Benzopyranones and Their Sulfate Esters fromPelargonium sidoides

Abstract

Investigation of the benzopyranones from the roots of PELARGONIUM SIDOIDES led to the identification of 15 benzopyranones, among them the novel compounds 12 and 14. Furthermore, benzopyranones 4 and 15 were detected in PELARGONIUM SIDOIDES for the first time. Structure determinations were performed by one- and two-dimensional NMR spectroscopy. An HPLC system for the discrimination of these benzopyranones has been developed.

Medicinal properties and conservation of Pelargonium sidoides DC.

“…The extensive use of Pelargonium sidoides in traditional medicine coupled with its popularisation in modern medical systems in Europe have led to an upsurge in scientific exploration of its chemical composition in an effort to identify the active principles. This has resulted in a considerable body of literature exploring the phytochemical properties of Pelargonium sidoides (Gödecke et al, 2003(Gödecke et al, , 2005Hauer et al, 2010;Kayser and Kolodziej, 1995;Latté et al, 2000;Schoetz et al, 2008). Details of the phytochemistry of the plant were comprehensively summarised in an excellent review by Kolodziej (2007).…”

“…The pharmacological efficacy of Pelargonium sidoides has been partly attributed to the biological activity of highly oxygenated coumarins (7-hydroxy-5, 6-di-methoxycoumarin; 6,8-dihydroxy-5,7-dimethoxycoumarin), gallic acid-derivatives, flavonoids, phenolic and hydroxycinnamic acid-derivatives (Kayser and Kolodziej, 1995;Kolodziej, 2007;Colling et al, 2010). Recently, 6-Methoxy-7-(sulfooxy)-2H-1-benzopyran-2-one and 6,8-Bis(sulfooxy)-7-methoxy-2H-1-benzopyran-2one were identified in Pelargonium sidoides for the first time (Hauer et al, 2010). Most significantly, Hauer et al (2010) characterised two novel compounds, 7-Hydroxy-6-methoxy-8-(sulfooxy)-2H-1-benzopyran-2-one and 8-Hydroxy-7-methoxy-6-(sulfooxy)-2H-1-benzopyran-2-one ( Fig.…”

“…Recently, 6-Methoxy-7-(sulfooxy)-2H-1-benzopyran-2-one and 6,8-Bis(sulfooxy)-7-methoxy-2H-1-benzopyran-2one were identified in Pelargonium sidoides for the first time (Hauer et al, 2010). Most significantly, Hauer et al (2010) characterised two novel compounds, 7-Hydroxy-6-methoxy-8-(sulfooxy)-2H-1-benzopyran-2-one and 8-Hydroxy-7-methoxy-6-(sulfooxy)-2H-1-benzopyran-2-one ( Fig. 2).…”

One New Phenolic Compound from Castanea mollissima Shells and its Suppression of HepatomaCell Proliferation and Inflammation by Inhibiting NF-κB Pathway

“…Compound 2 was identified as 7,8-dihydroxy-2H-chromen-3-one (2) (CAS: 56022-24-3), which physicochemical profiles was firstly reported. Then the structures of the other five compounds, after their physicochemical data were compared to reported literatures, were elucidatedas 7,8,9-trihydroxy-chromen-2-one(3) [5], 3-(3,4-dihydroxyphenyl)-4-hydroxycyclohexanone (4) [6], brevifolin carboxylic acid (5) [7], (3R,4R)-3-(3,4-dihydroxyphenyl)-4-hydroxycyclohexanone(6) [8], and (4R)-5-(1-(3,4-dihydrophenyl)-3-oxobutyl)-dihydrofuran-2(3H)-one(7) [6]. Of them, compounds (2)–(7) were identified the existence in C. mollissima for the first time (Figure 1).…”

Isoamericanoic Acid B from Acer tegmentosum as a Potential Phytoestrogen

“…The known compounds were identified as 4,4′-((1 R ,2 R )-3-hydroxy-1-methoxypropane-1,2-diyl)bis(2-methoxyphenol) ( 2 ) [26], 6- O -galloylsalidroside ( 3 ) [27], isoscopoletin ( 4 ) [28], 6,8-dihydroxy-7-methoxy-2 H -1-benzopyran-2-one ( 5 ) [29], trans -ferulic acid ( 6 ) [30], 4-hydroxybenzoic acid ( 7 ) [31], syringic acid ( 8 ) [32], 4-methoxycatechol ( 9 ) [33], and 4-hydroxyphenylethanol ( 10 ) [34] by comparing the spectroscopic data obtained in this study with values reported in previous studies. To the best of our knowledge, compounds 2 , 4 , 5 , and 9 were structurally identified from the bark of A. tegmentosum for the first time in this study.…”