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Challenges and delivery aspects
of phytomedicines and
bioactives
SECTION II
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3
Challenges in delivery of plant
actives
Mariana Neves Amaral
1, 2, #
, Jacinta O. Pinho
1, #
,
M. Manuela Gaspar
1
and Catarina Pinto Reis
1, 2
1
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de
Lisboa, Lisbon, Portugal;
2
Instituto de Biofísica e Engenharia Biomédica (IBEB), Faculdade de
Ciências, Universidade de Lisboa, Campo Grande, Lisbon, Portugal
1. Natural compounds with therapeutic potential
Natural active ingredients are sourced from plants or microorganisms and have a broad
spectrum of biological and pharmacological properties. The application of these natural com-
pounds in the treatment of human diseases dates back to traditional medicine of ancient civ-
ilizations [1]. Commonly, the bioactive compounds are isolated from plant extracts; however,
novel techniques have recently emerged, i.e., using biotechnology to produce and/or chem-
ically synthesize such plant-derived compounds [2]. Also, according to their biosynthetic
origin, plant-derived active ingredients can mainly fit into the following categories: alkaloids;
phenylpropanoids; polyketides; and terpenoids [3].
Alkaloids are the most explored for their therap eutic applications and represent the class
that englobes the biggest share of natural compounds [3e5]. These are nitrogen heterocyclic
compounds, conferring alkaline nature, that originate from the nucleoside metabolism, and
thus, amino acids [3,6]. In 1804, morphine was the first alkaloid to be discovered, being iso-
lated from Papaver somniferum (also known as opium poppy) in its crystalline form. Some
other well-known compounds that belong to this class includ e nicotine, quinine, atropine, co-
deine, caffeine, etc. [6]. Alkaloids belong to a broad spectrum of therapeutic plant products
with antimicrobial, antiviral, antimalarial, antioxidant, anti-inflammatory, antitussive,
muscular relaxing, and anesthetic properties [3e6]. Although many alkaloids have anesthetic
properties, their practical medical applications are limit ed due to the addictive nature of
CHAPTER
#
These authors contributed equally to this work.
35
Phytopharmaceuticals and Herbal Drugs
https://doi.org/10.1016/B978-0-323-99125-4.00008-1 © 2023 Elsevier Inc. All rights reserved.
https://t.me/med1917
several alkaloids (i.e., morphine) [6]. Moreover, some of these compounds act as stimulants of
the central nervous system (i.e., nicotine, cocaine, and caffeine) [6].
Phenylpropanoids are another class of natural compounds composed of the phenolic acids
most commonly found in plants [7]. These are abundantly present in some foods, as is the
case of many cereal grains, fruits, vegetables (i.e., potato), spices, and herbs (i.e., cinnamon),
and some beverages (i.e., coffee and red wine) [7]. Phenylpropanoids are very important for
plant homeostasis, including response to biotic and abiotic stimuli, defense against pathogens
and reproduction, and some types have proven to be beneficial to human health [8].
Flavonoids are a type of phenylpropanoids with low molecular weight and polyphenolic
structures found in many vegetables, fruits, and plants that are able to modulate the enzy-
matic activity of many cellular systems [9,10]. Flavonoids display interesting biologic activ-
ities, such as immunomodulation, antioxidant, anti-inflammatory, antimutagenic,
antimicrobial, antiviral, antiparasitic, and antitumoral properties [9,10]. The interest in this
class has increased in the past years as the specific antioxidant nature of these compounds
has proven beneficial for people suffering from Alzheimer disease, cancer, atherosclerosis,
and have been associated with overall improvement of cardiac and circulatory health [10].
These benefits arise from flavonoids’ ability of scavenging superoxide, hydroxyl, and lipid
radicals, greatly associated with oxidative stress [11].
Polyketides are another category of compounds that can be used as bioactives. They are
synthesized from simple acyl building blocks and present very heterogeneous structures
[12,13]. This heterogeneity results in a vast array of biologic activities of these compounds,
which includes antifungal, anticholesteremic, antitumoral, antibiotic, antiviral, anti-inflam-
matory, immunosuppressive, and antiparasitic properties [13,14]. Some of the most known
members of this class are doxorubicin, amphotericin B, rapamycin, erythromycin A, and
tetracycline [13,15]. Recently, polyketides, specially spirotetronate polyketides, have been
considered a good lead for drug discovery due to their enhanced antibacterial and antitu-
moral properties [16]. The growing interest in this class of plant-derived compounds is recog-
nized by the 20 billion US dollars that arise from the annual sales of polyketide-based
pharmaceuticals (i.e., doxorubicin, as a chemotherapy agent; amphotericin B, as an anti-
fungal; and rapamycin, as an immunosuppressant) [14].
Terpenoids belong to another class of plant actives. These are secondary metabolites that
can be further categorized into monoterpenes, sesquiterpenes, diterpenes, sesterpenes, and
triterpenes, according to their structure/composition [17]. These compounds display antitu-
moral, antimicrobial, antiviral, antimalarial, anti-inflammatory, antifungal, antioxidant, and
immunomodulatory properties, and are promoters of cardiovascular health [17e19]. The
most well-known compounds of this class are paclitaxel, a chemotherapeutic agent, and arte-
misinin, an antimalarial drug [18](Table 3.1).
1.1 Natural compounds and cancer
Cancer, which remains the main cause of death worldwide [32], is a multifactorial disease
characterized by different hallmarks, such as resistance to cell death, inductio n of angiogen-
esis, invasion and metastasis, sustainable proliferative signaling, genomic mutations and
3. Challenges in delivery of plant actives36
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TABLE 3.1 Examples of different natural compounds or derivatives with relevant biological activities
belonging to the above-mentioned classes.
Bioactive Biological activity
Class of natural
compounds References
Lobeline Antitussive Alkaloids [4]
Noscapine
Theophylline
Ephedrine
Codeine [3,4,6]
Vinblastine Antitumoral [3]
Vincristine
Vindestine
Camptothecin
Quinine Antimalarial [3,6]
Morphine Analgesic
Atropine Anticholinergic
Caffeine CNS stimulant
Phenethyl ester Antimicrobial Phenylpropanoids [7]
Caffeic acid Antimicrobial and antioxidant.
Feluric acid
Resveratrol Antioxidant, anti-inflammatory, cardioprotective, neuroprotective
and antidiabetic.
[20,21]
Curcumin Antioxidant, anti-inflammatory, antihypercholesterolemic,
antiatherosclerotic, chemoprotective, antibacterial, antifungal,
antiviral, antitumoral and antidepressant.
[22,23]
Rutin Anti-inflammatory, anticholinesterase, antioxidant and antitumoral. Flavonoids [10,24,25]
Quercetin Anticholinesterase, antioxidant, antimicrobial, anti-inflammatory,
cardioprotective and antitumoral.
[10,25]
Epicatechin Cardioprotective [25]
Nobiletin Anti-inflammatory, immunomodulatory and antitumoral. [26]
Apigenin Antioxidant, antihyperglycemic, anti-inflammatory and
antiapoptotic.
[27]
Luteolin Anti-inflammatory, antiallergic and antitumoral. [28]
Naringenin Antitumoral [29]
(Continued)
1. Natural compounds with therapeutic potential 37
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