Nematocidal Activity of Picrodendrins against a Species of Diplogastridae
To develop parasiticides, the nematocidal activity of 22 picrotoxane terpenoids, picrodendrins isolated from the Euphorbiaceae plant Picrodendron baccatum (L.) KLUG et URBAN, was measured using a species of Diplogastridae (Nematoda). Picrodendrin P displayed the most potent nematocidal activity with...
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| Veröffentlicht in: | Biological & pharmaceutical bulletin 1999/12/15, Vol.22(12), pp.1310-1313 |
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| creator | WATANABE, Ie KOIKE, Kazuo SATOU, Tadaaki NIKAIDO, Tamotsu |
| description | To develop parasiticides, the nematocidal activity of 22 picrotoxane terpenoids, picrodendrins isolated from the Euphorbiaceae plant Picrodendron baccatum (L.) KLUG et URBAN, was measured using a species of Diplogastridae (Nematoda). Picrodendrin P displayed the most potent nematocidal activity with a minimum lethal concentration (MLC) value of 4.4×10-3 M. The nematocidal activity of picrodendrin P was 9-fold more potent than that of kainic acid (4.0×10-2 M) and santonin (4.0×10-2 M) and 6-fold more potent than that of diethylcarbamazine citrate (3.0×10-2 M). Thus, picrodendrin P may eventually be used as a leading parasiticide. In light of the relationship between the structure of picrodendrins and their nematocidal activities, potent nematocidal activity was found to require the following elements within the picrotoxane skeleton : the γ-lactone that bridges C-3 and C-5, the epoxide group that bridges between C-6 and C-8, a cis-OCH3 group and a trans-CH2OH group related to carbonyl at α-methylene-γ-lactone ring (C-18), and the absence of 4- and 8-hydroxyl groups. These results are the first demonstration of nematocidal activity for these terpenes and thus are important in furthering our understanding. |
| doi_str_mv | 10.1248/bpb.22.1310 |
| format | Article |
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KLUG et URBAN, was measured using a species of Diplogastridae (Nematoda). Picrodendrin P displayed the most potent nematocidal activity with a minimum lethal concentration (MLC) value of 4.4×10-3 M. The nematocidal activity of picrodendrin P was 9-fold more potent than that of kainic acid (4.0×10-2 M) and santonin (4.0×10-2 M) and 6-fold more potent than that of diethylcarbamazine citrate (3.0×10-2 M). Thus, picrodendrin P may eventually be used as a leading parasiticide. In light of the relationship between the structure of picrodendrins and their nematocidal activities, potent nematocidal activity was found to require the following elements within the picrotoxane skeleton : the γ-lactone that bridges C-3 and C-5, the epoxide group that bridges between C-6 and C-8, a cis-OCH3 group and a trans-CH2OH group related to carbonyl at α-methylene-γ-lactone ring (C-18), and the absence of 4- and 8-hydroxyl groups. These results are the first demonstration of nematocidal activity for these terpenes and thus are important in furthering our understanding.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.22.1310</identifier><identifier>PMID: 10746162</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antinematodal Agents - chemistry ; Antinematodal Agents - pharmacology ; Antiparasitic agents ; Biological and medical sciences ; Diplogastridae ; General pharmacology ; Medical sciences ; nematocidal activity ; Nematoda ; Nematoda - drug effects ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. 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KLUG et URBAN, was measured using a species of Diplogastridae (Nematoda). Picrodendrin P displayed the most potent nematocidal activity with a minimum lethal concentration (MLC) value of 4.4×10-3 M. The nematocidal activity of picrodendrin P was 9-fold more potent than that of kainic acid (4.0×10-2 M) and santonin (4.0×10-2 M) and 6-fold more potent than that of diethylcarbamazine citrate (3.0×10-2 M). Thus, picrodendrin P may eventually be used as a leading parasiticide. In light of the relationship between the structure of picrodendrins and their nematocidal activities, potent nematocidal activity was found to require the following elements within the picrotoxane skeleton : the γ-lactone that bridges C-3 and C-5, the epoxide group that bridges between C-6 and C-8, a cis-OCH3 group and a trans-CH2OH group related to carbonyl at α-methylene-γ-lactone ring (C-18), and the absence of 4- and 8-hydroxyl groups. These results are the first demonstration of nematocidal activity for these terpenes and thus are important in furthering our understanding.</description><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antinematodal Agents - chemistry</subject><subject>Antinematodal Agents - pharmacology</subject><subject>Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Diplogastridae</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>nematocidal activity</subject><subject>Nematoda</subject><subject>Nematoda - drug effects</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>picrodendrin</subject><subject>Picrodendron baccatum</subject><subject>Plant Extracts - pharmacology</subject><subject>Rosales - chemistry</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0E1v1DAQBmALUdFt4cQdRQL1grLYztiJj1VpoVIFSMDZmvhj8SqbBNuL1H9fp7sqiIvn4Mcz45eQ14yuGYfuQz_3a87XrGH0GVmxBtpacCaekxVVrKslE90pOUtpSyltKW9ekFNGW5BM8hW5_eJ2mCcTLA7VpcnhT8j31eSrb8HEybrRxjCmCjdYSq6w-j47E1xayMcwD9MGU47ltXtJTjwOyb061nPy8-b6x9Xn-u7rp9ury7vayAZyzaVrOk4p2AbAKd8qiuh7Adx6C84qjwDWAvMMvFCd6lvjuJTe856C9M05uTj0neP0e-9S1ruQjBsGHN20T1oqkKIFUeDb_-B22sex7KYZQIkGhOiKen9Q5bspRef1HMMO471mVC_56pKv5lwv-Rb95thz3--c_cceAi3g3RFgMjj4iKMJ6a_jIFqmCrs5sG3KuHFP9xhzMINbZjKlmse5_HguCzwB8wujdmPzAHJjmjQ</recordid><startdate>19991201</startdate><enddate>19991201</enddate><creator>WATANABE, Ie</creator><creator>KOIKE, Kazuo</creator><creator>SATOU, Tadaaki</creator><creator>NIKAIDO, Tamotsu</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</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>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19991201</creationdate><title>Nematocidal Activity of Picrodendrins against a Species of Diplogastridae</title><author>WATANABE, Ie ; KOIKE, Kazuo ; SATOU, Tadaaki ; NIKAIDO, Tamotsu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c634t-26e382004d344e9f790aafb542dfd4ed9fa44dd41f14f5989b7ce266ff2b046f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antinematodal Agents - chemistry</topic><topic>Antinematodal Agents - pharmacology</topic><topic>Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Diplogastridae</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>nematocidal activity</topic><topic>Nematoda</topic><topic>Nematoda - drug effects</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>picrodendrin</topic><topic>Picrodendron baccatum</topic><topic>Plant Extracts - pharmacology</topic><topic>Rosales - chemistry</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>WATANABE, Ie</creatorcontrib><creatorcontrib>KOIKE, Kazuo</creatorcontrib><creatorcontrib>SATOU, Tadaaki</creatorcontrib><creatorcontrib>NIKAIDO, Tamotsu</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Biological & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>WATANABE, Ie</au><au>KOIKE, Kazuo</au><au>SATOU, Tadaaki</au><au>NIKAIDO, Tamotsu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nematocidal Activity of Picrodendrins against a Species of Diplogastridae</atitle><jtitle>Biological & pharmaceutical bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>1999-12-01</date><risdate>1999</risdate><volume>22</volume><issue>12</issue><spage>1310</spage><epage>1313</epage><pages>1310-1313</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>To develop parasiticides, the nematocidal activity of 22 picrotoxane terpenoids, picrodendrins isolated from the Euphorbiaceae plant Picrodendron baccatum (L.) KLUG et URBAN, was measured using a species of Diplogastridae (Nematoda). Picrodendrin P displayed the most potent nematocidal activity with a minimum lethal concentration (MLC) value of 4.4×10-3 M. The nematocidal activity of picrodendrin P was 9-fold more potent than that of kainic acid (4.0×10-2 M) and santonin (4.0×10-2 M) and 6-fold more potent than that of diethylcarbamazine citrate (3.0×10-2 M). Thus, picrodendrin P may eventually be used as a leading parasiticide. In light of the relationship between the structure of picrodendrins and their nematocidal activities, potent nematocidal activity was found to require the following elements within the picrotoxane skeleton : the γ-lactone that bridges C-3 and C-5, the epoxide group that bridges between C-6 and C-8, a cis-OCH3 group and a trans-CH2OH group related to carbonyl at α-methylene-γ-lactone ring (C-18), and the absence of 4- and 8-hydroxyl groups. 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| subjects | Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antinematodal Agents - chemistry Antinematodal Agents - pharmacology Antiparasitic agents Biological and medical sciences Diplogastridae General pharmacology Medical sciences nematocidal activity Nematoda Nematoda - drug effects Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments picrodendrin Picrodendron baccatum Plant Extracts - pharmacology Rosales - chemistry Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Structure-Activity Relationship |
| title | Nematocidal Activity of Picrodendrins against a Species of Diplogastridae |
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