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Gut Eect on Phytochemicals
Figure 1. Biotransformation of Ellagic acid into Urolithins (adapted from Al-Harbi et al., 2021)
Proantocyanidins
Proanthocyanidins are formed by the condensation of single or multi-component of flavan-3-ols and are found in grapes, apples and chocolate (Kawabata et al., 2019). In stomach partial degradation occurs due to acidic environment and oligomers are hydrolysed to epicatechin monomer and dimers. This was suggested to enhance the absorption in the small intestine (Spencer et al., 2000). However, only a small number of proanthocyanidins are bioaccessible in the small intestine (Del Rio et al., 2010). Meanwhile, microbiota can act on monomeric and oligomeric catechins in the gut. Microbial degradation forms 3-hydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, 3-(3-hydroxyphenyl)propionic acid, and 5-(30-hydroxyphenyl)-γ-valerolactone (Spencer et al., 2000). A feeding study (20 healthy human vol­unteers) also showed that gut microbiota transforms green tea flavan-3-ols into polyhydroxyphenyl-g­valerolactones (Del Rio et al., 2010).
Bioactive Peptides
Plant proteins can provide bioactive peptides which improve human health with their antioxidative, anti-inflammatory, antihypertensive, antihypercholesterolaemic, anticancer, antimicrobial effects. These bioactive compounds were also suggested to support delivery and bioavailability of many other bioactive compounds (Karaś et al., 2017). Food industry can provide various types bioactive protein by-products such as milk proteins or rice soy proteins. Following the intake, peptides encounter with many digestive enzymes in the mouth, stomach and the small intestine. In small intestine, many additional enzymes from the enterocytes are secreted as well. These enzymes are expressed in the microvilli of the brush border membrane and within the glycocalyx including dipeptidyl-peptidases 3 and 4, glutamyl aminoopeptidase, membrane metallo-endopeptidase, transmembrane protease serine 4 and transmembrane protease serine 15 (Lundquist & Artursson, 2016).
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Gut Eect on Phytochemicals
To show any biological effects, bioactive peptides should be absorbed from the gastrointestinal tract. Different mechanisms are in place to achieve uptake of these peptides. These mechanims can be listed as: Paracellular transport through intercellular tight junctions, direct penetration of the epithelial cell­membranes, endocytosis/phagocytosis by cells, and active transport by specific carrier proteins. Studies on bioactive peptides reported inadequate evidence on ability of the dietary bioactive peptides to enter the hepatic portal system in physiologically relevant concentrations whereas there is enough evidence on bioavailability of the dipeptides and tripeptides (Chakrabarti et al., 2018).
Peptides and aminoacids in the gut are also used to produce short chain fatty acids such as propionate and butyrate. It is estimated that low pH condition and presence of carbohydrates affect peptide and ami­noacid fermentation in proximal colon but distal colon serves a better environment (Louis & Flint, 2017).
As bioactive peptides can be produced by microbial fermentation. Using Lactic acid bacteria is ac­cepted as an effective way of producing bioactive peptides in fermentaton media or food fermentation processes. It is reported that around 13 g of protein and peptides/day was estimated to reach human colon (Louis & Flint, 2017). It is known that many peptides have the capacity to modulate human gut microbiota (Wu et al., 2021). Human gut microbiota should have capacity to produce bioactive peptides from ingested proteins reached colon. However, there is limited information on this subject, especially on plant derived ones. A study investigated the milk peptides released in the gastrointestinal tract of mini­pigs. Six different dairy food matrices were given to the pigs, later duodenal effluents were obtained over a 5 h-period and analyzed by tandem mass-spectrometry. Production of bioactive peptides were also reported and that approves bioactive peptide production by gut microbiota as suggested in in vivo experiments (Barbé et al., 2014).
Glucosinolates
Glucosinolates are sulphur containing glycosides found in cruciferous vegetables mainly belong to the Brassicaceae, Capparaceae and Caricaceae genera. These include broccoli, radish, cabbage, Brussels sprouts, cauliflower and turnip of the different Brassica species. Glucosinolates have little biological activity but their degradation products serve as a defence against herbivores including insects, birds, aphids and mammals. Glucosinolates are also responsible for the characteristic flavour and odour of these vegetables. It was reported that they have antifungal and antibacterial properties (Fahey et al., 2001). Glucosinolate research started with toxicological aspects of glucosinolates and methods for removing them from dietary sources and animal feed but nowadays, the studies are mainly focused on their potential health promoting effects (Narbad & Rossiter, 2018).
Glucosinolates (Figure 19.2) are degraded by plant myrosinases into bioactive isothiocyanates (ITCs) which have been recognised as potent anticancer compounds. Myrosinase (thioglucoside hydrolase EC
3.2.3.1) is the enzyme responsible for hydrolysis of glucosinolates. Normally, glucosinolate hydrolysis in plant is avoided by storing glucosinolate and the degradation enzyme in different plant compartments (Fahey et al., 2001). Glucosinolate can generate various types of metabolites such as ITCs, nitriles, epi- thionitriles and thiocyanates. Table 19.3 shows some of the common glucosinolates found in cruciferous plants and their degradation products, ITCs.
The plant myrosinases are well studied and characterised. However, during cooking plant myrosinases are heat inactivated and this biotranformation relies on specific gut bacteria and their myrosinase-like enzymes that can metabolise glucosinolates into ITCs (Narbad & Rossiter, 2018). In addition, reductases are also involved in glucosinolate metabolism. They can reduce sulphoxide groups and produce their
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Gut Eect on Phytochemicals
Figure 2. General Structure of Glucosinolates. R; variable side chain (adapted from Halkier & Gersh­enzon, 2006).
counterpart reduced glucosinolates (such as from glucoraphanin to glucoerucin) (Figure 19.3) (Cebeci,
2017). Glucosinolates are well studied phytochemicals especially due to their bioactive degradation prod-
ucts. As different cooking methods destroy myrosinase activity from plant itself, ITC production by human gut microbiota becomes important to confer health promoting effects. However, there is limited information about formation of ITCs by human gut bacteria. There are studies including human inter­vention, rat models (Elfoul et al., 2001) studies, gut community based in vitro fermentation models or in vitro fermentation assays using pure bacterial cultures (Luang-In et al., 2014; Mullaney et al., 2013b). These studies mainly show that there is an inter-individual difference in glucosinolate metabolism by human due to gut microbiota composition. It is known that many bacteria in human gut are involved in
Table 3. Some Important Glucosinolates and their Hydrolysis Products (adapted from (Luang-In et al.,
2014)
Glucosinolate Precursor Isothiocyanate Product Nitrile Product
Sinigrin Allylisothiocyanate Allyl nitrile
Glucoerucin Erucin Erucin nitrile
Glucoiberin Iberin Iberin nitrile
From Gluconasturtiin Phenethyl isothiocyanate Phenethyl nitrile
Glucoraphanin Sulforaphane Sulforaphane nitrile
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Gut Eect on Phytochemicals
Figure 3. Proposed metabolism of glucosinolates into isothiocyanates by gut microbiota (adapted from (Cebeci, 2017)
glucosinolate degradation and glycoside hydrolases are involved in the metabolism but the responsible enzyme in the human gut is yet to be identified.
In vitro fermentation assays use human gut microbiota to assess their impact on glucosinolates in vitro. There are pioneer studies reporting glucosinolate degradading ability of pure bacterial strains in vitro. For instance, Enterobacter cloacae was identified as a sinigrin degrading bacterium in 1974 (Tani
et al., 1974b). Another study reported glucosinolate degrading ability of Bacillus cereus strains (Huber et al., 1983) and Brabban & Edwards (1994) showed that Bacillus, Streptomyces, Staphylococcus isolates
and an unknown fungus can degradee sinigrin. These strains were not isolated from the human gut but Enterobacter, Bacillus and Staphylococcus genera are also members of human gut microbiota. Later, in vitro fermentation assays were performed using pure bacterial cultures of human origin but some of these could not detect ITCs. Cheng et al. (2004) studied Bifidobacterium pseudocatenulatum, Bifidobacterium adolescentis and Bifidobacterium longum for their ability to utilise sinigrin and glucotropaeolin in vitro. The study concluded that these Bifidobacterium strains are able to utilize both sinigrin and glucotropa­elin producing 3-butene-nitrile as main product. Phenylacetonitrile and AITC or benzyl isothicyanate (BITC) were hardly detectable.
Plant myrosinase (thioglucosidase) is a member of glycoside hydrolase family 1 (GH1). Studies also used bioinformatic tools to find myrosinase like enzymes of different bacterial species and determine myrosinase producers. Mullaney et al. (2013a) investigated three bacteria including Lactobacillus plan-
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Gut Eect on Phytochemicals
tarum KW30, Lactococcus lactis subsp. lactis KF147, and Escherichia coli Nissle 1917, and known myrosinase-producer Enterobacter cloacae to degrade the glucosinolates in broccoli extract. It was shown that Enterobacteriaceae degraded 65% of glucoiberin and 78% of glucoraphanin and transformed them mainly into their reduced counterparts glucoiberverin and glucoerucin, respectively. The study reported only a small amount of iberverin nitrile and erucin nitrile formation when Enterobacteriaceae was included. On the other hand, lactic acid bacteria consumed 30−33% of glucosinolates and produced nitriles such as iberverin nitrile, erucin nitrile, sulforaphane nitrile, and further unidentified metabolites (Mullaney et al., 2013).
Luang-In et al investigated the metabolism of glucoerucin, glucoiberin and glucoraphanin by gut
strains; Lactobacillus agilis R16, Enterococcus casseliflavus CP1, Escherichia coli VL8. Lactobacil-
lus agilis R16 metabolised only 10% of glucosinolates and did not produce any detectable products. E. casseliflavus CP1 metabolised 40-50% of glucoiberin and glucoraphanin and resulted in formation of
iberin and sulforaphane in low concentrations. Escherichia coli VL8 showed 80-90% degradation of glucoiberin and glucoraphanin. The metabolism by E. coli VL8 produced glucoiberverin from glucoi­berin and glucoerucin from glucoraphanin. Other metabolites were erucin, erucin nitrile and iberverin, iberverin nitrile respectively which points a reductase activity. This reductase activity was proposed to
2+
performed by a reductase requires both Mg
and NAD(P)H as cofactors (Luang-In et al., 2014). This study also supports the idea that reductases are also involved in glucosinolate metabolism by gut bacte­ria (Cebeci, 2017). A follow-up study using same Lactobacillus agilis R16, Enterococcus casseliflavus CP1 and Escherichia coli VL8 aimed to investigate the metabolic fates of sinigrin, glucotropaeolin, gluconasturtiin, and their corresponding desulfo-GSLs. Gluconasturtiin was completely degraded within 24 h to phenethyl isothiocyanate and phenethyl nitrile by all bacteria, excluding L. agilis R16 which produced only phenethyl nitrile. More than 80% of glucotropaeolin and sinigrin were degraded by all bacteria within 24 h to ITCs and nitriles. The total amount of the products only accounted for 3–53%
+2
of the initial glucosinolate amount. It was reported that Fe
promotes nitrile production, while Mg+2 does the same for ITC formation. In addition, the study showed that desulfoglucosinolates can only give rise to nitriles not ITCs or epithionitriles (Luang-In et al., 2016). Crucifer specialists were reported to have sulfatase activity which enables them to produce desulfoglucosinolates from glucosinolates. This biotransformation prevents myrosinases to act on glucosinolates and form toxic hydrolysis products to specialists (Ratzka et al., 2002).
Bacteroides thetaiotaomicron, a human digestive strain, was studied for its ability to degrade sinigrin in a gnotobiotic rat model. An oral dose of 50 µmol sinigrin was given to gnotobiotic rats harbouring B. thetaiotaomicron. Sinigrin was metabolised in the large bowel and, allyl isothiocyanate, hydrolysis product of sinigrin, was detected in digestive contents (Elfoul et al., 2001). Another study investigated glucoraphanin degradation by 5 Lactobacillus species (Lactobacillus gasseri, Lactobacillus acidophilus, Lactobacillus casei and two Lactobacillus plantarum species). The degradation rate by the Lactobacillus species ranged from 36 to 49% after 24 h incubation and the main degradation product was nitrile, no sulforaphane was detected (Lai et al., 2009).
Studies also investigate glucosinolate degradation by the microbial community instead of a certain type bacteria in rat models. For instance, Lai et al. (2009) showed that rat cecal microbiota was able to degrade 40% of the initial glucoraphanin in the medium after 24 h incubation. When rats were pretreated with glucoraphanin, degradation rate went up to 56%. The main hydrolysis product was reported to be nitrile. The study determined that isothiocyanate metabolites are formed and found in portal blood stream after introducing glucoraphanin directly to cecum. A following study to this examined ex vivo
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Gut Eect on Phytochemicals
degradation of glucoraphanin by rat cecal microbiota and reported evidence for glucoraphanin hydrolysis to sulforaphane and its absorption across the cecal walls of rats. Glucoraphanin (150 µmol/kg BW) was directly introduced to cecum and ITC were detected in the mesenteric plasma by 120 min and plasma levels keeping the stability for an hour (Lai et al., 2010). A rat model study investigated glucosinolate hydrolysis in gnotobiotic rats. Rats harbouring a whole human faecal flora (Flora+) was compared with that in germ-free rats (Flora-). To test the effect of plant myrosinase, myrosinase was either active (Myro+) or inactive (Myro-) in the diets given to the rats. Urinary mercapturic acids which are end products of isothiocyanate metabolism were used o estimate isothiocyanate formation. The study con­cluded that highest excretion of urinary mercapturic acids was found when plant myrosinase was active (Myro+) in grem-free rats (Flora-). The excretion was lower in rats with whole human feacal microbiota (Flora+) and given active myrosinase (Myro+). Excretion of urinary mercapturic acids was low in rats harbouring a whole human faecal flora (Flora+) but Flora+ treatments also show promising capacity to break down glucosinolates as no intact glucosinolates were detected in the faeces of rats (Rouzaud et al., 2003a). These results emphasize the importance of an active and efficient myrosinase to confer health benefits from glucosinolates.
Studies mostly report ITC formation and potential health benefits thanks to human gut microbiota (Krul et al., 2002). However, some studies focus on the fact that other metabolites but yet ITCs can be produced such as allyamine or benzylamine (Combourieu et al., 2001). Food matrix effect should also be taken into account when discussing bioavailability of bioactive compounds. For instance, plants include specifier proteins as they have myrosinases. In presence of specifier proteins, the hydrolysis of glucosinolates results in formation of nitriles, epithionitriles and organic thiocyanates instead of ITCs (Wittstock & Burow, 2007). Biological activity of these compounds are low compared to ITCs plus they can even show toxic effects such as thiocyanates (inhibit the uptake of iodide by the thyroid)(Eisenbrand & Gelbke, 2016; Wittstock & Burow, 2007).
Health claim on glucosinolates depends on ITC formation and its concentration but glucosinolate deg­radation not always end up by formation of ITCs. To determine the amounts of glucosinolate metabolite, a dynamic in vitro large-intestinal model was used. The study investigated sinigrin and its metabolites using human gut microbiota. Allyl isothiocyanate (from sinigrin) peak levels were observed between 9 and 12 h after the addition of sinigrin. The study reported that only 10% to 30% (mean 19%) of the sinigrin was converted into allyl isothiocyanate so rest of the sinigrin was supposed to be converted into unknown metabolites (Krul et al., 2002). Another in vitro fermentation assay using rat intestinal micro­biota reported degradation of up to 64% of the initial sinigrin amount during 12h. The study showed that major products were allyl isothiocyanate (15% of initial sinigrin) and allyl cyanide (20% of initial sinigrin) after 12h. 1-cyano-2,3-epithiopropane was also detected in trace amounts in culture medium (Lu et al., 2011). This result raises the question about rest of the degraded sinigrin. Similar results were reported in another study testing the effect of human gut microbiota on glucoraphanin. The amounts of the metabolites detected by combined HPLC and LC–MS/MS methods did not account for the initial amount of the glucoraphanin in the media.
A human intervention study inclued 18 healthy volunteers consumed broccoli soups from fresh or frozen broccoli florets (lightly cooked before freezing). The study showed that glucoraphanin was con­verted into sulforaphane and sulforaphane was found in the plasma and urine as free form or sulforaphane thio-conjugates. In addition, the study reported reductase activity of gut microbiota forming glucoerucin from glucoraphanin. As Erucin N-acetyl-cysteine conjugate was also determined as a urinary metabolite, it was proposed that human gut microbiota can show myrosinase and reductase activity (Saha et al., 2012).
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Clarke et al. (2011) investigated the bioavailability and excretion of the mercapturic acid pathway metabolites of isothiocyanates after human consumption of fresh broccoli sprouts or broccoli supple­ment. The study was designed as a cross-over study in which 12 subjects consumed 40 grams of fresh broccoli sprouts followed by a 1 month washout period and then the same 12 subjects consumed 6 pills of a broccoli supplement. Control group was given alfalfa sprouts during the first phase and placebo pills during the second phase. The bioavailability of sulforaphane and erucin, main ITC products of brocoli, is siginificantly higher in fresh broccoli sprout consuming group. Interconversion of sulforaphane and erucin was also observed within each subject but this conversion was variable among the subjects. This study also confirms the importance of an active myrosinase to produce ITCs as stated in previous rat model study (Rouzaud et al., 2003a).
Some of the studies reporting the effect of gut microbiota on glucosinolate metabolism are listed in Table 4. Briefly, many studies report the glucosinolate degradation by community based microbiota or pure bacterial cultures and glycoside hydrolases are suggested to be the responsible enzyme. Many attempts were also made to identify the gut microbial myrosinases (Liou et al., 2020; Luang-In et al.,
2014). Some of these studies reported myrosinase activity by only intact cells but some showed myrosi­nase activity in cell-free extracts as well (Cebeci, 2017; Luang-In et al., 2014).
MAIN FOCUS OF THE CHAPTER
This chapter mainly focus on biotransformation of phytochemicals by human gut microbiota. It discusses the studies (in vitro or in vivo) reporting or suggesting the gut microbial effect on different bioactive compounds.
SOLUTIONS AND RECOMMENDATIONS
The main concern regarding the effectiveness of phytochemicals in vivo raises from their low bio­availability profiles. Many studies report evidence for these bioactive compounds to show anticancer, antitumor, antiviral, antimicrobial, antiinflammatory and cardioprotective effects. Unfortunately, the concentration used in in vitro experiments are rarely applicable in vivo so this raises question about the real effectiveness of these molecules. To overcome this, further human feeding trials using in vivo applicable doses are needed.
FUTURE RESEARCH DIRECTIONS
As discussed in the chapter, human gut microbiota influences bioavailability of phytochemicals. However, our knowledge on this subject is limited for some phytochemicals. For instance, phenolic compounds are generally known to be metabolized by gut community but studies mostly lack identification of specific responsible microoorganisms. Identification of specific microorganism or responsible enzymes can help enhancing bioavailability of phytochemicals as some of them show very low bioavailability. In addi­tion, studies mostly focus on bacteria but the role of other micoorganisms such as fungi should also be adressed. Another issue, human feeding studies mostly use bioactives in pure forms however presence of
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other compounds change how microorganisms act on phytochemicals and which metabolites are formed. Briefly, more studies are needed to adress food matrix effect on bioavailability.
Table 4. Studies reporting the effect of certain microorganisms or community based gut microbiota on glucosinolate metabolism
Study Details
In vitro
fermentation
studies
Gnotobiotic rat model
Cecal microbiota from male F344 rats
Rat intestinal microbiota
In vitro fermentation using dynamic intestinal model
Human intervention study
Glucosinolates & (Source
if given)
Sinigrin Enterobacter cloacae
Glucosinolates, (defatted
rape seed meal)
Sinigrin
Sinigrin
Glucotropaeolin
Glucoraphanin
(broccoli extract)
Glucoerucin
Glucoiberin
Glucoraphanin
Sinigrin, Glucotropaeolin,
Gluconasturtiin Desulfo-
glucosinolates
Sinigrin Bacteriodes thetaiomicron
Glucoraphanin Not determined, colonic fermentation in gut suggested
Lactobacillus gasseri
Glucoraphanin
Desulfosinigrin Community based human gut microbiota (Lu et al., 2011)
Sinigrin Community based human gut microbiota
Glucoraphanin (broccoli sprouts or broccoli suplement
Glucoraphanin (broccoli soup)
Lactobacillus acidophilus Lactobacillus casei Lactobacillus plantarum strains
Community based human gut microbiota (inter-individual variation due to gut microbiota composition)
Community based human gut microbiota
Staphylococcus and unknown fungus
Bifidobacterium pseudocatenulatum,
Lactoccoccus lactis subsp. lactis KF147
Microorganisms Reference
Bacillus cereus strains
Trichosporon cutaneum (yeast)
Bacillus, Streptomyces
Bifidobacterium adolescentis,
Bifidobacterium longum
Lactobacillus plantarum KW30
Escherichia coli Nissle 1917
Enterobacter cloacae
Lactobacillus agilis R16
Enterococcus casseliflavus CP1
Escherichia coli VL8
Lactobacillus agilis R16
Enterococcus casseliflavus CP1
Escherichia coli VL8
(Tani et al., 1974a)
(Huber et al.,
1983)
(Brabban &
Edwards, 1994)
(Cheng et al.,
2004)
(Mullaney,
Kelly, et al.,
2013)
(Luang-In et al.,
2014)
(Luang-In et al.,
2016)
(Combourieu et al., 2001)
(Rouzaud et al., 2003b)
(Lai et al.,
2009)
(Krul et al.,
2002)
(Clarke et al.,
2011)
(Saha et al.,
2012)
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Gut Eect on Phytochemicals
CONCLUSION
The studies reveal that many microorganisms are involved in transformation of pytochemicals into their metabolites. Sometimes, these metabolites are more bioactive than parent compounds and in some cases they can be toxic to host as well. For certain phytochemicals, it was known that which enzymes in the gut are involved in biotansformation. For instance, α-rhamnosidase, exo-β-glucosidase, endo-β­glucosidase and/or β-glucuronidase are suggested to be involved in flavonoid degradation and gut bacterial myrosinases (possibly glycoside hydrolases), reductases (such as methionine reductases), sulfatases in glucosinolate degradation. However, further studies are needed. Various studies emphasize that there is inter-individual diffences among people in phytochemical metabolism. The knowledge we have about pytochemical bioavailability shoud enable us to develop better strategies. By doing so, it would be pos­sible to enhance the biavailability of these compounds and make the most of them.
In conclusion, it was aimed to provide a better understanding of microorganisms and their enzymes involved in pytochemical metabolism to maximise the health benefits. Such understanding can lead us identification of probiotic strains to enhance the bioavailability of phytochemicals. This would improve the efficiency of these bioactive compounds for people who are unable to utilise phyochemicals and benefit efficiently.
ACKNOWLEDGMENT
This research received no specific grant from any funding agency in the public, commercial, or not-for­profit sectors.
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