scholarly journals Isolation of Betulinic acid from the stem bark and root of Uapaca guineensis

Author(s):  
Abdulrazaq Ogunmoye

Uapaca guineensis Mull. Arg. (Euphorbiaceae) commonly called false mahogany and “Ewe akun” in the western part of Nigeria grows in humid localities, mixed evergreen forest and sea-level up to 1100 m altitude. The study was designed to isolate Betulinic acid (3?-hydroxylup-20-(29)-en-28-oic acid) which is a naturally occurring pentacyclic triterpenoid that exhibited antibacterial, antimalarial, anti-inflammatory, anthelmintic and antioxidant properties from the stem bark and root of Uapaca guineensis. The air-dried and pulverized stem bark and root of U. guineensis (0.5 kg each) were separately extracted with aqueous ethanol (80%) for 72 hour at room temperature, filtered, concentrated on rotatory evaporator at 37 oC and then stored in a desiccator. The ethanol extracts of the stem bark was partitioned successively with n-hexane, dichloromethane and methanol, while ethanol extract of the root was chromatographed directly. The dichloromethane and methanol extracts of the stem bark was also chromatographed. These results in the formation of whitish powder that are UV inactive and also gave single spot each with cerium sulphate. They are coded as DBG-D13 (25.0 mg), MBG-Q3 (6.1 mg) and ERG-E7 (20.0 mg) for dichloromethane, Methanol and Ethanol extracts respectively. The structure was unequivocally established by 1HNMR, 13CNMR, 2D-NMR, IR, UV and MS spectra analysis as well as by comparison of the spectra data with previously reported values. The dichloromethane, methanol and the ethanol extracts all yielded betulinic acid in substantial quantity. The isolated compound is a confirmation to existing information and an addition to the library of organic compounds.

2020 ◽  
Vol 10 (03) ◽  
pp. 109-115
Author(s):  
Shreya Udaya ◽  
Nishith Babu ◽  
Dechamma Pandyanda Nanjappa ◽  
Krithika Kalladka ◽  
Gunimala Chakraborty ◽  
...  

Abstract Objective This study was aimed at evaluating the toxicity and the antioxidant property of Cassia fistula stem bark extracts in zebrafish. Materials and Methods Crude aqueous and ethanol extracts of C. fistula stem bark were obtained following a standard solvent-based extraction method. The toxicity of these extracts on zebrafish embryonic development was determined and the LC50 values were calculated. Finally, the antioxidant property of C. fistula stem bark extracts was determined in arsenic-induced oxidative stress models of zebrafish. Results The aqueous extract of C. fistula stem bark showed a slightly larger LC50 value (213.6 ppm) compared with the ethanol extract (LC50 = 63.5 ppm), suggesting a lower toxicity of the aqueous extract. A significant reduction of reactive oxygen species (ROS) signal was observed in arsenic-exposed embryos treated with the aqueous extract, but not the ethanol extract, indicating that the antioxidant activity is present only in the aqueous extract of C. fistula stem bark. Conclusion Identification of antioxidants from natural sources is desirable because of increasing safety concerns associated with synthetic antioxidants. This study demonstrated that aqueous extract from C. fistula stem bark possesses antioxidant properties, which can be further characterized for mechanism of action and potential applications.


2019 ◽  
Vol 1 (4) ◽  
pp. 199-216 ◽  
Author(s):  
Khine Zar Wynn Lae ◽  
Su Swe Su ◽  
Nwet Nwet Win ◽  
Ni Ni Than ◽  
Hla Ngwe

A large number of the plants are claimed to possess the antibiotic properties in the traditional system and are also used extensively by the tribal people throughout the world. It is now mostly thought that nature has given the cure of every disease in one form or another. Plants have been known to cure people from various diseases in Ayurveda. This research focused on the screening of phytochemicals and some biological activities of Phyllanthus albizzioides. The research showed that the ethanol extracts were found to be greater chemical constituents than watery extracts. Among the chemical constituents, steroid compounds were observed in highest amount in ethanol extract and the second highest in flavonoid compounds followed by tannin compounds and pheolic compounds. Furthermore, the ethanol extracts were more effective than the watery extracts in all tested biological activities such as antioxidant, anti-diabetic, cytotoxicity, antimicrobial, antitumor and NO inhibition activities. A cyclohexanone compound was isolated from the chloroform extract of the stem bark of P. albizzioides. The relative structure was determined to be 4,5-dihydroxy-3-methyl-cyclohex-2-enone on the basic of HRESIMS, 1H NMR and 13C NMR spectroscopic analyses, including 2D NMR experiments.


2019 ◽  
Vol 9 (3) ◽  
pp. 80-86
Author(s):  
Hanane Megdad ◽  
Samuel Chiomokhare ◽  
Ahmed M’Hamedi ◽  
Paul L Chazot

Plant natural products have a long history of being a rich source of neuroactive drugs.The total phenolic and flavonoid content, and antioxidant activity of ethanol, chloroform and aqueous extracts of AlgerianMedicagoSativaL, leaves were measured to discover new potential sources of Algerian natural antioxidants and neuroactives. All extracts were non-neurotoxic up to 1 mg/ ml for 24 h exposure. The total phenolcontent of M.Sativa extracts ranged between 38 and 69 mg GAE per g extracts. All of the extracts displayed antioxidant capacityassessed by two methods, but at different levels depending on the concentration and the extraction solvent used. The overall antioxidant potency was in the order water > chloroform> ethanol extracts, and the phenolic content exhibited a positive correlation with the antioxidant activity of M. Sativa extracts.Despite a weaker antioxidant activity, the ethanol extract elicited a calcium spike and suppressed the KCl-induced depolarisation response in neurons, indicating effect on ligand-and/or voltage gated calcium channels. In contrast, the chloroform and water extractsdisplayed no apparent direct functional effects. In conclusion, the antioxidant and functional properties related to phenolic content of Algerian Medicago Sativa L. in water and ethanol extracts, respectively.


2019 ◽  
Vol 1 (1) ◽  
pp. 68-74
Author(s):  
Lenny Anwar

Pentacyclic triterpenoid, betulinic acid (1) and phenolic, p-hydroxybenzoic acid (2), had been isolated for the first time from the stem bark of Vitex pubescens Vahl. The structure of compounds 1 and 2 was determined based on the interpretation of spectroscopic data including UV, IR, NMR (1H-NMR, 13C-NMR, HMQC, HMBC, COSY) and MS, as well as by comparison with those reported data.


2008 ◽  
Vol 63 (11) ◽  
pp. 1335-1338 ◽  
Author(s):  
Herve M. P. Poumale ◽  
Rodrigue T. Kengap ◽  
Jean Claude Tchouankeu ◽  
Felix Keumedjio ◽  
Hartmut Laatsch ◽  
...  

Abstract Two new pentacyclic triterpenes 8,26-cyclo-urs-21-en-3β, 20β-diol (1) and 3β-acetoxy-8.26- cyclo-ursan-20β-ol (2) together with 3-friedelanone, oleanolic acid, betulinic acid, lupeol acetate, α- and β-amyrine, S.SJ^'-tetrahydroxyflavane, and 3,5,7,3',4'-pentahydroxyflavane were isolated from the stem bark of Ficus cordata (Moraceae). The structures of these secondary metabolites were established using ID and 2D NMR spectra and by comparison with published data or with authentic samples. Compounds 1 and 2 exhibited weak antibacterial and no antifungal activity.


Plants ◽  
2020 ◽  
Vol 9 (2) ◽  
pp. 142 ◽  
Author(s):  
Chloé Placines ◽  
Viana Castañeda-Loaiza ◽  
Maria João Rodrigues ◽  
Catarina G. Pereira ◽  
Azzurra Stefanucci ◽  
...  

Cakile maritima Scop. (sea rocket) is an edible halophyte plant with several ethnomedicinal uses. This work reports the chemical profile and bioactivities of food grade extracts from sea rocket organs. Toxicity was determined on mammalian cells, and phenolic profiling and the quantitation of the main metabolites were made by high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS). Enzymatic inhibition was determined towards acetyl- and butyrylcholinesterase (AChE, BuChE), α-glucosidase, α-amylase, and tyrosinase. Docking studies were performed to tyrosinase, on the major metabolites, and samples were tested for antioxidant properties. Extracts were not toxic, were constituted mainly by flavonoids, and some compounds (roseoside and oleuropein) are here described for the first time in the species. The aerial organs’ ethanol extract had relevant activity towards 2,2-diphenyl-1-picrylhydrazyl [DPPH, half maximal inhibitory concentration (IC50) = 0.59 mg/mL], and ferric-reducing activity power (FRAP, IC50 = 0.99 mg/mL). All samples were more active towards AChE than on BuChE. The ethanol fruits’ extract inhibited α-glucosidase [2.19 mmol of equivalent of acarbose (ACAE)/g]. Samples were active against tyrosinase, especially the aerial organs’ ethanol extracts [25.9 mg of equivalent of kojic acid (KAE)/g]. Quercetin and kaempferol glycosides fit well into the enzymatic pocket of tyrosinase. Our results suggest sea rocket as a candidate to be further explored as a source of bioactive products.


2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Vouffo Bertin ◽  
Hidayat Hussain ◽  
Simeon F. Kouam ◽  
Etienne Dongo ◽  
Gennaro Pescitelli ◽  
...  

Four compounds were isolated from the stem bark of Antiaris africana. One of them, a γ-lactone named antialactone (1a), is reported for the first time as a natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectra and EI MS data. The absolute configuration of antialactone acetate (1b) was established by TDDFT CD calculations and comparison with measured CD spectra. The remaining three known compounds were identified, by comparing their spectroscopic data with those reported in the literature, as lichenxanthone, β-sitosterol, and betulinic acid.


2014 ◽  
Vol 4 (17) ◽  
pp. 2116-2125 ◽  
Author(s):  
Ismet Jahan ◽  
Hemayet Hossain ◽  
Proity Akbar ◽  
Md. Rahman ◽  
Tanzir Khan ◽  
...  

2016 ◽  
Vol 11 (5) ◽  
pp. 1934578X1601100
Author(s):  
Martial F. E. Adjapmoh ◽  
Flavien A. A. Toze ◽  
Jules L. Songue ◽  
Moses K. Langat ◽  
Gilbert D. W. F. Kapche ◽  
...  

A new ceramide and a new biflavonoid named parinaramide (1) and sparinaritin (2), respectively, have been isolated along with ten known compounds, kaempferol, quercetin, taxifolin, taxifolin-3- O-rhamnoside, lupeol, betulinic acid, ursolic acid, 2α-hydroxy-ursolic acid, 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone, and sucrose, from the leaves of Parinari hypochrysea (Chrysobalanaceae). Structures were determined using 1D- and 2D-NMR, MS and by chemical analysis. The methanol extract of leaves, stem bark and roots of P. hypochrysea were screened for their antioxidant and lipoxygenase inhibition potential and found to be inactive.


2020 ◽  
Vol 24 (7) ◽  
pp. 785-797
Author(s):  
Yabo Dambagi Lawali ◽  
Akyuz Mehmet ◽  
Aydin Tuba ◽  
Cakir Ahmet

: Five metabolites were isolated by chromatographic methods from the fruit stems of P. vera and their chemical structures were characterized as masticadienonic acid (1), tirucallol (2), masticadienolic acid (3), pistachionic acid (4) and inulobiose (5) via FT-IR, 1H-NMR, 13C-NMR, 1D-NMR and 2D-NMR. Pistachionic acid (4), a new shikimic acid derivative, was isolated from the ethanol extract for the first time. The hexane, chloroform, ethanol extracts and pure metabolites exhibited antidiabetic properties by inhibiting α- glycosidase and α-amylase enzymes at different rates. Their inhibitory effects against the α- glycosidase enzyme were also higher than that of the acarbose (IC50=10.30 mg/mL). Masticadienolic acid (3) (IC50=0.03 mg/mL), masticadienonic acid (1) (IC50=0.13 mg/mL) and hexane extract (IC50=0.09 mg/mL) with the lowest IC50 values were found to be most active substances. Nevertheless, the inhibitory effect of acarbose against the α-amylase enzyme was determined to be higher than the inhibition effects of the extracts and pure metabolites. According to the IC50 values, the best inhibitors against the α-amylase were ethanol extract (IC50=5.17 mg/mL), pistachionic acid (4) (IC50=7.35 mg/mL), tirucallol (2) (IC50=7.58 mg/mL) and masticadienolic acid (3) (IC50=8.22 mg/mL), respectively among the applications. In addition, anticholinesterase properties of the extracts and pure metabolites were investigated by testing the inhibitory properties against acetylcholine esterase (AChE) and butrylcholine esterase (BChE) enzymes activities. The results showed that the anticholinesterase properties of all extracts and pure metabolites were weaker than those of the commercial cholinesterase inhibitors, neostigmine and galantamine, and all applications reduced the activity of these enzymes at very high concentrations.


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