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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Helvetica chimica acta | ||||
| Verlag: | Verl. Helvetica Chimica Acta | ||||
| Band: | 84 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 11 | ||||
| Seitenbereich: | S. 3380-3392 | ||||
| Datum: | 2001 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 136:164127 11-1 Plant Biochemistry 398119-08-9 (Furonewguinone B) Role: FMU (Formation, unclassified), PAC (Pharmacological activity), BIOL (Biological study), FORM (Formation, nonpreparative) (prenylated bi- and tricyclic phloroglucinol derivs. from Hypericum papuanum); 398119-01-2P (Enaimeone A); 398119-02-3P (Enaimeone B); 398119-03-4P (Enaimeone C); 398119-04-5P (1'-Hydroxyialibinone A); 398119-05-6P (1'-Hydroxyialibinone B); 398119-06-7P (1'-Hydroxyialibinone D) Role: NPO (Natural product occurrence), PAC (Pharmacological activity), PRP (Properties), PUR (Purification or recovery), BIOL (Biological study), OCCU (Occurrence), PREP (Preparation) (prenylated bi- and tricyclic phloroglucinol derivs. from Hypericum papuanum); 398119-07-8P (Furonewguinone A) Role: NPO (Natural product occurrence), PRP (Properties), PUR (Purification or recovery), BIOL (Biological study), OCCU (Occurrence), PREP (Preparation) (prenylated bi- and tricyclic phloroglucinol derivs. from Hypericum papuanum) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | New natural products (enaimeones A-C and furonewguinones A and B (phloroglucinols) Molecular structure (of enaimeones A-C and furonewguinones A and B (phloroglucinols) Antibacterial agents Antitumor agents Hypericum papuanum (prenylated bi- and tricyclic phloroglucinol derivs. from Hypericum papuanum) enaimeone hydroxyialibinone phloroglucinol deriv Hypericum | ||||
| 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: | 17200 |
Zusammenfassung
From the petroleum-ether ext. of the dried aerial parts of Hypericum papuanum, three new prenylated tricyclic and four new bicyclic acylphloroglucinol derivs. were isolated by bioactivity-guided fractionation. The structures of the bicyclic compds. enaimeone A, B, and C (e.g. I, enaimeone A) were elucidated as ...
Zusammenfassung
From the petroleum-ether ext. of the dried aerial parts of Hypericum papuanum, three new prenylated tricyclic and four new bicyclic acylphloroglucinol derivs. were isolated by bioactivity-guided fractionation. The structures of the bicyclic compds. enaimeone A, B, and C (e.g. I, enaimeone A) were elucidated as rel-(1R,5R,6S)-4-hydroxy-6-(1-hydroxy-1-methylethyl)-5-methyl-1-(3-methylbut-2-enyl)-3-(2-methylpropanoyl)bicyclo[3.2.1]oct-3-ene-2,8-dione, rel-(1R,5R,6R)-4-hydroxy-6-(1-hydroxy-1-methylethyl)-5-methyl-1-(3-methylbut-2-enyl)-3-(2-methylpropanoyl)bicyclo[3.2.1]oct-3-ene-2,8-dione, rel-(1R,5R,6R)-4-hydroxy-6-(1-hydroxy-1-methylethyl)-5-methyl-3-(2-methylbutanoyl)-1-(3-methylbut-2-enyl)bicyclo[3.2.1]oct-3-ene-2,8-dione, resp. The tricyclic isolates 8-hydroxy-3beta -(1-hydroxy-1-methylethyl)-4,4,7-trimethyl-9-(2-methylpropanoyl)-5beta H-tricyclo[5.3.1.01.5]undec-8-ene-10,11-dione , 8-hydroxy-3alpha -(1-hydroxy-1-methylethyl)-4,4,7-trimethyl-9-(2-methylpropanoyl)-5beta H-tricyclo[5.3.1.01.5]undec-8-ene-10,11-dione , and 8-hydroxy-3alpha -(1-hydroxy-1-methylethyl)-4,4,7-trimethyl-9-(2-methylbutanoyl)-5beta H-tricyclo[5.3.1.01.5]undec-8-ene-10,11-dione, and their corresponding tautomers were named 1'-hydroxyialibinones A (II), B, and D, resp. Oxidative decompn. of furonewguinone A (III) (2,3,3a,5-tetrahydro-3a-hydroxy-2-(1-hydroxy-1-methylethyl)-5-methyl-5-(3-methylbut-2-enyl)-7-(2-methylpropanoyl)-benzofuran-4,6-dione) led to furonewguinone B (3,3a,7,7a-tetrahydro-3a,6,7a-trihydroxy-2-(1-hydroxy-1-methylethyl)-7-methyl-7-(3-methylbut-2-enyl)-5-(2-methylpropanoyl)benzofuran-4(2H)-one). Structure elucidation was based on extensive 1D and 2D NMR studies, as well as on data derived from mass spectrometry. Furthermore, the cytotoxicity towards KB nasopharyngeal carcinoma cells and the antibacterial activity were detd.
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