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Further Prenylated Bi- and Tricyclic Phloroglucinol Derivatives fromHypericum papuanum

2001; Wiley; Volume: 84; Issue: 11 Linguagem: Inglês

10.1002/1522-2675(20011114)84

1522-2675

Karin Winkelmann, Jörg Heilmann, Oliver Zerbe, Topul Rali, Otto Sticher,

Synthesis of Organic Compounds

Helvetica Chimica ActaVolume 84, Issue 11 p. 3380-3392 Research Article Further Prenylated Bi- and Tricyclic Phloroglucinol Derivatives from Hypericum papuanum Karin Winkelmann, Karin Winkelmann Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this authorJörg Heilmann, Jörg Heilmann Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this authorOliver Zerbe, Oliver Zerbe Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this authorTopul Rali, Topul Rali PNG Biodiversity Research PTY Ltd., Port Moresby, Papua New GuineaSearch for more papers by this authorOtto Sticher, Otto Sticher Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this author Karin Winkelmann, Karin Winkelmann Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this authorJörg Heilmann, Jörg Heilmann Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this authorOliver Zerbe, Oliver Zerbe Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this authorTopul Rali, Topul Rali PNG Biodiversity Research PTY Ltd., Port Moresby, Papua New GuineaSearch for more papers by this authorOtto Sticher, Otto Sticher Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zürich, Winterthurerstrasse 190, CH-8057 ZürichSearch for more papers by this author First published: 06 December 2001 https://doi.org/10.1002/1522-2675(20011114)84:11 3.0.CO;2-OCitations: 31AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract From the petroleum-ether extract of the dried aerial parts of Hypericum papuanum, three new prenylated tricyclic and four new bicyclic acylphloroglucinol derivatives were isolated by bioactivity-guided fractionation. The structures of the bicyclic compounds enaimeone A, B, and C (1/1a, 2/2a, and 3/3a, resp.) 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 (1/1a), 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 (2/2a), 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 (3/3a). The tricyclic isolates 8-hydroxy-3β-(1-hydroxy-1-methylethyl)-4,4,7-trimethyl-9-(2-methylpropanoyl)-5βH-tricyclo[5.3.1.01,5]undec-8-ene-10,11-dione (4), 8-hydroxy-3α-(1-hydroxy-1-methylethyl)-4,4,7-trimethyl-9-(2-methylpropanoyl)-5βH-tricyclo[5.3.1.01,5]undec-8-ene-10,11-dione (5), and 8-hydroxy-3α-(1-hydroxy-1-methylethyl)-4,4,7-trimethyl-9-(2-methylbutanoyl)-5βH-tricyclo[5.3.1.01,5]undec-8-ene-10,11-dione (6), and their corresponding tautomers 4a, 5a, and 6a, were named 1′-hydroxyialibinones A, B, and D, respectively. Oxidative decomposition of furonewguinone A (=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; 7) 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; 8/8a). 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 determined. Citing Literature Volume84, Issue11November 14, 2001Pages 3380-3392 RelatedInformation