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医薬品候補の潜在的供給源としての野生塩生植物の利用

アハメドモハメドオスマンカミス AHMED MOHAMED OTHMAN KHAMIS 九州大学

2023.03.20

概要

九州大学学術情報リポジトリ
Kyushu University Institutional Repository

Utilization of halophytes as a potential source
of pharmaceutical candidates
アハメドモハメドオスマンカミス

https://hdl.handle.net/2324/6787673
出版情報：Kyushu University, 2022, 博士（農学）, 課程博士
バージョン：
権利関係：

Name
Title

：アハメドモハメドオスマンカミス
(AHMED MOHAMED OTHMAN KHAMIS)
：Utilization of halophytes as a potential source of pharmaceutical
candidates
(医薬品候補の潜在的供給源としての野生塩生植物の利用)

Category：Kou
Thesis Summary
Natural product research continues to play a vital role in paving the way toward the discovery of novel
bioactive drug leads and has been applied in many fields of pharmaceutical and functional food industry.
Recently, the scientific interest and particularly the economic significance of halophytes have been highly
demanding due to the medicinal and nutraceutical potential of its bioactive compounds. The xero-halophyte
herbs, Bassia indica and Agathophora alopecuroides, are deemed to be among the promising sources of
natural compounds without chemical or biological investigation.
Non-communicable diseases (NCDs) greatly burden societies and national governments owing to their
high mortality rates. NCDs cover a wide range of health issues, such as neurological disorders, cancer, and
dermatological conditions. In Alzheimer disease (AD), the deterioration and dysfunction of the cholinergic
system are accompanied by a marked decline in the main neurotransmitter, acetylcholine (ACh). Additionally,
the accumulation of amyloid-β plaques, overactivity of monoamine oxidase type B (MAO-B), and
phosphorylated tau-protein in the CNS result in neuroinflammation and cognitive impairments. Hence,
multi-targeting of such therapeutic targets has emerged as one of the promising strategies to develop AD
treatments.
The first part of this study (Chapters 2-4) was conducted to provide a more scientific basis for the
application of halophytes-derived chemicals, especially amide alkaloids, for fighting AD. Hence, the
chemical investigation of B. indica led to the isolation of twenty-five compounds. Their structures have been
determined by 1D, 2D NMR, and HR-MS analysis. Among the isolates, a novel acylated flavonol
tetraglycoside and an amide alkaloid, together with a new seco-glycosidic oleanane saponin, were identified
for the first time. Moreover, the study reports on the isolation and identification of seven amide alkaloids
from the aerial parts of B. indica and A. alopecuroides, namely N-trans-feruloyl-3-methoxytyramine, Ntrans-feruloyl

tyramine, S-(–)-N-trans-feruloylnormetanephrine, S-(–)-N-trans-feruloyloctopamine, R-(+)-N-

trans-feruloyloctopamine,

N-trans-caffeoyltyramine,

and

S-(–)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-

hydroxyphenyl)methoxyethyl]acrylamide.
Interestingly, 6,7-dihydroxy coumarin, which has been isolated from B. indica, showed a pronounced
anti-acetylcholinesterase activity. N-trans-feruloyl-3-methoxytyramine, N-trans-feruloyltyramine, and 3-(4hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)methoxyethyl]acrylamide

showed

potent

inhibitory

activity against β-secretase (BACE1), MAO-B, phosphorylated tau-protein, and anti-aggregation of Aβpeptides. Meanwhile, N-trans-caffeoyltyramine displayed a promising inhibition activity against MAO-B
enzyme.

Notably, inflammation is currently known to contribute to tumor cell proliferation, angiogenesis, and
inhibition of apoptosis. Recently, several studies have shown that among the effective approaches for
treatment of early tumor progression is anti-inflammatory therapy. Consequently, searching for the discovery
of compounds with remarkable anti-inflammatory and anti-tumor properties from halophytic plants is of
great importance for developing new anti-tumor drugs. Thus, the second part of thesis (Chapter 5) was aimed
to assess the anti-tumor and anti-inflammatory activity of isolated compounds from B. indica. The methanol
extract and oleanane saponin (23) displayed promising anti-inflammatory activity. Additionally,
N-trans-feruloyltyramine exhibited significant cytotoxicity against OVK-18 with IC50 = 1.74 μg/mL, while
6,7-dihydroxy coumarin exhibited a potent inhibition against MCF-7 cells with IC50 = 1.47 μg/mL.
Interestingly, compounds 1 and 25 exhibited remarkable cytotoxicity against HepG2 and HCT116 with IC50
< 0.1 μg/mL. Meanwhile, compounds 2, 4, 5, 6, and 9 exerted potent cytotoxicity against HepG2.
The human skin is the body’s first-line protection against environmental, chemical, and biological assaults.
Aged skin and several skin diseases such as xerosis, atopic dermatitis, and psoriasis are closely linked to the
disrupted skin barrier function and are associated with reduced levels of ceramides, which contribute to the
epidermal barrier function as the main lipids of the skin’s stratum corneum. Plant-derived compounds are
perceived to be safer than synthetic chemicals and are preferable to them for therapeutic and cosmetic
applications. Recently, research has been done to discover the beneficial effects of plant-derived compounds
on human skin to overcome the reduced levels of natural skin ceramides in diseased and aged skin. Therefore,
the third part of thesis (Chapter 6) was conducted to gain a more detailed view of the protective and
beneficial health effects of A. alopecuroides on the skin. Consequently, the study reports on the isolation and
structure elucidation of three previously undescribed compounds (glucosylceramide, flavonol triglycoside,
and triterpene oleanane saponin), along with eight known ones from the methanol extract of A.
alopecuroides. In addition, as ceramide synthase-3 (CerS3) plays a crucial role in epidermal hydration and
restoration of the skin barrier function, the influence of A. alopecuroides extract and its isolated compounds
on the mRNA expression levels of CerS3 in human keratinocyte cells (HaCaT) was evaluated. Importantly,
the methanol extract significantly increased the mRNA expression levels of CerS3 by 1.2-fold. Among the
isolates, isorhamnetin-3-O-glucoside significantly enhanced the expression levels of CerS3 by 4.3-fold. In
addition, β-sitosterol, β-sitosterol-glucoside, and solysaponin A, significantly upregulated the mRNA
expression levels of CerS3 by 1.9, 4.2, and 3.2-fold, respectively.
In conclusion, the area of research on halophytes is still emerging. The utilization of halophytes as a
potential source of value-added products supports the concept of circular economy, in addition to their role
in ecological restoration. They offer multiple opportunities as new crops, sustainable agriculture, and a
promising source of candidate leads for pharmaceutical and cosmetic applications. By reviewing literature,
there are no or limited studies regarding the valorization of halophytic herbs, B. indica and A. alopecuroides.
Part of the findings in this study will encourage natural product researchers to utilize more halophytic plants
in AD therapies. Importantly, the outcomes might be very helpful during the development of new inhibitor
molecules using the scaffold of the amide alkaloids reported here. Moreover, the study results demonstrated
that A. alopecuroides has the potential to stimulate epidermal ceramide synthesis via enhancing the mRNA
expression levels of CerS3. Thus, A. alopecuroides is a promising source of bioactive compounds with the
capacity to recover aged dry skin including xerosis, atopic dermatitis, and psoriasis, in addition to the ability
to restore the disrupted skin barrier function, which is great potential for applications in cosmetic therapy.

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