Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity

Zhang, Liuqiang; Zhu, Tiantian; Qian, Fei; Xu, Jin-Wen; Dorje, Gaawe; Zhao, Zhili; Guo, Fujiang; Li, Yiming

doi:10.1016/j.fitote.2014.07.005

Cited by 42 publications

(23 citation statements)

References 19 publications

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“…melissophyllum brought us to the isolation and the identification of five compounds namely monomelittoside (1) (Scarpati & Esposito 1967a), melittoside (2) (Bobbitt et al 1967;Scarpati & Esposito 1967b), harpagide (3) acetyl-harpagide (4) (Scarpati et al 1965), ajugoside (5) (Guiso et al 1974) and allobetonicoside (6) (Jeker et al 1989). These are iridoid glycosides occurring in many medicinal plants belonging to Lamiaceae, Plantaginaceae and Scrophulariaceae families, where they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy both in vitro and in vivo as well as to the antioxidant activity of these plants (Zhang et al 2011;Háznagy-Radnai et al 2012;Erukainure et al 2014;Zhang et al 2014). Compounds 1, 2, 3, 4 and 5 had been already evidenced in this species (Scarpati et al 1965;Scarpati & Esposito 1967a, 1967b, Guiso et al 1974 and their presence was also confirmed in this study.…”

Section: Resultssupporting

confidence: 81%

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

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Frezza

Guarcini

et al. 2015

Natural Product Research

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The analysis of the polar fraction of Melittis melissophyllum L. subsp. melissophyllum led to the identification of several iridoid glycosides: monomelittoside (1), melittoside (2), harpagide (3), acetyl-harpagide (4) and ajugoside (5). Compounds 3 and 4 are considered marker compounds for the genus and, as well as compounds 1, 2 and 5, were already evidenced in a previous study on the nominal species. It was noteworthy of the presence of allobetonicoside (6) which was never reported for this genus. The isolation of 6 is very relevant because of its allose residue on the structure. Allose has been often found in the species of the subfamily Lamioideae even if it mostly regarded flavonoids considered of chemotaxonomical relevance for some correlated genera of Lamiaceae. Same as allosyl-glycosidic flavonoids, the presence of allosyl-glycosidic iridoids may also be an additional chemosystematic evidence of botanical relationships among Lamiaceae species and genera.

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Section: Resultssupporting

confidence: 81%

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Venditti

Frezza

Guarcini

et al. 2015

Natural Product Research

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“…A number of promising new agents are in clinical development based on selective activity against cancer-related molecular targets, including flavopiridol and combretastatin a4 phosphate, while some agents which failed in earlier clinical studies are stimulating renewed interest [33]. Iridoid glycosides and their hydrolysed products which isolated from Scrophularia species have been shown to have cytotoxic and anticancer effects against gastric cancer, Hela Cervix carcinoma cell line, myeloid leukemia K562 and MNK-45 cell lines [34][35][36][37][38]. Natural anticancer and cytotoxic compounds are important in different area of cancer research and determining their possible mechanisms can leads to their proper use in cancer treatment.…”

Section: Discussionmentioning

confidence: 99%

Apoptosis and Caspase 3 Pathway Role on Anti-Proliferative Effects of Scrophulariaoxy Sepala Methanolic Extract on Caco-2 Cells

et al. 2017

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Colorectal cancer is one the most important malignancies worldwide and finding new treatment option for this cancer is of high priority. Natural compounds are common source of drugs for treatment of various diseases including cancers. The aim of this study was to investigate the effects of Scrophularia oxysepala extract on Caco-2 cells and explore the possible role of caspase 3 pathway in inducing cell death in this cancer cells in compare with chemotherapy agents of cisplatin and capecitabine. The methanolic extract of Scrophularia oxysepala (SO) was prepared by drench method. The IC50 of extract, cisplatin and capecitabine on Caco-2 cells were determined by MTT assay. The effect of SO extract on caspase 3 expression and inducing apoptosis were determined using TUNEL assay and caspase 3 ELISA methods, respectively. The IC50 of SO extract, cisplatin and capecitabine were 300, 195 and 80 µg/ml, respectively. Analysis for apoptosis revealed that SO methanolic extract increased apoptosis significantly (P<0.001) compared with control group. The effect of high doses of SO extract on apoptosis induction were comparable to cisplatin but significantly were higher than capecitabine. Only high doses of SO methanolic extract showed significant effects (P<0.05) on increasing caspase 3 compared to control group. The methanolic extract of SO showed inhibitory effect on Caco-2 cells and induced apoptosis in a dose-dependent manner comparable to cisplatin and higher than capecitabine 2 commonly used chemotherapeutic agent for various cancers.

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“…To our knowledge, distinct species of the Scrophularia genus have an anti-inflammatory potential. In this context, the iridoids (scropolioside B and scropolioside D) isolated from S. denata were shown to exhibit anti-inflammatory effects in an NF-κB-mediated reporter gene luciferase assay [39]. Verbascosaponin isolated from S. auriculata strongly inhibited the carrageenan paw edema and ear edema induced by 12-O-tetradecanoylphorbol 13-acetate (TPA test) [40].…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Scrophularia Tenuipes Coss and Durieu: Phytochemical Composition and Biological Activities

et al. 2020

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Scrophularia tenuipes is an Algerian-Tunisian endemic species, which has not been studied yet. Ethyl acetate (EA) and n-butanol (Bu) fractions obtained from Scrophularia tenuipes were investigated for their health benefit properties, in particular with respect to in vivo/in vitro anti-inflammatory and antioxidant activities, as well as their potential to inhibit key enzymes with impact in diabetes (α-glucosidase and α-amylase). The fractions had a distinct phytochemical composition, of which EA was richer in total phenolic compounds (225 mg GAE/g) and mostly composed of the phenylethanoid acetyl martynoside. Compared to EA, Bu had higher amounts of total flavonoids, and according to the result obtained from UHPLC-DAD-ESI-MSn analysis, harpagoside (iridoid) was its major phytochemical. EA fraction was quite promising with regard to the in vivo (at 200 mg/kg, po) anti-inflammatory effect (62% and 52% for carrageenan-induced rat paw edema and xylene-induced ear edema tests, respectively), while Bu fraction exhibited a stronger antioxidant capacity in all tests (IC50 = 68 µg/mL, IC50 = 18 µg/mL, IC50 = 18 µg/mL and A0.50 = 43 µg/mL for DPPH●, ABTS•+, O2•− scavenging assays and cupric-reducing antioxidant capacity method, respectively). Both fractions also showed a strong effect against α-amylase enzyme (IC50 = 8 µg/mL and 10 µg/mL for EA and Bu fraction, respectively).

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Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity

Cited by 42 publications

References 19 publications

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Apoptosis and Caspase 3 Pathway Role on Anti-Proliferative Effects of Scrophulariaoxy Sepala Methanolic Extract on Caco-2 Cells

Scrophularia Tenuipes Coss and Durieu: Phytochemical Composition and Biological Activities

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