- 3-Oxolup-20(29)-en-30-al, a New Lupane from Gymnosporia emarginata (Celastraceae)
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The steam bark of Gymnosporia emarginata (Willd.) Hook f. ex.Thw. (Celastraceae) contains a number of triterpenes including a new oxygenated lupane, 3-oxolup-20(29)-en-30-al (1) and two related lupanes, 3β-hydroxylup-20(29)-en-30-al (2) and 30-hydroxylup-20(29)-en-3-one (3).The structures of these compounds have been established by spectroscopic and chemical methods.
- Wijeratne, Dharmassree B. T.,Kumar, Vijaya,Sultanbawa, M. Uvais S.
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- Antidyslipidemic and antioxidant effects of novel lupeol-derived chalcones
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A series of Lupeol-based chalcones have been synthesized aiming to enhance the therapeutic efficacy of parent compound, the novel compounds were evaluated for their antidyslipidemic activity in triton-WR 1339 induced hyperlipidemic rats. Among the ten synthesized chalcones, the most active K4, K8, and K9 reversed the plasma levels of TC by (24, 25, 27 %), phospholipid by (25, 26, 25 %) and triacylglycerol by (27, 24, 24 %) respectively. In addition, the compounds showed significant in vitro antioxidant activity. The lipid lowering activity of these compounds were mediated through lipoprotein lipase activation (12-21 %) and enhanced post-heparin lipolytic activity (15-16 %). The compounds also displayed noteworthy inhibitory effect on 3-hydroxy-3-methyl-glutaryl reductase activity (in vitro). The in vitro effect of the most active compounds on MDI-induced adipogenesis using 3T3-L1 preadipocytes at 10 and 20 μM concentrations showed significant inhibition (20-32 %) of adipogenesis.
- Srivastava, Shishir,Sonkar, Ravi,Mishra, Sunil Kumar,Tiwari, Avinash,Balramnavar, Vishal,Mir, Snober,Bhatia, Gitika,Saxena, Anil K.,Lakshmi, Vijai
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- Isolation of lupeol, design and synthesis of lupeol derivatives and their biological activity
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The triterpenoid, lupeol (1) has been isolated from the leaves extract of Walsura trifoliate. Few novel derivatives (4a-j) were synthesized from the naturally occurring lupeol (1) and confirmed by spectroscopic methods, and tested for antimicrobial and anti-proliferative activity against MDAMB-231, IMR32and A549 cell lines. This all compound showed moderate activities.
- Rao, S. Devendra,Rao, B. Nageswara,Devi, P. Uma,Rao, A. Karteek
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- A new 3,4-seco-lupane derivative from Lasianthus gardneri
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A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, β-sitosterol, ursolic acid, and stigmasterol 3-O-β -D-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of 13C and 1H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.
- Dallavalle, Sabrina,Jayasinghe, Lalith,Kumarihamy,Merlini, Lucio,Musso, Loana,Scaglioni, Leonardo
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- Design and synthesis of new lupeol derivatives and their α-glucosidase inhibitory and cytotoxic activities
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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.
- 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
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- Oxidation at C-16 enhances butyrylcholinesterase inhibition in lupane triterpenoids
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A set of triterpenoids with different grades of oxidation in the lupane skeleton were prepared and evaluated as cholinesterase inhibitors. Allylic oxidation with selenium oxide and Jones's oxidation were employed to obtain mono-, di- and tri-oxolupanes, starting from calenduladiol (1) and lupeol (3). All the derivatives showed a selective inhibition of butyrylcholinesterase over acetylcholinesterase (BChE vs. AChE). A kinetic study proved that compounds 2 and 9, the more potent inhibitors of the series, act as competitive inhibitors. Molecular modeling was used to understand their interaction with BChE, the role of carbonyl at C-16 and the selectivity towards this enzyme over AChE. These results indicate that oxidation at C-16 of the lupane skeleton is a key transformation in order to improve the cholinesterase inhibition of these compounds.
- Castro, María Julia,Richmond, Victoria,Faraoni, María Belén,Murray, Ana Paula
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p. 301 - 309
(2018/05/28)
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- Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors
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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.
- Bhandari, Pamita,Patel, Neeraj Kumar,Bhutani, Kamlesh Kumar
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supporting information
p. 3596 - 3599
(2014/07/22)
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- Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD
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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.
- Gutierrez-Nicolas, Fatima,Gordillo-Roman, Barbara,Oberti, Juan C.,Estevez-Braun, Ana,Ravelo, Angel G.,Joseph-Nathan, Pedro
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experimental part
p. 669 - 676
(2012/06/29)
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- Oxidative deprotection of oximes, phenylhydrazones and semicarbazones using pyridinium chlorochromate in catalytic amount with t-butyl hydroperoxide and in the solid state on montmorillonite K-10 clay support under microwave irradiation
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Pyridinium chlorochromate (FCC) and other oxochromium(VI) reagents have been extensively employed in excess of the stoichiometric amount (2 equivalents or more) for efficient cleavage of oximes to carbonyl compounds. The aim of this study is to replace excess use of toxic chromium(VI) reagents and develop cleaner environment-friendly general methods of cleavage of imine derivatives such as oximes, phenylhydrazones and semicarbazones using PCC in catalytic or stoichiometric amount. Two approaches of greening the deprotection process with PCC are conceived of which the first one is based on the catalytic use of the reagent (0.1 equiv.) in combination with an excess of 70% t-butyl hydroperoxide as the cooxidant. Mild selective regeneration of carbonyl compounds from oximes, phenylhydrazones and semicarbazones has been accomplished in good-to-excellent yields (70-98%) by this method. With focus on rate enhancement coupled with efficiency of cleavage, an alternative microwave-assisted solid-state solventiess protocol of deprotection employing a stoichiometric amount of PCC dispersed on montmorillonite K-10 clay is also evaluated. It offers an expeditious efficient (74-98% yields) general route of cleavage of these procarbonyl compounds. Absence of overoxidation, particularly for oxidation-prone aryl aldehydes, is the key advantage of both these methods.
- Ganguly, Nemai C.,Datta, Mrityunjoy,De, Prithwiraj
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p. 308 - 312
(2007/10/03)
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- New ursane-type triterpenic esters from the stem bark of Thevetia peruviana
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Phytochemical studies on the stem bark of Thevetia peruviana resulted in the isolation of six new ursane-type triterpenes, named peruvianursenyl acetate A, peruvianursenyl acetate B, isolupenyl acetate, peruvianursenyl acetate C, lupedienyl acetate and peruvianursenyl glucoside along with two known triterpenoids, namely α-amyrin acetate and lupeol acetate. The structures of the new phytoconstituents have been established as 23 - nor methyl urs-12-en-4α-ethylenic-18α-H-3β-yl acetate, urs-5.21-dien-18α-H- 3β-yl acetate, lup-20 (29)-en-3α-yl acetate, urs-12 en-18α- H-3β-yl acetate, lup-5,20 (29)-dien-3β-yl acetate, and urs-12-en-18α-H-3-O-β-D- glucopyranoside, respectively.
- Ali,Ravinder,Ramachandram
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p. 385 - 389
(2007/10/03)
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- Studies on ketene dithioacetalization and hypervalent iodine oxidation of lupenone
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Ketene dithioacetalization at the activated C-2 centre of triterpenic lupenone 2 has been carried out successfully to yield α-oxoketenedithioacetal derivative 3. Compound 3 on ring closure reactions with guanidine hydrochloride and hydrazine hydrate furnished respectively the pyrimidine and pyrazole annealed heterocycles 4-6 of lupenone. Unlike these reactions hypervalent iodine oxidation of lupenone using Koser reagent [PhI(OH)OTs] gave various oxidised products 8-11 and did not show any regio-specificity.
- Roy, Kamal,Raj,Bhaduri
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p. 774 - 777
(2007/10/03)
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- Lupene derivatives from Skimmia laureola
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Three new lupenes, isolated from Skimmia laureola, have been characterized as 23-acetoxy-lup-20(29)-en-30-al-3-one, 3β,23-bisacetoxy-lup-20(29)-e.
- Razdan,Harkar,Qadri,Qurishi,Khuroo
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p. 1890 - 1892
(2007/10/02)
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- REDUCTION OF KETONES TO EPIMERIC ALCOHOLS WITH POTASSIUM HYDROXIDE-DIETHYLENE GLYCOL
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Triterpenoid ketones have been reduced to epimeric alcohols on boiling with potassium hydroxide in diethylene glycol. α,β-unsaturated ketone furnished saturated epimeric alcohols.
- Pradhan, B. P.,Hassan, A.,Ray, T.
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p. 2513 - 2516
(2007/10/02)
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- THE CHEMISTRY OF TOXIC PRINCIPLES FROM MAYTENUS NEMEROSA
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Maytenus nemerosa has been fractionated systematically by following the toxicity of extracts, partitioned solutions and column chromatographic fractions against coltured KB cells.Several compounds were isolated in this fashion, including 3-oxo-20(29)-lupen-30-al, β-amyrin, 29-hydroxyfriedelan-3-one, 30-hydroxy-20(29)-lupen-3-one, 30-hydroxyfriedelan-3-one and lup-20(29)-ene-3β,30-diol, as well as tingenone, 20-hydroxytingenone and galactitol. 3-Oxo-20(29)-lupen-30-al was shown to be cytotoxic for the first time; the structural basis of this cytotoxicity was investigated, in part, by bioassay of four products obtained by chemical transformation of single, isolated principles.Key Word Index - Maytenus nemerosa; Calestraceae; cytotoxic principles; antineoplastic agents; pentacyclic triterpenes.
- Fang, Sheng-Ding,Berry, David E.,Lynn, David G.,Hecht, Sidney M.,Campbell, James,Lynn, William S.
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p. 631 - 634
(2007/10/02)
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