Chiral resolution, absolute configuration, and bioactivity of a new racemic asarone derivative from the rhizome of Acorus tatarinowii.

Fitoterapia

Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China. Electronic address:

Published: October 2017


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

A new asarone-derived racemate (1) was isolated from the rhizome of Acorus tatarinowii. The structure of 1 was established by comprehensive spectroscopic analyses, and it was successfully resolved by chiral HPLC, demonstrating that it is racemic. The absolute configurations of 1a [(-)-acortatarone A] and 1b [(+)-acortatarone A] were determined using quantum chemical calculations. Compounds 1a and 1b were the first cases of asarone derivatives with the 5,7-dialkyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one core. The α-glucosidase inhibitory and acetylcholinesterase (AChE) inhibitory activities of 1 were evaluated, and it exhibited α-glucosidase inhibitory activity with potency close to that of the positive control (acarbose).

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.fitote.2017.08.004DOI Listing

Publication Analysis

Top Keywords

rhizome acorus
8
acorus tatarinowii
8
α-glucosidase inhibitory
8
chiral resolution
4
resolution absolute
4
absolute configuration
4
configuration bioactivity
4
bioactivity racemic
4
racemic asarone
4
asarone derivative
4

Similar Publications

Reporting negative Ames test results for Indian Acorus calamus L., rhizome, extracts, and beta asarone.

Indian J Pharmacol

September 2025

Department of Pharmacognosy and Phytochemistry, Bombay College of Pharmacy, Mumbai, Maharashtra, India.

Objective: Acorus calamus L. (Sweet Flag), known in India as "Vacha," is widely used in traditional medicine, particularly for cognitive enhancement in infants. While traditionally considered safe, β-asarone - a key constituent - has shown potential genotoxicity in some in vitro studies.

View Article and Find Full Text PDF

The primary objectives of this study were to evaluate the kinetics of Acori tatarinowii rhizoma (ATR) and to investigate how hot air drying at different temperatures affected the surface texture and sensory quality of the ATR. The drying kinetics of ATR were evaluated at five temperature levels (35, 45, 55, 65, and 75 ℃). Among the tested models, the Cubic model showed the best performance.

View Article and Find Full Text PDF

Alzheimer's disease (AD) is a degenerative disorder causing neuronal loss and cognitive deficits, which is associated with intestinal flora dysbiosis. Acori Tatarinowii Rhizoma (ATR) is the dried rhizome of Acorus tatarinowii Schott., and exhibits neuroprotective effects.

View Article and Find Full Text PDF

Metabolic dysfunction-associated steatotic liver disease (MASLD) is a global health issue that causes severe liver abnormalities and metabolic dysregulation, incurring substantial costs to healthcare systems. , a traditional remedy, has been studied for its anti-inflammatory and neuroprotective effects. However, its potential role in the management of metabolic disorders via its polysaccharide components remains unclear.

View Article and Find Full Text PDF

Chemical Composition, Anti-Tyrosinase and Antioxidant Potential of Essential Oils from (L.) and (L.).

Molecules

May 2025

Faculty of Natural Sciences, Institute of Biological Sciences, University of Siedlce, 14 Prusa St., 08-110 Siedlce, Poland.

The essential oils (EOs) represent a natural source of diverse phytoconstituents that may exert a wide range of health-promoting effects, including antioxidative, anti-inflammatory, antimicrobial, and immunomodulatory activities. Compounds with antioxidative and anti-tyrosinase properties present in EOs may suppress excessive melanin production and protect skin cells from oxidative stress factors that often aggravate the pigmentation process. L.

View Article and Find Full Text PDF