Die Flavonglykoside von <i>Veronicastrum sibiricum</i> Pennell var. <i>japonicum</i> Hara und Synthese des Luteolin‐7‐neohesperidosids (Veronicastrosid)

Inouye, Hiroyuki; Aoki, Yasuhiko; Wagner, Hildebert; Hörhammer, L.; Aurnhammer, Gerold; Budweg, Wolfgang

doi:10.1002/cber.19691020917

Cited by 17 publications

(1 citation statement)

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“…Modern pharmacological studies have shown that Veronicastrum species have versatile beneficial pharmacological properties, such as anti-inflammatory, analgesic, antibiosis and immunosuppressive activities (Gao et al, 2004;Huang et al, 2009;Zhou & Meng, 1992a). Several kinds of chemical constituents have been isolated from these plants, including flavonoids, phenols, phenylpropanoids and terpenoids (Inouye & Aoki, 1968;Inouye et al, 1969;Lin et al, 1995;Liu et al, 1999;Nohara et al, 2010;Shang et al, 1997;Shimada et al, 1971;Zhao & Shi, 2007;Zhou & Meng, 1992b). Recently, several studies revealed that Veronicastrum axillare exhibited potential antiulcer effects on gastric ulcer in rats induced by ethanol (Du et al, 2013;Shen et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Monoterpenoids from the whole herb of Veronicastrum axillare

Deng

Fang

Zheng

et al. 2014

Pharmaceutical Biology

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Context: Veronicastrum axillare (Sieb. et Zucc.) Yamazaki (Scrophulariaceae) embraces varieties of bioactivities such as anti-inflammatory, anti-pyresis and detoxification activity, while little is known of the phytochemical components of this medicinal plant. Objective: To isolate and identify bioactive constituents from the whole herb of V. axillare. Materials and methods: Ethanol extract of the whole herb of V. axillare was subjected to successive column chromatography. Chemical structures of the compounds were elucidated by detailed spectroscopic analyses on the basis of NMR, IR and HR-MS data. Results: A new monoterpenoid, axillacetal A (1) and a known analogue, tarumal (2), were isolated from the whole herb of V. axillare. The structure of tarumal (2) was also revised according to our NMR data. Discussion and conclusion: This is the first report on the isolation and authentication of novel chemical constituents from V. axillare.

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Section: Introductionmentioning

confidence: 99%

Monoterpenoids from the whole herb of Veronicastrum axillare

Deng

Fang

Zheng

et al. 2014

Pharmaceutical Biology

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Transacylierungsreaktionen in der Flavonoid‐Reihe, VI. Synthese von Luteolin‐7‐β‐rutinosid (Scolymosid) sowie 3′.4′‐Di‐O‐methyl‐luteolin‐7‐β‐neohesperidosid und ‐7‐β‐rutinosid

Wagner¹,

Budweg²,

Hörhammer³

et al. 1971

Chem. Ber.

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Die Struktur des aus Cynara Scolymus L. isolierten Scolymosids (la) wurde durch Kupplung von 7-Hydroxy-5.3'.4'-tribenzoyloxy-flavon (7) mit a-Acetobromrutinose und anschlidende Entfernung der Schutzgruppen endgultig bewiesen. AuRerdem wurden 3'.4'-Di-O-methyl-luteoh-7-P-neohesperidosid (4a) und das damit isomere -7-a-rutinosid @a) auf zwei verschiedenen Wegen synthetisiert. Transacylation Reactions in the Flavonoid Series *), VISynthesis of Luteolin-7-P-rutinoside (Scolymoside) and 3' .4'-Di-O-methyl-luteolin-7-Pneohesperidoside and -7-P-rutinosideThe structure of scolymoside (1 a), isolated from Cynara scolymns L., was unambiguously proved by condensation of a-acetobromorutinose with 5,3',4'-tri(benzoyloxy)-7-hydroxyflavone (7), and subsequent removal of the protecting groups. 3',4'-di-O-methyl-luteolin-7-~-neohesperidoside (4a) and the corresponding isomeric -7-P-rutinoside (8a) were prepared by two different routes.Im Jahre 1956 isolierten Masquelier und Michaudz) aus Cynaru scolymus L. ein bisher nicht beschriebenes Glykosid, das bei der Hydrolyse Luteolin (5a) und das Disaccharid Rhamnoglucose ergab. Die Autoren nannten es Scolymosid. 1961 gewannen Nakaoki, Morita und Lsetani3) aus Lonicera japonica Thunb. ein Glykosid gleicher Zusammensetzung, dem sie den Namen Lonicerin**) gaben und das sie nach Permethylierung als ein Luteolin-7-O-rhamnogl~1cosid identifizierten. Die Verkniip-*) Teil der Dissertation W. Budweg, Univ. Miinchen 1970. **)Nicht zu verwechseln mit dem Alkaloid gleichen Namens.

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