Secoiridoid glucosides from fraxinus ornus bark

Iossifova, Tanya; Vogler, Bernhard; Kostova, I.

doi:10.1016/s0031-9422(98)00097-1

Cited by 21 publications

(10 citation statements)

References 4 publications

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“…Lonicera japonica (Caprifoliaceae). 12) 46.9 (C-9), 118.6 (C-10), 168.4 (C-11), 55.0 (OMe), 97.9 (C-1Ј), 73.0 (C-2Ј), 76.7 (C-3Ј), 70.0 (C-4Ј), 77.0 (C-5Ј), 61.1 (C-6Ј). Gentiana scabra (Gentianaceae).…”

Section: Biological and Pharmacological Activity Of Naturally Occurrimentioning

confidence: 99%

Naturally Occurring Secoiridoids and Bioactivity of Naturally Occurring Iridoids and Secoiridoids. A Review, Part 2

Debnath²,

2007

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This is a second part of a review 1) and is mainly a compilation of new secoiridoids reported in the literature during 1994-2005 as well as a high-light of biological and pharmacological activity of iridoids and secoiridoids published during 1998--2005. The earlier first part of review 1) included new naturally occurring iridoids (glycosides, aglycones, derivatives and dimers) reported during 1994-2005. Secoiridoids are monoterpenoids based on the 7,8-secocyclopenta[c]-pyranoid skeleton and represented by 1a. They are possibly derived in plants from iridoid, loganin 1b by oxidative cleavage with redox enzyme to 1c and then undergo various secondary modifications of the basic skeleton namely, epoxidation, oxidation, hydroxylation and esterification of the generated hydroxyl groups leading a group of compounds which constitute the class. The main aim of this review is for rapid identification of isolated secoiridoids by comparison of spectral data as well as to draw attention of the natural product chemists for evaluation of biological and pharmacological activity of the isolated iridoids and secoiridoids in order to justify the use of medicinal plants containing these metabolites in folk medicines. In certain plants, the isolated metabolites showed biological activities other than the use of the concerned plants in traditional system of medicine. The high-light of pharmacological activity may possibly draw the attention of the synthetic chemists for design of new drugs using known iridoids as raw materials.A number of review articles on plant secoiridoids are available. Listings of naturally occurring secoiridoids together with spectroscopic data and plant source (review of El-Naggar and Beal covering the literature through January, 1980 2) and of Boros and Stermitz covering the literature through December, 1989 3) ), and without spectroscopic data (review of Hazimi and Alkhathlan covering through December, 1993 4) ) are available. The reviews on biological activity of plant iridoids, namely of Sticher, covering the works reported up to 1976, 5) of Ghisalberti and of Mandal et al. covering the literature up to a part of 1997 6,7) are also available. Secoiridoids are listed in Table 1 in a fashion similar to that of the Boros and Stermitz review.3) All the new secoiridoids are arranged in four groups. Group 1 contains simple secoiridoids; whereas group 2 contains terpene-conjugated secoiridoids; group 3 contains aromatic conjugated secoiridoids and group 4 contains bis-, tris-and tetrakis-secoiridoids. The oxidation state of C-10 and C-11 guides the arrangement of compounds in each group except group 4. The available data for each compound were listed in the following order: name; structure; molecular formula; calculated molecular weight as per atomic weight of most abundant isotopic atoms of C, H, O, etc.; melting point (°C); optical rotation, [a] D (with concentration and solvent); UV (solvent, l max in nm, log e); IR (medium, n max in cm C-NMR data to the first decimal point. Assignments with the s...

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Section: Biological and Pharmacological Activity Of Naturally Occurrimentioning

confidence: 99%

Naturally Occurring Secoiridoids and Bioactivity of Naturally Occurring Iridoids and Secoiridoids. A Review, Part 2

Debnath²,

2007

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“…The remaining ten resonances consisted of three quaternary carbon signals, two of which were for carbonyl carbons, three methine signals, with one of the methine carbons being involved in a double bond, three methylene signals, two of which bear an oxygen atom, and an allylic methyl group signal. COSY, HSQC, and HMBC experiments showed that this ten-carbon unit formed a monocyclic planar structure characteristic of secoiridoids previously reported for Fraxinus species [2][3][4][5][6][7]. However, several features of the NMR spectral data exhibited some significant differences for the skeleton of 1 in comparison with the previously reported class of secoiridoids.…”

Section: Resultsmentioning

confidence: 52%

“…In addition, the following COSY correlations were also observed: between the oxymethylene protons (H 2 -11) at d [2][3][4][5][6][7], an anomeric proton signal at d H 4.70 (1H, d, J = 8 Hz), a signal due to a methoxyl group at d H 3.72 (3H, s), and a hydroxymethylene signal at d H 3.74 (2H, t, J = 7 Hz), together with signals due to para-substituted aromatic protons at d H 6.97 and d H 7.24 (each 2H, d, J = 9 Hz) ( Table 1). The 13 C-NMR spectral data displayed 25 resonances ( Table 2), six of which were attributable to a b-glucopyranosyl moiety, eight to a para-hydroxyphenethyl moiety, one to a methoxyl moiety, and the remaining ten signals to a secoiridoid skeleton [2][3][4][5][6][7]. Inspection of the other 1 H-and 13 C-NMR spectral data of 2 revealed similar patterns to those of formoside (9) (Tables 1, 2) [6,7].…”

Section: Resultsmentioning

confidence: 99%

“…Since the HR-ESI-MS spectrum showed a single molecular ion peak, it was inferred that the two compounds had the same molecular formula but differed in the configuration around a chiral center. The 13 C-NMR spectral data can then be interpreted to display 33 resonances, six of which are attributable to a b-glucopyranosyl moiety, eight to a para-hydroxyphenylethyl moiety, eight to a 1,3,4-trisubstituted phenylethyl moiety, one to a methoxy group, and the remaining ten signals to a secoiridoid skeleton [2][3][4][5][6][7]. Comparison of the 1 H-NMR spectral pattern with those of other secoiridoids isolated from the same plant revealed a similarity to that of safghanoside D (7) [8] except for differences in the chemical shifts attributed to the phenylethyl group, esterified to the carboxyl group at the 11-position, as well as the presence of a methoxyl group (d H 3.23, 3H, s) ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

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Secoiridoid and iridoid glucosides from the leaves of Fraxinus griffithii

Macahig¹,

Harinantenaina²,

Matsunami³

et al. 2009

J Nat Med

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Phytochemical investigation of the dried leaves of Fraxinus griffithii collected in Okinawa has led to the isolation of three new secoiridoid glucosides, griffithosides A-C (1-3), and one new iridoid glucoside, 7-epi-7-O-(E)-caffeoylloganic acid (4), along with eight known secoiridoid glucosides (5-12). The structures of these compounds were elucidated by means of NMR, MS, and other spectroscopic techniques, as well as comparison with literature data. The isolated compounds were tested for radical-scavenging activity. Among them, compounds 3, 4, and 7 exhibited substantial radical-scavenging activity.

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“…1, and named dilatioside B. The thirteen known secoiridoid glucoside derivatives were identified as oleoside dimethyl ester (3), 11) ligustroside (4), 11) oleuropein (5), 17) (2″R)-2″-methoxyoleuropein (6), 18) fraxamoside (7), 19) hydroxyframoside A (8), 20) syringalactone A (9), 21) syringalactone B (10), 21) (8E)-nüzhenide (11), 22) (8Z)-nuezhenide A (12), 23) jaspolyanoside (13), 13) jaspolyoside (14), 24) oleonuezhenide (15) 25) by comparison of their spectroscopic data with the data reported in the literatures.…”

Section: Resultsmentioning

confidence: 99%