Further sesquiterpene lactones from Anthemis carpatica
A new germacranolide, ( E)-1α,10β-epoxy-3β-acetoxy-6α-hydroxygermacra-4,11(13)-dien-12,8α-olide, together with nine new highly oxygenated guaiadien-12,6α-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering Anthemis carpatica. In...
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| Published in: | Phytochemistry (Oxford) Vol. 54; no. 6; pp. 625 - 633 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
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01-07-2000
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| Abstract | A new germacranolide, (
E)-1α,10β-epoxy-3β-acetoxy-6α-hydroxygermacra-4,11(13)-dien-12,8α-olide, together with nine new highly oxygenated guaiadien-12,6α-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering
Anthemis carpatica. In addition, six known guaianolides belonging to the same groups, also isolated previously from
A. carpatica, along with two guaianolides, 2β-hydroxyepiligustrin and cumambrin B, not found before in this species, were isolated this time. |
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| AbstractList | A new germacranolide, (E)-1alpha, 10beta-epoxy-3beta-acetoxy-6alpha-hydroxygermacra-4,11 (13)-dien-12,8alpha-olide, together with nine new highly oxygenated guaiadien-12,6alpha-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering Anthemis carpatica. In addition, six known guaianolides belonging to the same groups, also isolated previously from A. carpatica, along with two guaianolides, 2beta-hydroxyepiligustrin and cumambrin B, not found before in this species, were isolated this time. A new germacranolide, ( E)-1α,10β-epoxy-3β-acetoxy-6α-hydroxygermacra-4,11(13)-dien-12,8α-olide, together with nine new highly oxygenated guaiadien-12,6α-olides of anthemolide, and cumambrin type were identified in the repeated examination of the aerial parts of the flowering Anthemis carpatica. In addition, six known guaianolides belonging to the same groups, also isolated previously from A. carpatica, along with two guaianolides, 2β-hydroxyepiligustrin and cumambrin B, not found before in this species, were isolated this time. |
| Author | Vajs, Vlatka Macura, Slobodan Milosavljević, Slobodan Juranić, Nenad Todorović, Nina Menković, Nebojša Bulatović, Vanja |
| Author_xml | – sequence: 1 givenname: Vlatka surname: Vajs fullname: Vajs, Vlatka organization: Institute for Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Yugoslavia – sequence: 2 givenname: Nina surname: Todorović fullname: Todorović, Nina organization: Institute for Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Yugoslavia – sequence: 3 givenname: Vanja surname: Bulatović fullname: Bulatović, Vanja organization: Institute for Medicinal Plant Research, “Dr. Josif Pančić”, Tadeuša Košćuška 1, 11000 Belgrade, Yugoslavia – sequence: 4 givenname: Nebojša surname: Menković fullname: Menković, Nebojša organization: Institute for Medicinal Plant Research, “Dr. Josif Pančić”, Tadeuša Košćuška 1, 11000 Belgrade, Yugoslavia – sequence: 5 givenname: Slobodan surname: Macura fullname: Macura, Slobodan organization: Mayo Foundation, Rochester, MN 55905, USA – sequence: 6 givenname: Nenad surname: Juranić fullname: Juranić, Nenad organization: Mayo Foundation, Rochester, MN 55905, USA – sequence: 7 givenname: Slobodan surname: Milosavljević fullname: Milosavljević, Slobodan email: smilo@helix.chem.bg.ac.yu organization: Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O. Box 158, 11001 Belgrade, Yugoslavia |
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| Cites_doi | 10.1016/0305-1978(73)90030-6 10.1016/S0031-9422(00)88654-9 10.1016/S0031-9422(96)00846-1 10.1016/S0031-9422(00)83588-8 10.1021/np970185w 10.1039/a705725c 10.1016/0031-9422(91)80087-H 10.1016/S0031-9422(98)00504-4 10.1002/mrc.1270220312 10.1016/S0031-9422(00)84954-7 10.1016/0031-9422(96)00142-2 10.1021/jo01296a020 10.1016/S0040-4039(00)90765-2 10.1039/np9920900289 10.1007/BF00472018 10.1016/S0040-4020(01)90687-8 |
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| Keywords | Anthemolides 9α-Oxygenated cumambrins 3β-Acetoxydeacetyltulirinol Sesquiterpene lactones Asteraceae Anthemis carpatica Guaidienolides ( E)-1α,10β-Epoxy-3β-acetoxy-6α-hydroxygermacra-4,11-dien-12,8α-olide Molecular structure Dicotyledones Sesquiterpenes Angiospermae Isolation Lactone Above ground plant part Spermatophyta Compositae |
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| References | Doskotch, Fairchaild, Huang, Wilton, Beno, Christoph (BIB8) 1980; 45 Milosavljević, Vajs, Bulatović, Djoković, Aljančić, Juranić, Macura (BIB13) 1998; 2 Ph.D. Thesis, Faculty of Chemistry, University of Belgrade Sutherland (BIB15) 1974; 30 Yoshioka, Mabry, Timmermann (BIB18) 1973 Iriuchijima, S., Tamura, S., 1967. Stereochemical structures of pyrethrosin, cyclopyrethrosin acetate and isocyclopyrethrosin. Tetrahedron Letters, 1965–1969 Bulatoviić, V., 1998. Comparative study of chemical constituents of plant species di Benedetto, Menichini, Gacs-Baitz, Delle Monache (BIB7) 1991; 30 Todorova, Krasteva (BIB16) 1996; 42 Bruno, Bondi, Vassalo, Gedris, Herz (BIB2) 1997; 45 Geissman, Lucas, Saitoh, Payne (BIB9) 1973; 1 Casteel (BIB6) 1999; 16 Bohlmann, Zdero, King, Robinson (BIB1) 1984; 23 and Zdero, Bohlmann, Müller (BIB19) 1987; 26 Bulatović, Vajs, Macura, Juranić, Milosavljević (BIB4) 1997; 60 Knappe, Peteri (BIB12) 1962; 190 Rodrigues, Garcia, Rabi (BIB14) 1978; 17 Casteel (BIB5) 1992; 9 Joseph-Nathan, Wesener, Günther (BIB11) 1984; 22 Vajs, Bulatović, Fodulović-Šavikin, Menković, Macura, Juranić, Milosavljević (BIB17) 1999; 50 Doskotch (10.1016/S0031-9422(00)00160-6_BIB8) 1980; 45 Zdero (10.1016/S0031-9422(00)00160-6_BIB19) 1987; 26 Bruno (10.1016/S0031-9422(00)00160-6_BIB2) 1997; 45 Vajs (10.1016/S0031-9422(00)00160-6_BIB17) 1999; 50 Yoshioka (10.1016/S0031-9422(00)00160-6_BIB18) 1973 di Benedetto (10.1016/S0031-9422(00)00160-6_BIB7) 1991; 30 Knappe (10.1016/S0031-9422(00)00160-6_BIB12) 1962; 190 Casteel (10.1016/S0031-9422(00)00160-6_BIB5) 1992; 9 Milosavljević (10.1016/S0031-9422(00)00160-6_BIB13) 1998; 2 Bulatović (10.1016/S0031-9422(00)00160-6_BIB4) 1997; 60 Sutherland (10.1016/S0031-9422(00)00160-6_BIB15) 1974; 30 Bohlmann (10.1016/S0031-9422(00)00160-6_BIB1) 1984; 23 Todorova (10.1016/S0031-9422(00)00160-6_BIB16) 1996; 42 10.1016/S0031-9422(00)00160-6_BIB3 Rodrigues (10.1016/S0031-9422(00)00160-6_BIB14) 1978; 17 Casteel (10.1016/S0031-9422(00)00160-6_BIB6) 1999; 16 Joseph-Nathan (10.1016/S0031-9422(00)00160-6_BIB11) 1984; 22 Geissman (10.1016/S0031-9422(00)00160-6_BIB9) 1973; 1 10.1016/S0031-9422(00)00160-6_BIB10 |
| References_xml | – volume: 30 start-page: 3657 year: 1991 end-page: 3659 ident: BIB7 article-title: Three guaianolides from publication-title: Phytochemistry contributor: fullname: Delle Monache – volume: 30 start-page: 1651 year: 1974 end-page: 1660 ident: BIB15 article-title: Regio- and stereo-specificity in the cyclisation of medium rings 1,5-dienes publication-title: Tetrahedron contributor: fullname: Sutherland – volume: 9 start-page: 289 year: 1992 end-page: 312 ident: BIB5 article-title: Peroxy natural products publication-title: Natural Product Reports contributor: fullname: Casteel – volume: 23 start-page: 1979 year: 1984 end-page: 1988 ident: BIB1 article-title: Pseudoguaianolides and other sesquiterpene lactones from publication-title: Phytochemistry contributor: fullname: Robinson – volume: 45 start-page: 375 year: 1997 end-page: 377 ident: BIB2 article-title: Guaianolides and other terpenoids from publication-title: Phytochemistry contributor: fullname: Herz – volume: 16 start-page: 55 year: 1999 end-page: 73 ident: BIB6 article-title: Peroxy natural products publication-title: Natural Product Reports contributor: fullname: Casteel – volume: 1 start-page: 13 year: 1973 end-page: 20 ident: BIB9 article-title: Sesquiterpene lactones of publication-title: Biochemical Systematics contributor: fullname: Payne – volume: 60 start-page: 1222 year: 1997 end-page: 1228 ident: BIB4 article-title: Highly oxygenated guaianolides from publication-title: Journal of Natural Products contributor: fullname: Milosavljević – volume: 45 start-page: 1441 year: 1980 end-page: 1446 ident: BIB8 article-title: Tulirinol, an antifeedant sesquiterpene lactone for the gipsy moth larvae from publication-title: Journal of Organic Chemistry contributor: fullname: Christoph – volume: 50 start-page: 287 year: 1999 end-page: 291 ident: BIB17 article-title: Highly oxygenated guaianolides from publication-title: Phytochemistry contributor: fullname: Milosavljević – volume: 26 start-page: 2763 year: 1987 end-page: 2775 ident: BIB19 article-title: Sesquiterpene lactones and other constituents from publication-title: Phytochemistry contributor: fullname: Müller – volume: 17 start-page: 953 year: 1978 end-page: 954 ident: BIB14 article-title: Facile biomimetic synthesis of costunolide-1,10-epoxide, santamarin and reynosin publication-title: Phytochemistry contributor: fullname: Rabi – volume: 22 start-page: 190 year: 1984 end-page: 191 ident: BIB11 article-title: A two-dimensional NMR study of angelic and tiglic acid publication-title: Organic Magnetic Resonance contributor: fullname: Günther – volume: 190 start-page: 386 year: 1962 end-page: 389 ident: BIB12 article-title: Dünnschichtchromatographische Identifizierung organischer Peroxide publication-title: Zeitschrift für Analytische Chemie contributor: fullname: Peteri – volume: 42 start-page: 1231 year: 1996 end-page: 1233 ident: BIB16 article-title: Sesquiterpene lactones from publication-title: Phytochemistry contributor: fullname: Krasteva – volume: 2 start-page: 383 year: 1998 end-page: 395 ident: BIB13 article-title: Application of two-dimensional nuclear magnetic resonance methods for structure elucidation of sesquiterpene lactones (guaianolides) from publication-title: Recent Research Developments in Phytochemistry contributor: fullname: Macura – start-page: 345 year: 1973 ident: BIB18 publication-title: Sesquiterpene Lactones contributor: fullname: Timmermann – volume: 1 start-page: 13 year: 1973 ident: 10.1016/S0031-9422(00)00160-6_BIB9 article-title: Sesquiterpene lactones of Ambrosia chamissonis publication-title: Biochemical Systematics doi: 10.1016/0305-1978(73)90030-6 contributor: fullname: Geissman – volume: 17 start-page: 953 year: 1978 ident: 10.1016/S0031-9422(00)00160-6_BIB14 article-title: Facile biomimetic synthesis of costunolide-1,10-epoxide, santamarin and reynosin publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)88654-9 contributor: fullname: Rodrigues – volume: 45 start-page: 375 year: 1997 ident: 10.1016/S0031-9422(00)00160-6_BIB2 article-title: Guaianolides and other terpenoids from Anthemis aetnensis publication-title: Phytochemistry doi: 10.1016/S0031-9422(96)00846-1 contributor: fullname: Bruno – volume: 26 start-page: 2763 year: 1987 ident: 10.1016/S0031-9422(00)00160-6_BIB19 article-title: Sesquiterpene lactones and other constituents from Eriocephalus species publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)83588-8 contributor: fullname: Zdero – volume: 60 start-page: 1222 year: 1997 ident: 10.1016/S0031-9422(00)00160-6_BIB4 article-title: Highly oxygenated guaianolides from Anthemis carpatica publication-title: Journal of Natural Products doi: 10.1021/np970185w contributor: fullname: Bulatović – volume: 16 start-page: 55 year: 1999 ident: 10.1016/S0031-9422(00)00160-6_BIB6 article-title: Peroxy natural products publication-title: Natural Product Reports doi: 10.1039/a705725c contributor: fullname: Casteel – volume: 30 start-page: 3657 year: 1991 ident: 10.1016/S0031-9422(00)00160-6_BIB7 article-title: Three guaianolides from Anthemis hydruntina publication-title: Phytochemistry doi: 10.1016/0031-9422(91)80087-H contributor: fullname: di Benedetto – volume: 50 start-page: 287 year: 1999 ident: 10.1016/S0031-9422(00)00160-6_BIB17 article-title: Highly oxygenated guaianolides from Anthemis cretica subsp. cretica publication-title: Phytochemistry doi: 10.1016/S0031-9422(98)00504-4 contributor: fullname: Vajs – ident: 10.1016/S0031-9422(00)00160-6_BIB3 – volume: 22 start-page: 190 year: 1984 ident: 10.1016/S0031-9422(00)00160-6_BIB11 article-title: A two-dimensional NMR study of angelic and tiglic acid publication-title: Organic Magnetic Resonance doi: 10.1002/mrc.1270220312 contributor: fullname: Joseph-Nathan – volume: 23 start-page: 1979 year: 1984 ident: 10.1016/S0031-9422(00)00160-6_BIB1 article-title: Pseudoguaianolides and other sesquiterpene lactones from Gaillardia species publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)84954-7 contributor: fullname: Bohlmann – volume: 42 start-page: 1231 year: 1996 ident: 10.1016/S0031-9422(00)00160-6_BIB16 article-title: Sesquiterpene lactones from Artemisia lerchiana publication-title: Phytochemistry doi: 10.1016/0031-9422(96)00142-2 contributor: fullname: Todorova – volume: 45 start-page: 1441 year: 1980 ident: 10.1016/S0031-9422(00)00160-6_BIB8 article-title: Tulirinol, an antifeedant sesquiterpene lactone for the gipsy moth larvae from Liriodendron tulipifera publication-title: Journal of Organic Chemistry doi: 10.1021/jo01296a020 contributor: fullname: Doskotch – start-page: 345 year: 1973 ident: 10.1016/S0031-9422(00)00160-6_BIB18 contributor: fullname: Yoshioka – ident: 10.1016/S0031-9422(00)00160-6_BIB10 doi: 10.1016/S0040-4039(00)90765-2 – volume: 9 start-page: 289 year: 1992 ident: 10.1016/S0031-9422(00)00160-6_BIB5 article-title: Peroxy natural products publication-title: Natural Product Reports doi: 10.1039/np9920900289 contributor: fullname: Casteel – volume: 190 start-page: 386 year: 1962 ident: 10.1016/S0031-9422(00)00160-6_BIB12 article-title: Dünnschichtchromatographische Identifizierung organischer Peroxide publication-title: Zeitschrift für Analytische Chemie doi: 10.1007/BF00472018 contributor: fullname: Knappe – volume: 2 start-page: 383 year: 1998 ident: 10.1016/S0031-9422(00)00160-6_BIB13 article-title: Application of two-dimensional nuclear magnetic resonance methods for structure elucidation of sesquiterpene lactones (guaianolides) from Anthemis carpatica and diterpenes from Achillea clypeolata publication-title: Recent Research Developments in Phytochemistry contributor: fullname: Milosavljević – volume: 30 start-page: 1651 year: 1974 ident: 10.1016/S0031-9422(00)00160-6_BIB15 article-title: Regio- and stereo-specificity in the cyclisation of medium rings 1,5-dienes publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)90687-8 contributor: fullname: Sutherland |
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| Snippet | A new germacranolide, (
E)-1α,10β-epoxy-3β-acetoxy-6α-hydroxygermacra-4,11(13)-dien-12,8α-olide, together with nine new highly oxygenated... A new germacranolide, (E)-1alpha, 10beta-epoxy-3beta-acetoxy-6alpha-hydroxygermacra-4,11 (13)-dien-12,8alpha-olide, together with nine new highly oxygenated... |
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| SubjectTerms | ( E)-1α,10β-Epoxy-3β-acetoxy-6α-hydroxygermacra-4,11-dien-12,8α-olide 3β-Acetoxydeacetyltulirinol 9α-Oxygenated cumambrins Anthemis carpatica Anthemolides Asteraceae Asteraceae - chemistry Biological and medical sciences Chemical constitution Fundamental and applied biological sciences. Psychology Guaidienolides Lactones - chemistry Lactones - isolation & purification Magnetic Resonance Spectroscopy Plant physiology and development Plants, Medicinal - chemistry Sesquiterpene lactones Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification |
| Title | Further sesquiterpene lactones from Anthemis carpatica |
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