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Metabolites
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Gut Metabolism of Natural Products
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Gut Metabolism of Natural Products

A special issue of Metabolites (ISSN 2218-1989). This special issue belongs to the section "Microbiology and Ecological Metabolomics".

Deadline for manuscript submissions: closed (15 December 2019) | Viewed by 31690

Special Issue Editor

Prof. Dr. Jaehong Han

E-Mail Website
Guest Editor
Metalloenzyme Research Group and Department of Plant Science and Biotechnology, Chung-Ang University, Anseong, Korea
Interests: biotransformation; natural products; metabolite; flavonoids; mechanism

Special Issue Information

Dear Colleagues,

With the increasing interest in and significance of the gut metabolism in human health, a Special Issue of Metabolites has been launched on the topic of the “Gut Metabolism of Natural Products”. I would like to invite all those working on the gut metabolism of bioactive compounds from natural products and foods at the molecular level to submit their recent progress, significant discoveries, and insightful reviews. The areas of research covered include the intestinal bacterial metabolism of natural compounds, structural characterization of gut metabolites produced by in vivo or in vitro studies, chemical synthesis, and the pharmacokinetic study of gut metabolites. Works on the biological activity of gut metabolites are especially welcome.

Prof. Dr. Jaehong Han
Guest Editor

Manuscript Submission Information

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Keywords

  • Gut metabolism
  • Natural products
  • Intestinal bacteria
  • Biotransformation
  • Biological activity
  • Gut metabolites

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Published Papers (7 papers)

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Research

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12 pages, 1425 KiB  
Article
Gut Microbiota Is the Key to the Antidepressant Effect of Chaihu-Shu-Gan-San
by Meng Yu, Hong-Mei Jia, Tao Zhang, Hai Shang, Hong-Wu Zhang, Li-Yan Ma and Zhong-Mei Zou
Metabolites 2020, 10(2), 63; https://doi.org/10.3390/metabo10020063 - 10 Feb 2020
Cited by 11 | Viewed by 3449
Abstract
Accumulating evidence highlights the link between gut microbiota and depression. As an antidepressant herbal drug in clinic, Chaihu-Shu-Gan-San (CSGS) has also been used in China for the treatment of various gastrointestinal disorders. Therefore, we hypothesize that the gut microbiota might be involved in [...] Read more.
Accumulating evidence highlights the link between gut microbiota and depression. As an antidepressant herbal drug in clinic, Chaihu-Shu-Gan-San (CSGS) has also been used in China for the treatment of various gastrointestinal disorders. Therefore, we hypothesize that the gut microbiota might be involved in the effect of CSGS. Here, we investigated the antidepressant effects of CSGS against chronic variable stress (CVS)-induced depression rats with and without antibiotic treatment using 16S rRNA gene sequencing and ultra-performance liquid chromatography coupled with time of flight mass spectrometry (UPLC-Q-TOF/MS) based metabolomics approaches. As a result, the prominent effects of CSGS against the depression-like behavioral disorder of CVS-induced rats were significantly weakened when the gut microbiota was changed after oral administration of the broad-spectrum antibiotic. The mediation of CSGS on hippocampal levels of serotonin (5-HT) and glutamic acid (Glu) was also receded with the antibiotic treatment. Further investigation on the diversity of microbiome indicated that the improvement effect of CSGS on gut microbiota dysbiosis—especially the phylum level of Firmicutes—was attenuated after the CSGS combined antibiotic treatment. Moreover, 3-hydroxypicolinic acid (H4) and inosine (H8) in the hippocampus were considered as important biomarkers for depression and are also associated with gut microbiota mediated CSGS efficacy. Taken together, our current study indicated that gut microbiota is a critical factor in the antidepressant effect of CSGS, which improve depression-related metabolic disturbance partly through gut microbiota. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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16 pages, 3027 KiB  
Article
Biotransformation of Silymarin Flavonolignans by Human Fecal Microbiota
by Kateřina Valentová, Jaroslav Havlík, Pavel Kosina, Barbora Papoušková, José Diógenes Jaimes, Kristýna Káňová, Lucie Petrásková, Jitka Ulrichová and Vladimír Křen
Metabolites 2020, 10(1), 29; https://doi.org/10.3390/metabo10010029 - 9 Jan 2020
Cited by 31 | Viewed by 4848
Abstract
Flavonolignans occur typically in Silybum marianum (milk thistle) fruit extract, silymarin, which contains silybin, isosilybin, silychristin, silydianin, and their 2,3-dehydroderivatives, together with other minor flavonoids and a polymeric phenolic fraction. Biotransformation of individual silymarin components by human microbiota was studied ex vivo, using [...] Read more.
Flavonolignans occur typically in Silybum marianum (milk thistle) fruit extract, silymarin, which contains silybin, isosilybin, silychristin, silydianin, and their 2,3-dehydroderivatives, together with other minor flavonoids and a polymeric phenolic fraction. Biotransformation of individual silymarin components by human microbiota was studied ex vivo, using batch incubations inoculated by fecal slurry. Samples at selected time points were analyzed by ultrahigh-performance liquid chromatography equipped with mass spectrometry. The initial experiment using a concentration of 200 mg/L showed that flavonolignans are resistant to the metabolic action of intestinal microbiota. At the lower concentration of 10 mg/L, biotransformation of flavonolignans was much slower than that of taxifolin, which was completely degraded after 16 h. While silybin, isosilybin, and 2,3-dehydrosilybin underwent mostly demethylation, silychristin was predominantly reduced. Silydianin, 2,3-dehydrosilychristin and 2,3-dehydrosilydianin were reduced, as well, and decarbonylation and cysteine conjugation proceeded. No low-molecular-weight phenolic metabolites were detected for any of the compounds tested. Strong inter-individual differences in the biotransformation profile were observed among the four fecal-material donors. In conclusion, the flavonolignans, especially at higher (pharmacological) doses, are relatively resistant to biotransformation by gut microbiota, which, however, depends strongly on the individual structures of these isomeric compounds, but also on the stool donor. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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17 pages, 1633 KiB  
Article
Quantification of Urinary Phenyl-γ-Valerolactones and Related Valeric Acids in Human Urine on Consumption of Apples
by Andrea Anesi, Pedro Mena, Achim Bub, Marynka Ulaszewska, Daniele Del Rio, Sabine E. Kulling and Fulvio Mattivi
Metabolites 2019, 9(11), 254; https://doi.org/10.3390/metabo9110254 - 29 Oct 2019
Cited by 32 | Viewed by 4527
Abstract
Flavan-3-ols are dietary bioactive molecules that have beneficial effects on human health and reduce the risk of various diseases. Monomeric flavan-3-ols are rapidly absorbed in the small intestine and released in the blood stream as phase II conjugates. Polymeric flavan-3-ols are extensively metabolized [...] Read more.
Flavan-3-ols are dietary bioactive molecules that have beneficial effects on human health and reduce the risk of various diseases. Monomeric flavan-3-ols are rapidly absorbed in the small intestine and released in the blood stream as phase II conjugates. Polymeric flavan-3-ols are extensively metabolized by colonic gut microbiota into phenyl-γ-valerolactones and their related phenylvaleric acids. These molecules are the main circulating metabolites in humans after the ingestion of flavan-3-ol rich-products; nevertheless, they have received less attention and their role is not understood yet. Here, we describe the quantification of 8 phenyl-γ-valerolactones and 3 phenylvaleric acids in the urine of 11 subjects on consumption of apples by using UHPLC-ESI-Triple Quad-MS with pure reference compounds. Phenyl-γ-valerolactones, mainly as sulfate and glucuronic acid conjugates, reached maximum excretion between 6 and 12 after apple consumption, with a decline thereafter. Significant differences were detected in the cumulative excretion rates within subjects and in the ratio of dihydroxyphenyl-γ-valerolactone sulfate to glucuronide conjugates. This work observed for the first time the presence of two distinct metabotypes with regards to the excretion of phenyl-γ-valerolactone phase II conjugates. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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12 pages, 1552 KiB  
Article
Effects of Gut Microbiota on the Bioavailability of Bioactive Compounds from Ginkgo Leaf Extracts
by Min Sun Choi, Jeon-Kyung Kim, Dong-Hyun Kim and Hye Hyun Yoo
Metabolites 2019, 9(7), 132; https://doi.org/10.3390/metabo9070132 - 5 Jul 2019
Cited by 17 | Viewed by 4285
Abstract
Ginkgo leaf extract (GLE) is a popular herbal medicine and dietary supplement for the treatment of various diseases, including cardiovascular disease. GLE contains a variety of secondary plant metabolites, such as flavonoids and terpenoids, as active components. Some of these phytochemicals have been [...] Read more.
Ginkgo leaf extract (GLE) is a popular herbal medicine and dietary supplement for the treatment of various diseases, including cardiovascular disease. GLE contains a variety of secondary plant metabolites, such as flavonoids and terpenoids, as active components. Some of these phytochemicals have been known to be metabolized by gut microbial enzymes. The aim of this study was to investigate the effects of the gut microbiota on the pharmacokinetics of the main constituents of GLE using antibacterial-treated mice. The bilobalide, ginkgolide A, ginkgolide B, ginkgolide C, isorhamnetin, kaempferol, and quercetin pharmacokinetic profiles of orally administered GLE (600 mg/kg), with or without ciprofloxacin pretreatment (150 mg/kg/day for 3 days), were determined. In the antibacterial-treated mice, the maximum plasma concentration (Cmax) and area under the curve (AUC) of isorhamnetin were significantly (p < 0.05) increased when compared with the control group. The Cmax and AUC of kaempferol and quercetin (other flavonol glycosides) were slightly higher than those of the control group, but the difference was not statistically significant, while both parameters for terpenoids of GLE showed no significant difference between the antibacterial-treated and control groups. These results showed that antibacterial consumption may increase the bioavailability of isorhamnetin by suppressing gut microbial metabolic activities. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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13 pages, 1839 KiB  
Article
Role of Intestinal Microbiota in Metabolism of Gastrodin In Vitro and In Vivo
by Mahesh Raj Nepal, Ki Sun Jeong, Geon Ho Kim, Dong Ho Cha, Mi Jeong Kang, Jin Sung Kim, Ju-Hyun Kim and Tae Cheon Jeong
Metabolites 2019, 9(4), 69; https://doi.org/10.3390/metabo9040069 - 8 Apr 2019
Cited by 11 | Viewed by 3689
Abstract
Alteration in the number and composition of intestinal microbiota affects the metabolism of several xenobiotics. Gastrodin, isolated from Gastrodia elata, is prone to be hydrolyzed by intestinal microbiota. In the present study, the role of intestinal microbiota in gastrodin metabolism was investigated in [...] Read more.
Alteration in the number and composition of intestinal microbiota affects the metabolism of several xenobiotics. Gastrodin, isolated from Gastrodia elata, is prone to be hydrolyzed by intestinal microbiota. In the present study, the role of intestinal microbiota in gastrodin metabolism was investigated in vitro and in vivo. Gastrodin was incubated in an anaerobic condition with intestinal contents prepared from vehicle- and antibiotics-treated rats and the disappearance of gastrodin and formation of 4-hydroxybenzyl alcohol (4-HBA) was measured by liquid chromatography coupled to mass spectroscopy (LC-MS/MS). The results showed that almost all gastrodin incubated with control intestinal contents was metabolized to its aglycone in time- and concentration-dependent manners. In contrast, much less formation of 4-HBA was detected in intestinal contents from antibiotics-treated rats. Subsequently, in vivo pharmacokinetic study revealed that the antibiotic pretreatment of rats significantly affected the metabolism of gastrodin to 4-HBA. When administered orally, gastrodin was rapidly absorbed rapidly into plasma, metabolized to 4-HBA, and disappeared from the body within six hours. Interestingly, the pharmacokinetic parameters of 4-HBA were changed remarkably in antibiotics-treated rats, compared to control rats. The results clearly indicated that the antibiotics treatment of rats suppressed the ability of intestinal microbiota to metabolize gastrodin to 4-HBA and that, thereby, the pharmacodynamic action was significantly modulated. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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15 pages, 3286 KiB  
Article
Effects of Early Intervention with Maternal Fecal Microbiota and Antibiotics on the Gut Microbiota and Metabolite Profiles of Piglets
by Chunhui Lin, Jiajia Wan, Yong Su and Weiyun Zhu
Metabolites 2018, 8(4), 89; https://doi.org/10.3390/metabo8040089 - 6 Dec 2018
Cited by 27 | Viewed by 4875
Abstract
We investigated the effects of early intervention with maternal fecal microbiota and antibiotics on gut microbiota and the metabolites. Five litters of healthy neonatal piglets (Duroc × Landrace × Yorkshire, nine piglets in each litter) were used. Piglets in each litter were orally [...] Read more.
We investigated the effects of early intervention with maternal fecal microbiota and antibiotics on gut microbiota and the metabolites. Five litters of healthy neonatal piglets (Duroc × Landrace × Yorkshire, nine piglets in each litter) were used. Piglets in each litter were orally treated with saline (CO), amoxicillin treatment (AM), or maternal fecal microbiota transplantation (MFMT) on days 1–6, with three piglets in each treatment. Results were compared to the CO group. MFMT decreased the relative abundances of Clostridium sensu stricto and Parabacteroides in the colon on day 7, whereas the abundance of Blautia increased, and the abundance of Corynebacterium in the stomach reduced on day 21. AM reduced the abundance of Arcanobacterium in the stomach on day 7 and reduced the abundances of Streptococcus and Lachnoclostridium in the ileum and colon on day 21, respectively. The metabolite profile indicated that MFMT markedly influenced carbohydrate metabolism and amino acid (AA) metabolism on day 7. On day 21, carbohydrate metabolism and AA metabolism were affected by AM. The results suggest that MFMT and AM discriminatively modulate gastrointestinal microflora and alter the colonic metabolic profiles of piglets and show different effects in the long-term. MFMT showed a location-specific influence on the gastrointestinal microbiota. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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Review

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6 pages, 1347 KiB  
Review
Chemical Aspects of Gut Metabolism of Flavonoids
by Jaehong Han
Metabolites 2019, 9(7), 136; https://doi.org/10.3390/metabo9070136 - 10 Jul 2019
Cited by 11 | Viewed by 4432
Abstract
The intestine is a small world where all the chemical reactions are operated by gut microbiota. Study on the gut metabolism of natural products is a new and expanding research area that leads to new bioactive metabolites, as well as novel chemical reactions. [...] Read more.
The intestine is a small world where all the chemical reactions are operated by gut microbiota. Study on the gut metabolism of natural products is a new and expanding research area that leads to new bioactive metabolites, as well as novel chemical reactions. To provide exemplary cases, flavonoid biotransformation by intestinal bacteria with focus on S-equol biosynthesis and aryl methyl ether cleavage reaction, is described in this review. Full article
(This article belongs to the Special Issue Gut Metabolism of Natural Products)
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