Inuloxins A–D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: Potential for broomrapes and field dodder management

Andolfi, Anna; Zermane, Nadjia; Cimmino, Alessio; Avolio, Fabiana; Boari, Angela; Vurro, Maurizio; Evidente, Antonio

doi:10.1016/j.phytochem.2012.10.003

Cited by 82 publications

(114 citation statements)

References 33 publications

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“…2014, 62, 10485−10492 mainly a phytotoxic effect, was due to the different organization of the carbon skeleton and also to their different functionalities and stereochemistry. These results were in agreement with those reported previously testing the same compounds on O. crenata 16. …”

supporting

confidence: 94%

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Effect of Fungal and Plant Metabolites on Broomrapes (Orobanche and Phelipanche spp.) Seed Germination and Radicle Growth

Cimmino¹,

Fernández‐Aparicio

Andolfi³

et al. 2014

J. Agric. Food Chem.

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Orobanche and Phelipanche species (the broomrapes) are root parasitic plants, some of which cause heavy yield losses on important crops. The development of herbicides based on natural metabolites from microbial and plant origin, targeting early stages on parasitic plant development, might contribute to the reduction of broomrape seed bank in agricultural soils. Therefore, the effect of metabolites belonging to different classes of natural compounds on broomrape seed germination and radicle development was assayed in vitro. Among the metabolites tested, epi-sphaeropsidone, cyclopaldic acid, and those belonging to the sesquiterpene class induced broomrape germination in a species-specific manner. epi-Epoformin, sphaeropsidin A, and cytochalasans inhibited germination of GR24-treated broomrape seeds. The growth of broomrape radicle was strongly inhibited by sphaeropsidin A and compounds belonging to cyclohexene epoxide and cytochalasan classes. Broomrape radicles treated with epi-sphaeropsidone developed a layer of papillae while radicles treated with cytochalasans or with sphaeropsidin A turned necrotic. These findings allow new lead natural herbicides for the management of parasitic weeds to be identified.

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supporting

confidence: 94%

“…Similar activity was also shown by some fungal terpenoids and their hemisynthetic derivatives, 13−15 while inhibitory effect was exhibited from four new sesquiterpenoids recently isolated from Inula viscosa. 16 These results prompted testing of the effect of some plant allelochemicals and several phytotoxins with very different…”

mentioning

confidence: 99%

Effect of Fungal and Plant Metabolites on Broomrapes (Orobanche and Phelipanche spp.) Seed Germination and Radicle Growth

Cimmino¹,

Fernández‐Aparicio

Andolfi³

et al. 2014

J. Agric. Food Chem.

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“…Antifeedant activity of its pyrrolizidine alkaloids (Sicilliano et al 2005). Antidiabetic activity of its aqueous extract in STZ-diabetic rats (Muhammed & Ari 2012;Al-Snafi 2014 Talib et al 2012); chlorogenic-and caffeic acids, rutin, myricetin, quercetin, luteolin and kaempferol (Gökbulut et al 2013); bi-and tri-cyclic sesquiterpene lactones; inuloxins A-D (Andolfi et al 2013). …”

Section: Introductionmentioning

confidence: 99%

“…Antioxidative, fungicidal and phytoxic effects (Andolfi et al 2013;Askarne et al 2013;Gökbulut et al 2013). Selecive antiproliferative and proapoptotic capacity in breast cancer cells; cytotoxic and genotoxic effect in A. cepa.…”

Section: Introductionmentioning

confidence: 99%

The use of medicinal herbs in gynecological and pregnancy-related disorders by Jordanian women: a review of folkloric practice vs. evidence-based pharmacology

Akour

Kasabri

Afifi

et al. 2016

Pharmaceutical Biology

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Context National statistical reports in Jordan indicate a decrease in the total fertility rate along with a parallel increase in contraceptive use. The folkloric use of medicinal herbs in gynecological disorders has been growing in Jordan, despite of deficient reports on the evidence-based safety and efficacy of these practices. Objective The aim of this comprehensive article is to review medicinal plants with claimed ethnonpharmacological usage in various gynecological and pregnancy-related issues in Jordan, and to assess their evidence-based pharmacological studies as well as their phytochemistry. Methods The published literature was surveyed using Google Scholar entering the terms ''ethnopharmacology AND Jordan AND infertility AND gynecology OR gestation''. We included ethnopharmacological surveys in Jordan with available full-text. Results Twelve articles were reviewed. Plant species which are commonly used for female gynecological issues such as Artemisia monosperma Del. and A. herba-alba Asso. (Asteraceae) have been found to exert an antifertility effect. Ricinus communis L. (Euphorbiaceae) and Citrullus colocynthis (L.) Schrad. (Cucurbitaceae) had antifertility effects in male rats, but Nigella sativa oil L. (Ranunculaceae) and Cinnamon zeylanicum J. Presl (Lauraceae) were found to enhance it. Conclusion Using plants for gynecological disorders is a common practice in Jordan. Many of them, whether utilised for gynecological or non-gynecological conditions equally, were found to have detrimental effects on female or male fertility. Thus, couples planning pregnancy should be discouraged from the consumption of these herbs. Further local studies are warranted to confirm the appreciable beneficial pharmacological effects and safety of these plants. ARTICLE HISTORY

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“…Phytotoxins can be grouped into three main classes: terpenoids, N-containing compounds, and phenolic compounds (Huang et al, 2010). Eremophilane sesquiterpenes have been shown to be an important class of secondary metabolites responsible for phytotoxic activities (Andolfi et al, 2013; Masi et al, 2014; Miranda et al, 2015; Wang et al, 2015). Various skeletons of eremophilane sesquiterpenes have been identified as major secondary metabolites in the genus Ligularia (Yang et al, 2011; Kuroda et al, 2012; Saito, 2012; Tori, 2016), and some have been reported to display phytotoxicity (Cantrell et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Phytotoxic Terpenoids from Ligularia cymbulifera Roots

et al. 2017

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Ligularia cymbulifera is one of the predominant species in the Hengduan Mountains, China, and has led to a decrease in the amount of forage grass in this area. However, little is known about the mechanism behind its predominance. In this study, two novel eremophilane sesquiterpenes, ligulacymirin A and B (1 and 2), together with seven other known terpenoids (3–9), were isolated from the roots of L. cymbulifera. The structures of 1 and 2 were determined by spectroscopic methods and single-crystal X-ray diffraction. Each compound showed phytotoxic activities against Arabidopsis thaliana, and each was detected and identified in rhizosphere soil by UHPLC-MS. Compound 3 was the most potent phytotoxin, showing remarkable inhibition against both seedling growth (EC50 = 30.33 ± 0.94 μg/mL) and seed germination (EC50 = 155.13 ± 0.52 μg/mL), with an average content in rhizosphere soil of 3.44 μg/g. These results indicate that terpenoids in L. cymbulifera roots might be released as phytotoxins in rhizosphere soil to interfere with neighboring plants.

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Inuloxins A–D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: Potential for broomrapes and field dodder management

Cited by 82 publications

References 33 publications

Effect of Fungal and Plant Metabolites on Broomrapes (Orobanche and Phelipanche spp.) Seed Germination and Radicle Growth

Effect of Fungal and Plant Metabolites on Broomrapes (Orobanche and Phelipanche spp.) Seed Germination and Radicle Growth

The use of medicinal herbs in gynecological and pregnancy-related disorders by Jordanian women: a review of folkloric practice vs. evidence-based pharmacology

Phytotoxic Terpenoids from Ligularia cymbulifera Roots

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