cyclase.
Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis
Vieira, Patrícia De Brum,Silva, Nícolas Luiz Feijó,Da Silva, Gloria Narjara Santos,Silva, Denise Brentan,Lopes, Norberto Peporine,Gnoatto, Simone Cristina Baggio,Da Silva, Márcia Vanusa,MacEdo, Alexandre José,Bastida, Jaume,Tasca, Tiana
, p. 2229 - 2236 (2016/04/26)
Trichomonas vaginalis causes trichomoniasis; the most common but overlooked non-viral sexually transmitted disease worldwide. The treatment is based at 5′-nitroimidazoles, however, failure are related to resistance of T. vaginalis to chemotherapy. Caatinga is a uniquely Brazilian region representing a biome with type desert vegetation and plants present diverse biological activity, however, with few studies. The aim of this study was to investigate the activity against T. vaginalis of different plants from Caatinga and identify the compounds responsible by the activity. A bioguided fractionation of Manilkara rufula was performed and four major compounds were identified: caproate of α-amyrin (1b), acetate of β-amyrin (2a), caproate of β-amyrin (2b), and acetate of lupeol (3a). In addition, six derivatives of α-amyrin (1), β-amyrin (2) and lupeol (3) were synthesized and tested against the parasite. Ursolic acid (5) reduced about 98% of parasite viability after 2 h of incubation and drastic ultrastructural alterations were observed by scanning electron microscopy. Moreover, 5 presented high cytotoxicity to HMVII and HeLa cell line and low cytotoxicity against Vero line at 50 μM (MIC against the parasite). Metronidazole effect against T. vaginalis resistant isolate was improved when in association with 5.
Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors
Bhandari, Pamita,Patel, Neeraj Kumar,Bhutani, Kamlesh Kumar
supporting information, 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.
Molecular modeling, structure activity relationship and immunomodulatory properties of some lupeol derivatives
Shahlaei, Mohsen,Ghanadian, Syed Mustafa,Ayatollahi, Abdul Majid,Mesaik, M. Ahmed,Abdalla, Omer Mohamed,Afsharypour, Suleiman,Rabbani, Mohammed
, p. 1795 - 1803 (2013/07/26)
Currently, scientists are focused on developing drug-like compounds as an alternative to the available immunosuppressive drugs with less side effects. Therefore, in the current study we tried to generate derivatives of lupeol and investigate their primary effects on the immune system. In the second part, a computational approach, integrating molecular docking, and molecular dynamics simulation was used to assess the likely mechanism of action and the preliminary analysis of the structure activity relationship (SAR). Our goal for this research was to develop an in-depth SAR for the design of future immunosuppressive lupeol analogs with the potential clinical use.
Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD
Gutierrez-Nicolas, Fatima,Gordillo-Roman, Barbara,Oberti, Juan C.,Estevez-Braun, Ana,Ravelo, Angel G.,Joseph-Nathan, Pedro
experimental part, p. 669 - 676 (2012/06/29)
Lupane triterpenoids 2 and 5-12 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure-activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.
Synthesis and structure of an acetylene derivative of lupeol
Kazakova,Medvedeva,Suponitskii
experimental part, p. 408 - 410 (2011/10/09)
The synthesis and x-ray crystal structure of 3-acetoxy-29-norlup-20(30)-yne were carried out.
