Characterization of stable and reactive metabolites of piperine formed on incubation with human liver microsomes
Black pepper, though commonly employed as a spice, has many medicinal properties. It consists of volatile oils, alkaloids, pungent resins, etc., of which piperine is a major constituent. Though safe at low doses, piperine causes alteration in the activity of drug metabolising enzymes and transporter...
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| Veröffentlicht in: | Journal of mass spectrometry. 2019-09, Vol.54 (9), p.738-749 |
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| creator | Praneetha, Pammi Balhara, Ankit Ladumor, Mayur K. Singh, Dilip Kumar Patil, Amol Preethi, Jalvadi Pokharkar, Sunil Deshpande, Abhijeet Yashwantrao Giri, Sanjeev Singh, Saranjit |
| description | Black pepper, though commonly employed as a spice, has many medicinal properties. It consists of volatile oils, alkaloids, pungent resins, etc., of which piperine is a major constituent. Though safe at low doses, piperine causes alteration in the activity of drug metabolising enzymes and transporters at high dose and is known to precipitate liver toxicity. It has a potential to form reactive metabolite(s) (RM) owing to the presence of structural alerts, such as methylenedioxyphenyl (MDP), α, β‐unsaturated carbonyl group (Michael acceptor), and piperidine. The present study was designed to detect and characterize stable and RM(s) of piperine formed on in vitro incubation with human liver microsomes. The investigation of RMs was done with the aid of trapping agents, viz, glutathione (GSH) and N‐acetylcysteine (NAC). The samples were analysed by ultra‐high performance liquid chromatography coupled with high resolution mass spectrometry (UHPLC‐HRMS) using Thermo Scientific Q Exactive Plus Orbitrap. Full scan MS followed by data‐dependent MS2 (Full MS‐ddMS2) mode was used to establish mass spectrometric fragmentation pathways of protonated piperine and its metabolites. In total, four stable metabolites and their isomers (M1a‐c, M2a‐b, M3a‐c, and M4a‐b) were detected. Their formation involved removal of carbon (3, M1a‐c), hydroxylation (2, M2a‐b), hydroxylation with hydrogenation (3, M3a‐c), and dehydrogenation (2, M4a‐b). Out of these metabolites, M1, M2, and M3 are reported earlier in the literature, but their isomers and two M4 variants are novel. In addition, six novel conjugates of RMs, including three GSH conjugates of m/z 579 and three NAC conjugates of m/z 435, were also observed. |
| doi_str_mv | 10.1002/jms.4424 |
| format | Article |
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It consists of volatile oils, alkaloids, pungent resins, etc., of which piperine is a major constituent. Though safe at low doses, piperine causes alteration in the activity of drug metabolising enzymes and transporters at high dose and is known to precipitate liver toxicity. It has a potential to form reactive metabolite(s) (RM) owing to the presence of structural alerts, such as methylenedioxyphenyl (MDP), α, β‐unsaturated carbonyl group (Michael acceptor), and piperidine. The present study was designed to detect and characterize stable and RM(s) of piperine formed on in vitro incubation with human liver microsomes. The investigation of RMs was done with the aid of trapping agents, viz, glutathione (GSH) and N‐acetylcysteine (NAC). The samples were analysed by ultra‐high performance liquid chromatography coupled with high resolution mass spectrometry (UHPLC‐HRMS) using Thermo Scientific Q Exactive Plus Orbitrap. Full scan MS followed by data‐dependent MS2 (Full MS‐ddMS2) mode was used to establish mass spectrometric fragmentation pathways of protonated piperine and its metabolites. In total, four stable metabolites and their isomers (M1a‐c, M2a‐b, M3a‐c, and M4a‐b) were detected. Their formation involved removal of carbon (3, M1a‐c), hydroxylation (2, M2a‐b), hydroxylation with hydrogenation (3, M3a‐c), and dehydrogenation (2, M4a‐b). Out of these metabolites, M1, M2, and M3 are reported earlier in the literature, but their isomers and two M4 variants are novel. In addition, six novel conjugates of RMs, including three GSH conjugates of m/z 579 and three NAC conjugates of m/z 435, were also observed.</description><identifier>ISSN: 1076-5174</identifier><identifier>EISSN: 1096-9888</identifier><identifier>DOI: 10.1002/jms.4424</identifier><identifier>PMID: 31368246</identifier><language>eng</language><publisher>England: Wiley Subscription Services, Inc</publisher><subject>Acetylcysteine ; Acetylcysteine - chemistry ; Alkaloids ; Alkaloids - analysis ; Alkaloids - metabolism ; Benzodioxoles - analysis ; Benzodioxoles - metabolism ; Carbonyl compounds ; Carbonyl groups ; Carbonyls ; Chromatography, High Pressure Liquid ; Conjugates ; Dehydrogenation ; Essential oils ; Glutathione ; Glutathione - chemistry ; Hepatotoxicity ; High performance liquid chromatography ; HPLC ; Humans ; Hydroxylation ; Incubation ; Incubation period ; Isomerism ; Isomers ; Liquid chromatography ; Liver ; Mass spectrometry ; Mass spectroscopy ; Medicinal plants ; Metabolites ; Microsomes ; Microsomes, Liver - metabolism ; N‐acetyl‐L‐cysteine ; orbitrap ; Piper nigrum ; Piperidine ; Piperidines - analysis ; Piperidines - metabolism ; Piperine ; Polyunsaturated Alkamides - analysis ; Polyunsaturated Alkamides - metabolism ; reactive metabolite ; Resins ; Ribosomes ; Spices ; Tandem Mass Spectrometry ; Toxicity</subject><ispartof>Journal of mass spectrometry., 2019-09, Vol.54 (9), p.738-749</ispartof><rights>2019 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3864-f2f3f121cb7029f558b2ae0d7c034d1f7eddd14379bc1931243890f63fbb08e13</citedby><cites>FETCH-LOGICAL-c3864-f2f3f121cb7029f558b2ae0d7c034d1f7eddd14379bc1931243890f63fbb08e13</cites><orcidid>0000-0002-8433-4598</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjms.4424$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjms.4424$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31368246$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Praneetha, Pammi</creatorcontrib><creatorcontrib>Balhara, Ankit</creatorcontrib><creatorcontrib>Ladumor, Mayur K.</creatorcontrib><creatorcontrib>Singh, Dilip Kumar</creatorcontrib><creatorcontrib>Patil, Amol</creatorcontrib><creatorcontrib>Preethi, Jalvadi</creatorcontrib><creatorcontrib>Pokharkar, Sunil</creatorcontrib><creatorcontrib>Deshpande, Abhijeet Yashwantrao</creatorcontrib><creatorcontrib>Giri, Sanjeev</creatorcontrib><creatorcontrib>Singh, Saranjit</creatorcontrib><title>Characterization of stable and reactive metabolites of piperine formed on incubation with human liver microsomes</title><title>Journal of mass spectrometry.</title><addtitle>J Mass Spectrom</addtitle><description>Black pepper, though commonly employed as a spice, has many medicinal properties. It consists of volatile oils, alkaloids, pungent resins, etc., of which piperine is a major constituent. Though safe at low doses, piperine causes alteration in the activity of drug metabolising enzymes and transporters at high dose and is known to precipitate liver toxicity. It has a potential to form reactive metabolite(s) (RM) owing to the presence of structural alerts, such as methylenedioxyphenyl (MDP), α, β‐unsaturated carbonyl group (Michael acceptor), and piperidine. The present study was designed to detect and characterize stable and RM(s) of piperine formed on in vitro incubation with human liver microsomes. The investigation of RMs was done with the aid of trapping agents, viz, glutathione (GSH) and N‐acetylcysteine (NAC). The samples were analysed by ultra‐high performance liquid chromatography coupled with high resolution mass spectrometry (UHPLC‐HRMS) using Thermo Scientific Q Exactive Plus Orbitrap. Full scan MS followed by data‐dependent MS2 (Full MS‐ddMS2) mode was used to establish mass spectrometric fragmentation pathways of protonated piperine and its metabolites. In total, four stable metabolites and their isomers (M1a‐c, M2a‐b, M3a‐c, and M4a‐b) were detected. Their formation involved removal of carbon (3, M1a‐c), hydroxylation (2, M2a‐b), hydroxylation with hydrogenation (3, M3a‐c), and dehydrogenation (2, M4a‐b). Out of these metabolites, M1, M2, and M3 are reported earlier in the literature, but their isomers and two M4 variants are novel. In addition, six novel conjugates of RMs, including three GSH conjugates of m/z 579 and three NAC conjugates of m/z 435, were also observed.</description><subject>Acetylcysteine</subject><subject>Acetylcysteine - chemistry</subject><subject>Alkaloids</subject><subject>Alkaloids - analysis</subject><subject>Alkaloids - metabolism</subject><subject>Benzodioxoles - analysis</subject><subject>Benzodioxoles - metabolism</subject><subject>Carbonyl compounds</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Conjugates</subject><subject>Dehydrogenation</subject><subject>Essential oils</subject><subject>Glutathione</subject><subject>Glutathione - chemistry</subject><subject>Hepatotoxicity</subject><subject>High performance liquid chromatography</subject><subject>HPLC</subject><subject>Humans</subject><subject>Hydroxylation</subject><subject>Incubation</subject><subject>Incubation period</subject><subject>Isomerism</subject><subject>Isomers</subject><subject>Liquid chromatography</subject><subject>Liver</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Medicinal plants</subject><subject>Metabolites</subject><subject>Microsomes</subject><subject>Microsomes, Liver - metabolism</subject><subject>N‐acetyl‐L‐cysteine</subject><subject>orbitrap</subject><subject>Piper nigrum</subject><subject>Piperidine</subject><subject>Piperidines - analysis</subject><subject>Piperidines - metabolism</subject><subject>Piperine</subject><subject>Polyunsaturated Alkamides - analysis</subject><subject>Polyunsaturated Alkamides - metabolism</subject><subject>reactive metabolite</subject><subject>Resins</subject><subject>Ribosomes</subject><subject>Spices</subject><subject>Tandem Mass Spectrometry</subject><subject>Toxicity</subject><issn>1076-5174</issn><issn>1096-9888</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kc1q3DAUhUVJyEymhT5BEWSTjSf6s2wty5CflgldNFkL2b5iNNiWK9kJ6dNXzkxaKGQlIX3nQ7oHoc-UrCkh7GrfxbUQTHxAS0qUzFRZlifzvpBZTguxQOcx7gkhSgl5hhacclkyIZdo2OxMMPUIwf02o_M99hbH0VQtYNM3OEC6dE-AO0iHvnUjxBkZ3JAiPWDrQwcNTkHX11N1cDy7cYd3U2d63KZwwJ2rg4--g_gRnVrTRvh0XFfo8eb6YXOXbX_cftt83WY1L6XILLPcUkbrqiBM2TwvK2aANEVNuGioLaBpGip4oaqaKk6Z4KUiVnJbVaQEylfo8uAdgv81QRx152INbWt68FPUjMmiEFJxltCL_9C9n0KfXqcZJ7kgIpfyn3D-SQxg9RBcZ8KLpkTPLejUgp5bSOiXo3Cq0nD-gm9jT0B2AJ5dCy_vivT3-5-vwj-IHZG-</recordid><startdate>201909</startdate><enddate>201909</enddate><creator>Praneetha, Pammi</creator><creator>Balhara, Ankit</creator><creator>Ladumor, Mayur K.</creator><creator>Singh, Dilip Kumar</creator><creator>Patil, Amol</creator><creator>Preethi, Jalvadi</creator><creator>Pokharkar, Sunil</creator><creator>Deshpande, Abhijeet Yashwantrao</creator><creator>Giri, Sanjeev</creator><creator>Singh, Saranjit</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7QR</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7TK</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H97</scope><scope>JG9</scope><scope>JQ2</scope><scope>K9.</scope><scope>KR7</scope><scope>L.G</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8433-4598</orcidid></search><sort><creationdate>201909</creationdate><title>Characterization of stable and reactive metabolites of piperine formed on incubation with human liver microsomes</title><author>Praneetha, Pammi ; Balhara, Ankit ; Ladumor, Mayur K. ; Singh, Dilip Kumar ; Patil, Amol ; Preethi, Jalvadi ; Pokharkar, Sunil ; Deshpande, Abhijeet Yashwantrao ; Giri, Sanjeev ; Singh, Saranjit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3864-f2f3f121cb7029f558b2ae0d7c034d1f7eddd14379bc1931243890f63fbb08e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acetylcysteine</topic><topic>Acetylcysteine - chemistry</topic><topic>Alkaloids</topic><topic>Alkaloids - analysis</topic><topic>Alkaloids - metabolism</topic><topic>Benzodioxoles - analysis</topic><topic>Benzodioxoles - metabolism</topic><topic>Carbonyl compounds</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Conjugates</topic><topic>Dehydrogenation</topic><topic>Essential oils</topic><topic>Glutathione</topic><topic>Glutathione - chemistry</topic><topic>Hepatotoxicity</topic><topic>High performance liquid chromatography</topic><topic>HPLC</topic><topic>Humans</topic><topic>Hydroxylation</topic><topic>Incubation</topic><topic>Incubation period</topic><topic>Isomerism</topic><topic>Isomers</topic><topic>Liquid chromatography</topic><topic>Liver</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>Medicinal plants</topic><topic>Metabolites</topic><topic>Microsomes</topic><topic>Microsomes, Liver - metabolism</topic><topic>N‐acetyl‐L‐cysteine</topic><topic>orbitrap</topic><topic>Piper nigrum</topic><topic>Piperidine</topic><topic>Piperidines - analysis</topic><topic>Piperidines - metabolism</topic><topic>Piperine</topic><topic>Polyunsaturated Alkamides - analysis</topic><topic>Polyunsaturated Alkamides - metabolism</topic><topic>reactive metabolite</topic><topic>Resins</topic><topic>Ribosomes</topic><topic>Spices</topic><topic>Tandem Mass Spectrometry</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Praneetha, Pammi</creatorcontrib><creatorcontrib>Balhara, Ankit</creatorcontrib><creatorcontrib>Ladumor, Mayur K.</creatorcontrib><creatorcontrib>Singh, Dilip Kumar</creatorcontrib><creatorcontrib>Patil, Amol</creatorcontrib><creatorcontrib>Preethi, Jalvadi</creatorcontrib><creatorcontrib>Pokharkar, Sunil</creatorcontrib><creatorcontrib>Deshpande, Abhijeet Yashwantrao</creatorcontrib><creatorcontrib>Giri, Sanjeev</creatorcontrib><creatorcontrib>Singh, Saranjit</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Civil Engineering Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of mass spectrometry.</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Praneetha, Pammi</au><au>Balhara, Ankit</au><au>Ladumor, Mayur K.</au><au>Singh, Dilip Kumar</au><au>Patil, Amol</au><au>Preethi, Jalvadi</au><au>Pokharkar, Sunil</au><au>Deshpande, Abhijeet Yashwantrao</au><au>Giri, Sanjeev</au><au>Singh, Saranjit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of stable and reactive metabolites of piperine formed on incubation with human liver microsomes</atitle><jtitle>Journal of mass spectrometry.</jtitle><addtitle>J Mass Spectrom</addtitle><date>2019-09</date><risdate>2019</risdate><volume>54</volume><issue>9</issue><spage>738</spage><epage>749</epage><pages>738-749</pages><issn>1076-5174</issn><eissn>1096-9888</eissn><abstract>Black pepper, though commonly employed as a spice, has many medicinal properties. It consists of volatile oils, alkaloids, pungent resins, etc., of which piperine is a major constituent. Though safe at low doses, piperine causes alteration in the activity of drug metabolising enzymes and transporters at high dose and is known to precipitate liver toxicity. It has a potential to form reactive metabolite(s) (RM) owing to the presence of structural alerts, such as methylenedioxyphenyl (MDP), α, β‐unsaturated carbonyl group (Michael acceptor), and piperidine. The present study was designed to detect and characterize stable and RM(s) of piperine formed on in vitro incubation with human liver microsomes. The investigation of RMs was done with the aid of trapping agents, viz, glutathione (GSH) and N‐acetylcysteine (NAC). The samples were analysed by ultra‐high performance liquid chromatography coupled with high resolution mass spectrometry (UHPLC‐HRMS) using Thermo Scientific Q Exactive Plus Orbitrap. Full scan MS followed by data‐dependent MS2 (Full MS‐ddMS2) mode was used to establish mass spectrometric fragmentation pathways of protonated piperine and its metabolites. In total, four stable metabolites and their isomers (M1a‐c, M2a‐b, M3a‐c, and M4a‐b) were detected. Their formation involved removal of carbon (3, M1a‐c), hydroxylation (2, M2a‐b), hydroxylation with hydrogenation (3, M3a‐c), and dehydrogenation (2, M4a‐b). Out of these metabolites, M1, M2, and M3 are reported earlier in the literature, but their isomers and two M4 variants are novel. In addition, six novel conjugates of RMs, including three GSH conjugates of m/z 579 and three NAC conjugates of m/z 435, were also observed.</abstract><cop>England</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31368246</pmid><doi>10.1002/jms.4424</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-8433-4598</orcidid></addata></record> |
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| ispartof | Journal of mass spectrometry., 2019-09, Vol.54 (9), p.738-749 |
| issn | 1076-5174 1096-9888 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Acetylcysteine Acetylcysteine - chemistry Alkaloids Alkaloids - analysis Alkaloids - metabolism Benzodioxoles - analysis Benzodioxoles - metabolism Carbonyl compounds Carbonyl groups Carbonyls Chromatography, High Pressure Liquid Conjugates Dehydrogenation Essential oils Glutathione Glutathione - chemistry Hepatotoxicity High performance liquid chromatography HPLC Humans Hydroxylation Incubation Incubation period Isomerism Isomers Liquid chromatography Liver Mass spectrometry Mass spectroscopy Medicinal plants Metabolites Microsomes Microsomes, Liver - metabolism N‐acetyl‐L‐cysteine orbitrap Piper nigrum Piperidine Piperidines - analysis Piperidines - metabolism Piperine Polyunsaturated Alkamides - analysis Polyunsaturated Alkamides - metabolism reactive metabolite Resins Ribosomes Spices Tandem Mass Spectrometry Toxicity |
| title | Characterization of stable and reactive metabolites of piperine formed on incubation with human liver microsomes |
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