Trilobolide and its analogues belong to the guaianolide type of sesquiterpene lactones, which are characteristic and widely distributed within the families Asteraceae and Apiaceae. Certain guaianolides are receiving continuously increasing attention for their promising sarco-endoplasmic reticulum Ca2+-ATPase (SERCA)-inhibitory activity. However, because of their alkylation capabilities, they are generally toxic. Therefore, the search for compounds with significant immunobiological properties but with decreased cytotoxicities suitable for use in immune-based pharmacotherapy is ongoing. Therefore, we extended our previous investigation of the immunobiological effects of trilobolide to a series of structurally related guaianolides and germacranolides. To evaluate the relationship, we tested a series of selected derivatives containing α-methyl lactone or exomethylene lactone ring. For a wider comparison, we also included some of their glycosidic derivatives. We assessed the in vitro immunobiological effects of the tested compounds on nitric oxide (NO) production, cytokine secretion, and prostaglandin E2 (PGE2) release by mouse peritoneal cells, activated primarily by lipopolysaccharide (LPS), and evaluated their viability. The inhibitory effects of the apparently most active substance, 8-deoxylactucin, seem to be the most promising.

• Klíčová slova
• 8-deoxylactucin, 8-epiisoamberboin, germacranolides, guaianolides, immune-modulatory effects,
• MeSH
• butyráty MeSH
• cytokiny metabolismus   MeSH
• dinoproston metabolismus   biosyntéza   MeSH
• furany MeSH
• laktony * farmakologie   chemie   MeSH
• lipopolysacharidy farmakologie   MeSH
• myši MeSH
• oxid dusnatý * metabolismus   MeSH
• peritoneální makrofágy účinky léků   metabolismus   MeSH
• seskviterpeny germakranové * farmakologie   chemie   MeSH
• seskviterpeny guajanové * farmakologie   chemie   MeSH
• seskviterpeny farmakologie   chemie   MeSH
• zvířata MeSH
• Check Tag
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• butyráty MeSH
• cytokiny MeSH
• dinoproston MeSH
• furany MeSH
• germacranolide MeSH Prohlížeč
• laktony * MeSH
• lipopolysacharidy MeSH
• oxid dusnatý * MeSH
• seskviterpeny germakranové * MeSH
• seskviterpeny guajanové * MeSH
• seskviterpeny MeSH
• trilobolide MeSH Prohlížeč

Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of Allium porrum L. (garden leek). Two of them were identical with the already known leek plant constituents: aginoside (1) and 6-deoxyaginoside (2). The third one was identified as new component of A. porrum; however, it was found identical with yayoisaponin A (3) obtained earlier from a mutant of elephant garlic Allium ampeloprasun L. It is a derivative of the aginoside (1) with additional glucose in its glycosidic chain, identified by MS and NMR analysis as (2α, 3β, 6β, 25R)-2,6-dihydroxyspirostan-3-yl β-D-glucopyranosyl-(1 → 3)-β-D-glucopranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl]-(1 → 4)-β-D-galactopyranoside, previously reported also under the name alliporin. The leek native saponins were tested together with other known and structurally related saponins (tomatonin and digitonin) and with their related aglycones (agigenin and diosgenin) for in vitro cytotoxicity and for effects on NO production in mouse peritoneal cells. The highest inhibitory effects were exhibited by 6-deoxyaginoside. The obtained toxicity data, however, closely correlated with the suppression of NO production. Therefore, an unambiguous linking of obtained bioactivities of saponins with their expected immunobiological properties remained uncertain.

• Klíčová slova
• Allium porrum, NO production, aginoside, alliporin, cytotoxicity, leek flowers, steroid saponins,
• MeSH
• Allium chemie   MeSH
• buněčné linie MeSH
• květy chemie   MeSH
• lipopolysacharidy antagonisté a inhibitory   farmakologie   MeSH
• molekulární konformace MeSH
• myši inbrední C57BL MeSH
• myši MeSH
• oxid dusnatý antagonisté a inhibitory   biosyntéza   MeSH
• peritoneální makrofágy účinky léků   metabolismus   MeSH
• saponiny chemie   izolace a purifikace   farmakologie   MeSH
• spirostany chemie   izolace a purifikace   farmakologie   MeSH
• viabilita buněk účinky léků   MeSH
• zvířata MeSH
• Check Tag
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• lipopolysacharidy MeSH
• oxid dusnatý MeSH
• saponiny MeSH
• spirostany MeSH