Secoiridoids and Xanthones in the Genus Centaurium

Abstract

Two new acyl secoiridoid glucosides, named decentapicrins A and B, accumulating in the fruits of Centaurium littorale Gilmour spp. littorale, have been isolated by means of preparative column chromatography. Another new compound, named decentapicrin C, could also be detected but in minute amounts and was prepared from decentapicrin B. The close interrelation between these three compounds and the strongly bitter centapicrin (Ia) and desacetylcentapicrin (Ib), accumulating in the fruits of Centaurium erythraea R AFN. [1, 2], have been demonstrated by means of TLC analysis of the products obtained under alkaline treatment. Under these conditions not only hydrolysis, but also acyl migrations, took place. Decentapicrin A is partly converted into desacetylcentapicrin (Ib) and decentapicrin C; decentapicrin B is converted into decentapicrin C. On the basis of this chemical information and spectroscopical data ( (1)H-NMR, (13)C-NMR, UV and IR) the structures of decentapicrins A, B and C are postulated to be Ic, Id and Ie respectively. The single acylation at C (3)-OH and C (4)-OH of the glucose moiety as shown in the structures of decentapicrins A and B is new in iridoid chemistry. Unlike centapicrin (Ia) and desacetylcentapicrin (Ib) the new compounds decentapicrins A, B and C are only weak bitter principles like sweroside (I).

Xanthones and Secoiridoids from Hairy Root Cultures ofCentaurium erythraea and C. pulchellum

“…Ratio between drug and solvent was 1 : 10. TLC and HPLC conditions and standard supstances were published previously [7], [10], [1]1, [16]. Quantification was performed using HPLC.…”

Purification, cDNA cloning and functional expression of NADPH‐cytochrome P450 reductase from Centaurium erythraea cell cultures

“…Extracts from this medicinal plant are traditionally used as bitter tonics and stomachics for increasing the secretion of gastric juices and for treatment of chronic gastric disorders (Wichtl 2004). Constituents of C. erythraea are intensely bitter‐tasting secoiridoid glycosides, such as centapicrin, and polymethoxylated xanthones, such as eustomin (van der Sluis & Labadie 1981; Baresova 1989). The biosynthetic pathways leading to these two classes of secondary products include several P450‐catalysed reactions.…”

PHYTOCHEMICAL INVESTIGATION OF THE AERIAL PARTS OF CENTAURIUM SPICATUM WITH HEPATOPROTECTIVE AND mRNA ENZYMATIC INHIBITION ACTIVITIES

“…Alkaloids of pyridine type (e.g. gentianine), spicatine and the series of amides derived from the secoiridoid glucoside swertiamarin and kantaurin were also shown to be present 3 . Among the most important pharmacological activities of the genus Centaury were the hepatoprotective and the antioxidant activities attributed to secoiridoides and flavonoid glycosides 5 .…”

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Five compounds (1)(2)(3)(4)(5) were firstly reported from the genus Centaurium family Gentianaceae. They were identified as Lisianthoside 1, Secoxyloganin 2, Secologanin dimethyl acetal 3, 1,5,6,5,6,7, 5.

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