4′-Deoxy iridoid glycosides from Centranthus longiflorus

Kuruüzüm-Uz, Ayşe; Güvenalp, Zühal; Demirezer, L. Ömür; Bergere, Isabelle; Ströch, Karsten; Zeeck, Axel

doi:10.1016/s0031-9422(02)00476-4

Cited by 21 publications

(9 citation statements)

References 14 publications

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“…Known compounds were identified as volvalerenal C ( 4 ) [ 13 ], (+) pinoresinol-4,4'-di- O - β -D-glucopyranoside ( 5 ) [ 14 ], (+) pinoresinol-8- O - β -D-glucopyranoside ( 6 ) [ 15 ], 8-hydroxypinoresinol-4,4'-di- O -β-D-glucopyranoside ( 7 ) [ 16 ], (+) 8-hydroxypinoresinol-4'- O - β -D-glucopyranoside ( 8 ) [ 14 ], (+) pinoresinol-4- O - β -D-glucopyranoside ( 9 ) [ 17 ], (+) 8-hydroxypinoresinol ( 10 ) [ 14 ], (+) 8-hydroxypinoresinol-4- O - β -D-glucopyranoside ( 11 ) [ 14 ], patrinoside ( 12 ) [ 18 ], and kanokoside A ( 13 ) [ 19 ] by comparing their NMR spectroscopic data with the literature values. The structures of compounds 1-13 are shown in Figure 3 .…”

Section: Resultsmentioning

confidence: 99%

Compounds from the Roots and Rhizomes of Valeriana amurensis Protect against Neurotoxicity in PC12 Cells

Wang

Zuo

et al. 2012

Molecules

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Three new germacrane-type sesquiterpenoids, heishuixiecaoline A–C (compounds 1–3), were isolated along with ten known compounds 4–13 from fraction of Valeriana amurensis roots and rhizomes effective against Alzheimer’s disease (AD). The structures of 1–3 were elucidated on the basis of their spectroscopic data. We also investigated the protective effect of compounds 1–13 on the neurotoxicity of PC12 cells induced by amyloid-beta (Aβ25–25), respectively. As a result, germacrane-type sesquiterpenoids 1–4 and lignans 5–7 were seen to afford protection against Aβ-induced toxicity in PC 12 cells. This study will contribute to revealing the chemical basis for the therapeutic effect of V. amurensis against AD.

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Section: Resultsmentioning

confidence: 99%

Compounds from the Roots and Rhizomes of Valeriana amurensis Protect against Neurotoxicity in PC12 Cells

Wang

Zuo

et al. 2012

Molecules

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“…and all these compounds showed weak cytostatic/cytotoxic activity (GI 50 : 1-9 mg/ml) against cancer cell lines, HM02 (stomach carcinoma), Hep G2 (liver carcinoma) and MCF7 (mamma carcinoma) according to NCI-directives. 87) This plant is used in folk medicine for sedative and antispasmodic purposes. The iridoids containing aqueous extract of this plant (100 mg/kg) growth over the full range (100 to 0.78 mg/ml) of concentrations tested.…”

Section: )mentioning

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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“…The EtOAc-soluble fraction (211 g) was subjected to silica gel (500 g; 70-230 mesh) column chromatography, using gradient of EtOAc in n-Hexane to give 10 fractions (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) Bioassay Procedure PC12D cells were dissociated by incubation with 1 mmol of ethylene glycol-bis(2-aminoethyl ether)-N,N,NЈ,NЈ-tetraacetic acid (EGTA) in phosphate-buffered saline (PBS) for 30 min and then were seeded in 24-well culture plates (2ϫ10 4 cells/well) coated with poly-L-lysine. After 24 h, the medium was changed to test medium containing various concentrations of NGF (50 ng/ml for positive control, 2 ng/ml for test samples and significant difference control), 1% fetal calf serum, 2% horse serum, and various concentrations of test compounds (10, 30, 100 mmol).…”

Section: Extraction and Isolationmentioning

confidence: 99%

Iridoids and Sesquiterpenoids with NGF-Potentiating Activity from the Rhizomes and Roots of Valeriana fauriei

Guo

et al. 2006

Chem. Pharm. Bull.

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4′-Deoxy iridoid glycosides from Centranthus longiflorus

Cited by 21 publications

References 14 publications

Compounds from the Roots and Rhizomes of Valeriana amurensis Protect against Neurotoxicity in PC12 Cells

Compounds from the Roots and Rhizomes of Valeriana amurensis Protect against Neurotoxicity in PC12 Cells

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

Iridoids and Sesquiterpenoids with NGF-Potentiating Activity from the Rhizomes and Roots of Valeriana fauriei

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