Die Phloroglucide von drei Dryopteris‐Arten von den Azoren sowie zwei Arten von Madeira und den Kanarischen Inseln zum Vergleich

Abstract

und Tadeus Reichsteind) (13. I. 75) Uneercm Freund, Herrn Prof. F. Santavf (Olornouc), zu seincm 60. Geburtstag (23.4. 1975) gewidmet. Summary. Thc phloroglucinols of Dvyopevis aemda from the Azores and from Brittany (France), D. aaorica and D. crispifolia, a new tctraploid specks endemic t o the Azores [a], have been investigatcd. Thc following two species recently analysed with insufficient amounts of material have bcen reinvestigatcd using improvcd methods: D. maderensis and 'D. dilatata' from Tenerife, a new species cndemic t o the Canary islands and described by Gibby et al. [s] as B.guanchim Gibby & Jemy.W c have now found that both these specks also contain much albaspidin, particularly the homologuc BA. Former results for these. and other species differing in somc details were corrected (sec Table 1) after careful reexamination of the old chromatograms.D . aemulu from all origins contains relatively large amounts of two new compounds: aemulin(1) and trisaemulin (20), thc structures of which werc provcd by degradation, NMR.-and massspectroscopy. Trisaemulin was present as a mixture of two hornologucs BBB and BAB. The latter is the first three-ring phloroglucinol found in nature which carries am acetyl group in the middle ring. so far only butyryl-groups were found in this position.D. azodca is diploid like D. madevsnsis and D. inkrmedia and a11 3 taxa contain practically the same range of phloroglucinols. These facts are in agreement with conclusions based on morphology and cytology, which suggest that thew three taxa arc essentially cbnspecific. ).-_.._

Phloroglucinol compounds of natural origin

“…52,323, 324 Margaspidins PP (461), BP (462), PB (463), BB (464), BV (465) and VB (466) were reported from ferns Dryopteris aemula, Dryopteris marginata, Dryopteris inaequalis and Dryopteris pseudo-abbreviata. 319,323, 325 Abbreviatin BB (467), PB (468) and AB (469) were isolated from Dryopteris abbreviata 326,327 and aemulin BB (470) from Dryopteris aemula and D. pseudo-abbreviata. 325,328 Phloraspins AB (471), VB (472), BV (473) and BB (474) were reported from Ctenitis apiciflora 239 and various Dryopteris spp.…”

“…319,323, 325 Abbreviatin BB (467), PB (468) and AB (469) were isolated from Dryopteris abbreviata 326,327 and aemulin BB (470) from Dryopteris aemula and D. pseudo-abbreviata. 325,328 Phloraspins AB (471), VB (472), BV (473) and BB (474) were reported from Ctenitis apiciflora 239 and various Dryopteris spp. 241 Similarly, phloraspidinols AB (475), VB (476), BV (477) and BB (478) were reported from various Dryopteris spp.…”

Studies on the Biosynthetic Origin of the Acyl Side Chains of Dryopteris Fern Constituents

“…The phloroglucinol derivatives were isolated from the plant material by the MgO-method [6,8,91. Preliminary radioactivity measurements (Table I) gave positive results only for the phloroglucinol derivatives prepared from D. carthusiana specimens offered 1-14C sodium acetate and methyl-14C methionine, and from D. filix mas specimens given I-14C sodium acetate (methyl-14C methionine was not tried).…”

The Phloroglucinols of Dryopteris aitoniana PICHI SERM. (Dryopteridaceae, Pteridophyta)

“…It was recorded at similar values forpuva-aspidin BB (7-BB) [16], filixic acid BBB (19-BBB) [28] and other compounds with such partial structures. The signal of the CH, group between two aromatic rings was found at still lower field, 6 % 3.70-3.84 depending on substitution [29]. In tris-para-aspidin BBB (20-BBB) the two main signals at 6 = 3.56 and 3.79 ppm are well separated [16].…”

“…25. The MeOH phases were worked up in groups and processed further as follows: [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] and 36-45 (1.195 Fr. 6 (218 mg, eluted with pentane) gave 30 mg ofcrystals, m.p.…”