Structures of the natural products blumenols A, B, and C

Galbraith, M. N.; Horn, D. H. S.

doi:10.1039/c39720000113

Cited by 72 publications

(29 citation statements)

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“…The spectroscopic data of the disaccharide moiety and those of the aglycone, compared with literature data (Galbraith and Horn, 1972;Miyase et al, 1988), unambiguously identified blumenin as a new natural blumenol C glycoside. With regard to the elucidation of the structure and its occurrence, there is no systematic distribution of blumenol C and its conjugates in plants.…”

Section: Discussionmentioning

confidence: 97%

“…With regard to the elucidation of the structure and its occurrence, there is no systematic distribution of blumenol C and its conjugates in plants. The aglycone of blumenin, blumenol C, was found for the first time, together with its possible deriv a t' ives blumenol A and B, in leaves of Podocarpus blumei (Podocarpaceae) (Galbraith and Horn, 1972). A blumenin-related glycoside, blumenol C glucoside, has been isolated from leaves of Nicotiana rustica (Solanaceae) (Kodama et al, 1984) and Isatis tinctoria (Brassicaceae) (Hartleb and Seifert, 1994) and the aerial parts of Epimedium grandiflorum (Berberidaceae) (Miyase et al, 1988).…”

Section: Discussionmentioning

confidence: 99%

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Levels of a Terpenoid Glycoside (Blumenin) and Cell Wall-Bound Phenolics in Some Cereal Mycorrhizas

et al. 1995

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~Four cereals, Hordeum vulgare (barley), Triticum aestivum (wheat), Secale cereale (rye), and Avena safiva (oat), were grown in a defined nutritional medium with and without the arbuscular mycorrhizal fungus Glomus intraradices. Levels of soluble and cell wall-bound secondary metabolites in the roots of mycorrhizal and nonmycorrhizal plants were determined by high-performance liquid chromatography during the first 6 to 8 weeks of plant development. Whereas there was no difference in the levels of the cell wall-bound hydroxycinnamic acids, 4-coumaric and ferulic acids, there was a fungus-induced change of the soluble secondary root metabolites. The most obvious effect observed in all four cereals was the induced accumulation of a terpenoid glycoside. This compound was isolated and identified by spectroscopic methods (nuclear magnetic resonance, mass spectrometry) to be a cyclohexenone derivative, i.e. blumenol C 9-0(2'-D~-glucuronosyl)-~-glucoside. The level of this compound was found to be directly correlated with the degree of root colonization.Arbuscular mycorrhizas are universally found symbiotic associations between plant roots and certain fungi, and there is ample evidence that these symbioses are of significant benefit for plants (reviewed by Powell and Bagyaraj, 1984; Gianinazzi and Schüepp, 1994). These benefits include enhanced nutrient supply (e.g. phosphate) and increased resistance to pathogen attack (e.g. root pathogenic fungi) or stress (e.g. drought). Despite increasing efforts in research on arbuscular mycorrhiza at the cellular and molecular levels within the last years Dixon, 1993, 1994;Dumas-Gaudot et al., 1994), very little is known about the basic biochemical interactions between the symbionts leading to formation of arbuscular mycorrhiza and maintenance of an active symbiotic relationship. This is in sharp contrast to our knowledge about pathogenic plantfungus interactions .There is increasing evidence that secondary compounds in particular play a significant role in the interactions occurring between plants and their natural environment (Harborne, 1988). In this respect, secondary metabolites of roots might play an important role in mycorrhizal symbiosis. It has been documented, for example, that flavonoids promote spore germination of arbuscular mycorrhizal 'This work was supported by the Fonds der Chemischen * Corresponding author; fax 49-345-5582-106.Industrie.fungi (Gianinazzi-Pearson et al., 1989;Tsai and Phillips, 1991). Colonization of plants with arbuscular mycorrhizal fungi may lead to marked systemic reactions in terpenoid metabolism. Thus, Glomus intraradices induces accumulation of significant amounts of leaf sesquiterpenoids in Citrus jambkiri (Nemec and Lund, 1990). The sesquiterpenoid ABA reaches considerably higher levels in Glomus-colonized maize than in control plants (Danneberg et al., 1993).As part of our studies of arbuscular mycorrhizal fungiinduced changes in secondary metabolism of cereals, we report here quantitative changes of root secondary products during form...

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Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

Levels of a Terpenoid Glycoside (Blumenin) and Cell Wall-Bound Phenolics in Some Cereal Mycorrhizas

et al. 1995

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“…,32) The asymmetric center in the side chain of the isolated compound displayed an optical rotation and the absolute configuration at C(9) was shown to be R. This fact indicates that in the degradation pathway of carotenoids to (45) OH o (39) o (56) (25) The numbers in parentheses express the compound number in Table II. 3-oxo-a-ionol, at least one enzymatic reaction is probable. Thus, the elucidation of the stereochemistry of the side chain in 3-hydroxy-,'1-ionol and 3-hydroxy-7,8-dehydro-,'1-ionol seem to be of great interest from the view point of the degradation mechanism of carotenoids.…”

Section: Lomentioning

confidence: 99%

“…12 ) 3-0xo-7,8-dihydroa-ionol (Blumenol C) has been reported to be present in the leaves of Rodocarpus blumei. 25 ) With respect to the configuration of the hydroxyl group, 3-hydroxy-{i-ionone has the same configuration as zeaxanthin. 26 ) This supports the assumption that 3-hydroxy-pionone is formed by the oxidative degradation of carotenoids such as zeaxanthin which has 3-hydroxyl group.…”

Section: Degradation Products Of Carotenoidsmentioning

confidence: 99%

Neutral Aroma Constituents in Burley Tobacco

Fujimori

Kasuga

Matsushita

et al. 1976

Agricultural and Biological Chemistry

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“…The aglycone of blumenin, blumenol C, was first isolated from leaves of Podocarpus blumei. 43) Blumenin and a number of related cyclohexenone derivatives have been found in the AM roots of most gramineous plants, O. umbellatum, and solanaceous tobacco and tomato, and also the model legumes L. japonicus and Medicago truncatula. [44][45][46][47] These compounds differ in ring substitutions and in the nature and degree of glycosylation, including sugar moieties modified with a malonyl group.…”

Section: Am-specific Accumulation Of Mycorradicin and Cyclohexenomentioning

confidence: 99%

Chemical Identification and Functional Analysis of Apocarotenoids Involved in the Development of Arbuscular Mycorrhizal Symbiosis

Akiyama

2007

Bioscience, Biotechnology, and Biochemistry

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Arbuscular mycorrhizae formed between more than 80% of land plants and arbuscular mycorrhizal (AM) fungi represent the most widespread symbiosis on the earth. AM fungi facilitate the uptake of soil nutrients, especially phosphate, by plants, and in return obtain carbohydrates from hosts. Apocarotenoids, oxidative cleavage products of carotenoids, have been found to play a critical role in the establishment of AM symbiosis. Strigolactones previously isolated as seed-germination stimulants for root parasitic weeds act as a chemical signal for AM fungi during presymbiotic stages. Stimulation of carotenoid metabolism, leading to massive accumulation of mycorradicin and cyclohexenone derivatives, occurs during root colonization by AM fungi. This review highlights research into the chemical identification of arbuscular mycorrhiza-related apocarotenoids and their role in the regulation and establishment of AM symbiosis conducted in the past 10 years.

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Structures of the natural products blumenols A, B, and C

Cited by 72 publications

References 0 publications

Levels of a Terpenoid Glycoside (Blumenin) and Cell Wall-Bound Phenolics in Some Cereal Mycorrhizas

Levels of a Terpenoid Glycoside (Blumenin) and Cell Wall-Bound Phenolics in Some Cereal Mycorrhizas

Neutral Aroma Constituents in Burley Tobacco

Chemical Identification and Functional Analysis of Apocarotenoids Involved in the Development of Arbuscular Mycorrhizal Symbiosis

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