Neurotrophic and anti-neuroinflammatory constituents from the aerial parts of Coriandrum sativum

Article abstract of DOI:10.1016/j.bioorg.2020.104443

In the course of our continuing search for biologically active compounds from medicinal sources, we investigated the MeOH extract of the aerial parts of Coriandrum sativum Linn. An extended phytochemical investigation of the aerial parts of C. sativum led to the isolation and identification of seven compounds (1–7) including two new isocoumarin glycosides (1–2) and a new phenolic glycoside (5). The chemical structures of the new compounds (1, 2, and 5) were elucidated by analysis of 1D and 2D NMR (¹H and ¹³C NMR, COSY, HSQC, and HMBC) and HRESIMS data as well as by using chemical methods. All the isolates were evaluated not only for their potential neurotrophic activity by means of induction of nerve growth factor (NGF) in C6 glioma cells but also for production of nitric oxide (NO) levels in lipopolysaccharide (LPS)-activated murine microglia BV-2 cells to assess their anti-neuroinflammatory activity. Compounds 1–3 and 7 were stimulants of NGF release, with levels of NGF stimulated at 127.23 ± 1.89%, 128.22 ± 5.45%, 121.23 ± 6.66%, and 120.94 ± 3.97%, respectively. Furthermore, the aglycones of 1 and 2 (1a and 2a) showed more potent NGF secretion activity and anti-neuroinflammatory effect than did their glycosides (1a: 130.81 ± 5.45% and 2a: 134.44 ± 5.45%).

Full text of DOI:10.1016/j.bioorg.2020.104443

Bioorganic Chemistry 105 (2020) 104443
Contents lists available at ScienceDirect
Bioorganic Chemistry
journal homepage: www.elsevier.com/locate/bioorg
Neurotrophic and anti-neuroinflammatory constituents from the aerial
parts of Coriandrum sativum
,
,
,*
Joon Min Chaa, DaHye Yoonb c, Sun Yeou Kimb c, Chung Sub Kima, Kang Ro Leea
a Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea
b Gachon Institute of Pharmaceutical Science, Gachon University, 191 Hambakmoero, Yeonsu-gu, Incheon 21936, Republic of Korea
c College of Pharmacy, Gachon University, 191 Hambakmoero, Yeonsu-gu, Incheon 21936, Republic of Korea
A R T I C L E I N F O
A B S T R A C T
Keywords:
In the course of our continuing search for biologically active compounds from medicinal sources, we investigated
the MeOH extract of the aerial parts of Coriandrum sativum Linn. An extended phytochemical investigation of the
aerial parts of C. sativum led to the isolation and identification of seven compounds (1–7) including two new
isocoumarin glycosides (1–2) and a new phenolic glycoside (5). The chemical structures of the new compounds
(1, 2, and 5) were elucidated by analysis of 1D and 2D NMR (1H and 13C NMR, COSY, HSQC, and HMBC) and
HRESIMS data as well as by using chemical methods. All the isolates were evaluated not only for their potential
neurotrophic activity by means of induction of nerve growth factor (NGF) in C6 glioma cells but also for pro-
duction of nitric oxide (NO) levels in lipopolysaccharide (LPS)-activated murine microglia BV-2 cells to assess
their anti-neuroinflammatory activity. Compounds 1–3 and 7 were stimulants of NGF release, with levels of NGF
stimulated at 127.23 ± 1.89%, 128.22 ± 5.45%, 121.23 ± 6.66%, and 120.94 ± 3.97%, respectively. Further-
Coriandrum sativum
Apiaceae
Structural elucidation
Neurotrophic
Anti-inflammation
more, the aglycones of
1 and 2 (1a and 2a) showed more potent NGF secretion activity and anti-
neuroinflammatory effect than did their glycosides (1a : 130.81 ± 5.45% and 2a : 134.44 ± 5.45%).
1. Introduction
we screened the nerve growth factor (NGF) production in astrocyte C6
cells. C6 cells are rat-derived glial cells and are the most abundant cells
Neurodegenerative diseases, including Alzheimer s disease (AD),
Parkinson s disease (PD), Huntington s disease, and multiple sclerosis
(MS), deteriorate the human body s activity for multiplex reasons with
aging and led to cognitive/memory disorders [1]. These diseases can
result from the structural breakdown and dysfunction of neurons
including neuroinflammation and depletion of neurotrophic factors.
Therefore, much studies have been focused on finding neuroprotective
and neurotrophic substances for neurodegenerative diseases. BV-2 cells,
mouse-derived microglial cells, are important cells involved in the
central nervous system (CNS), and the increase in nitric oxide (NO) and
cytokines is a major biomarker of neuroinflammation [2,3]. Activation
of microglia by lipopolysaccharide (LPS) results in cytotoxicity and
neuroinflammation through an increase in inflammatory mediators such
NO, cytokines and reactive oxygen species (ROS). In addition, increase
of cytokines such as interleukin6 (IL6), nuclear factor kappa-light-chain-
in the brain. These cells play a very important function in repairing brain
tissue when being damaged [5]. NGF is one of main neurotrophic factor
which is related with nerve growth, maintenance, proliferation and
neuronal survive. It is also responsible for the extension and mainte-
nance of axons in neurons. Thus, the efficacy of NGF for neuronal repair
may be a better alternative for the treatment of various neuronal dis-
orders [6].
Coriandrum sativum Linn. (Apiaceae) generally known as “coriander”
or “cilantro” is an annual plant native to regions spanning from Southern
Europe and Northern Africa to Southwestern Asia [7]. In addition to the
wide usage of C. sativum as a spice around the world, the aerial parts of
this plant have been used in a traditional medicine for treating hyper-
tension, gastrointestinal disorders, and anti-inflammation [8,9]. Previ-
ous phytochemical investigations have isolated isocoumarins, aliphatic
lactones, and monoterpene derivatives [10–12] with a variety of bio-
logical effects such as cytotoxic, antioxidant, antibacterial, gastric
mucosal protective, and anti-inflammatory activities [13–15]. In this
study, an extended phytochemical investigation of the aerial parts of
enhancer of activated B cells (NF-KB), tumor necrosis factor-α (TNF-α) by
LPS lead to neuronal cell death [4]. Thus, we did screening of anti-
neuroinflammatory effect of the compound in BV-2 cells. Additionally,
* Corresponding author.
E-mail address: krlee@skku.edu (K.R. Lee).
https://doi.org/10.1016/j.bioorg.2020.104443
Received 21 August 2020; Received in revised form 22 October 2020; Accepted 28 October 2020
Available online 1 November 2020
0045-2068/© 2020 Elsevier Inc. All rights reserved.

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Bioorganic Chemistry, 105 (2020) 104443. doi:10.1016/j.bioorg.2020.104443

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Bioorganic Chemistry, 105 (2020) 104443. doi:10.1016/j.bioorg.2020.104443

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Bioorganic Chemistry, 105 (2020) 104443. doi:10.1016/j.bioorg.2020.104443