An iridoid diglycoside isolated from Scrophularia scorodonia

Fernández, L.; Dı́az-Lanza, Ana Marı́a; Ollivier, Évelyne; Faure, Robert; Balansard, G.

doi:10.1016/0031-9422(95)00305-q

Cited by 17 publications

(5 citation statements)

References 11 publications

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“…The 13 C NMR spectrum showed that all the signals arising from the aromatic part were doubled, while the remaining signals were not. This part of the spectrum was very similar to that of scorodioside (6a) from Scrophularia scorodonia L. (Fernandez et al, 1995), which is a 3 00 -acetyl-2 00 -cinnamoyl diester of 6-a-O-rhamnopyranosylcatalpol (see Table 1), except for the signals arising from the aromatic part. From the spectrum, however, it was obvious that this part of 6b was a p-coumaroyl moiety, and therefore the compound was an isomer of the two known diesters: scrophuloside A 2 (a 2 00 -acetyl-4 00 -p-coumaroyl diester) and scrophuloside A 3 (a 3 00 -acetyl-4 00 -p-coumaroyl diester) found in Scrophularia nodosa L. (Miyase and Mimatsu, 1999).…”

Section: Resultsmentioning

confidence: 75%

“…The LC was coupled to a LCT of a TOF MS (Micromass, Manchester, UK) operated in the positive electrospray ion mode using 5-leucineenkephalin as lock mass. The isolated compounds were identified by their 1 H and 13 C NMR spectra by comparison with spectra of known standards: 1, 2, 4, 5, 5a and 7 (Taskova et al, 2006); ajugol esters 2a and 2b (Nishimura et al, 1989); 3 and 3a (Chaudhuri et al, 1980); scorodioside (6a) (Fernandez et al, 1995).…”

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confidence: 99%

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Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae)

Jensen

Albach

et al. 2008

Phytochemistry

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The relationships between the genera Triaenophora, Oreosolen and Rehmannia were investigated. All three genera were previously included in tribe Veroniceae which was part of Scrophulariaceae but which is now included in Plantaginaceae. With regard to the content of iridoid glucosides, Triaenophora rupestris and the much-investigated Rehmannia were almost identical in containing catalpol, ajugol and 6-feruloylajugol. Oreosolen wattii was rather different in having compounds typical for the tribe Scrophularieae (Scrophulariaceae), namely aucubin, harpagide, harpagoside as well as two diesters of rhamnopyranosylcatalpol, one of which, here named oreosolenoside, had not previously been described in the literature. These results are consistent with recent analyses based on DNA sequencing and a phylogenetic tree illustrating the taxonomic relationships is presented.

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Section: Resultsmentioning

confidence: 75%

mentioning

confidence: 99%

Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae)

Jensen

Albach

et al. 2008

Phytochemistry

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“…In this context, the ratio harpagoside (HS)/8- O -( p -coumaroyl)harpagide (8-PCHG) was described as a chemotaxonomical marker allowing the differentiation between H. procumbens and H. zeyheri . Compound 3 , the ( Z ) isomer of 8-PCHG, represents a new natural product with structurally closely related derivatives already described from different sources. ,, The co-occurrence of ( Z ) and ( E ) cinnamoyl derivatives of iridoids and phenylethanoids has been frequently reported and has been unequivocally associated with light-induced isomerization processes in the case of p -methoxycinnamoyl derivatives . The biological relevance of this isomerization process is unknown, and it is not understood whether the ( Z ) derivatives are indeed biogenic entities.…”

Section: Resultsmentioning

confidence: 99%

LC-DAD-MS/SPE-NMR Hyphenation. A Tool for the Analysis of Pharmaceutically Used Plant Extracts: Identification of Isobaric Iridoid Glycoside Regioisomers from Harpagophytum procumbens

et al. 2004

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LC-DAD-MS monitored fractionation of aHarpagophytum procumbens DC. (Pedaliaceae) root extract was combined with a hyphenated LC-DAD-MS/SPE-NMR technique, thus providing the spectral data needed for structure elucidation. This approach allowed the characterization of isobaric iridoid glycoside regioisomers present only as minor constituents. The analytes were identified as the (E/Z) pairs of 6′-O-(p-coumaroyl)harpagide (6′-PCHG) and 8-O-(p-coumaroyl)-harpagide (8-PCHG). The fact that 8-(Z)-PCHG constitutes a new natural product underlines the analytical power of this combined approach. Furthermore, derivatives 6′-(Z)-and 6′-(E)-PCHG are new constituents for H. procumbens.

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“…Scrophularia scorodonia L. is widespread in the southwestern parts of Spain and in the northwest of Africa [ 142 ] . Seven iridoid glycosides isolated from different extracts of S. scorodonia , namely, aucubin ( 14 ), harpagoside ( 19 ), harpagide ( 20 ), 8-acetylharpagide ( 42 ), scorodioside ( 43 ), scropolioside B ( 44 ) and bartsioside ( 45 ), were evaluated for their in vitro anti-inflammatory activity in cellular systems generating COX and LOX metabolites.…”

Section: Iridoid Chemistry and Researched Anti-inflammatory Iridoid-cmentioning

confidence: 99%

Anti-Inflammatory Iridoids of Botanical Origin

Viljoen

Mncwangi²,

Vermaak³

2012

CMC

175

110

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Inflammation is a manifestation of a wide range of disorders which include; arthritis, atherosclerosis, Alzheimer’s disease, inflammatory bowel syndrome, physical injury and infection amongst many others. Common treatment modalities are usually non-steroidal anti-inflammatory drugs (NSAIDs) such as aspirin, paracetamol, indomethacin and ibuprofen as well as corticosteroids such as prednisone. These however, may be associated with a host of side effects due to non-selectivity for cyclooxygenase (COX) enzymes involved in inflammation and those with selectivity may be highly priced. Thus, there is a continuing search for safe and effective anti-inflammatory molecules from natural sources. Research has confirmed that iridoids exhibit promising anti-inflammatory activity which may be beneficial in the treatment of inflammation. Iridoids are secondary metabolites present in various plants, especially in species belonging to the Apocynaceae, Lamiaceae, Loganiaceae, Rubiaceae, Scrophulariaceae and Verbenaceae families. Many of these ethnobotanicals have an illustrious history of traditional use alluding to their use to treat inflammation. Although iridoids exhibit a wide range of pharmacological activities such as cardiovascular, hepatoprotection, hypoglycaemic, antimutagenic, antispasmodic, anti-tumour, antiviral, immunomodulation and purgative effects this review will acutely focus on their anti-inflammatory properties. The paper aims to present a summary for the most prominent iridoid-containing plants for which anti-inflammatory activity has been demonstrated in vitro and / or in vivo.

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An iridoid diglycoside isolated from Scrophularia scorodonia

Cited by 17 publications

References 11 publications

Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae)

Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae)

LC-DAD-MS/SPE-NMR Hyphenation. A Tool for the Analysis of Pharmaceutically Used Plant Extracts: Identification of Isobaric Iridoid Glycoside Regioisomers from Harpagophytum procumbens

Anti-Inflammatory Iridoids of Botanical Origin

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