Hans Dietmar Zinsmeister

Biflavonoids and 4,2′-epoxy-3-phenylcoumarins from the moss Mnium hornum

Abstract From gametophytes of Mnium hornum have been isolated a sophorotriose caffeate, three biflavonoids, among them the first biflavone methyl ether from a moss, and six derivatives of 4,2′-epoxy-3-phenylcoumarin — a group of isoflavone-related compounds — that has been found so far only in some seed plants. The structures of all compounds were elucidated and confirmed spectroscopically.

The first biaurone, a triflavone and biflavonoids from two Aulacomnium species☆

Abstract The flavonoid pattern of two Aulacomnium spp. has been studied. Besides seven known biflavonoids the new aulacomniumbiaureusidin and aulacomniumtriluteolin have been isolated; their structures have been established by spectroscopic methods.

Hypnogenols and other dihydroflavonols from the moss Hypnum cupressiforme

Abstract Six new aromadendrin-derived flavanoids have been isolated from Hypnum cupressiforme; hypnogenol A; hypnogenol B; 3,5,7,4′,3″,5″,7″,3″′4″−nonahydroxy-3′-6″-biflavanone, 3,5,7,4′,3″,5″,7″-heptahydroxy-3′-O-4″ -biflavanone; 1″′,2″′,3″′,4″′-tetrahydro-3,3″,5,5″,7,7″-hexahydroxy-4″′-keto-3′-1″′,4′-O-2″′-biflavanone and 3,5,7, 4′-tetrahydroxy-3′-(3″-formyl-6″-hydroxyphenyl)-flavanone.

Prenylated bibenzyl derivatives from Lethocolea glossophylla and Radula voluta

Abstract Phytochemical investigation of the liverwort, Lethocolea glossophylla , yielded five new prenylated bibenzyl derivatives. Their structures were elucidated by spectral analysis as 2-carboxy-3-methoxy-4,6-di-(3-methyl-2-butenyl)-5,4′-dihydroxy- bibenzyl, 2,4-di-(3-methyl-2-butenyl)-3,5,4′-trihydroxy-bibenzyl, 2,2-dimethyl-5-hydroxy-6-(3-methyl-2-butenyl)-7-[2-(4′- hydroxyphenyl)-ethyl]-chromene, 2,2-dimethyl-5-hydroxy-7-[2-(4′-hydroxyphenyl)-ethyl]-8-(3-methyl-2-butenyl)-chromene and as a bisprenylated bisbibenzyl (glossophyllin) with a chromene and a chromane moiety. From Radula voluta , the previously known bibenzyls, 2-(3-methyl-2-butenyl)-3,5-dihydroxy-bibenzyl and 2-geranyl-3,5-dihydroxy-bibenzyl, were isolated and identified.

Biflavonoids from the moss Homalothecium lutescens

Abstract From gametophytes of Homalothecium lutescens 3′,3‴-binaringenin and the hitherto unknown 2,3-dihydro-3′,3‴-biapigenin have been isolated. 3′,3‴-Biapigenin has been obtained synthetically. The structures of the new compounds have been elucidated spectroscopically.

The biflavonoids of Plagiomnium undulatum

Abstract The biflavonoid pattern of Plagiomnium undulatum has been studied. Besides two known biflavonoids the new 3‴-desoxydicranolomin, 2,3-dihydro-3‴-desoxydicranolomin and 2,3-dihydro-5′,3‴-dihydroxyrobustaflavone have been isolated, and their structures elucidated spectroscopically.

Tri- and tetrahydroxycoumarin derivatives from Tetraphis pellucida

Abstract From gametophytes of Tetraphis pellucida have been isolated eight different tri- and tetrahydroxycoumarin derivatives; three of them are new natural products, the structures of which were elucidated spectroscopically. The taxonomic relevance of the results is discussed.

New Three- and Tetraoxygenated Coumarin Glucosides from the Mosses Atrichum undulatum and Polytrichum formosum

Atrichum undulatum as well as Polytrichum formosum are containing each six different coumarin glycosides of which three are common to both species. From the nine different glycosides eight are new natural compounds. The structures have been elucidated spectroscopically.

Isomeric triluteolins from Bartramia stricta and Bartramia pomiformis

From Bartramia stricta and B. pomiformis the new triluteolins epibartramiatriluteolin and strictatriluteolin along with the known bartramiatriluteolin were isolated. The structures and relative stereochemistry of these triluteolins have been elucidated spectroscopically.

Isolation and synthesis of rufulamide, an oligopeptide analogue from Metzgeria rufula☆

Abstract An oligopeptide analogue consisting of l -glutamic, malonic and 2 molecules of anthranilic acid combined via amide bonds was isolated from the liverwort Metzgeria rufula . Its structure was elucidated by spectroscopic methods and by chemical synthesis.