Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety....
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| Veröffentlicht in: | Chemical biology & drug design 2016-09, Vol.88 (3), p.354-362 |
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| creator | Kharbanda, Chetna Alam, Mohammad Sarwar Hamid, Hinna Javed, Kalim Bano, Sameena Ali, Yakub Dhulap, Abhijeet Alam, Perwez Pasha, M. A. Qadar |
| description | Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ‐induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a‐h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR‐γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side‐effects.
Twenty synthesized piperine derivatives are potential antidiabetic agents. Maximum antidiabetic effect was observed for compounds 6c and 6d. |
| doi_str_mv | 10.1111/cbdd.12760 |
| format | Article |
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Twenty synthesized piperine derivatives are potential antidiabetic agents. Maximum antidiabetic effect was observed for compounds 6c and 6d.</description><identifier>ISSN: 1747-0277</identifier><identifier>EISSN: 1747-0285</identifier><identifier>DOI: 10.1111/cbdd.12760</identifier><identifier>PMID: 27037532</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>amide linkage ; Animals ; antidiabetic ; Blood Glucose - analysis ; Blood Glucose - metabolism ; Diabetes Mellitus, Experimental - drug therapy ; Diabetes Mellitus, Experimental - genetics ; Diabetes Mellitus, Experimental - metabolism ; gene expression ; Gene Expression Regulation - drug effects ; HEK293 Cells ; Humans ; Hypoglycemic Agents - chemistry ; Hypoglycemic Agents - pharmacology ; Hypoglycemic Agents - therapeutic use ; Lipid Peroxidation - drug effects ; Male ; Molecular Docking Simulation ; Piper nigrum ; Piper nigrum - chemistry ; Piperidines - chemistry ; Piperidines - pharmacology ; Piperidines - therapeutic use ; piperine ; PPAR gamma - agonists ; PPAR gamma - genetics ; PPAR gamma - metabolism ; PPAR-γ ; Rats, Wistar</subject><ispartof>Chemical biology & drug design, 2016-09, Vol.88 (3), p.354-362</ispartof><rights>2016 John Wiley & Sons A/S</rights><rights>2016 John Wiley & Sons A/S.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3850-d67612cd32a6b01ec56b2459554cddf8326d9e37b3ebbeb05066855ec47d499e3</citedby><cites>FETCH-LOGICAL-c3850-d67612cd32a6b01ec56b2459554cddf8326d9e37b3ebbeb05066855ec47d499e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fcbdd.12760$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fcbdd.12760$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27037532$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kharbanda, Chetna</creatorcontrib><creatorcontrib>Alam, Mohammad Sarwar</creatorcontrib><creatorcontrib>Hamid, Hinna</creatorcontrib><creatorcontrib>Javed, Kalim</creatorcontrib><creatorcontrib>Bano, Sameena</creatorcontrib><creatorcontrib>Ali, Yakub</creatorcontrib><creatorcontrib>Dhulap, Abhijeet</creatorcontrib><creatorcontrib>Alam, Perwez</creatorcontrib><creatorcontrib>Pasha, M. A. Qadar</creatorcontrib><title>Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists</title><title>Chemical biology & drug design</title><addtitle>Chem Biol Drug Des</addtitle><description>Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ‐induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a‐h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR‐γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side‐effects.
Twenty synthesized piperine derivatives are potential antidiabetic agents. Maximum antidiabetic effect was observed for compounds 6c and 6d.</description><subject>amide linkage</subject><subject>Animals</subject><subject>antidiabetic</subject><subject>Blood Glucose - analysis</subject><subject>Blood Glucose - metabolism</subject><subject>Diabetes Mellitus, Experimental - drug therapy</subject><subject>Diabetes Mellitus, Experimental - genetics</subject><subject>Diabetes Mellitus, Experimental - metabolism</subject><subject>gene expression</subject><subject>Gene Expression Regulation - drug effects</subject><subject>HEK293 Cells</subject><subject>Humans</subject><subject>Hypoglycemic Agents - chemistry</subject><subject>Hypoglycemic Agents - pharmacology</subject><subject>Hypoglycemic Agents - therapeutic use</subject><subject>Lipid Peroxidation - drug effects</subject><subject>Male</subject><subject>Molecular Docking Simulation</subject><subject>Piper nigrum</subject><subject>Piper nigrum - chemistry</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Piperidines - therapeutic use</subject><subject>piperine</subject><subject>PPAR gamma - agonists</subject><subject>PPAR gamma - genetics</subject><subject>PPAR gamma - metabolism</subject><subject>PPAR-γ</subject><subject>Rats, Wistar</subject><issn>1747-0277</issn><issn>1747-0285</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtOwzAQQC0E4r_hAChLhJRiO_5lWVooSChUFQh2VmxPwJA2JU4LnIt7cCYC_SzxZizNm7d4CB0R3CHtO7PGuQ6hUuANtEskkzGmim-u_1LuoL0QXjBmjFO1jXaoxInkCd1Fg6yaQxkN_RRqP4Go34553vg5hOjdN89Rd9J453MDjbfRRVGAbaI8RMNhdxR_f0Xdp2riQxMO0FaRlwEOl3Mf3V9e3PWu4pvbwXWvexPbRHEcOyEFodYlNBcGE7BcGMp4yjmzzhUqocKlkEiTgDFgMMdCKM7BMulY2m720cnCO62rtxmERo99sFCW-QSqWdBEEaJSSRhv0dMFausqhBoKPa39OK8_NcH6N5z-Daf_wrXw8dI7M2Nwa3RVqgXIAnj3JXz-o9K9835_JY0XN20h-Fjf5PWrFrLV6odsoLNHlamHwUiz5Af_X4ay</recordid><startdate>201609</startdate><enddate>201609</enddate><creator>Kharbanda, Chetna</creator><creator>Alam, Mohammad Sarwar</creator><creator>Hamid, Hinna</creator><creator>Javed, Kalim</creator><creator>Bano, Sameena</creator><creator>Ali, Yakub</creator><creator>Dhulap, Abhijeet</creator><creator>Alam, Perwez</creator><creator>Pasha, M. A. Qadar</creator><general>Blackwell Publishing Ltd</general><scope>BSCLL</scope><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>201609</creationdate><title>Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists</title><author>Kharbanda, Chetna ; Alam, Mohammad Sarwar ; Hamid, Hinna ; Javed, Kalim ; Bano, Sameena ; Ali, Yakub ; Dhulap, Abhijeet ; Alam, Perwez ; Pasha, M. A. Qadar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3850-d67612cd32a6b01ec56b2459554cddf8326d9e37b3ebbeb05066855ec47d499e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>amide linkage</topic><topic>Animals</topic><topic>antidiabetic</topic><topic>Blood Glucose - analysis</topic><topic>Blood Glucose - metabolism</topic><topic>Diabetes Mellitus, Experimental - drug therapy</topic><topic>Diabetes Mellitus, Experimental - genetics</topic><topic>Diabetes Mellitus, Experimental - metabolism</topic><topic>gene expression</topic><topic>Gene Expression Regulation - drug effects</topic><topic>HEK293 Cells</topic><topic>Humans</topic><topic>Hypoglycemic Agents - chemistry</topic><topic>Hypoglycemic Agents - pharmacology</topic><topic>Hypoglycemic Agents - therapeutic use</topic><topic>Lipid Peroxidation - drug effects</topic><topic>Male</topic><topic>Molecular Docking Simulation</topic><topic>Piper nigrum</topic><topic>Piper nigrum - chemistry</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Piperidines - therapeutic use</topic><topic>piperine</topic><topic>PPAR gamma - agonists</topic><topic>PPAR gamma - genetics</topic><topic>PPAR gamma - metabolism</topic><topic>PPAR-γ</topic><topic>Rats, Wistar</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kharbanda, Chetna</creatorcontrib><creatorcontrib>Alam, Mohammad Sarwar</creatorcontrib><creatorcontrib>Hamid, Hinna</creatorcontrib><creatorcontrib>Javed, Kalim</creatorcontrib><creatorcontrib>Bano, Sameena</creatorcontrib><creatorcontrib>Ali, Yakub</creatorcontrib><creatorcontrib>Dhulap, Abhijeet</creatorcontrib><creatorcontrib>Alam, Perwez</creatorcontrib><creatorcontrib>Pasha, M. A. Qadar</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Chemical biology & drug design</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kharbanda, Chetna</au><au>Alam, Mohammad Sarwar</au><au>Hamid, Hinna</au><au>Javed, Kalim</au><au>Bano, Sameena</au><au>Ali, Yakub</au><au>Dhulap, Abhijeet</au><au>Alam, Perwez</au><au>Pasha, M. A. Qadar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists</atitle><jtitle>Chemical biology & drug design</jtitle><addtitle>Chem Biol Drug Des</addtitle><date>2016-09</date><risdate>2016</risdate><volume>88</volume><issue>3</issue><spage>354</spage><epage>362</epage><pages>354-362</pages><issn>1747-0277</issn><eissn>1747-0285</eissn><abstract>Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ‐induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a‐h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR‐γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side‐effects.
Twenty synthesized piperine derivatives are potential antidiabetic agents. Maximum antidiabetic effect was observed for compounds 6c and 6d.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>27037532</pmid><doi>10.1111/cbdd.12760</doi><tpages>9</tpages></addata></record> |
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| subjects | amide linkage Animals antidiabetic Blood Glucose - analysis Blood Glucose - metabolism Diabetes Mellitus, Experimental - drug therapy Diabetes Mellitus, Experimental - genetics Diabetes Mellitus, Experimental - metabolism gene expression Gene Expression Regulation - drug effects HEK293 Cells Humans Hypoglycemic Agents - chemistry Hypoglycemic Agents - pharmacology Hypoglycemic Agents - therapeutic use Lipid Peroxidation - drug effects Male Molecular Docking Simulation Piper nigrum Piper nigrum - chemistry Piperidines - chemistry Piperidines - pharmacology Piperidines - therapeutic use piperine PPAR gamma - agonists PPAR gamma - genetics PPAR gamma - metabolism PPAR-γ Rats, Wistar |
| title | Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists |
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