Arbuscular mycorrhizal fungus-induced changes in the accumulation of secondary compounds in barley roots

Peipp, Heinrich; Maier, W.; Schmidt, Jürgen; Wray, Victor; Strack, Dieter

doi:10.1016/s0031-9422(96)00561-4

Cited by 101 publications

(64 citation statements)

References 35 publications

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“…The absolute stereochemistry of C-9 was determined to be 9S by comparison of the chemical shift values of the related compounds, which have same planer structure except for 13-OH. 8) As described above, the 13 C-NMR chemical shifts of C-9 in (9R)-and (9S)-megastigma-4,7-dien-3-on-9-ol 9-O-b-D-glucopyranoside to be d C 77.0 and 74.7, respectively. 8) Therefore, the absolute configuration at C-9 (d C 74.9) of 5 was assigned as 9S.…”

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confidence: 85%

“…As a result, the structure of compound 2 was established to be (6S,9R)-megastigman-4-en-3-one-6,9-diol 9-O-(6Ј-O-galloyl)-b-D-glucopyranoside. Macarangioside B (3) was obtained as an amorphous powder and its elemental composition was determined to be C 26 H 34 O 12 by HR-FAB-MS. 1 H-and 13 C-NMR spectra indicated that macarangioside B (3) also have a megastigmane skeleton (Tables 1, 2). However, one of the methyl signals was converted to an oxygenated methylene carbon.…”

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confidence: 99%

“…Thus, the position of the glucopyranosyl and galloyl moieties was determined to be the same as compound 1 and 2. 13 C chemical shift value of C-9 is diagnostic in assigning the absolute configuration at C-9 in ionol glucosides, i.e., an upfield shift of C-9 is indicative for the (9S)-configuration whereas lower field signal for 9R. For example, 13 C-NMR chemical shifts of C-9 in (9R)-and (9S)-megastigma-4,7-dien-3-one-9-ol 9-O-b-D-glucopyranoside are d C 77.0 and 74.7, respectively.…”

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confidence: 99%

“…13 C chemical shift value of C-9 is diagnostic in assigning the absolute configuration at C-9 in ionol glucosides, i.e., an upfield shift of C-9 is indicative for the (9S)-configuration whereas lower field signal for 9R. For example, 13 C-NMR chemical shifts of C-9 in (9R)-and (9S)-megastigma-4,7-dien-3-one-9-ol 9-O-b-D-glucopyranoside are d C 77.0 and 74.7, respectively. 8) Therefore, the absolute configuration of 3 at C-9 was determined to be 9R by the comparison of chemical shift value (d C 78.0 at C-9).…”

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confidence: 99%

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Radical-Scavenging Activities of New Megastigmane Glucosides from Macaranga tanarius (L.) MUELL.-ARG.

et al. 2006

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Megastigmanes and its glycosides are a currently expanding class of compounds. In our continuation of the studies on the sub-tropical plants collected on Okinawa Island, we have phytochemically investigated the leaves of Macaranga tanarius (L.) MÜLL.-ARG. (Euphorbiaceae). M. tanarius is well known as a pioneer tree and also an ant-plant. It is defended by ants against herbivores by producing the ant-attracting food body.1) This plant can be found throughout eastern and southern Asia, especially in southern China, Korea and Japan. In China, root and bark of this plant are used for hemoptysis and dysentery, respectively.2) In this paper, we describe the isolation and structure elucidation of four new megastigmane glucosides (2-5) together with five known compounds (1, 6-9), and then discuss about the structural feature on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicalscavenging activity of these compounds. Results and DiscussionAir-dried leaves (12.1 kg) of M. tanarius were extracted with MeOH (15 lϫ3) by maceration, and then the combined methanolic extracts were evaporated under reduced pressure. The MeOH extract concentrated to 3 l was defatted with nhexane (3 l), and the remaining MeOH extract was concentrated to viscous gum. The residue was suspended in H 2 O (3 l) and partitioned with EtOAc (3 l) and n-BuOH (3 l) successively to give EtOAc-(801 g) and n-BuOH-(374 g) soluble fractions, respectively. Part of the n-BuOH-soluble fraction (181 g) was subjected to various kinds of column chromatography on a highly porous synthetic polymer (Diaion HP-20), silica gel, ODS, droplet counter-current chromatography (DCCC) and HPLC (ODS) to give the above-mentioned nine compounds (1-9) (Fig. 1).Compound 1 was obtained as an amorphous powder. Methanolysis of 1 with 0.1 M NaOMe gave 1a, (6S,9R)-roseoside.3) The presence of D-glucose was also confirmed by acid hydrolysis of 1a and derivatization with (S)-(Ϫ)-amethylbenzylamine.4) The 13 C-and 1 H-NMR spectra indicated the presence of a galloyl moiety (Tables 1, 2). From these results, compound 1 was identified as mallophenol B isolated from Mallotus furetianus.5) It is noteworthy that a 6Ј-O-galloyl moiety doesn't influence the chemical shift values of aglycone moiety and the cotton effect of CD spectrum by comparison of the physical data of 1 and 1a.Macarangioside A (2) was obtained as an amorphous powder and its elemental composition was determined to be C 26 Nishihara-cho, Nakagami-gun, Okinawa 903-0129, Japan: c Iriomote Station, Tropical Biosphere Research Center, University of the Ryukyus; 870 Aza Uehara, Taketomi-cho, Yaeyama-gun, Okinawa 907-1541, Japan: d Division of Foods, National Institute of Health Sciences; Japan: and e

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confidence: 85%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Radical-Scavenging Activities of New Megastigmane Glucosides from Macaranga tanarius (L.) MUELL.-ARG.

et al. 2006

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“…The high abundance of hordatines in the young barley seedling (Stoessl, 1967) suggests that hordatines are preformed infection inhibitors (Stoessl & Unwin, 1970;Smith & Best, 1978). Recent studies showed that the biosynthesis of hydroxycinnamoyl agmatine derivatives, the precursors of hordatines, are strongly induced in response to fungal inocculation even in older leaves of barley (Peipp et al, 1997, von Roepenack, Parr & Schulze-Lefert, 1998.…”

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Correlation between hordatine accumulation, environmental factors and genetic diversity in wild barley (Hordeum spontaneum C. Koch) accessions from the Near East Fertile Crescent

et al. 2006

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Wild barley shows a large morphological and phenotypic variation, which is associated with ecogeographical factors and correlates with genotypic differences. Diversity of defense related genes and their expression in wild barley has been recognized and has led to attempts to exploit genes from H. spontaneum in breeding programs. The aim of this study was to determine the variation in the accumulation of hordatines, which are Hordeum-specific preformed secondary metabolites with strong and broad antimicrobial activity in vitro, in 50 accessions of H. spontaneum from different habitats in Israel. Differences in the accumulation of hordatines in the seedling stage were significant between different H. spontaneum genotypes from different regional locations and micro-sites. Variation in the hordatine accumulation within genotypes was between 9% and 45%, between genotypes from the same location between 13% and 38%, and between genotypes from different locations up to 121%. Principal component analysis showed that water related factors explain 39%, temperature related factors explain 33% and edaphic factors account for 11% of the observed variation between the populations of H. spontaneum. Genetic analysis of the tested accessions with LP-PCR primers that are specific for genes involved in the biosynthetic pathway of hordatines showed tight correlations between hordatine abundance and genetic diversity of these markers. Multiple regression analyses indicated associations between genetic diversity of genes directly involved in hordatine biosynthesis, ecogeographical factors and the accumulation of hordatines.

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Combined mass spectrometric and chromatographic methods for in-depth analysis of phenolic secondary metabolites in barley leaves

et al. 2015

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Structural analysis via HPLC-ESI-MSn, UPLC-HESI-MS/MS and NMR reported 152 phenolic secondary metabolites in spring barley seedlings (Hordeum vulgare L.). Flavonoids with various patterns of glycosylation and acylation, as well as hydroxycinnamic acid glycosides, esters and amides, were identified in methanolic extracts from leaves of nine varieties of barley originating from different regions of the world. Hordatines derivatives, flavones acylated directly on the aglycone, and hydroxyferulic acid derivatives deserve special attention. Preparative chromatography enabled characterization of a number of compounds at trace levels with the 6-C-[6″-O-glycosyl]-glycosides and the 6-C-[2″,6″-di-O-glycosides]-glucoside structure of flavones. Derivatives of flavonols, quercetin and isorhamnetin were observed only in Syrian varieties. The ultra performance liquid chromatography profiles of UV-absorbing secondary metabolites were used for chemotaxonomic comparison between nine varieties of barley from different climatic conditions. The hierarchical clustering of bred lines from the Fertile Crescent and European and American varieties indicates a great diversity of chemical phenotypes within barley species.

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Arbuscular mycorrhizal fungus-induced changes in the accumulation of secondary compounds in barley roots

Cited by 101 publications

References 35 publications

Radical-Scavenging Activities of New Megastigmane Glucosides from Macaranga tanarius (L.) MUELL.-ARG.

Radical-Scavenging Activities of New Megastigmane Glucosides from Macaranga tanarius (L.) MUELL.-ARG.

Correlation between hordatine accumulation, environmental factors and genetic diversity in wild barley (Hordeum spontaneum C. Koch) accessions from the Near East Fertile Crescent

Combined mass spectrometric and chromatographic methods for in-depth analysis of phenolic secondary metabolites in barley leaves

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