Iridoids with Anti-Inflammatory Activity from Vitex peduncularis

Suksamrarn, Apichart; Kumpun, Saowanee; Kirtikara, Kanyawim; Yingyongnarongkul, Boon‐ek; Suksamrarn, Sunit

doi:10.1055/s-2002-20048

Cited by 61 publications

(33 citation statements)

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“…28) However, iridoid compounds 2-4 did not inhibit platelet aggregation, indicating a different inhibition mechanism on the BF decrease. There have been many reports on the anti-allergic effects of iridoid derivatives which inhibit the production of COX-2 29) or NO, 30) or the expression of iNOS and COX-2. 31) Inhibition of the BF decrease by iridoid derivatives may occur in a similar manner.…”

Section: Discussionmentioning

confidence: 99%

Allergy-Preventive Effects of Chlorogenic Acid and Iridoid Derivatives from Flower Buds of Lonicera japonica

Oku

Ogawa

Iwaoka

et al. 2011

Biological & Pharmaceutical Bulletin

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Flower buds of Lonicera japonica THUNB. (Caprifoliaceae), one of the most common traditional Chinese medicines, are used to treat various diseases including arthritis, diabetes mellitus, fever, infections, sores and swelling. 1)Pharmacological studies have indicated that the extract of these flower buds have a broad spectrum of biological activities, including antibacterial, anti-inflammatory, antioxidant, antipyretic, antiviral and hepato-protective effects.1,2) A number of chemical constituents including flavonoids, iridoids and saponins have been obtained from this plant. [3][4][5][6][7][8] In our continuing search for allergy-preventive substances from natural sources, 9) we have been using our previously developed in vivo assay method to estimate effects on complex allergies. 10,11) This time, we found that the 35% EtOH extract of flower buds of L. japonica exhibited allergy-preventive activity. Our in vivo assay method monitors the decrease in blood flow (BF) in the tail vein of mice subjected to hen eggwhite lysozyme (HEL) sensitization alone without the HELchallenge as a guide.10) The BF in HEL-sensitized mice (control group) gradually and significantly decreased to about 70% of that in normal mice on day 9. Thus, the induction phase (promotion stage) of allergy caused by xenobiotics can be dynamically and easily measured using BF monitoring. This BF decrease is considered to be due to the contraction of peripheral blood vessels and an increase in blood viscosity, because no relationship with blood pressure was observed. Although anti-HEL immunoglobulin E (IgE) antibody significantly increased after HEL sensitization, there was no significant increase in the number of leukocytes. Thus, a decrease in BF reflects the promoter process of an allergic reaction. The BF decrease is regulated by various factors such as nitric oxide (NO), thromboxane (TX) A 2 , prostacyclin (PGI 2 ), and endothelin (ET)-1, together with granulocytic elastase (GE), cyclooxygenase (COX)-1 and -2, inducible nitric oxide synthase (iNOS), and constitutive nitric oxide synthase (cNOS).10) In addition, the BF decrease occurs via both pathways of iNOS-independent and -dependent responses.11) Therefore this monitoring system should be useful when searching for substances that can prevent complicated inflammatory allergies involving NO, TXA 2 , PGI 2 , ET-1, GE, COX-1, and COX-2. This paper describes the evaluation of the allergy-preventive effects of a 35% EtOH extract (LJ) of flower buds of L. japonica and the following compounds isolated from LJ: chlorogenic acid (1) and three iridoid derivatives, loganin (2), secoxyloganin (3) and sweroside (4).The structure-activity relationships of iridoid derivatives, morroniside (5), geniposide (6), asperuloside (7), aucubin (8) and catalpol (9) were also examined, as iridoid glucosides (2-4) isolated from LJ showed allergy-preventive effects. MATERIALS AND METHODS General Experimental ProceduresMelting points were determined on a Yanagimoto micro-point apparatus. IR spectra were recorded on a Shim...

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Section: Discussionmentioning

confidence: 99%

Allergy-Preventive Effects of Chlorogenic Acid and Iridoid Derivatives from Flower Buds of Lonicera japonica

Oku

Ogawa

Iwaoka

et al. 2011

Biological & Pharmaceutical Bulletin

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“…It was not toxic to vero cells (IC 50 Ͼ50 mg/ml). 109) As this iridoid, 224 contains a C-5 hydroxy group, possibly it is the structural requirement for an iridoid to exhibit anti HSV-1 activity.…”

Section: (Z)-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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“…8) No phytochemical study of this plant has been reported so far. In our search for biologically active substances of new structural types from Thai natural resources, [9][10][11][12] we investigated the chemical constituents and biological activities of this plant species and have found that the ethyl acetate extract of the root bark of Z. cambodiana showed pronounced in vitro antimalarial potential against Plasmodium falciparum. In this paper, we report the isolation and characterization of a new tritrpene ester (1), together with five known lupane constituents: lupeol (2), 13) betulinaldehyde (3), 14) the major metabolite betulinic acid (4), 13) 2-O-E-p-coumaroylalphitolic acid (5), 1) and alphitolic acid (6), 1) and three ceanothane triperpenes: zizyberanalic acid (7), 15) zizyberenalic acid (8) 15) and ceanothic acid (9), 16) as the antiplasmodial and antituberculosis constituents of the root bark of this plant species.…”

mentioning

confidence: 99%

Ceanothane- and Lupane-Type Triterpenes with Antiplasmodial and Antimycobacterial Activities from Ziziphus cambodiana

et al. 2006

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One new and eight known ceanothane-and lupane-type triterpenes were isolated from the root bark of Ziziphus cambodiana PIERRE (Rhamnaceae). Based on spectral analyses, the structure of the new compound was elucidated as 3-O-(4-hydroxy-3-methoxybenzoyl)ceanothic acid (3-O-vanillylceanothic acid) (1), while the known compounds were identified as lupeol (2), betulinaldehyde (3), betulinic acid (4), 2-O-E-p-coumaroyl alphitolic acid (5), alphitolic acid (6), zizyberanalic acid (7), zizyberenalic acid (8) and ceanothic acid (9). Compounds 1, 5 and 8 exhibited significant in vitro antiplasmodial activity against the parasite Plasmodium falciparum, with inhibitory concentration (IC 50 ) values of 3.7, 0.9 and 3.0 m mg/ml, respectively. Compounds 1 and 3-8 showed antimycobacterial activity against Mycobacterium tuberculosis with respective MIC values of 25, 25, 25, 12.5, 50, 50 and 100 m mg/ml.

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Iridoids with Anti-Inflammatory Activity from Vitex peduncularis

Cited by 61 publications

References 3 publications

Allergy-Preventive Effects of Chlorogenic Acid and Iridoid Derivatives from Flower Buds of Lonicera japonica

Allergy-Preventive Effects of Chlorogenic Acid and Iridoid Derivatives from Flower Buds of Lonicera japonica

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

Ceanothane- and Lupane-Type Triterpenes with Antiplasmodial and Antimycobacterial Activities from Ziziphus cambodiana

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