The quantitative isolation and antimicrobial activity of the aglycone of aucubin

Davini, Enrico; Javarone, Carlo; Trogolo, Corrado; Aureli, Paolo; Pasolini, Beatrice

doi:10.1016/s0031-9422(00)81711-2

Cited by 60 publications

(28 citation statements)

References 14 publications

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“…Antimicrobial activity of iridoid aglycones has previously been documented for a variety of different iridoid compounds (Ishiguro et al 1982;Van der Sluis et al 1983) and for a variety of different microorganisms (Rombouts and Links 1956;Davini et al 1986). The strength of inhibitory effects appears to depend both on the type of iridoid and on the type of micro-organism.…”

Section: Discussionmentioning

confidence: 96%

Two herbivore-deterrent iridoid glycosides reduce the in-vitro growth of a specialist but not of a generalist pathogenic fungus of Plantago lanceolata L

2002

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Many secondary plant compounds are involved in defense against both insect herbivores and pathogens. Two secondary plant compounds of Plantago lanceolata, the iridoid glycosides catalpol and its precursor aucubin, are well known for their deterrent effects on generalist and nonadapted specialist insect herbivores. We tested the effects of these compounds on the in-vitro growth of a specialist and generalist fungal pathogen of this host species. Two chemical forms of these iridoids were tested. The glycosides and their aglycones, the products of enzymatic conversion by specific β-glucosidase enzymes. The glycosides enhanced growth of both the specialist fungus Diaporthe adunca and the generalist fungus Fusarium moniliforme var. subglutinans. The positive effect of these glycosides on the generalist fungus is in sharp contrast with the generally negative effects of these glysosides on generalist insect herbivores. The aglycones of aucubin and catalpol reduced the growth of the specialist fungus D. adunca, but, contrary to expectation, enhanced the growth of the generalist fungus F. moniliforme var. subglutinans. Effects of aucubin on D. adunca were stronger than effects of catalpol. This was true both for the growth stimulating effects of the glycosides and for the fungitoxic effects of the aglycones. We therefore expect that the effects of these iridoids in P. lanceolata on the specialist fungus will strongly depend on the ratio between catalpol and its precursor aucubin and the chemical form (glycoside or aglycone) in which these compounds are encountered by the fungus during growth. Our results suggest that iridoid glycosides in P. lanceolata can be used as defense against both herbivores and pathogens, but that their effects are highly specific with respect to the natural enemy species that is encountered.

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Section: Discussionmentioning

confidence: 96%

Two herbivore-deterrent iridoid glycosides reduce the in-vitro growth of a specialist but not of a generalist pathogenic fungus of Plantago lanceolata L

2002

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“…Solid phase extraction of the polar extract from S. umbrosa pursued HPLC analysis of the MeOH extract of aerial parts (10% fraction) and MeOH extract of seed (40% fraction) led to identification of iridoid and flavonoid structures. Compounds 1 and 2 were identified as aucubin (A) and Luteolin-7-Orutinoside (B) through straight analogy of spectroscopic results with data published in the literature (18)(19)(20)(43)(44)(45)(46).…”

Section: Discussionmentioning

confidence: 64%

Evaluation of Phytochemistry and Some Biological Activities of Aerial Parts and Seed of Scrophularia Umbrosa Dumort

Nikkhah

Afshar

Babaei

et al. 2017

Jundishapur J Nat Pharm Prod

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Background: Scrophularia umbrosa is a plant used as a traditional herb. Objectives: This study was designed to investigate the antimalarial activity and free radical scavenging of methanol, DCM and nHexane extract of aerial parts and seed, as well as total phenol, total flavonoid content, and phytochemical identification. Methods: GC-MS techniques were used for identification of the chemical composition of the DCM and n-Hexane extract as well as HPLC and NMR techniques for methanolic extract. The hemozoin formation has been suggested as a desirable drug target to antimalaria sieve scheme. In the present study, we used the spectrophotometric assay to screen plant extracts. The DPPH method has been used for antioxidant activity screening of the extracts and fractions. AlCl3 and Folin -Ciocalteu reagents, respectively, were used for total flavonoid and total phenol content of the samples. Results: Our results showed that n-hexane and the MeOH extracts, aerial part, and seed did not display any impressive prevention of heme biocrystallization confidants, however, the DCM extract of aerial part, in comparison with the blank, showed slightly antimalarial effects. Furthermore, fractions (20%, 40%, and 60%) of MeOH extracts of aerial part and seed of S. umbrosa had moderate to strong antioxidant activity and it is possible to conclude that there is a positive relation between phenolic and flavonoid composition as well as antioxidant activity. GC-MS data showed that volatile portions of DCM and n-Hexane extracts of various organs from S. umbrosa are containing few identifiable compounds. In addition, Aucubin and Luteolin-7-O-rutinoside were also recognized from MeOH extracts. Conclusions: Based on the results, the fractions of extracts could be evaluated by 1HNMR for predicting of groups of natural compounds as well as interfacing chemical and biological assessments.

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“…Besides anticancer activity, iridoids have additional pharmaceutical potentials that provide valuable resources for the development of novel drugs and therapeutic strategies against diverse diseases [7][8][9]. In the natural environment, iridoids benefit plants by preventing microbial invasions [10][11][12][13][14], and by repelling herbivorous vertebrates and invertebrates [10,15,16].…”

Section: Introductionmentioning

confidence: 99%

Deciphering the route to cyclic monoterpenes in Chrysomelina leaf beetles: source of new biocatalysts for industrial application?

Burse

Boland

2017

Zeitschrift Für Naturforschung C

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Abstract:The drastic growth of the population on our planet requires the efficient and sustainable use of our natural resources. Enzymes are indispensable tools for a wide range of industries producing food, pharmaceuticals, pesticides, or biofuels. Because insects constitute one of the most species-rich classes of organisms colonizing almost every ecological niche on earth, they have developed extraordinary metabolic abilities to survive in various and sometimes extreme habitats. Despite this metabolic diversity, insect enzymes have only recently generated interest in industrial applications because only a few metabolic pathways have been sufficiently characterized. Here, we address the biosynthetic route to iridoids (cyclic monoterpenes), a group of secondary metabolites used by some members of the leaf beetle subtribe Chrysomelina as defensive compounds against their enemies. The ability to produce iridoids de novo has also convergently evolved in plants. From plant sources, numerous pharmacologically relevant structures have already been described. In addition, in plants, iridoids serve as building blocks for monoterpenoid indole alkaloids with broad therapeutic applications. As the commercial synthesis of iridoidbased drugs often relies on a semisynthetic approach involving biocatalysts, the discovery of enzymes from the insect iridoid route can account for a valuable resource and economic alternative to the previously used enzymes from the metabolism of plants. Hence, this review illustrates the recent discoveries made on the steps of the iridoid pathway in Chrysomelina leaf beetles. The findings are also placed in the context of the studied counterparts in plants and are further discussed regarding their use in technological approaches.

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The quantitative isolation and antimicrobial activity of the aglycone of aucubin

Cited by 60 publications

References 14 publications

Two herbivore-deterrent iridoid glycosides reduce the in-vitro growth of a specialist but not of a generalist pathogenic fungus of Plantago lanceolata L

Two herbivore-deterrent iridoid glycosides reduce the in-vitro growth of a specialist but not of a generalist pathogenic fungus of Plantago lanceolata L

Evaluation of Phytochemistry and Some Biological Activities of Aerial Parts and Seed of Scrophularia Umbrosa Dumort

Deciphering the route to cyclic monoterpenes in Chrysomelina leaf beetles: source of new biocatalysts for industrial application?

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