ChemInform Abstract: IRIDOIDS PART 13, AJUGOSIDE AND AJUGOL, STRUCTURE AND CONFIGURATION

Guiso, Marcella; Marini-Bettolo, R.; Agostini, Alessandro

doi:10.1002/chin.197428467

Cited by 9 publications

(10 citation statements)

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“…These are iridoid glycosides occurring in many medicinal plants belonging to Lamiaceae, Plantaginaceae and Scrophulariaceae families, where they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy both in vitro and in vivo as well as to the antioxidant activity of these plants (Zhang et al 2011;Háznagy-Radnai et al 2012;Erukainure et al 2014;Zhang et al 2014). Compounds 1, 2, 3, 4 and 5 had been already evidenced in this species (Scarpati et al 1965;Scarpati & Esposito 1967a, 1967b, Guiso et al 1974 and their presence was also confirmed in this study. Actually, these compounds and in particular harpagide (3) and its acetyl derivative (4) are considered chemotaxonomic markers for this genus and also for other related genera in the Lamiaceae family such as Ajuga (Assaad & Lahloub 1988;Breschi et al 1992), Stachys (Kotsos et al 2001;Munoz et al 2001;Háznagy-Radnai et al 2006;Venditti et al 2013aVenditti et al , 2013cVenditti et al , 2014 and Galeopsis (Wieffering & Fikenscher 1974;Venditti et al 2013b).…”

Section: Resultssupporting

confidence: 79%

“…melissophyllum brought us to the isolation and the identification of five compounds namely monomelittoside (1) (Scarpati & Esposito 1967a), melittoside (2) (Bobbitt et al 1967;Scarpati & Esposito 1967b), harpagide (3) acetyl-harpagide (4) (Scarpati et al 1965), ajugoside (5) (Guiso et al 1974) and allobetonicoside (6) (Jeker et al 1989). These are iridoid glycosides occurring in many medicinal plants belonging to Lamiaceae, Plantaginaceae and Scrophulariaceae families, where they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy both in vitro and in vivo as well as to the antioxidant activity of these plants (Zhang et al 2011;Háznagy-Radnai et al 2012;Erukainure et al 2014;Zhang et al 2014).…”

Section: Resultsmentioning

confidence: 99%

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Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Venditti

Frezza

Guarcini

et al. 2015

Natural Product Research

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The analysis of the polar fraction of Melittis melissophyllum L. subsp. melissophyllum led to the identification of several iridoid glycosides: monomelittoside (1), melittoside (2), harpagide (3), acetyl-harpagide (4) and ajugoside (5). Compounds 3 and 4 are considered marker compounds for the genus and, as well as compounds 1, 2 and 5, were already evidenced in a previous study on the nominal species. It was noteworthy of the presence of allobetonicoside (6) which was never reported for this genus. The isolation of 6 is very relevant because of its allose residue on the structure. Allose has been often found in the species of the subfamily Lamioideae even if it mostly regarded flavonoids considered of chemotaxonomical relevance for some correlated genera of Lamiaceae. Same as allosyl-glycosidic flavonoids, the presence of allosyl-glycosidic iridoids may also be an additional chemosystematic evidence of botanical relationships among Lamiaceae species and genera.

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Section: Resultssupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Venditti

Frezza

Guarcini

et al. 2015

Natural Product Research

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“…Compound 4 showed similarities to 1 in its spectral data except for an extra signal at d = 2.89 (1H, m) due to a proton at carbon 5; however, the resonance positions of the H6-proton (see Materials and Methods) and the carbons 4, 5 and 6 in the iridoid moiety ( Table 1) differ from 1 in that they are almost identical with NMR data of 8-O-acetylmyoporoside [13] in the corresponding positions; when compared to laterioside [14] and ajugoside [15], which are 6-epimers of myoporoside, an upfield shift of the H-6 and downfield shifts of the C-6 of 4 indicate an a-configuration of the C-6-OH group; this was corroborated by positive NOEs between H-6 and H-5, H-7a and H-9. Finally, CE analysis of the hydrolyzed compound revealed D-glucose.…”

Section: Resultsmentioning

confidence: 94%

New and Known Iridoid- and Phenylethanoid Glycosides fromHarpagophytum procumbensand theirin vitroInhibition of Human Leukocyte Elastase

Boje

Lechtenberg²,

Nahrstedt³

2003

Planta med

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Ten compounds, harpagoside (1), 8- p-coumaroylharpagide (2), 8-feruloylharpagide (3), 8-cinnamoylmyoporoside (4), pagoside (5), acteoside (6), isoacteoside (7), 6'- O-acetylacteoside (8), cinnamic acid (9) and caffeic acid (10) were isolated from the storage roots of Harpagophytum procumbens, Pedaliaceae. Compounds 1, 2, 6, 7 and 9 are known for H. procumbens; 3 and 10 were isolated the first time from H. procumbens; compounds 4, 5 and 8 are new natural products. Their structures were elucidated using spectroscopic data (NMR, with NOE, COSY and HMBC experiments, UV, [alpha]). The inhibitory activity of aqueous extracts of the roots of H. procumbens and H. zeyheri as well as the main compounds isolated from H. procumbens was tested on human neutrophile elastase. Although inhibition was comparatively weak a dose-dependence was observed. An IC (50) of 542 microg/mL was determined for the aqueous extract of H. procumbens, but 1012 microg/mL for that of H. zeyheri. 6'- O-Acetylacteoside (8), that is not present in H. zeyheri, inhibited the enzyme with an IC (50) of 47 microg/mL (70 microM), compound 7 with 179 microg/mL (286 microM), 2 with 179 microg/mL (331 microM), 5 with 154 microg/mL (260 microM) and 10, which was also used as reference compound, with an IC (50) of 86 microg/mL (475 microM). The IC (50) values of acteoside, harpagoside, cinnamic acid and stachyose were higher than 300 microg/mL and thus not further determined.

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“…perfoliata ten compounds were isolated. On the basis of 1D, 2D NMR and UV-Vis spectral analyses their structures were elucidated as acteoside (1) (Birkofer et al, 1968), leucosceptoside A (2) (Miyase et al, 1982), martynoside (3) (Sasaki et al, 1978), lavandulifolioside (4) (Nishimura et al, 1991) (Chari et al, 1981;Lenherr et al, 1984) (Lenherr et al, 1984), (Lenherr and Mabry 1987) (Lenherr and Mabry, 1987), caffeic acid (9) and ajugoside (10) (Boros and Stermitz, 1990;Guiso et al, 1974).…”

Section: Resultsmentioning

confidence: 99%

Antioxidant and antiinflammatory activities of Sideritis perfoliata subsp. perfoliata (Lamiaceae)

Charami

Lazari

Karioti

et al. 2008

Phytotherapy Research

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Sideritis perfoliata L. subsp. perfoliata is a plant widely used in folk medicine in Greece since antiquity because of its antiinflammatory, antirheumatic, antiulcer, digestive and vasoprotective properties. Phytochemical investigations of the polar extracts afforded four flavonoid glycosides, four phenylpropanoic glycosides, caffeic acid and one iridoid, ajugoside. Reactive oxygen species (ROS) are implicated in the aetiology of several inflammatory processes. In the present study polar fractions and isolated compounds from S. perfoliata subsp. perfoliata were evaluated for their antioxidant activity using DPPH spectrophotometric and TBA lipid peroxidation assays, as well as for their antiinflammatory activity using the soybean lipoxygenase bioassay. All extracts and isolated compounds showed significant antioxidant and inhibitory activity against soybean lipoxygenase. These findings give support to the ethnopharmacological use of the plant in the treatment of several inflammatory ailments.

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ChemInform Abstract: IRIDOIDS PART 13, AJUGOSIDE AND AJUGOL, STRUCTURE AND CONFIGURATION

Cited by 9 publications

References 0 publications

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

New and Known Iridoid- and Phenylethanoid Glycosides fromHarpagophytum procumbensand theirin vitroInhibition of Human Leukocyte Elastase

Antioxidant and antiinflammatory activities of Sideritis perfoliata subsp. perfoliata (Lamiaceae)

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