Structural characterization, hepatoprotective and antihyperlipidemic activities of alkaloid derivatives from Murraya koenigii

doi:10.1016/j.phytol.2019.11.001

Phytochemistry Letters

Volume 35, February 2020, Pages 135-140

https://doi.org/10.1016/j.phytol.2019.11.001 Get rights and content

Highlights

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Murraya koenigii is not only an ingredient, but also a medical plant for people.
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Three new alkaloids and a new natural alkaloid were isolated from M. koenigii.
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Thirteen known alkaloids were obtained from M. koenigii for the first time.
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Compounds 1, 15, 16, and 17 (10 μM) showed moderate hepatoprotective activities.
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Compounds 2, 3, 9, and 13 showed moderate activation of PPARα and PPARγ receptors.

Abstract

Three new alkaloids (1-3) and a new natural alkaloid (4), named (1′R,3′R,4′R,6′S)-endocycliomurrayamine-A (1), 3-formyle-7-hydroxy-9H-carbazole-1-O-β-d-glucopyranoside (2), 4′-hydroxyphenyl-6-ethyl-1H-pyrrole-2-carboxaldehyde (3), and 4-hydroxyphenoxy-N-methyl-propanamide (4), together with thirteen known alkaloid derivatives (5–17) were isolated from Murraya koenigii. Among them, compounds (8–17) were isolated from this plant for the first time. The structures of compounds (1–17) were elucidated on the basis of their spectroscopic analysis and references. Compounds 1, 15, 16, and 17 (10 μM) showed moderate hepatoprotective activities against d-galactosamine-induced HL-7702 cells damage. Compounds 2, 3, 9, and 13 showed moderate activation of PPARα and PPARγ receptors.

Graphical abstract

Introduction

Murraya koenigii (L.) Spreng, belonging to the Rutaceae family, is popular as an ingredient in the Southeast Asia (Ma et al., 2013). It is mainly distributed Yunnan, Guangxi, and Hainan provinces in China. The leaf of M. koenigii is well known as curry leaf, and its dried powder is traditionally added to Indian gravy and other vegetables for the delicious taste (Mani and Milind, 2009). Previous phytochemical studies on M. koenigii afforded structurally-diverse compounds, such as phenylpropanoids, alkaloids, sesquiterpenes, alkenes, and volatile oils (Ma et al., 2019). M. koenigii has been known for its medical properties for the treatment of nephroprotective (Mahipal and Pawar, 2017), antiinflammatory (Rautela et al., 2018), hepatoprotective (Ma et al., 2014), antioxidative (Ma et al., 2016), antilisterial (Kumar et al., 2017) PTP1B inhibitory (Rahman and Gray, 2005), immunomodulatory (Priyanka et al., 2011) inhibitory activity by measuring IL-6-induced STAT3 promoter activity in HepG2 cells, and inhibition against lipopolysaccharide (LPS)-induced NO production in RAW264.7 macrophages functions (Ma et al., 2019). Inspired by the functions of M. koenigii in the treatment of many diseases, we carried out a bioactivity-guided investigation of M. koenigii in order to evaluate their further pharmacological potentials. As a result, three new alkaloids (1–3) and a new natural alkaloid (4), together with thirteen known alkaloids derivatives (5–17) were isolated from the active fractions of M. koenigii. Meanwhile, compounds (1–17) were evaluated for their hepatoprotective and antihyperlipidemic activities in this work. Described herein are the isolation, structural elucidation, and bioactivity evaluation of these alkaloid derivatives (1–17) from M. koenigii in this paper (Supporting information: Fig. 1).

Section snippets

Structure elucidation

Compound 1 was obtained as colorless oil. Its molecular formula was determined to be C₂₃H₂₅NO₃, established by HR-ESI-MS at m/z 364.1905 [M+H]⁺ (calcd. for C₂₃H₂₆NO₃, 364.1907) corresponding to twelve degrees of unsaturation. The UV spectrum showed at λ_max 202, 237, 267, and 319 nm, indicating the presence of the carbazole alkaloid skeleton (Sim and Teh, 2011). The IR spectrum implied the presence of amino (3343 cm⁻¹), hydroxyl (2923 cm⁻¹), benzene ring (1620 cm⁻¹) functionalities. In the ¹H

General experimental procedures

The IR spectra were recorded on a Nicolet 5700 FT-IR microscope spectrometer (Shanghai Xiangrun Industry Co. Ltd., Shanghai, China). The UV spectra were taken with a Hitachi UV-240 spectrophotometer (GBC Scientific Equipment Pty. Ltd., Braeside, Australia). The optical rotations were recorded on a Perkin-Elmer 241 digital polarimeter at 20℃ (PerkinElmer, America). The NMR spectra were performed on Varian Mercury-300, Inova-501, DD2-500,VNS-600 spectrometers with tetramethylsilane as an internal

Declaration of Competing Interest

There are no conflicts of interest to declare.

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (81803843), the Standard Revision Research Project of National Pharmacopoeia Committee (2018Z090), the Key Scientific Research Project of Colleges and Universities in Henan Province (19A350006), the Science and Technology Project of Jiangxi Health Commission (20195648, 20195650), the Science and Technology Project of Jiangxi Provincial Department of Education (GJJ180662, GJJ180688), the Scientific Research

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Structural characterization, hepatoprotective and antihyperlipidemic activities of alkaloid derivatives from Murraya koenigii

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Structure elucidation

General experimental procedures

Declaration of Competing Interest

Acknowledgements

Phytochemistry

Phytochemistry

Fitoterapia

Carbohydr. Res.

LWT-Food Sci. Technol.

Asian Pac. J. Trop. Med.

Fitoterapia

Bioorg. Chem.

Bioorg. Med. Chem. Lett.

Chin. J. Nat. Med.

Phytochemistry

Livest. Sci.

J. Ethnopharmacol.

Phytochemistry