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Phytochemistry, Pharmacology, and Applications of Phytoecdysteroids
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CHAPTER 6
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BIOAVAILABILITY OF PENTACYCLIC
TRITERPENE
CONTENTS
6.1. Introduction .................................................................................... 184
6.2. Triterpenes: Natural Occurrence and Chemical Structures ..............186
6.3. Pentacyclic Triterpenes Bioavailability ............................................. 188
References .............................................................................................204
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Natural Compounds: An Introduction
6.1. INTRODUCTION
Triterpenes are some of the most prolific natural products, including over
30,000 structures found so far (Muffler et al., 2011). Pentacyclic triterpenes
have gotten more attention from a biological standpoint. Several of them
are being marketed as dietary supplements or therapeutic agents all over
the world, inclusive of pentacyclic triterpene derivatives (Sheng and Sun,
2011). These compounds have been contained in a wide range of vegetables,
vegetable oils, and cereals, and they are natural components of the human
diet. Individual human consumption of triterpenes in the western world is
estimated to be around 250 mg per day, while average intake in Mediterranean
countries could be as high as 400 mg per day (Figure 6.1) (Moreau et al.,
2002; Siddique and Saleem, 2011).
Figure 6.1: Triterpene structural formula.
Source: https://en.wikipedia.org/wiki/Triterpene.
Triterpene content has also been correlated to the health benets of
vegetables and fruits. The number of patents and manuscripts relating
to triterpenes, therapeutic potential and biological activities is growing
as evidenced by Thomson Reuters (2103 references), PubMed (2908
references), Web of Science (2223 references), and SciFinder Scholar (6910
references). Indeed, this group of compounds has a variety of biological
effects, such as anti-viral, antioxidant, cardioprotective, anti-diabetic, anti-
tumor, anti-inammatory, and hepato-protective activities (Szakiel et al.,
2012; Pádua et al., 2014).
There is also evidence that pentacyclic triterpenes can help with obesity,
hypertension, diabetes, and atherosclerosis-related vascular difculties.
They could be used as anti-ulcer drugs, in cancer treatment, and to prevent
and treat metabolic diseases. As a consequence, clinical trials are currently
being conducted on several triterpenes (Cichewicz and Kouzi, 2004; Smina
et al., 2011).
Bioavailability of Pentacyclic Triterpene
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185
Although triterpenes showed remarkable biological activity in some
animal models and in vitro assays, the in vivo efcacy in humans is still
being debated. Certainly, it is based on various factors such as metabolism
and absorption. The barriers in oral bioavailability include permeation, rst-
pass metabolism, pre-systemic excretion from the liver or intestine, and
solubility and/or dissolution (Hu and Li, 2011; Alqahtani et al., 2013).
This review aims to provide an overview of in vivo and in vitro studies
that have been conducted to nd the pentacyclic triterpenes bioavailability,
as well as to highlight the research that has been conducted to enhance the
absorption and dissolution properties of these compounds (Dewick, 2009;
Jäger et al., 2009). For the below pentacyclic triterpenes, the available
literature data is introduced: the lupine group consists of betulinic acid,
betulin, and lupeol; the oleanane group contains alpha-boswellic acids,
maslinic, and oleanolic; while the ursane group contains Asiatic, ursolic,
beta-boswellic acids, and corosolic (Figure 6.2).
Figure 6.2: Some bioactive pentacyclic triterpenes chemical structures.
Source: https://pubmed.ncbi.nlm.nih.gov/28273859/.
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Natural Compounds: An Introduction
6.2. TRITERPENES: NATURAL OCCURRENCE AND
CHEMICAL STRUCTURES
Triterpenes relate to the family of terpenes, which is the most widely used
natural product group. They are obtained from C
categorized according to the number of isoprene units they contain, such
as sesquiterpenes (C
) monoterpenes (C10), tetraterpenes (C40), and sesterterpenes (C25).
(C
5
), triterpenes (C30), diterpenes (C20), hemiterpenes
15
Triterpenoids are frequently found in nature as tetra- or pentacyclic
structures. However, acyclic, monocyclic, bicyclic, tricyclic, and hexacyclic
triterpenes exist (Laszczyk, 2009; Morrissey, 2009). There are three main
classes of pentacyclic triterpenes: ursane, oleanane, and lupane, each of
which includes precious bioactive compounds (Figure 6.2). Triterpenes
are mostly found on plant surfaces like leaves, fruit peels, and stem bark.
They are made in the cytosol by cyclizing epoxidized squalene, which is
the precursor to a wide range of polycyclic triterpenes. Triterpenes that are
free or conjugated can form these polycyclic structures. Triterpenes can be
acylated (for example, with hydroxycinnamic acids) or glycosylated, and
are known as triterpenoid saponins in this state (Andre et al., 2013, 2016).
Saponin is derived from the Latin word “Sapo,” which means “soap.”
When agitated in a solution(aqueous), this leads to the surfactant property
of producing foam (Prasad et al., 2007). It occurs because a lipophilic
moiety (triterpenoid aglycone, also known as a sapogenin) is attached to
a hydrophilic moiety (sugar). Saponins also trigger hemolysis of the red
blood cells by enhancing the permeability of the plasma membrane, and as a
result, are poisonous when inserted into the bloodstream. On the other hand,
saponins are relatively safe when consumed, and many nutritious foods,
such as oats, beans, soybeans, lentils, and spinach, contain large amounts of
saponins. For instance, many medicinal plants contain triterpenoid saponins
like Medicago sativa L. and Aesculus turbinata Blume, which have been
utilizing due to their hypocholesterolemic effect and anti-glucose absorption
activity, respectively. The sugar moiety of triterpenoid saponins is digested
by gastrointestinal microorganisms in the gut, allowing the aglycone
(triterpene) to be absorbed (Figure 6.3) (Andre et al., 2012; Netala et al.,
2015).
isoprene units. They are
5
Bioavailability of Pentacyclic Triterpene
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Figure 6.3: Pentacyclic triterpenes extracted from Euphorbia microsciadia
(1–3).
Source: https://www.researchgate.net/gure/Pentacyclic-triterpenes-from-Euphorbia-microsciadia-1-3_g1_258703532.
187
Pentacyclic triterpenes have been discovered in consumed fruits, e.g.,
strawberries, mango, mulberry, guava, olives, pear peel, green pepper,
and apple peel. They are also found in aromatic herbs, such as lavender,
oregano, basil, and rosemary. They have also been found in trees, like birch
bark and eucalyptus leaves. Additionally, herbs are widely distributed all
over the world in some traditional and oriental medicine. Aside from their
lower water solubility, they can be found as an ingredient in medicinal plant
decoctions, where their bioavailability is thought to be enough to enhance
biological activity (Yamaguchi et al., 2008; Wang et al., 2016). In terms of
health benets, boswellic acids have attracted a lot of attention. They are
the main active constituents in the gum resin extract of Boswellia serrata
Roxb. The extract of gum resin is also known as Indian frankincense. In
traditional Eastern medicine, this has been used for curing inammatory
diseases. In European pharmacopeias, this extract is also listed. According
to Joos et al. (2006), alternative, and complementary medicine is used by
52% of surveyed German patients with inammatory bowel disease. While,
B. serrata extracts have been used to treat inammatory bowel disease in
36% of German patients (Romero et al., 2010).
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Natural Compounds: An Introduction
Pentacyclic triterpenes from the maslinic acid, lupane, ursane groups,
and oleanane can also be found in Mediterranean spices and fruits. For
instance, it is the main pentacyclic triterpene found in the fruits and leaves
of Olea europaea L. As a potential nutraceutical, this compound is gaining
popularity (Liu, 2005; Sánchez-Avila et al., 2009).
6.3. PENTACYCLIC TRITERPENES
BIOAVAILABILITY
“The term bioavailability refers to the percentage of an orally administered
dose that enters as an intact drug to the systemic circulation, after accounting
for absorption as well as local metabolic degradation” (Dale and Rang,
2007). To determine absolute oral bioavailability (F), the concentration
of plasma drug versus time curves are measured in a group of subjects
following intravenous and oral administration. To estimate the fraction
oral
/AUC
intravenous
AUC
(AUC) are utilized, and corrected by the intravenous and oral dose by the
following formula (Pérez-Camino and Cert, 1999):
, areas under the concentration of plasma time curve
When it comes to pentacyclic triterpenes, which are found in foods and
medicinal plants, the evaluation of their bioaccessibility is the rst step in
nding their bioavailability. Which is the proportion of nutrients ingested
released from the gastrointestinal lumen food matrix and thus available for
intestinal absorption (Heaney, 2001; Rein et al., 2013).
Triterpenes undergo digestion in the duodenum, mouth, and stomach
before entering the small intestine because medicinal plant and food matrices
play an important role in their bioavailability. As a result, they are subjected
to a variety of pH conditions, enzymatic activities, and mechanical forces.
Furthermore, foods containing minerals, proteins, ber, carbohydrates, and
fats are frequently consumed in combination with other foods containing
these nutrients. Phytochemical compounds are capable of interacting with
bers, carbohydrates, and Proteins (Van Willige et al., 2000). Thus, they
reduce the absorption of lipophilic compounds, like triterpenes. Because
micellization and solubilization of lipophilic compounds are required steps
before absorption, so, the existence of fat shows to be very crucial (Riedl et
al., 1999).
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