Cytotoxic Prenyl and Geranyl Coumarins from the Stem Bark of Casimiroa edulis

Phytochemical investigation of the methanolic extract of the stem bark of Casimiroa edulis afforded four coumarins. Various spectroscopic experiments were used to characterize the isolated coumarins. The structures were identified as auraptene (K-1), suberosin (K-2), 5-geranyloxypsoralen (bergamottin) (K-3), and 8-geranyloxypsoralen (K-4), based on the chemical and spectral analysis. Among these compounds, suberosin (K-2) and 5-geranyloxypsoralen (bergamottin) (K-3) were isolated for the first time from this genus, and auraptene (K-1) was isolated from this plant for the first time. Cytotoxicity of pure compound K-4 and sub-fraction MD-3 was evaluated against HeLa and T47D cell lines and moderate activity was found with an IC50 value in the range 17.4 to 72.33 μg/mL.

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Isolation and Characterization of Secondary Metabilites and Evaluation of Antimicrobial, Antioxidant and Thrombolytic Potentials of Erythrina variegata L. Bark

Asian Journal of Chemistry ◽

10.14233/ajchem.2019.21993 ◽

2019 ◽

Vol 31 (8) ◽

pp. 1842-1846

Author(s):

Fatema Tabassum ◽

Choudhury Mahmood Hasan ◽

Mohammad Mehedi Masud ◽

Md. Imran Nur Manik ◽

Monira Ahsan

Keyword(s):

Methanolic Extract ◽

Authentic Sample ◽

Stem Bark ◽

Moderate Activity ◽

Zone Of Inhibition ◽

Nmr Studies ◽

Erythrina Variegata ◽

Isolation And Characterization ◽

Ic50 Value

Six compounds, sitosta-4-en-3-one (1), 3β,28-dihydroxyolean-12-en (2), scandenone (3), alpinum isoflavone (4), stigmasterol (5) and lupeol (6) were isolated from the methanol soluble extract of the stem bark of Erythrina variegata. The structure of the compounds was established by extensive NMR studies as well as co-TLC with authentic sample. The petroleum ether, carbon tetrachloride, chloroform and aqueous soluble fractions of the methanolic extract of Erythrina variegata were evaluated for antimicrobial, antioxidant and thrombolytic properties. In the antimicrobial study, most of the fractions of the extract exhibited mild to moderate antimicrobial activity where the zone of inhibition were ranging from 7.69 to 19.51 mm. The chloroform soluble fraction showed significant antioxidant activity with IC50 value 66.28 μg/mL as compared to standard BHT (IC50 value 23.09 μg/mL). The thrombolytic property of different extracts of E. variegata exhibited moderate activity ranging from 31.25 to 57.78 %.

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chemical constituents from methanolic extract of Garcinia mackeaniana leaves and their antioxidant activity

Vietnam Journal of Science and Technology ◽

10.15625/2525-2518/58/4/14680 ◽

2020 ◽

Vol 58 (4) ◽

pp. 411

Author(s):

Ha Nguyen Thi Thu ◽

Cuong Pham Van ◽

Tra Nguyen Thanh ◽

Anh Le Thi Tu ◽

Cham Ba Thi ◽

...

Keyword(s):

Methanolic Extract ◽

Chemical Constituents ◽

Spectroscopic Method ◽

Acetyl Derivative ◽

Antioxidant Assay ◽

Chemical Structures ◽

Phytochemical Investigation ◽

Ic50 Value ◽

First Time

A phytochemical investigation of the methanolic extract of Garcinia mackeaniana leaves led to the isolation, and determination of five secondary metabolites, including one benzophenone 4,3',4'-trihydroxy-2,6-dimethoxybenzophenone (1), two flavone C-glucosides vitexin (2) and its 2''-O-acetyl derivative (3), one biflavone amentoflavone (4), and one mono-phenol methyl protocatechuate (5). The chemical structures of these compounds were characterized by the NMR-spectroscopic method. These isolated compounds were isolated from G. mackeaniana species for the first time. Benzophenone derivative 1 has shown to be associated with a significant IC50 value of 14.97±0.8 µg/mL in the DPPH-antioxidant assay.

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Mammalian Arginase Inhibitory Activity of Methanolic Extracts and Isolated Compounds from Cyperus Species

Molecules ◽

10.3390/molecules26061694 ◽

2021 ◽

Vol 26 (6) ◽

pp. 1694

Author(s):

Kamel Arraki ◽

Perle Totoson ◽

Alain Decendit ◽

Andy Zedet ◽

Justine Maroilley ◽

...

Keyword(s):

Inhibitory Activity ◽

Methanolic Extract ◽

Significant Inhibition ◽

Isolation And Identification ◽

Vasorelaxant Effect ◽

Methanolic Extracts ◽

Phytochemical Investigation ◽

Ic50 Values ◽

First Time

Polyphenolic enriched extracts from two species of Cyperus, Cyperus glomeratus and Cyperus thunbergii, possess mammalian arginase inhibitory capacities, with the percentage inhibition ranging from 80% to 95% at 100 µg/mL and 40% to 64% at 10 µg/mL. Phytochemical investigation of these species led to the isolation and identification of two new natural stilbene oligomers named thunbergin A-B (1–2), together with three other stilbenes, trans-resveratrol (3), trans-scirpusin A (4), trans-cyperusphenol A (6), and two flavonoids, aureusidin (5) and luteolin (7), which were isolated for the first time from C.thunbergii and C. glomeratus. Structures were established on the basis of the spectroscopic data from MS and NMR experiments. The arginase inhibitory activity of compounds 1–7 was evaluated through an in vitro arginase inhibitory assay using purified liver bovine arginase. As a result, five compounds (1, 4–7) showed significant inhibition of arginase, with IC50 values between 17.6 and 60.6 µM, in the range of those of the natural arginase inhibitor piceatannol (12.6 µM). In addition, methanolic extract from Cyperus thunbergii exhibited an endothelium and NO-dependent vasorelaxant effect on thoracic aortic rings from rats and improved endothelial dysfunction in an adjuvant-induced arthritis rat model.

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Synthesis of N-methyl-4-piperidone Curcumin Analogues and Their Cytotoxicity Activity against T47D Cell Lines

Indonesian Journal of Chemistry ◽

10.22146/ijc.24174 ◽

2018 ◽

Vol 18 (2) ◽

pp. 362 ◽

Cited By ~ 1

Author(s):

Yum Eryanti ◽

Rudi Hendra ◽

Tati Herlina ◽

Adel Zamri ◽

Unang Supratman

Keyword(s):

Condensation Reaction ◽

Yellow Crystal ◽

T47d Cell ◽

Crystal Form ◽

Moderate Activity ◽

Light Yellow Powder ◽

Cytotoxicity Activity ◽

Curcumin Analogues ◽

Light Yellow ◽

Ic50 Value

Three piperidone curcumin analogues (N-methyl-(3E,5E)-3,5-bis-(2-chlorobenzylidene)-4-piperidone (1), N-methyl-(3E,5E)-3,5-bis-(3-bromobenzylidene)-4-piperidone (2) and N-methyl-(3E,5E)-3,5-bis-(4-chlorobenzylidene)-4-piperidone (3)) were synthesized from N-methyl-4-piperidone with halogenbenzaldehyde, 2-chlorobenzaldehyde, 3-bromobenzaldehyde and 4-chlorobenzaldehyde. The Claisen-Schmidt condensation reaction was used in alkali condition with combinatorial. All the compounds showed light yellow needle, light yellow powder, and yellow crystal form with percentage of yield 39, 66, and 40%, respectively. All the structure compounds were confirmed by using UV, IR, 13C-NMR, 1H-NMR and MS. Apart from that, the cytotoxicity results against breast cancer cell (T47D) showed strong to moderate activity with the IC50 value 8, 4, and 45 µg/mL, respectively.

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

Natural Product Communications ◽

10.1177/1934578x211035851 ◽

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.

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Cytotoxic Sesquiterpenoids from the Stem Bark of Aglaia harmsiana (Meliaceae)

Indonesian Journal of Chemistry ◽

10.22146/ijc.47808 ◽

2020 ◽

Vol 20 (6) ◽

pp. 1448

Author(s):

Hersa Milawati ◽

Winda Sukmawati ◽

Desi Harneti ◽

Rani Maharani ◽

Nurlelasari Nurlelasari ◽

...

Keyword(s):

Cytotoxic Activity ◽

Stem Bark ◽

Hydroxyl Group ◽

Breast Cancer Cell Lines ◽

Spectroscopy Analysis ◽

Chemical Structures ◽

Ic50 Value ◽

First Time ◽

Mass Spectroscopy Analysis ◽

Mcf 7

Three aromadendrane-type sesquiterpenoids, spathulenol (1), 4β,10α-dihydroxyaromadendrane (2), and 4α,10α-dihydroxyaromadendrane (3) were isolated from the stem bark of Aglaia harmsiana (Meliaceae). Compound 3 was isolated for the first time from Aglaia genus. The chemical structures of isolated compounds were elucidated by various spectroscopic methods, including one and two-dimensional NMR, as well as mass spectroscopy analysis. These sesquiterpenoids 1-3 were evaluated for their cytotoxic activity against MCF-7 breast cancer cell lines. The IC50 value of compound 1-3 were 31.65 ± 0.1, 8.41 ± 0.04 and 2.80 ± 0.02 µM, respectively. Among the aromadendrane-type sesquiterpenoids, compounds 2 and 3, which do not have a double bond, showed higher activity than compound 1. Whereas, compound 3 showed the strongest activity indicate that α configuration of hydroxyl group increases the cytotoxic activity.

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STUDY ON CHEMICAL CONSTITUENTS AND CYTOTOXICITY OF ASPIDISTRA LETREAE

HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE ◽

10.26459/hueuni-jns.v129i2a.5656 ◽

2020 ◽

Vol 129 (1B) ◽

Author(s):

Duc Viet Ho

Keyword(s):

Methanol Extract ◽

Human Cancer ◽

Chemical Constituents ◽

Hep G2 ◽

Pure Compound ◽

Human Cancer Cell Lines ◽

Phytochemical Investigation ◽

Reported Data ◽

First Time

A phytochemical investigation of whole Aspidistra letreae plants led to the isolation of 2H-chromen-2-one (1), α-tocopherol (2), (E)-phytol (3), asparenydiol (4) and (25S)-spirost-1β,3α,5β-triol (5). Their structures were determined on the basis of NMR spectral evidences and in comparison with the reported data. Of these, asparenydiol (4) was isolated from the genus Aspidistra for the first time. This is also the first report on the separation and structural determination of (25S)-spirost-1β,3α,5β-triol (5) as a pure compound. The methanol extract exhibited a moderate cytotoxicity against the LU-1, HeLa, MDA-MB-231, Hep-G2, and MKN-7 human cancer cell lines with IC50 values ranging from 52.58 ± 3.65 to 64.78 ± 4.89 μg/mL.

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Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽

10.3390/molecules24183336 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3336 ◽

Cited By ~ 2

Author(s):

Ping-Chen Tu ◽

Han-Chun Tseng ◽

Yu-Chia Liang ◽

Guan-Jhong Huang ◽

Te-Ling Lu ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Isolation And Characterization ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Anti Inflammatory ◽

New Compounds ◽

First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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Phytochemical Study of Fagraea spp. Uncovers a New Terpene Alkaloid with Anti-Inflammatory Properties

Australian Journal of Chemistry ◽

10.1071/ch10421 ◽

2011 ◽

Vol 64 (4) ◽

pp. 489 ◽

Cited By ~ 11

Author(s):

Suciati ◽

Lynette K. Lambert ◽

Benjamin P. Ross ◽

Myrna A. Deseo ◽

Mary J. Garson

Keyword(s):

Cell Line ◽

Stem Bark ◽

Moderate Activity ◽

Additional Species ◽

Leukaemia Cell Line ◽

Phytochemical Study ◽

Phytochemical Investigation ◽

Amino Acid Component ◽

Chemotaxonomic Markers ◽

Secoiridoid Glycosides

Phytochemical investigation of the stem bark of F. racemosa JACK ex WALL (Loganiaceae) from East Java, Indonesia, has resulted in the isolation of a new alkaloid fagraeoside along with the iridoid glycoside secologanoside. Fagraeoside may be derived from the condensation of secologanin with L-asparagine, and represents a rare example of a terpene alkaloid in which the amino acid component is non-aromatic. Investigation of three additional species of Fagraea provided known lignans, iridoid or secoiridoid glycosides, and flavanol-6-C-glucosides, thus it is likely that iridoid and secoiridoid glucosides are chemotaxonomic markers for the Fagraea genus. Fagraeoside inhibited the production of prostaglandin E2 in 3T3 murine fibroblasts (IC50 ~5.1 µM), and was not cytotoxic to this cell line or to a P388 murine leukaemia cell line. Selected isolated compounds, including fagraeoside, showed low to moderate activity in anti-acetylcholinesterase screening.

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An Ellagic Acid Derivative and Its Antioxidant Activity of Stem Bark Extracts of Syzygium polycephalum Miq. (Myrtaceae)

Indonesian Journal of Chemistry ◽

10.22146/ijc.25467 ◽

2018 ◽

Vol 18 (1) ◽

pp. 26

Author(s):

Tukiran Tukiran ◽

Andika Pramudya Wardana ◽

Nurul Hidayati ◽

Kuniyoshi Shimizu

Keyword(s):

Antioxidant Activity ◽

Acid Derivative ◽

Ellagic Acid ◽

Methanol Extract ◽

Stem Bark ◽

Spectroscopic Studies ◽

Chloroform Fraction ◽

Ic50 Value ◽

Isolated Compound ◽

First Time

The investigation of the Syzygium polycephalum Miq. (Myrtaceae) aimed to assess the phytochemical contents and antioxidant activity of the chloroform fraction. In this study, the fraction was obtained from methanol extract of S. polycephalum stem bark partitionated by chloroform. An ellagic acid derivative was successively isolated from the chloroform fraction. The molecular structure of isolated compound was elucidated and established as 3,4,3’-tri-O-methylellagic acid through extensive spectroscopic studies including UV-Vis, FTIR, NMR and LC-MS analyses and by comparison with literature data. The finding of the isolated compound is the first time from the plant, although the isolated compound previously have been found in the other Syzygium species such as S. cumini together with ellagic acid and 3,3’-di-O-methylellagic acid. The chloroform fraction, isolated compound, and vitamin C showed antioxidant activity against 2,2’-diphenyl-1-picrylhydrazyl (DPPH) with IC50 value of 163.6, 72.1, and 11.5 μg/mL, respectively.

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