Antimycobacterial cycloartane derivatives from the roots of Trichilia welwistchii C. DC (Meliaceae)

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Armelle Tontsa Tsamo ◽  
Edwige P. Fodja Saah ◽  
Moses K. Langat ◽  
Pierre Mkounga ◽  
Alain François Kamdem Waffo ◽  
...  
Keyword(s):  
2D Nmr ◽  
Spectroscopic Methods ◽  
Moderate Activity ◽  
Chemical Transformations ◽  
Nmr Analysis ◽  
Pure Compound ◽  
Weak Activity ◽  
Synthetic Reaction ◽  
First Time ◽  
Related Compounds

Abstract Chemical investigation of the roots of Trichilia welwitschii yielded a cycloartane type terpenoid 28,29-bis-norcycloart-24-en-3β,4α,6α-triol (1), isolated as pure compound for the first time, three coumarins and three sterols. New cycloartane derivatives (1a) and (1b+1c) were obtained by hemi-synthetic reaction of compound 1. The structures of 1a–c were established by spectroscopic methods including 1D and 2D-NMR analysis, HR-EIMS, chemical transformations and by comparison of these data with those of related compounds. Evaluated for their antimycobacterial potential, compound 1 and 1b+1c were determined to show significant activities against Mycobacterium tuberculosis MIC values of 6.25 μg mL−1 while compound 1a displayed weak activity showing MIC > 100 μg mL−1. Compounds 2–4 displayed moderate activity with MIC values range from 12.5 to 50 μg mL−1.

scholarly journals Phenolic Constituents of Knautia arvensis Aerial Parts

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Jaroslaw Moldoch ◽  
Barbara Szajwaj ◽  
Milena Masullo ◽  
Lukasz Pecio ◽  
Wieslaw Oleszek ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
First Time

A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

scholarly journals CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  
Keyword(s):  
Mental Disorders ◽  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Tree Roots ◽  
Chemical Structures ◽  
Phytochemical Investigation ◽  
First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

scholarly journals New Neuritogenic Steroid Glycosides from the Vietnamese Starfish Linckia Laevigata

2007 ◽  
Vol 2 (1) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Alla A. Kicha ◽  
Natalia V. Ivanchina ◽  
Anatoly I. Kalinovsky ◽  
Pavel S. Dmitrenok ◽  
Natalia V. Palyanova ◽  
...  
Keyword(s):  
Neuronal Differentiation ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Chemical Transformations ◽  
Steroid Glycosides ◽  
New Compounds ◽  
Neuritogenic Activity ◽  
Linckia Laevigata

Two new steroid glycosides, linckosides L1 (1) and L2 (2), were isolated, along with the previously known echinasteroside C (3) from the ethanolic extract of the Vietnamese blue starfish, Linckia laevigata. The structures of the new compounds were elucidated by spectroscopic methods (mainly 2D NMR) and chemical transformations. Lifetime observations and analyses of silver impregnated preparations on the culture of neuroblastoma C-1300 cells showed that glycosides 1, 2, and 3 are capable of inducing neuronal differentiation similar to that of neurotrophins and of enhancing substantially the neuritogenic activity of NGF.

scholarly journals New Glycosides and Trypanocidal Metabolites from Vangueria edulis

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Shaymaa M. M. Mohamed ◽  
Khaled M. Elokely ◽  
Enaam Y. Bachkeet ◽  
Soad A. L. Bayoumi ◽  
Vincenzo Carnevale ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
Candida Glabrata ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Brucei ◽  
Iridoid Glucoside ◽  
Iridoid Glucosides ◽  
Monoterpene Glycoside ◽  
First Time

A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1′'→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively.

Antimicrobial and Antioxidant Isoflavonoid Derivatives from the Roots of Amphimas pterocarpoides

2013 ◽  
Vol 68 (8) ◽  
pp. 931-938 ◽  
Author(s):  
Edwige P. Fodja Saah ◽  
Valerie Tedjon Sielinou ◽  
Victor Kuete ◽  
Stephen T. Lacmata ◽  
Augustin E. Nkengfack
Keyword(s):  
Antioxidant Properties ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Spectroscopic Methods ◽  
Chemical Transformations ◽  
Spectroscopic Evidence ◽  
Wide Range ◽  
Bacteria And Fungi

A new bis-isoflavone derivative, named amphiisoflavone (1), was isolated from the roots of Amphimas pterocarpoides, together with three known isoflavones, namely 8-methoxyisoformononetin (2), 6-methoxyisoformononetin (3) and isoformononetin (4). Chemical transformations carried out on compound 3 led to two new derivatives, 4´-acetoxy-6,7-dimethylisoflavone (3a) and 4´-O-prenyl- 6,7-dimethylisoflavone (3p), along with a known compound, 4´,6,7-trimethoxyisoflavone (3m). The structures of all compounds were elucidated from spectroscopic evidence, in particular by 1D and 2D NMR spectroscopic methods. These compounds were evaluated for their antioxidant properties and for their antimicrobial activities against a wide range of bacteria and fungi.

Chemical Constituents from Euphorbia helioscopia

2011 ◽  
Vol 396-398 ◽  
pp. 1337-1340 ◽  
Author(s):  
Di Geng ◽  
Lian Jin Weng ◽  
Yuan Yuan Han ◽  
Xin Yang
Keyword(s):  
Silica Gel ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Nmr Spectrum ◽  
Euphorbia Helioscopia ◽  
First Time ◽  
Spectrum Data

AIM: To study the chemical constituents of Euphorbia helioscopia. METHODS: Compounds 1-10 were isolated and purified by silica gel, Sephadex LH-20 and Rp-18 chromatogarphy. Their structures were elucidated mainly by spectroscopic methods. RESULTS: Ten known compounds, helioscopinolide A(1), helioscopinolide B(2), scopoletin(3), scoparone(4), isoscopoletin(5), licochalone A(6), quercelin(7), 7, 4’-dihydroxy-5-methoxy flacanone(8), 2’, 4’-dihydroxy-6’-methoxydihydrochalcone(9) and pinocembrin(10), were isolated and structurally elucidated. CONCLUSION: Compound 3-5 and 8-10 were isolated from this plant for the first time. 2D NMR spectrum data of 2 were also reported in this paper.

scholarly journals Antimycobacterial Activity of the Extract and Isolated Compounds From the Stem Bark of Zanthoxylum leprieurii Guill. and Perr.

2021 ◽  
Vol 16 (8) ◽  
pp. 1934578X2110358
Author(s):  
Benson Oloya ◽  
Jane Namukobe ◽  
Matthias Heydenreich ◽  
Willy Ssengooba ◽  
Bernd Schmidt ◽  
...  
Keyword(s):  
Antimycobacterial Activity ◽  
Stem Bark ◽  
Multidrug Resistant ◽  
Moderate Activity ◽  
Spectroscopic Techniques ◽  
Minimum Inhibitory Concentrations ◽  
Mdr Tb ◽  
Weak Activity ◽  
First Time ◽  
Chloroform Methanol

Zanthoxylum leprieurii Guill. and Perr. (Rutaceae) stem bark is used locally in Uganda for treating tuberculosis (TB) and cough-related infections. Lupeol (1), sesamin (2), trans-fagaramide (3), arnottianamide (4), ( S)-marmesinin (5), and hesperidin (6) were isolated from the chloroform/methanol (1:1) extract of Z. leprieurii stem bark. Their structures were elucidated using spectroscopic techniques and by comparison with literature data. Furthermore, the extract and isolated compounds were subjected to antimycobacterial activity. The extract exhibited moderate activity against the susceptible (H37Rv) TB strain, but weak activity against the multidrug resistant (MDR)-TB strain with minimum inhibitory concentrations (MICs) of 586.0 and 1172.0 μg/mL, respectively. Compound 3 (trans-fagaramide) showed significant antimycobacterial activity against the susceptible (H37Rv) TB strain (MIC 6 μg/mL), but moderate activity against the MDR-TB strain (MIC 12.2 μg/mL). Compounds 2, 5, 6, and 1 showed moderate activities against the susceptible (H37Rv) strain (MIC 12.2-98.0 μg/mL) and moderate to weak activities against the MDR-TB strain (MIC 24.4-195.0 μg/mL). This study reports for the first time the isolation of compounds 1 to 6 from the stem bark of Z leprieurii. trans-Fagaramide (3) may present a vital template in pursuit of novel and highly effective TB drugs.

scholarly journals Four Flavan-3-ol Compounds From The Stembark of Chisocheton balansae C.DC. (MELIACEAE)

Molekul ◽  
2021 ◽  
Vol 16 (1) ◽  
pp. 9
Author(s):  
Unang Supratman ◽  
Mohamad Fajar ◽  
Supriatno Salam ◽  
Rani Maharani ◽  
Desi Harneti ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
13C Nmr ◽  
Chemical Structure ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Endemic Plants ◽  
North Sulawesi ◽  
First Time

Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1), epicatechin (2), epigallocatechin-3-O-gallate (3), and epicatechin-3-O-gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods (1H-NMR, 13C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.

scholarly journals Steroidal Glycosides from Veronica chamaedrys L. Part I. The Structures of Chamaedrosides C, C1, C2, E, E1 and E2

2012 ◽  
Vol 7 (5) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Alexandra Marchenko ◽  
Pavel Kintya ◽  
Bozena Wyrzykiewicz ◽  
Elena Gorincioi
Keyword(s):  
2D Nmr ◽  
Spectroscopic Methods ◽  
Steroidal Glycosides ◽  
Ms Analysis ◽  
The Given ◽  
First Time ◽  
Chemical Evidence

Two new spirostane glycosides, chamaedrosides C (1) and C1 (2), two new furostane glycosides, chamaedrosides E (4) and E1 (5), and two new furospirostane glycosides, chamaedrosides C2 (3) and E2 (6), have been isolated from Veronica chamaedrys L. plants. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR experiments, as well as MS analysis. The given compounds have been found for the first time.

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