Glucosides of ionone-related compounds in several nicotiana species

Kodama, Hisashi; Fujimori, Takahiro; Katö, Kunio

doi:10.1016/s0031-9422(00)80386-6

Cited by 41 publications

(19 citation statements)

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“…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). The most obvious effect observed in changes of secondary products of a11 four cereal roots was the fungus-induced accumulation of blumenin.…”

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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~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: 99%

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

et al. 1995

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“…Analyses of eight species of the genus Nicotiana revealed that they were present as glycosides also in the fresh leaves, and that part of the free ionone-related compounds in tobacco was derived from those glycosides by pglucosidase during the ageing and curing process. 45 The glycosides proved to have a high smoke transfer rate (about 10%) influencing the smoke flavour. Furthermore, the bound character of the aroma compounds is essential for inducing an improved flavour.…”

Section: Glycosidically Bound Volatiles In Tobacco and Black Teamentioning

confidence: 99%

Glycosidically bound volatiles—a review 1986–1991

Stahl‐Biskup

Intert

Holthuijzen

et al. 1993

Flavour & Fragrance J

147

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Five years ago, in 1986, only a limited number of glycosidically bound volatiles were known and little could be reported on the distribution of those compounds in the plant kingdom. Since then an explosion of research activities in this field has led to the publication of many interesting results concerning structurally diverse terpenoid and non-terpenoid glycosides, their occurrence, and their role in different plant species. Up to now, about 200 different aglycone structures have been found in about 150 species belonging to 35 different families including ferns, gymnosperms, dicotyledons, and monocotyledons.All the diverse results concerning the role of these compounds in the plants should not lead us into ascribing to them an exclusive role, such as being involved in essential oil metabolism, as early workers have postulated. Although considering new electron microscopical observations of a transformation of carbohydrate-rich substances into lipophilic droplets at the tonoplast of Menha x piperitu secretory cells, the range of possible roles should not be underestimated. New experimental work should not only provide new analytical data but should also attempt to throw more light on the role of the glycosides.

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“…Isomeric glucosides of 3-hydroxy-5,6-epoxy-Pionol (18) have been characterized in Nicotiuna ssp. ,29 Prunus s p i n o s~'~ and apple tree leaves.% The free aglycon has been also found in nature.…”

Section: I 44 45mentioning

confidence: 99%

C₁₃‐Norisoprenoid glycosides in plant tissues: An overview on their occurrence, composition and role as flavour precursors

Winterhalter

Schreier

1994

Flavour & Fragrance J

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Glucosides of ionone-related compounds in several nicotiana species

Cited by 41 publications

References 5 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

Glycosidically bound volatiles—a review 1986–1991

C₁₃‐Norisoprenoid glycosides in plant tissues: An overview on their occurrence, composition and role as flavour precursors

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Glucosides of ionone-related compounds in several nicotiana species

Cited by 41 publications

References 5 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

Glycosidically bound volatiles—a review 1986–1991

C13‐Norisoprenoid glycosides in plant tissues: An overview on their occurrence, composition and role as flavour precursors

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C₁₃‐Norisoprenoid glycosides in plant tissues: An overview on their occurrence, composition and role as flavour precursors