Essential Oil Composition of Beilschmiedia insignis from Malaysia

Azhar, Muhammad Ammar Mohd; Salleh, Wan Mohd Nuzul Hakimi Wan; Khamis, Shamsul

doi:10.1007/s10600-021-03361-7

Cited by 3 publications

(4 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Melting points were measured using melting point apparatus equipped with a microscope, Leica Gallen III and were uncorrected. The 1 H-NMR (400 MHz) and 13 C-NMR (100 MHz) spectra were recorded on a Bruker Avance 400 Spectrometer. Chemical shifts were reported in ppm and CDCl3 as the solvent.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…We have recently reported the chemical composition of the leaf oil of B. insignis [13]. Analysis of the essential oil revealed the presence of twenty-six components, accounting for 85.7%, and characterized by the presence of high concentrations of oxygenated sesquiterpenes (61.1%).The major components identified were (E)-nerolidol (32.4%), spathulenol (12.9%), bicyclogermacrene (5.2%), globulol (5.0%), and viridiflorol (4.4%).…”

Section: Introductionmentioning

confidence: 99%

“…Brownish amorphous powder; m.p. 183-185 °C;1 H NMR (400 MHz, CDCl3): δH 2.45-2.50 (2H, m, H-4), 2.50 (3H, s, N-CH3), 2.65-2.70 (2H, dd, J = 16.6, 3.2 Hz, H-7), 2.95-3.04 (2H, m, H-5), 3.12-3.20 (1H, m, H-6a), 3.68 (3H, s, 1-OCH3), 3.88 (3H, s, 2-OCH3), 3.90 (3H, s, 10-OCH3), 6.68 (1H, s, H-3), 6.80 (1H, d, J = 8.0 Hz, H-8), 6.85 (1H, d, J = 8.0 Hz, H-9);13 C NMR (100 MHz, CDCl3): δC 29.2 (C-4), 35.8 (C-7), 43.5 (N-CH3), 52.6 (C-5), 55.8 (2-OCH3), 56.2 (10-OCH3), 62.0 (1-OCH3), 62.8 (C-6a), 111.0 (C-3), 111.2 (C-9), 119.0 (C-8), 120.2 (C-11a), 125.8 (C-1a), 129.2 (C-1b), 130.0 (C-3a), 130.2 (C-7a), 142.0 (C-1), 144.0 (C-11), 149.5 (C-10), 151.2 (C-2); MS m/z 342 [M + , C20H24NO4] [21]. (+)-Norisocorydine (2).…”

mentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl3): δC 28.5 (C-4), 35.0 (C-7), 43.2 (N-CH3), 53.0 (C-5), 56.0 (10-OCH3), 60.5 (1-OCH3), 62.5 (C-6a), 110.0 (C-11), 113.0 (C-3), 114.0 (C-8), 123.5 (C-11c), 126.0 (C-11b), 126.5 (C-11a), 130.0 (C-3a), 130.0 (C-7a), 142.0 (C-1), 145.0 (C-9), 145.2 (C-10), 148.0 (C-2); MS m/z 328 [M + , C19H21NO4] [11].…”

mentioning

confidence: 99%

See 3 more Smart Citations

Chemical constituents and acetylcholinesterase inhibitory activity of Beilschmiedia insignis Gamble

Salleh¹,

Nafiah²,

Jauri³

et al. 2022

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

ABSTRACT. Secondary metabolites from natural products are potential sources of acetylcholinesterase inhibitors, which are key enzymes in the treatment of many neurodegenerative diseases. Inspired by the reported activities of alkaloids herein we report the chemical investigation on the chemical constituents from Beilschmiedia insignis and their acetylcholinesterase inhibitory activity. Isolation of the stem bark of B. insignis led to the isolation and identification of five aporphine alkaloids, namely isocorydine (1), norisocorydine (2), (+)-laurotetanine (3), (+)-N-methyllaurotetanine (4), and (+)-boldine (5), together with β-sitosterol (6), β-sitostenone (7), lupeol (8), and lupenone (9). The chemical structures of these compounds were obtained by analysis of their spectroscopic data, as well as the comparison with that of reported data. Acetylcholinesterase inhibitory activity revealed that all isolated alkaloids were found to inhibit AChE with percentage inhibition values ranged from 44.9 to 74.5%. This is the first report on phytochemicals from B. insignis. KEY WORDS: Lauraceae, Beilschmiedia insignis, Alkaloid, Acetylcholinesterase, Alzheimer Bull. Chem. Soc. Ethiop. 2021, 35(3), 685-691. DOI: https://dx.doi.org/10.4314/bcse.v35i3.19

show abstract

Section: General Experimental Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Chemical constituents and acetylcholinesterase inhibitory activity of Beilschmiedia insignis Gamble

Salleh¹,

Nafiah²,

Jauri³

et al. 2022

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

show abstract

Chemical Constituents of Beilschmiedia maingayi

et al. 2021

View full text Add to dashboard Cite

The Leaf Oils of Beilschmiedia tonkinensis (Lecomte) Ridl. and Lindera gracilipes H. W. Li: Chemical Composition, Cytotoxicity, Antimicrobial Activity, and Docking Study

Huan,

Luyen,

et al. 2024

Natural Product Communications

View full text Add to dashboard Cite

Objective The Lauraceae plants comprised high amounts of essential oils, some of which established pharmacological potentials such as anticancer and antimicrobial activities. The Lauraceae essential oils are also used in cuisines and perfumes. The present study provides the chemical analysis of the leaf oils of Beilschmiedia tonkinensis and Lindera gracilipes, collected from Vietnam. Method Chemical components in the obtained oils were identified by the GC-FID/MS. The MTT and broth microdilution assays were used to evaluate cytotoxic and antimicrobial effects, respectively. The protein interactions were viewed by a docking study. Result Beilschmiedia tonkinensis leaf oil was characterized by sesquiterpene hydrocarbons (66.0%), in which bicyclogermacrene (23.3%), ( E)-caryophyllene (21.9%), caryophyllene oxide (9.9%), and spathulenol (6.0%) were the main components. The major chemical class in L gracilipes leaf oil was still sesquiterpene hydrocarbons (64.2%) with bicyclogermacrene (32.2%) being the principal component. Both 2 oil samples (IC50 41.2-44.12 µg/mL) were actively cytotoxic against the proliferation of A-549 cancer cells. In particular, B tonkinensis leaf oil strongly controlled Hep-G2 and MCF-7 cancerous cells with the IC50 values of 20.6 and 9.36 µg/mL, respectively. Beilschmiedia tonkinensis leaf oil also strongly inhibited the Gram (–) bacterium Pseudomonas aeruginosa and the fungus Aspergillus niger with the MIC values of 16 and 32 µg/mL, respectively. By molecular docking approach, bicyclogermacrene interacted with the p38α MAPK cancer protein (PDB ID: 4FA2) with a potential binding affinity of −8.019 kcal/mol, whereas ( E)-caryophyllene tends to bind 2 bacterial proteins P aeruginosa QS regulator (PDB ID: 6B8A) and glucosamine-6-phosphate synthase (GlmS) (PDB ID: 2VF5) with the better binding affinities of −6.740 and −6.521 kcal/mol, respectively. The most preferable binding mode was due to hydrophobic π-alkyl and alkyl interactions. Conclusion The current result can be seen as a basic foundation in the applications of essential oils of B tonkinensis and L gracilipes for anticancer and antimicrobial treatments. Further phytochemical studies and mechanisms of action are needed.

show abstract

Essential Oil Composition of Beilschmiedia insignis from Malaysia

Cited by 3 publications

References 10 publications

Chemical constituents and acetylcholinesterase inhibitory activity of Beilschmiedia insignis Gamble

Chemical constituents and acetylcholinesterase inhibitory activity of Beilschmiedia insignis Gamble

Chemical Constituents of Beilschmiedia maingayi

The Leaf Oils of Beilschmiedia tonkinensis (Lecomte) Ridl. and Lindera gracilipes H. W. Li: Chemical Composition, Cytotoxicity, Antimicrobial Activity, and Docking Study

Contact Info

Product

Resources

About