Neue Untersuchung über Inhaltsstoffe der Kreuzdornrinde, 2. Mitt.¹⁾ Isolierung und Charakterisierung der blau fluoreszierenden Leitstoffe aus der Rinde von Rhamnus catharticus L.²⁾

Abstract

Aus der Rinde von Rhamnus catharticus L. wurden die Naphthalidprimveroside 6-Methoxysorinin (lb) und Sorinin (2b) als Heptaacetylderivate isoliert und charakterisiert. Die Strukturen wurden vorwiegend mit spektroskopischen Methoden ermittelt. lb und 2b fungieren in der Ph. Eur. I1 als Leitstoffe der Kreuzdornrinde bei der dc-Priifung der offizinellen Rhamnus-Drogen: sie sind verantwortlich fiir die^ blaue Fluoreszenz der Zone mit Rf = 0,25. New Investigation of the Constituents ofRhprrmi catbartiu Cortex, II: Isolation and Characterization of the Blue Fluorescing Leading Substances from the Cortex of Rhamnus catharticus The naphthalide primverosides 6-methoxysorinin (lb) and sorinin (2b) were isolated as heptaacetates from the stem bark of Rhamnus catharticus L. (purging buckthorn). Their structures were established mainly by spectroscopic methods. These glycosides are leading substances in Ph. Eur. I1 for Rhamni cathartici cortex in the TLC analysis of Frangulae and Rhamni purshiani cortices: they are responsible for the blue fluorescence of the spot at Rf = 0.25. Die Ph. Eur. I1 priift bei Frangulae cortex und Rhamni purshiani cortex auf Verfdschung oder Verunreinigung durch Rhamni cathartici cortex mit Hilfe der Dunnschicht-Chromatographie: Im langwelligen UV darf das Chromatogramm keine blau fluoreszierenden Zonen mit Rf 0,25" und 0,404) zeigen. Der Zone mit Rf 0,25 liegen zwei lactonische Naphthalindiglykoside zugrunde, deren Isolierung und Strukturaufldarung im folgenden beschrieben werden. Spektroskopische Daten naturlich vorkommender 1.8-Dihydroxynaphthalidglykoside liegen in der Literatur nicht vor. Bei der DC des MeOH-Extraktes gelagerter Rinde von Rhamnus catharticus L. entsprechend der Monographie ,,Frangulae cortex" nach Ph. Eur. I1 ergeben die im 0365-6233/83/05054399 $ M.5WO

Flavonol and Naphthalene Glycosides from Rhamnus nakaharai

“…6-methoxysorigenin-8-0-ot-L-rhamnosyl (1-»6)-glucoside [2] and kaempferol 3-0-[ot-Lrhamnopyranosyl (1 ->4)-a-L-rhamnopyranosyl (1 -»6)]-P-D-galactopyranoside (kaempferol 3isorhamninoside) [3]• In a previous paper (1), we reported the isolation and characterization of a new anthraquinone glycoside, chrysophanol 8-0-xylosyl-( 1 ->6)-glucoside, and a new naphthalene glycoside, 2-acetyl-3methyl-6-methoxynaphthalene-1,8-diol 8-0-xylosyl-( 1 -»6)-glucoside, from the root bark of Rhamnus nakaharai (Rhamnaceae). In a continuation of this work, a known naphthalene glucoside, 6methoxysorigenin-8-0-3-D-glucoside[l} (2), a new naphthalene glycoside {2], a new flavonol triglycoside [3], and five known compounds, taraxerol, chrysophanol, physcion, rhamnocitrin, and kaempferol, were further isolated from the root bark and leaf of this plant. In this paper, we report the isolation and characterization of the two new glycosides 2 and 3 and the characterization of 1 by more detailed spectroscopic methods.…”

“…1 R=glc 2 R=glc(6->l)rha 7.14 (s, H-4). The 13C nmrofl (Table 1) was assigned by ^-decoupling spectra, the DEPT pulse sequence, comparison with the chemical shifts of 6methoxysorinin (3), and reported values in the literature (4). The above 3Hand 13C-nmr spectra further supported the characterization of 1 as 6-methoxysorigenin-8-0-p-D-glucoside.…”

Nakahalene and Cytotoxic principles of Formosan Rhamnus Species

“…The assignments of l3C-nmr spectra of 4 were obtained by 'H-decoupling spectra and DEPT pulse sequence and assigned by comparison with data reported in the literature (6,7). The presence of peaks at mtz 127 and 128 in the eims of 4 also clearly indicated that 4 possessed the naphthalene skeleton (6). Based on the above evidence, compound 4 was characterized as 2-acetyl-3-methyl-6-methoxy naphthalene-1,8-diol.…”

Antioxidative Effects of 6-Methoxysorigenin and Its Derivatives from Rhamnus nakaharai

“…8,9,18,19) To date, bioactivities of 6-methoxysorigenin and its derivatives remain largely unknown. This is the first report on their antioxidant activities.…”

“…1) and is rich in glycosides. 9) To evaluate the antioxidant effect of 2 and its derivatives, glycosides from the wood of R. nakaharai were isolated and characterized. They were 6-methoxysorigenin-8-O-glucoside (3), a-sorinin (4), 6-methoxysorigenin-8-O-rutinoside (5).…”