Struktur der Marsectobiose. Desoxyzucker, 46. Mitteilung

Saner, A.; Allgeier, Hans

doi:10.1002/hlca.19690520623

Cited by 17 publications

(6 citation statements)

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“…SSR 11,6. (9) Aynechi, Y., Sormaghi, M., Salehi, M., Amin, G. H., Soltani, A., Qumehr, N. (1982) zusãtzlich Quercetin 3-13-glucogalacturonid isoliert (2)(3)(4)(5). Ziel der vorliegenden Untersuchung war die Isolierung und Identifizierung weiterer, im DC der IdentitUts-bzw.…”

Section: Literaturunclassified

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Flavonoidglycoside ausArnica montanaundArnica chamissonis¹

Merfort

Wendisch²

1987

Planta Med

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Five flavonoid glycosides were identified from flowers of ARNICA MONTANA, four from A. CHAMISSONIS subsp. FOLIOSA var. INCANA. The structures were established on the basis of total acid hydrolysis and spectral data (UV, (1)H-NMR, (13)C-NMR, MS) as hispidulin 7- O-beta-glucoside, isorhamnetin 3- O-beta-glucoside, 3- O-beta- D-glucopyranosides of spinacetin, 6-methoxykaempferol and patuletin and querectin 3- O-(6''- O-acetyl)-beta- D-glucopyranoside. The latter compound can serve as distinctive marker between these two ARNICA species. The (1)H-NMR spectra in CD (3)OD are discussed.

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Section: Literaturunclassified

“…II, 2 u. 5) liegt das Signal bei tieferem Feld alsbei 3',3,4,[6][7][8]. Weiter gilt, daB das Signal von H-i" bei der Auf-Tabelle 1.…”

unclassified

Flavonoidglycoside ausArnica montanaundArnica chamissonis¹

Merfort

Wendisch²

1987

Planta Med

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“…Da der Unterschied in der 17B-Seitenkette fur diesen Effekt keine Bedeutung hat, durfte er von der 8p-HO-Gruppe verursacht werden, da diese HO-Gruppe mit dem 11p-H in 1,3-diaxialer Wechselwirkung steht. Die gleiche Verschiebung beobachtet man beim Vergleich der Lage des 118-H-Signals im 3,11,12,Fig. 6) Im Massenspektrum (Fig.…”

Section: Marsectohexol (Q) (7) Dieser Wenig Loslicheunclassified

“…The poorly characterised acyl-genin A-4 is most probably a mixture of the esters 16a+ 16b, also derived from 17@-marsdenin. [3]. Aus dem Gemisch der rohen Genine konnten neben ,&Sitosteryl-~-D-glucopyranosid und wenig Marsectohexol (7) 5 verschiedene krist.…”

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confidence: 97%

Glykoside von Marsdenia erecta R. Br. 2. Mitteilung: Versuche zur Strukturbestimmung der Genine. Glykoside und Aglykone, 330. Mitteilung

Saner

Stöckel

Reichstein

1972

Helvetica Chimica Acta

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Summary. Structures for the genins of the ester glycosides of Marsdenia erecta are suggested. They are based on the behaviour in alkaline hydrolysis of these ester glycosides, their NMR. and mass spectra and ORD. data. All genins are derived from three acyl-free pregnane derivatives, i.e. drevogenin-P (l), 17B-marsdenin (3) and marsectohexol (7). The structure of 1 is known, 3 and 7 arc new compounds, i . e. 3 = 38, 88, llcr, 128, 14~-pentahydroxy-d6-pregnen-20-one and 7 = 3 8 , 88, lla, 128,14/?, 20&hexahydroxy-d6-pregnene.Formulae 13-17 were attributed to the acyl-genins A-1, A-2, A-3, A-4 and A-5, but only two of them were pure compounds, i. e . acyl-genin A-3 = 11,12-di-O-tiglyl-17~-marsdenin (15) and acyl-genin A-5 = 11,12-di-O-acetyl-marsectohexol (17). Acyl-genin A-1 is a mixture of the two esters 13af 13b derived from drevogenin-P, and similarly acyl-genin A-2 is a mixture of the esters 14a+ 14b derived from 178-marsdenin. The poorly characterised acyl-genin A-4 is most probably a mixture of the esters 16a+ 16b, also derived from 17@-marsdenin. [3]. Aus dem Gemisch der rohen Genine konnten neben ,&Sitosteryl-~-D-glucopyranosid und wenig Marsectohexol (7) 5 verschiedene krist. Praparate, die Acylgenine A1-A5, isoliert werden, von denen aber nur das Acylgenin A5 (17) rein war. A l (13) und A2 (14) bestanden jeweils aus zwei Komponenten, auch A3 (15) und A4 (16) waren kaum ganz einheitlich. -Nach alkalischer Verseifung der rohen Acylgenine konnten neben Sauren (Essigsaure, Tiglinsaure und Benzoesaure) die folgenden vier Desacylgenine in reinen Kristallen gefasst werden : 17-iso-Drevogenin-P (2), 17b-Marsdenin (3), Marsdenin (= 17~-Marsdenin) (5) und Marsectohexol (7). Diese Stoffe waren in kleinen Mengen schon vor der alkalischen Verseifung im rohen Geningemisch enthalten. Die Struktur des 17-iso-Drevogenins-P (2) ist bekannt [4]

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“…Up to now the following flavonoid glycosides are known in flowers of both Arnica species: kaempferol-3f3-glucoside, quercetin-313-glucoside, luteolin-713-glucoside, and luteolin-713rutinoside (3)(4)(5). Besides these quercetin-313-glucogalacturonide was found in A. montana.…”

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Flavonol Glycosides of Arnicae Flos DAB 9

Merfort¹

1986

Planta Med

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The combination of positive ion and negative ion chemical ionization (PlC! and NICI) GC-MS of trimethylsilyl derivatives of pyrrolizidine alkaloids (PAs) offers a rapid insight in the structure of such compounds in plant material [1,2].PlC!, using NH3 as the reactant gas, furnishes information concerning the molecular weight because of the presence of MH ions in a relatively high abundance; elimination of the necic acid produces a fragment which may carry a substituent at C7 of the necine base.NICI, with OH-as the reactant ion, cleaves the ester bounds, which may be present at C7 and C9 of the necine base or at the 13-C atom of the necic acid like trachelanthic/viridifloric acid.A number of other fragments originate according to a characteristic fragmentation pattern. This will be shown by means of the PICI and NICI mass spectra of a number of TMS derivatives of (un)known PAs, present in Symphytum species Anchusa officinalis L. and Eupatorium cannabinum L., from which conclusions can be drawn concerning the presence of 0, 1 or 2 (pyrrols) double bounds in the necine base, which is, in our examples, always esterified with trachelanthic/viridifloric acid at C9. In addition the location of acetyl, (iso)butyryl, angelyl/tiglyl and (iso) valeryl esters functions at C7 of the necine base or at the 3-C atom of trachelanthic/viridifloric moiety of the molecule can be unambiguously ascertained. References 1. H.Arnicae fibs DAB 9 originate from Arnica montana L. and Arnica chamissonis Less. ssp. foliosa (Nutt.) Maguire. Sesquiterpene lactones are the essential biologically active compounds (1). As further active compounds for local anti-inflammatory effect flavonoids have to be discussed (2). Furthermore flavonoid glycosides are used for examination of purity by TLC in DAB 9.Up to now the following flavonoid glycosides are known in flowers of both Arnica species: kaempferol-3f3-glucoside, quercetin-313-glucoside, luteolin-713-glucoside, and luteolin-713rutinoside (3-5). Besides these quercetin-313-glucogalacturonide was found in A. montana. In this paper the isolation and identification of other flavonoid glycosides in flowers of both Arnica species are described.Air-dried powdered flowers were extracted with MeOH (80%, 50%). The aq. methanolic extracts were concd. under red. pres. until only H20 remained, which was extracted with n-hexane, CHC13, and EtOAc. From the EtOAc extract flavonol glycosides were isolated using RLCC, followed by column chromatography (Polyclar AT, cellulose, silicagel 60, sephadex LH-20). The identity of the compounds was confirmed by melting point, UV spectroscopy, MS, 'H-NMR, and '3C-NMR. Hydrolysis was carried out on silicagel plates, additionally to the common procedures. Five flavonol glycosides have been identified in flowers of A. montana: spinacetin-313-glucoside (1), 6-methoxykaempferol-313-glucoside (2), patuletin-3f3-glucoside (3), isorhamnetin-313glucoside (4), and the already known kaempferol-313-glucoside (5). From flowers of A. chamissonis ssp. foliosa var. incana quercetin-3-(6"-O-...

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Struktur der Marsectobiose. Desoxyzucker, 46. Mitteilung

Abstract: Marsectobiose (1), a disaccharide isolated from Marsdenia erecta R. Br., is shown to be 4‐O‐(3‐O‐methyl‐6‐deoxy‐β‐D‐glucopyranosyl)‐3‐O‐methyl‐2, 6‐dideoxy‐D‐arabinohexose.

Cited by 17 publications

References 28 publications

Flavonoidglycoside ausArnica montanaundArnica chamissonis¹

Flavonoidglycoside ausArnica montanaundArnica chamissonis¹

Glykoside von Marsdenia erecta R. Br. 2. Mitteilung: Versuche zur Strukturbestimmung der Genine. Glykoside und Aglykone, 330. Mitteilung

Flavonol Glycosides of Arnicae Flos DAB 9

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Struktur der Marsectobiose. Desoxyzucker, 46. Mitteilung

Abstract: Marsectobiose (1), a disaccharide isolated from Marsdenia erecta R. Br., is shown to be 4‐O‐(3‐O‐methyl‐6‐deoxy‐β‐D‐glucopyranosyl)‐3‐O‐methyl‐2, 6‐dideoxy‐D‐arabinohexose.

Cited by 17 publications

References 28 publications

Flavonoidglycoside ausArnica montanaundArnica chamissonis1

Flavonoidglycoside ausArnica montanaundArnica chamissonis1

Glykoside von Marsdenia erecta R. Br. 2. Mitteilung: Versuche zur Strukturbestimmung der Genine. Glykoside und Aglykone, 330. Mitteilung

Flavonol Glycosides of Arnicae Flos DAB 9

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Flavonoidglycoside ausArnica montanaundArnica chamissonis¹

Flavonoidglycoside ausArnica montanaundArnica chamissonis¹