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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Journal of natural products | ||||
| Verlag: | American Chemical Society | ||||
| Band: | 65 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 11 | ||||
| Seitenbereich: | S. 1530-1534 | ||||
| Datum: | 2002 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 137:353190 30-20 Terpenes and Terpenoids 55623-34-2P Role: BSU (Biological study, unclassified), PRP (Properties), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (oxidn. of abietic acid and its Me ester under various storage conditions and cytotoxicity of the oxidn. products); 1802-09-1P; 17751-36-9P Role: BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (oxidn. of abietic acid and its Me ester under various storage conditions and cytotoxicity of the oxidn. products); 86788-25-2DP; 155205-64-4P; 474511-09-6P; 474511-10-9P; 474511-11-0P; 474511-12-1P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (oxidn. of abietic acid and its Me ester under various storage conditions and cytotoxicity of the oxidn. products); 127-25-3 (Abietic Acid methyl ester); 514-10-3 (Abietic Acid) Role: RCT (Reactant), RACT (Reactant or reagent) (oxidn. of abietic acid and its Me ester under various storage conditions and cytotoxicity of the oxidn. products); 86788-23-0P; 86788-25-2P; 104915-32-4P Role: SPN (Synthetic preparation), PREP (Preparation) (oxidn. of abietic acid and its Me ester under various storage conditions and cytotoxicity of the oxidn. products) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | NMR (chem. shift, proton and carbon-13 of the oxidn. products obtained via oxidn. of abietic acid and its Me ester under various storage conditions) Overhauser effect (correlation for a abietic acid deriv. obtained via oxidn. of abietic acid Me ester) Oxidation (of abietic acid and its Me ester under various storage conditions) Reaction mechanism (of oxidn. of abietic acid and its Me ester under various storage conditions) Cytotoxicity (of the oxidn. products obtained via oxidn. of abietic acid and its Me ester under various storage conditions) Diterpenes Role: BSU (Biological study, unclassified), PRP (Properties), RCT (Reactant), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (podocarpane oxidn. of abietic acid and its Me ester under various storage conditions and cytotoxicity of the oxidn. products) abietic acid methyl ester oxidn cytotoxicity product | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Nein | ||||
| Dokumenten-ID: | 17205 |
Zusammenfassung
Abietic acid and its Me ester were investigated under various storage conditions to provide an indication of their preferred oxidn. mechanisms and to investigate the most susceptible positions for modification in the abietane skeleton. Six known compds., Me 7alpha ,13beta -dihydroxyabiet-8(14)-enoate, Me 7alpha ,13alpha -dihydroxyabiet-8(14)-enoate, Me 12-oxoabietate (I), Me 7-oxodehydroabietate ...
Zusammenfassung
Abietic acid and its Me ester were investigated under various storage conditions to provide an indication of their preferred oxidn. mechanisms and to investigate the most susceptible positions for modification in the abietane skeleton. Six known compds., Me 7alpha ,13beta -dihydroxyabiet-8(14)-enoate, Me 7alpha ,13alpha -dihydroxyabiet-8(14)-enoate, Me 12-oxoabietate (I), Me 7-oxodehydroabietate [II; R = O (III)], Me 7alpha -hydroxydehydroabietate II [R = alpha -OH, H (IV)], and 13,14-seco-13,14-dioxoabiet-7(8)-enoic acid, were identified. Compds. III and IV are regarded as potent allergens. In addn., six new oxidn. products were isolated, Me 13beta -ethoxy-7alpha -hydroxyabiet-8(14)-enoate, Me 13alpha -ethoxy-7alpha -hydroxyabiet-8(14)-enoate, Me 7alpha -hydroperoxy-13alpha -hydroxyabiet-8(14)-enoate or Me 13alpha -hydroperoxy-7alpha -hydroxyabiet-8(14)-enoate, 7alpha ,13beta -dihydroxyabiet-8(14)-enoic acid, 7alpha ,13alpha -dihydroxyabiet-8(14)-enoic acid, and 7alpha ,15-dihydroxydehydroabietic acid. Their structures were characterized on the basis of spectroscopic data interpretation. The cytotoxicity of several compds. against KB cells was evaluated, and weak activity was obsd. for I, III, and IV with IC50 values of 12.5, 4.5, and 5.8 micro g/mL, resp.
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