Neue Flavonoid-Glykoside aus Crataegus monogyna und Crataegus pentagyna

Abstract

From the leaves and flowers of Crataegus monogyna and C. Pentagyna six new flavonoid-C- and O-glycosides respectively have been isolated and identified as 2''-O-rhamnosyl-orientin, 2''-O-rhamnosyl-isoorientin, 2''-O-rhamnosyl-isovitexin, rutin, spiraeosid, 8-methoxy-kämpferol and 8-methoxy-kämpferol-3-O-glucoside. The structure of O-rhamnosyl-vitexin and O-acetyl-O-rhamnosyl-vitexin isolated previously, have been elucidated unambigiously mainly by NMR- and MS-spectroscopy.

4′′′‐Acetylvitexin‐2″‐O‐rhamnoside, Isoorientin, Orientin, and 8‐Methoxykaempferol‐3‐O‐glucoside as Markers for the Differentiation of Crataegus monogyna and Crataegus pentagyna from Crataegus laevigata (Rosaceae)

“…HPLC Analysis revealed a major unknown compound with an UV spectrum indicating a vitexin or isovitexin derivative. Cochromatography with reference compounds finally resulted in 4'''-acetylvitexin-2''-O-rhamnoside (13), which was in good agreement with the reports of Nikolov et al [9], and Lamaison and Carnat [23]. Although our samples contained 13, Rehwald et al [12] could not detect this compound in their sample, whereas Kurzmann [11] indicated that C. monogyna includes both 13-containing as well as 13-free samples, the latter ones being extremely dominated by 1.…”

“…Compound 12, isolated from C. pentagyna, and its co-chromatography with kaempferol-3-O-glucoside (14) also confirmed traces of these compounds in C. monogyna, which is in good agreement with the results reported in [9], as well as with those of Dauguet et al [22], who reported these compounds from C. monogynas bee pollen. Whereas Nikolov et al [9] isolated spiraeoside (15) and quercetin (16) Kurzmann [11] stated, that 7 and 8 were only present in the stems of flowers and stems of leaves of C. monogyna, whereas they represented main flavonoids in the leaves of C. pentagyna. As already mentioned above, C. pentagyna revealed a very rich pattern of flavonoids in the HPLC chromatogram.…”

“…Hence, the rotameric partners of 9 and 11 can also be observed in the 13 C-NMR spectrum of our samples. Compounds 9, 10, and 11 had already been described for C. pentagyna [9], whereas the isolation of 12 is reported for the first time from this species.…”

“…Already 25 years ago, the flavonoid pattern of C. monogyna and C. pentagyna had been intensively investigated by Nikolov et al [9]. During the last years, systems for the characterization of numerous Crataegus species by TLC, HPLC [6] [10 -12], and capillary electrophoresis (CE) [13] had been established, some focusing, in addition, on the flavonoid contents in different parts/organs of the respective samples as well as their changes during the vegetation period.…”

Quantitative LC/MS/MS method and in vivo pharmacokinetic studies of vitexin rhamnoside, a bioactive constituent on cardiovascular system from hawthorn

“…Chemical composition of the hawthorn is characterized by the presence of pentacyclic triterpenoid acids, phenolic acids (Svedstrom et al, 2006), flavonoids (Ammon et al, 1981;Markham and Temai, 1978;Nikolov et al, 1982;Temai and Markham, I976;Zhang and Xu, 2000) and proanthocyanidins (Handel, 1981). The cardiovascular bioactive constituents of hawthorn mainly include flavonoids, which are a group of natural benzo-pyran derivatives and are ubiquitous in photosynthesizing cells (Mashour et al, 1998).…”