Iridoid Glucosides and p-Coumaroyl Iridoids from Viburnum luzonicum and Their Cytotoxicity

Fukuyama, Yoshiyasu; Minoshima, Yuka; Kishimoto, Yoshiko; Chen, Ih-Sheng; Takahashi, Hironobu; Esumi, Tomoyuki

doi:10.1021/np040138l

Cited by 40 publications

(33 citation statements)

References 16 publications

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“…Although some of the tested flavonoids did not show a cytotoxicity in the present assay against MT-4 cells, some of them have been however shown to be toxic to a number of tumor cell lines supporting thus their important role in the prevention of prostate, breast, and colon cancers (Gâlvez et al, 2003;Kobayashi et al, 2002;Le Bail et al, 1998) or against human leukemia cell line HL-60 (Sonoda et al, 2004). The four new iridoids isolated from Morinda morindoides did not show a cytototoxic effect against MT-4 cells and this is in good agreement with Murakami et al (2002) who reported the same effect for other iridoids against the same cell-lines However, other types of iridoids isolated from other plant species have been reported to be toxic against different cell lines (Fukuyama et al, 2004(Fukuyama et al, , 2005Kumarasamy et al, 2003).…”

Section: Discussionsupporting

confidence: 81%

Cytotoxicity and in vitro susceptibility of Entamoeba histolytica to Morinda morindoides leaf extracts and its isolated constituents

Cimanga

Kambu

Tona

et al. 2006

Journal of Ethnopharmacology

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Section: Discussionsupporting

confidence: 81%

Cytotoxicity and in vitro susceptibility of Entamoeba histolytica to Morinda morindoides leaf extracts and its isolated constituents

Cimanga

Kambu

Tona

et al. 2006

Journal of Ethnopharmacology

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“…Furthermore, the presence of terpenes as major components in the ethyl acetate extract may explain its high cytotoxic activity. In fact, the anti-cancer potential of these products has been recently reported (23)(24)(25)(26). The molecular mechanisms of these purified components have not been well characterized.…”

Section: Discussionmentioning

confidence: 99%

Anti-tumor properties of blackseed (Nigella sativa L.) extracts

Mbarek

Mouse

Elabbadi

et al. 2007

Braz J Med Biol Res

170

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The objective of the present study was to evaluate the in vitro and in vivo anti-cancer effect of Nigella sativa L. seed extracts. The essential oil (IC 50 = 0.6%, v/v) and ethyl acetate (IC 50 = 0.75%) extracts were more cytotoxic against the P815 cell line than the butanol extract (IC 50 = 2%). Similar results were obtained with the Vero cell line. Although all extracts had a comparable cytotoxic effect against the ICO1 cell line, with IC 50 values ranging from 0.2 to 0.26% (v/v), tests on the BSR cell line revealed a high cytotoxic effect of the ethyl acetate extract (IC 50 = 0.2%) compared to the essential oil (IC 50 = 1.2%). These data show that the cytotoxicity of each extract depends on the tumor cell type. In vivo, using the DBA2/P815 (H 2 d ) mouse model, our results clearly showed that the injection of the essential oil into the tumor site significantly inhibited solid tumor development. Indeed, on the 30th day of treatment, the tumor volume of the control animals was 2.5 ± 0.6 cm 3 , whereas the tumor volumes of the essential oil-treated animals were 0.22 ± 0.1 and 0.16 ± 0.1 cm 3 when the animals were injected with 30 µL (28.5 mg)/mouse and 50 µL (47.5 mg)/mouse per 48 h (six times), respectively. Interestingly, the administration of the essential oil into the tumor site inhibited the incidence of liver metastasis development and improved mouse survival. CorrespondenceA. Zyad

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“…Iridoid glucosides 181 and 182 and their aglycones (185-189) exhibited moderate inhibitory activity with IC 50 values of 3-7 mM, whereas compound 183 and 184 showed no cytoxicity even at 100 mM. 84) Furthermore, cytotoxic iridoids 181, 182 and 185-189 also inhibited the growth and the cell viability in primary-cultured rat cortical neurons at 10 mM. 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.…”

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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Iridoid Glucosides and p-Coumaroyl Iridoids from Viburnum luzonicum and Their Cytotoxicity

Cited by 40 publications

References 16 publications

Cytotoxicity and in vitro susceptibility of Entamoeba histolytica to Morinda morindoides leaf extracts and its isolated constituents

Cytotoxicity and in vitro susceptibility of Entamoeba histolytica to Morinda morindoides leaf extracts and its isolated constituents

Anti-tumor properties of blackseed (Nigella sativa L.) extracts

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

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