ALTOSID, EIN HERZAKTIVES GLYKOSID AUSURGINEA ALTISSIMABAKER¹

Abstract

h t i , A. von W a r t b u r g U. J. R e n z Unter dem Begriff "Herzaktive Glykoside" versteht der Chemiker eine Gruppe von Naturstoffen, die sich durch eine starke und spezifische Wirkung auf die Herzmuskulatur von Mensch und Tier auszeichnen. Diese Glykoside finden sich in recht verschiedenen Pflanzenfamilien, wobei die Afiocynaceen und die Asclepiadaceen besonders reich vertreten sind.Die ersten chemischen Arbeiten über herzaktive Glykoside stammen aus dem 19. Jahrhundertabgesehen von einigen Versuchen im 18. Jahrhundert; doch haben Isolierung und Konstitutionsermittlung erst vor etwa dreißig Jahren auf breiterer Basis eingesetzt. J a c o b s (1935), T s ch es C h e (1934, 1935) und ' Vorgetragen auf der 7. Vortragstagung der Dtsch. Ges. für Arzneipflanzenforsdiung in Münster am 24. 10. 1959.Heruntergeladen von: NYU. Urheberrechtlich geschützt.

Antiproliferative Homoisoflavonoids and Bufatrienolides from Urginea depressa

“…Urgineanin B ( 2 ), [α] 21 D +18 ( c 0.12, MeOH), was also isolated as a light yellow oil; its composition was established as C 19 H 20 O 7 by positive ion HRESIMS. Comparison of 1 H and 13 C NMR spectroscopic data of 2 with those of 1 (Table 1) indicated that both compounds had the same skeleton and substitution pattern, and differed only in that 2 had a hydroxy group in place of one of the O -methyl groups of 1 .…”

“…Urgineanin C ( 3 ), [α] 21 D +9, was identified as the homoisoflavonoid (3 S )-5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one by comparison of its experimental and reported physical and spectroscopic data. 14,15 Based on the positive π→π* Cotton effect (Δε = 5.6) at 286 nm and a negative n→ π * Cotton effect (Δε = −2.8) at 251 nm, the absolute configuration of C-3 was assigned as S , enantiomeric with the reported compound.…”

“…Urgineanin D ( 4 , [α] 21 D +23, light yellow oil) had the molecular formula C 20 H 20 O 8 as determined by the HRESIMS. Comparison of the NMR spectroscopic data of 4 with those of 1 indicated that the only difference was the B-ring substitution pattern.…”

“…Urgineanin E ( 5 ) was obtained as a light yellow oil with [α] 21 D +12 ( c 0.12, MeOH). Its molecular formula was deduced as C 20 H 20 O 7 by HREIMS.…”

“…21 To complete the partially reported NMR spectroscopic data reported in the literature, and to enable comparison with the NMR data of 8 and 10 , we list its complete 1 H and 13 C NMR spectroscopic data (Table 2), as well as its key HMBC correlations (Figure 2a). …”