Studies on the Constituents of Syringa Species. X. Five New Iridoid Glycosides from the Leaves of Syringa reticulata (BLUME) HARA.

Machida, Koichi; Kaneko, Atsuko; Hosogai, Tomokazu; Kakuda, Rie; Yaoita, Yasunori; Kikuchi, Masao

doi:10.1248/cpb.50.493

Cited by 43 publications

(28 citation statements)

References 10 publications

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“…This biopharmaceutical quality of the root extract has been proved by clinical study on the treatment of osteoarthiritis pain by Chrubasik et al 72,73) c. Anti-inflammatory Activity Patrinia saniculaefolia HEMSLEY (Valerianaceae) is a perennial herb and endemic in Korea. The roots of this plant and other species of this genus have been used in Korean traditional medicine for treatment of various diseases including inflammation and edema, ap- 157.0 (C-3), 103.1 (C-4), 34.5 (C-5), 26.1 (C-6), 71.1 (C-7), 133.9 (C-8), 43.9 (C-9), 119.9 (C-10), 169.0 (C-11). Strychnos cathayensis (Loganiaceae).…”

Section: Biological and Pharmacological Activity Of Naturally Occurrimentioning

confidence: 99%

“…Gentiana scabra (Gentianaceae). 104.4 (C-4), 22.9 (C-5), 28.9 (C-6), 93.1 (C-7), 133.0 (C-8), 43.4 (C-9), 121.5 (C-10), 165.9 (C-11), 100.4 (C-1Ј), 74.7 (C-2Ј), 78.1 (C-3Ј), 71.4 (C-4Ј), 78.3 (C-5Ј), 62.6 (C-6Ј), 175.9 (C-1Љ), 42.0 (C-2Љ), 27.6 (C-3Љ), 11.8 (C-4Љ), 16.8 (C-5Љ). Chelonanthus chelonoides (Gentianaceae).…”

Section: Biological and Pharmacological Activity Of Naturally Occurrimentioning

confidence: 99%

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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%

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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“…As part of our continuing studies on the constituents of oleaceous plants, we previously reported the isolation of seven new iridoid glycosides, including the first identification of an (8Z)-oleoside-type secoiridoid [(8Z)-ligustroside, (8Z)-nuzhenide] and iridoid di-glycosides containing isomaltose and melibiose, from the leaves of Syringa reticulata (Oleaceae) [1,2]. This plant has been used as a traditional Chinese medicine for the treatment of bronchial asthma and as an expectorant [3].…”

Section: Introductionmentioning

confidence: 99%

Two new phenolic glycosides from Syringa reticulata

et al. 2008

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“…11,12) Syringopicroside (S-7) was obtained from the leaves of Syringa reticulate (Blume) HARA. 13) All other reagents were the highest quality available. Evaluation of Neurite Outgrowth ---PC12h cells were generously donated by the late Dr. H. Hatanaka of Osaka University, Japan, and were cultured in Dulbecco's modified Eagle medium supplemented with precolostrum calf serum and heat-inactivated horse serum for growth, as described previously.…”

Section: Introductionmentioning

confidence: 99%

“…The neurite outgrowth of these cells was evaluated by measuring the length of the longest neurite of individual cells following 48 hr of treatment with the test compounds, as described previously. 13) One hundred cells in ten random fields in two culture dishes were averaged for each treatment.…”

Section: Introductionmentioning

confidence: 99%

Neuritogenesis of Herbal Geniposide-Related Compounds in PC12h Cells

Chiba

Yamazaki

Kikuchi

et al. 2006

JOURNAL OF HEALTH SCIENCE

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Previously, we have reported that geniposide, a compound isolated from an extract of Gardenia fructus, has neuritogenic activity in PC12h cells, a subclone of the rat pheochromocytoma cell. In this study, we have examined the effects of seven geniposide-related compounds (S-1, 6α-hydroxygeniposide; S-2, 6β-hydroxygeniposide; S-3, 6α-methoxygeniposide; S-4, 6β-methoxygeniposide; S-5, loganin; S-6, 7-ketologanin; and S-7, syringopicroside) isolated from various medicinal herbs. The geniposide-type iridoids S-1, S-2, S-3, and S-4, and S-7 induced neurite outgrowth that was similar or more potent to that of geniposide. S-2 and S-4, which are optical isomers of S-1 and S-3, respectively, were particularly potent. The 2 loganin-type iridoids, S-5 and S-6, showed less activity than geniposide. The neuritogenic activity of geniposide-type iridoids appears to be not necessarily correlated directly to their hydrophobicity. These results suggest that geniposide-type iridoids have potent neuritogenic activity and that specific configurations for the interactions between iridoid compounds and the target molecule are necessary for neuritogenic function.

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Studies on the Constituents of Syringa Species. X. Five New Iridoid Glycosides from the Leaves of Syringa reticulata (BLUME) HARA.

Cited by 43 publications

References 10 publications

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

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

Two new phenolic glycosides from Syringa reticulata

Neuritogenesis of Herbal Geniposide-Related Compounds in PC12h Cells

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