Identification and anti-inflammatory activity of chemical constituents and a pair of new monoterpenoid enantiomers from the fruits of Litsea cubeba
10.16438/j.0513-4870.2023-1216
- VernacularTitle:荜澄茄化学成分及一对新的单萜对映异构体的鉴定和抗炎活性研究
- Author:
Mei-lin LU
1
;
Wan-feng HUANG
1
;
Yu-ming HE
1
;
Bao-lin WANG
1
;
Fu-hong YUAN
1
;
Ting ZHANG
1
;
Qi-ming PAN
1
;
Xin-ya XU
2
;
Jia HE
3
;
Shan HAN
3
;
Qin-qin WANG
3
;
Shi-lin YANG
1
,
4
;
Hong-wei GAO
1
Author Information
1. College of Pharmacy, Guangxi University of Chinese Medicine, Nanning 530200, China
2. Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China
3. College of Pharmacy, Jiangxi University of Chinese Medicine, Nanchang 330000, China
4. College of Pharmacy, Jiangxi University of Chinese Medicine, Nanchang 330000, China
- Publication Type:Research Article
- Keywords:
Lauraceae;
italic>Litsea cubeba;
italic>Litsea cubeba fruit;
monoterpenoid;
enantiomer;
anti-inflammatory activity
- From:
Acta Pharmaceutica Sinica
2024;59(5):1348-1356
- CountryChina
- Language:Chinese
-
Abstract:
Eighteen compounds were isolated from the methanol extract of the fruits of Litsea cubeba by silica gel, ODS, Sephadex LH-20 column chromatography, semi-preparative RP-HPLC, chiral HPLC and recrystallization. Their structures were elucidated by spectroscopic analyses and by comparison with reported spectroscopic data and physicochemical properties, and the absolute configurations of the enantiomers were established by experimental and calculated electronic circular dichroism spectra. These compounds were identified as (+)-(R)-4-hydroxypiperitenone (1a), (-)-(S)-4-hydroxypiperitenone (1b), (3S,4S,6R)-3,6-dihydroxy-1-menthene (2), (4S,5R)-4-hydroxy-5-isopropyl-2-methylcyclohex-2-en-1-one (3), (R)-6-hydroxy-3-(2-hydroxypropan-2-yl)-6-methylcyclohex-2-enone (4), (4S,6R)-4-hydroxy-6-isopropyl-3-methylcyclohex-2-enone (5), (1R,3S,4R)-3-hydroxy isopulegol (6), subamone (7), (6S)-3,7-dimethyl-7-hydroxy-2(Z)-octen-6-olide (8), (6S)-6,7-dihydroxy-3,7-dimethyloct-2(Z)-enoate (9), holostylactone (10), sesamin (11), dimethylmatairesinol (12), p-hydroxybenzoylcarbinol (13), syringaldehyde (14), p-hydroxybenzaldehyde (15), 4-hydroxy-3-methoxybenzaldehyde (16), 5,4ʹ-dihydroxy-7-methoxyflavone (17). Among them, compounds 1a and 1b were a pair of new monoterpenoid enantiomers, 8 and 9 were new natural products, 2-7, 10, 11 and 17 were isolated from Litsea genus for the first time. The in vitro anti-inflammatory effects of compounds 1-17 were evaluated using lipopolysaccharide-stimulated RAW264.7 cells, the results showed that compound 14 exhibited significant anti-inflammatory activity with NO inhibitory rate of 66.27% at a concentration of 40 μmol·L-1.
