scholarly journals 21,28-Epoxy-18β,21β-Dihydroxbaccharan-3-one and Other Terpenoids from the Liverwort Lepidozia Chordulifera T. Taylor

2008 ◽  
Vol 3 (11) ◽  
pp. 1934578X0800301
Author(s):  
Hildegard Zapp ◽  
Kerstin Orth ◽  
Josef Zapp ◽  
Joseph D. Connolly ◽  
Hans Becker
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Properties ◽  
Betulonic Acid ◽  
Side Chain

A new triterpenoid, 21,28-epoxy-18β,21β-dihydroxybaccharan-3-one (1), with a spiro-hemiketal side-chain, has been isolated from the liverwort Lepidozia chordulifera. The plant also yielded (6S*, 7S*)-3-norhimachal-1-en-3-one (3), an epimer of a known norhimachalane, the rare 3β-hydroxy-22,23,24,25,26,27-hexanordammaran-20-one and the triterpenoids shoreic acid, taraxerol, betulinic acid, betulonic acid and ursolic acid. Their structures have been assigned on the basis of their spectroscopic properties.

Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L.

2003 ◽  
Vol 17 (2) ◽  
pp. 129-134 ◽  
Author(s):  
C. Chandramu ◽  
Rao D. Manohar ◽  
David G. L. Krupadanam ◽  
Reddy V. Dashavantha
Keyword(s):  
Biological Activity ◽  
Ursolic Acid ◽  
Betulinic Acid ◽  
Vitex Negundo

scholarly journals Characterization and Quantification of Triterpenes in the Neotropical Medicinal Plant Souroubea sympetala (Marcgraviaceae) by HPLC-APCI-MS

2008 ◽  
Vol 3 (11) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Martha Mullally ◽  
Kari Kramp ◽  
Ammar Saleem ◽  
Marco Otorola Rojas ◽  
Pablo Sanchez Vindas ◽  
...  
Keyword(s):  
Medicinal Plant ◽  
Ursolic Acid ◽  
Betulinic Acid ◽  
Plant Organs ◽  
Immature Fruit ◽  
Pentacyclic Triterpenes ◽  
Wood Bark

A rapid, two-solvent, HPLC-APCI-MS method was developed to identify and quantify four pentacyclic triterpenes (betulinic acid, ursolic acid, α-amyrin and β-amyrin) in extracts of the neotropical medicinal plant Souroubea sympetala. Analysis of plant organs, wood, bark, leaves, immature fruit and flowers, indicated that the phytochemical distribution and quantity of triterpenes varies across the plant, with betulinic acid and ursolic acid the major constituents in the bark, wood, fruit and flowers and the amyrins the major constituents of the leaves.

Studies on Enaminoketones

1974 ◽  
Vol 52 (1) ◽  
pp. 55-65 ◽  
Author(s):  
Ivo Jirkovsky
Keyword(s):  
Cyanogen Bromide ◽  
Spectroscopic Properties ◽  
Phenyl Isocyanate ◽  
Biologically Active ◽  
Side Chain ◽  
Phenyl Isothiocyanate ◽  
Methyl Isothiocyanate ◽  
Synthetic Utility ◽  
Concentrated Sulfuric Acid ◽  
Biologically Active Derivatives

A series of N-substituted 3-amino-2-cyclohexen-1-ones and 3-amino-5,5-dimethyl-2-cyclohexen-1-ones (1–9) has been prepared. Halogenation of these compounds with bromine, NBS, cyanogen bromide, and iodine is described. The tendency of enaminoketones to form salts of the corresponding enol-ketimine form was observed and structures of the salts are supported by their p.m.r. and i.r. properties. The reaction of 3-benzylamino-2-bromo-5,5-dimethyl-2-cyclohexen-1-one with concentrated sulfuric acid effected debenzylation. Treatment of 3-benzylamino-2-iodo-5,5-dimethyl-2-cyclohexen-1-one with dibenzoyl peroxide gave 8,8a-dihydro-5-iodo-8,8-dimethyl-2,3-diphenyl-4H-1,4-benzoxazine-6,7-diol. The above secondary enaminoketones 1–9 were shown to react with phenyl isocyanates, phenyl isothiocyanate. and methyl isothiocyanate under fusion conditions to yield substituted 2-amino-6-oxo-1-cyclo-hexene-1-carboxamides and corresponding thiocarboxamides. 2-Benzylamino-6-oxo-N-phenyl-1-cyclohexene-1-carboxamide and its 5,5-dimethyl analog were found to undergo facile transamination in position 2, when heated with a primary amine. This reaction is of synthetic utility for the preparation of biologically active derivatives with a basically substituted side chain. Addition of 4-methylamino-3-pentene-2-one to phenyl isocyanate afforded 2-acetyl-3-methylaminoisocrotonanilide; the spectroscopic properties of this product are discussed.

scholarly journals Platelet Antiaggregating Activity and Chemical Constituents of Salvia x Jamensis J. Compton

2008 ◽  
Vol 3 (6) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Angela Bisio ◽  
Giovanni Romussi ◽  
Eleonora Russo ◽  
Nunziatina De Tommasi ◽  
Nicola Mascolo ◽  
...  
Keyword(s):  
Data Analysis ◽  
Platelet Aggregation ◽  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Data ◽  
Chemical Constituents ◽  
Isopimaric Acid ◽  
Phytochemical Study ◽  
Rat Platelets ◽  
Significant Concentration

A phytochemical study has been carried out on the surface exudate of Salvia x jamensis, which showed a significant platelet antiaggregating activity. The known compounds isopimaric acid (2), 14-α-hydroxy-isopimaric acid (3), 3β-hydroxy-isopimaric acid (4), 7,8β-dihydrosalviacoccin (5), betulinic acid (6), and ursolic acid (7) were isolated together with the new diterpene 1. The structure of 1 was determined as 15,16-epoxy-cleroda-3-en-7α,10β-dihydroxy-12,17;19,18-diolide on the basis of spectroscopic data analysis. Among all tested compounds, 2 showed a significant concentration-dependent antiaggregating activity when ADP (3 μM) was used as agonist on rat platelets. Conversely, 1 increased ADP–induced platelet aggregation.

scholarly journals Pharmacokinetic Comparisons of Multiple Triterpenic Acids from Jujubae Fructus Extract Following Oral Delivery in Normal and Acute Liver Injury Rats

2018 ◽  
Vol 19 (7) ◽  
pp. 2047 ◽  
Author(s):  
Yao Li ◽  
Sheng Guo ◽  
Quanjin Ren ◽  
Dandan Wei ◽  
Ming Zhao ◽  
...  
Keyword(s):  
Liver Injury ◽  
Betulinic Acid ◽  
Oral Delivery ◽  
Acute Liver Injury ◽  
Betulonic Acid ◽  
Pharmacokinetic Parameters ◽  
Pharmacokinetic Studies ◽  
Bioactive Constituents ◽  
Biological Studies ◽  
Triterpenic Acids

Jujubae Fructus, the dried fruit of Ziziphus jujuba, has been used as Chinese medicine and food for centuries. Triterpenic acids have been found to be the major bioactive constituents in Jujubae Fructus responsible for their hepatoprotective activity in previous phytochemical and biological studies, while few pharmacokinetic studies have been conducted. To reveal the kinetics of the triterpenic acids under the pathological liver injury state, an established ultra-performance liquid chromatography coupled with a mass spectrometry method was applied for the simultaneous quantitation of seven triterpenic acids (ceanothic acid, epiceanothic acid, pomonic acid, alphitolic acid, maslinic acid, betulinic acid, and betulonic acid) in plasma samples of normal and acute liver injury rats induced by CCl4. The results showed that there were significant differences (p < 0.05) in the pharmacokinetic parameters of seven triterpenic acids between model and normal groups. The AUC0–t and AUC0–∞ of epiceanothic acid (5227 ± 334 μg⋅h/L vs. 1478 ± 255 μg⋅h/L and 6127 ± 423 μg⋅h/L vs. 1482 ± 255 μg⋅h/L, respectively) and pomonic acid (4654 ± 349 μg⋅h/L vs. 1834 ± 225 μg⋅h/L and 4776 ± 322 μg⋅h/L vs. 1859 ± 230 μg⋅h/L, respectively) in model rats were significantly higher than those in normal rats, and the CLz/F of them were significantly decreased (0.28 ± 0.02 L/h/kg vs. 1.36 ± 0.18 L/h/kg and 19.96 ± 1.30 L/h/kg vs. 53.15 ± 5.60 L/h/kg, respectively). In contrast, the above parameters for alphitolic acid, betulinic acid and betulonic acid exhibited the quite different trend. This pharmacokinetic research might provide useful information for the clinical usage of triterpenic acids from Jujubae Fructus.

Lupane-Triterpene Esters from the Leaves of Ceriops decandra (Griff.) Ding Hou

2005 ◽  
Vol 58 (8) ◽  
pp. 615 ◽  
Author(s):  
Chanita Ponglimanont ◽  
Pakakrong Thongdeeying
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Methods ◽  
Ceriops Decandra ◽  
New Compounds ◽  
First Time ◽  
Triterpene Esters

Two novel triterpene esters were isolated from the leaves of Ceriops decandra in addition to 16 known triterpenes: lupenone 3, lupeol 4, betulinaldehyde 5, 3β-Z-coumaroyllupeol 6, 3β-E-coumaroyllupeol 7, 3-epi-betulinic acid 8, betulin 9, betulinic acid 10, 3β-E-feruloylbetulin 11, 30-nor-lup-3β-ol-20-one 12, 3β-E-caffeoyllupeol 13, lup-20(29)-en-3β,30-diol 14, 3β-hydroxylupan-29-oic acid 15, 3β,20-dihydroxylupane 16, and a mixture of oleanolic and ursolic acid 17 and 18. The new compounds were determined by spectroscopic methods to be 3β-E-feruloyllupeol 1 and 3β-Z-feruloyllupeol 2. Compounds 3 and 5–16 were reported for the first time as metabolites of C. decandra.

scholarly journals In silico screening of W. salutaris bioactive constituents reveal betulinic acid, ursolic acid acetate and eucosterol as potential M. tuberculosis antagonists targeting FabF

2021 ◽  
Author(s):  
Nokukhanya Gumede ◽  
Kgothatso E. Machaba ◽  
Umar Ndagi ◽  
Hezekiel M. Kumalo ◽  
Ndumiso N. Mhlongo
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
In Silico ◽  
Fatty Acid Biosynthesis ◽  
Binding Energies ◽  
Active Site Residues ◽  
Bioactive Constituents ◽  
Inhibitory Potential ◽  
Dynamics Simulations ◽  
Potential Inhibitors

Abstract Tuberculosis (TB) remains a long-standing burdening disease to control worldwide. The lengthy current TB treatment, which boasts with unbearable adverse effects, and frequent emergence of drug resistant strains of M. tuberculosis lays an increasing burden. This behests urgent discovery and development of alternative novel medicine to alleviate TB. In this report, in silico methods were applied to examine the propensity of W. salutaris active compounds as potential inhibitors of M. tuberculosis fatty acid biosynthesis protein (FabF). Thirteen compounds were virtually screened against FabF and subjected to molecular dynamics simulations and post-dynamics analyses to examine their inhibitory potential. Betulinic acid, ursolic acid and ursolic acid acetate had the best binding energies and hence the best inhibitory potential against FabF and desirable cytotoxicity profile. These compounds bind and interact with FabF active site residues to exert their inhibitory potential. Findings in this preliminary report warrant further experimental validation towards the development of these compounds as potential drugs targeting FabF in the treatment of tuberculosis.

scholarly journals Phytochemical Investigation and Antioxidative Capacity of Triterpenes Present in Plant Species Belonging to Lamiaceae Family

2020 ◽  
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
Analytical Determination ◽  
Antioxidative Capacity ◽  
Dpph Method ◽  
Wide Range ◽  
Ic50 Values ◽  
Hexane Extracts ◽  
Dpph Scavenging ◽  
Rosmarinus Officinalis L

Triterpenes are persistently associated with observed bioactivities of extracts obtained from plant material that contains these very important natural products. Many species belonging to Lamiaceae family have been used for the presence of essential oil and very little is known about the presence of the triterpene substances in this family. Qualitative and quantitative analyses of this very important substances, in the aerial parts of eight species, all belonging to Lamiaceae family, were investigated in this study. Different extracts containing triterpene substances were tested by DPPH method to evaluate their antioxidative capacity. TLC and HPLC methods, used for the analytical determination of triterpenes, showed the presence of betulin, betulinic acid, ursolic acid and oleanolic acid. Betulin (3.2 mg/g) and betulinic acid (37.1 mg/g) were the most abundant triterpene components in the hexane extracts of Rosmarinus officinalis L. Ursolic acid (0.14 mg/g) was the most abundant triterpene compound in the hexane extract of Thymus pulegioides L. All tested samples demonstrated DPPH scavenging activity in a concentration dependant manner, with a wide range of IC50 values from 0.4 mg/mL to 3.3 mg/mL.

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