Acyl secoiridoids and antifungal constituents from Gentiana macrophylla

Tan, Ren Xiang; Wolfender, Jean‐Luc; Zhang, L X; G,W,,Mack,; Fuzzati, Nicola; Marston, Andrew; Hostettmann, Kurt

doi:10.1016/0031-9422(96)00149-5

Cited by 99 publications

(75 citation statements)

References 26 publications

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“…2 In the Chinese Pharmacopoeia, the roots of four plants from the genus Gentiana (Gentianaceae), G. macrophylla, G. crassicaulis, G. straminea, G. duhurica, are used as the original materials of "Qin-Jiao". 3 Among them, G. macrophylla have been chemically and biological investigation by several groups, [4][5][6] whose results suggested that the water extract of G. macrophylla could obviously resist RA. 7 The mechanism might be the inhibition of not only phagocyte to produce and release prostaglandin E2 (PGE2), but also the activity of cyclooxygenase-2 (COX-2).…”

Section: Introductionmentioning

confidence: 99%

The chemical constituents from the roots of Gentiana crassicaulis and their inhibitory effects on inflammatory mediators NO and TNF-α

Wang

et al. 2012

Nat. Prod. Bioprospect.

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Abstract:Chemical study on the roots of Gentiana crassicaulis Duthie ex Burk (Gentianaceae) afforded 15 compounds, including two new iridoid glycosides, qinjiaosides B (1) and C (2). Their structures were elucidated by spectroscopic methods and chemical evidence. The isolated iridoid glycosides 1, 4-6 and 8-11 were tested for their anti-inflammatory activity by the inhibitory effects on LPS-induced NO and TNF-α production in macrophage RAW264.7 cells. All of them showed inhibitory effects on inflammatory mediators NO at a concentration of 15 μM, while 5 and 9 displayed the most potential inhibitory effects on TNF- with IC 50 of 0.06 and 0.05 μM, respectively. The structure-activity relationships (SARs) of these iridoid derivatives were discussed.

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Section: Introductionmentioning

confidence: 99%

The chemical constituents from the roots of Gentiana crassicaulis and their inhibitory effects on inflammatory mediators NO and TNF-α

Wang

et al. 2012

Nat. Prod. Bioprospect.

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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%

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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“…It widely exists in plants of many families [1][2][3] and shows a wide variety of biological activities such as hepatoprotective effect, antitumor, antibacterial, antifungal. [4][5][6][7] Sweroside is also the main ingredient of purified herbal extracts from the flower buds of Lonicera japonica THUNB. (IGEs-1) which were demonstrated to possess perfect hepatoprotective effect in our preliminary experiments.…”

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confidence: 99%

Determination of Sweroside in Rat Plasma and Bile for Oral Bioavailability and Hepatobiliary Excretion

Luo

Cao

Wen

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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79 Notes Sweroside (C 16 H 22 O 9 , molecular weight 358.344), an iridoid glycoside, belongs to a large group of natural monoterpenoids with a glucose moiety attached to C-1 in the pyrane ring. It widely exists in plants of many families [1][2][3] and shows a wide variety of biological activities such as hepatoprotective effect, antitumor, antibacterial, antifungal. 4-7)Sweroside is also the main ingredient of purified herbal extracts from the flower buds of Lonicera japonica THUNB. (IGEs-1) which were demonstrated to possess perfect hepatoprotective effect in our preliminary experiments. Since sweroside and its correlative plant extracts have exhibited these pharmacological effects, it would be hopeful that sweroside and IGEs-1 to be developed to some promising preparations of herbal medicinal products (HMPs).Recently, HMPs are getting more common in the main stream in previously skeptical markets such as the United States and United Kingdom. 8) Establishing the pharmacological basis for efficacy of HMPs is a constant challenge. Of particular interest is the question of bioavailability to assess to what degree and how fast compounds are absorbed after administration of HMPs. Of further interest are the elucidation of metabolic pathways, and the assessment of elimination routes and their kinetics. These data become an important issue to link data from pharmacological assays and clinical effects. A better understanding of the pharmacokinetics and bioavailability of HMPs can also help in designing rational dosage regimens. Despite a wide range of research in either sweroside or L. japonica, 9,10) to our best knowledge, there is no information available on the pharmacokinetics of sweroside orally and intravenously administered to investigate its oral bioavailability and hepatobiliary excretion. Moreover, no report has been published to elucidate the metabolites and the metabolic pathways of sweroside.Furthermore, the development of sampling technique has been a focus in vivo experiment.11) Microdialysis system is a sampling technique that can reduce endogenous interference and can be easy to couple with detector for on-line analysis. A series of papers reported the successful application of microdialysis system to pharmacokinetic study.12-15) However, there is no paper to present the application of microdialysis for the preparation of bile samples of sweroside in rat.In the present study, a simple, stable and accurate HPLC-UV method was developed to determine sweroside in rat plasma, urine, feces and bile simultaneously. The method was applied to basic pharmacokinetic and oral bioavailability studies after intravenous administration of sweroside and oral administration of sweroside and IGEs-1. A sampling method through a validated bile microdialysis system coupled with this HPLC-UV determination was developed to evaluate the hepatobiliary excretion of sweroside in rat. ExperimentalPreparation of IGEs-1 and Sweroside The flower buds of Lonicera japonica THUNB. were collected at the middle of May from Mi county, Hena...

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Acyl secoiridoids and antifungal constituents from Gentiana macrophylla

Cited by 99 publications

References 26 publications

The chemical constituents from the roots of Gentiana crassicaulis and their inhibitory effects on inflammatory mediators NO and TNF-α

The chemical constituents from the roots of Gentiana crassicaulis and their inhibitory effects on inflammatory mediators NO and TNF-α

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

Determination of Sweroside in Rat Plasma and Bile for Oral Bioavailability and Hepatobiliary Excretion

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