Acetylcholinesterase inhibitory activity of volatile oil from Peltophorum dasyrachis Kurz ex Bakar (yellow batai) and bisabolane-type sesquiterpenoids
Abstract
In this study, the chemical compositions and acetylcholinesterase (AChE) inhibitory activitiy of the volatile oil from the bark of Peltophorum dasyrachis Kurz ex Bakar (yellow batai) were evaluated. As a result, 68 compounds, accounting for 88.0% of the total oil, were identified. The main characteristic constituent in P. dasyrachis was isolated by silica gel column chromatography and found to be a sesquiterpenoid, (+)-(S)-ar-turmerone (1). In the AChE inhibitory assay, the volatile oil showed potent inhibitory activity with the IC(50) value of 83.2 +/- 2.8 microg/mL. Among the volatile oil components and characteristic sesquiterpenoids, (+)-(S)-ar-turmerone (1) and (+)-(S)-dihydro-ar-turmerone (2) were potent compounds, inhibiting AChE in a dose-dependent manner, with IC(50) values of 191.1 +/- 0.3 and 81.5 +/- 0.2 microM, respectively. (+)-(S)-Dihydro-ar-turmerone (2), in particular, was found to be the most potent AChE inhibitor. Also, bisabolane-type sesquiterpenoid derivatives, (+)-(7S,9S)-ar-turmerol (3), (+)-(7S,9R)-ar-turmerol (4), (+)-(7S,9S)-dihydro-ar-turmerol (5), (+)-(7S,9R)-dihydro-ar-turmerol (6), (+)-(S)-ar-curcumene (7), and (+)-(S)-dihydro-ar-curcumene (8), were synthesized and tested for their AChE inhibitory effect, and their structure-activity relationships were evaluated. All sesquiterpenoids exhibited AChE inhibitory activity. The order of AChE inhibitory potency by bisabolane-type sesquiterpenoids was as follows: ketones > alcohols > hydrocarbons. Furthermore, the inhibition kinetics analyzed by Dixon plots indicated that (+)-(S)-ar-turmerone (1) is a competitive inhibitor, with a K(i) value of 882.1 +/- 2.1 microM, whereas (+)-(S)-dihydro-ar-turmerone (2) is a non-competitive inhibitor.
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Bisabolane-type sesquiterpenoid derivatives exhibit AChE inhibitory activity in the order hydrocarbons < alcohols < ketones.
“Furthermore, the bisabolane-type sesquiterpenoid derivatives from plants, such as (+)-(7S,9S)-ar-turmerol, (+)-(7S,9R)-ar-turmerol, (+)-(7S,9S)-dihydro-ar-turmerol, (+)-(7S,9R)-dihydro-ar-turmerol, (+)-(S)-ar-curcumene, and (+)-(S)-dihydro-ar-curcumene, were synthesized which were found to exhibit the acetylcholinesterase inhibitory activity in the order hydrocarbons <alcohols < ketones.”
From Acetylcholinesterase Inhibitory Potential of Various Sesquiterpene Analogues for Alzheimer’s Disease Therapy (2021) · cites this paper as [90]
Maximum AChE inhibitory activity among bisabolane derivatives was observed through oxidation of the functional group at C9 and the C10-C11 single-bond moiety, (+)-(S)-dihydro-ar-turmerone.
“The maximum activity was observed through the oxidation of the functional group at C9 position and C10–C11 structure of single-bond moiety, (+)-(S)-dihydro-ar-turmerone.”
From Acetylcholinesterase Inhibitory Potential of Various Sesquiterpene Analogues for Alzheimer’s Disease Therapy (2021) · cites this paper as [90]
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“[90] evaluated the essential oil obtained from the bark of Peltophorum dasyrachis Kurz ex Bakar and the main sesquiterpenoids found were, (+)(S)-ar-turmerone (9) and (+)-(S)-dihydro-ar-turmerone (10).”
Background
- Authors
- Fujiwara, M., Yagi, N., & Miyazawa, M.
- Affiliations
- Kindai University (JP)
- Picaso Cosmetic Laboratory Limited, 9-20 Ikea-cho, Nishinomia-shi, Hyogo 662-0911, Japan
- Corresponding author
- Miyazawa, Mitsuo
- ORCID
- Miyazawa, Mitsuo
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-02-10
- Volume
- 58
- Issue
- 5
- Pages
- 2824-2829
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2025292382
- Cited by
- 75
- References
- 24
- Citations by year
- 2026: 4 · 2025: 1 · 2024: 7 · 2023: 6 · 2022: 3 · 2021: 7 · 2020: 2 · 2019: 6 · 2018: 8 · 2017: 2 · 2016: 4 · 2015: 6 · 2014: 7 · 2013: 4 · 2012: 3
- FWCI
- 6.37
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Agricultural and Food Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Food Science › Essential Oils and Antimicrobial Activity
- Health Sciences › Medicine › Pharmacology › Cholinesterase and Neurodegenerative Diseases
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Keywords
- essential oils, acetylcholinesterase inhibition, bisabolane sesquiterpenoids, ar-turmerone, ar-curcumene, structure-activity relationship, competitive inhibition, chemical composition, bark constituents, Alzheimer's disease, cholinesterase inhibitors
- MeSH terms
- Acetylcholinesterase, Cholinesterase Inhibitors, Fabaceae, Plant Oils, Sesquiterpenes, Volatilization
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