The fenugreek odor of<i>Lactarius helvus</i>

Rapior, Sylvie; Fons, Françoise; Bessière, Jean‐Marie

doi:10.1080/00275514.2000.12061159

Cited by 7 publications

(8 citation statements)

References 19 publications

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“…In the present work we were unable to find the HIL oxidative deamination product (10). However, the compound 3-amino-4,5-dimethyl-2(5)-furanone, previously found in L. helvus (29), with a molecular weight and mass spectrum close to those of sotolone, was clearly present in the hairy root cultures ( Figure 5; Table 2). It is unknown whether these compounds in this system were produced by chemical degradation, due to the action of the air upon the biomass components, or whether an enzymatic mechanism is involved.…”

Section: Time Course Of Growth Of Hairy Roots In Conical Flaskscontrasting

confidence: 70%

“…From GC-MS analyses of the oleoresin extracts, 48 compounds were detected (Figure 3), but only 9 were truly identified using authentic compounds as standards ( Table 2). The mass spectra analysis of the compounds from those extracts containing the fenugreek aroma clearly revealed the presence of sotolone and the compound 3-amino-4,5-dimethyl-2(5H)-furanone (Figures 4 and 5), which had been previously postulated as a compound structurally related to sotolone (28,29). The lack of the aroma in the essential oil agrees with reports in the literature that some kinds of Trigonella seeds do not produce the characteristic fenugreek aroma and typically do not contain sotolone (27).…”

Section: Time Course Of Growth Of Hairy Roots In Conical Flasksmentioning

confidence: 97%

“…This hydroxylated amino acid is usually present in T. foenumgraecum (59,60) and L. helvus (29), a mushroom from Europe. On the other hand, Blank et al (27) found that sotolone was generated in model systems by thermally induced oxidative deamination of HIL through 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone, using different carbonyl compounds as carbonyl reactant.…”

Section: Time Course Of Growth Of Hairy Roots In Conical Flasksmentioning

confidence: 98%

“…Sauvaire et al (31) suggested that HIL, an unusual amino acid that represents nearly 80% of free amino acids of dry fenugreek seeds, could be the natural precursor of sotolone in fenugreek. Recently, the presence of 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone was confirmed in fenugreek seeds (27), and afterward Rapior et al (29) reported the presence of 3-amino-4,5-dimethyl-2(5H)-furanone in Lactarius helvus cultures producing sotolone. The first of the two above amino compounds has been postulated as the putative precursor of sotolone; however, the second one has been related only with the fenugreek aroma (32), but its possible role in the metabolic pathway of sotolone has not been investigated.…”

Section: Introductionmentioning

confidence: 95%

“…Several synthetic pathways for sotolone have been postulated (10,(25)(26)(27)(28)(29). Early studies suggested that sotolone might originate by degradation of threonine (30) and from acetaldehyde and R-ketobutyric acid in sake and wine (12), or it might be thermally induced by oxidative deamination of 4-hydroxyisoleucine (HIL) or its corresponding lactone, 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone (10).…”

Section: Introductionmentioning

confidence: 99%

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Sotolone Production by Hairy Root Cultures of Trigonella foenum-graecum in Airlift with Mesh Bioreactors

Peraza-Luna

Rodríguez-Mendiola²,

Arias-Castro³

et al. 2001

J. Agric. Food Chem.

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3-Hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) and 3-amino-4,5-dimethyl-2(5H)-furanone, the postulated precursor of sotolone, were detected in hairy root cultures of Trigonella foenum-graecum (fenugreek) by GC-MS. The hairy root cultures in both conical flasks and airlift with mesh bioreactors were achieved from hypocotyl of seedling by infection with Agrobacterium rhizogenes. In flasks, the mathematical relationship between hairy root growth and conductivity was established and afterward used to evaluate the biomass evolution in bioreactor cultures due to the difficulty of obtaining direct biomass samples from the bioreactor. The GC-MS analyses of ethanolic extracts from hairy roots revealed the presence of two important compounds: sotolone (1.2% of the volatile fraction) and 3-amino-4,5-dimethyl-2(5H)-furanone (17% of the volatile fraction). These results point out that biotechnological production of sotolone in bioreactors is possible. Additionally, these hairy root cultures offer, for the first time, an excellent biological model to study the biosynthetic pathway of sotolone in fenugreek.

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Section: Time Course Of Growth Of Hairy Roots In Conical Flaskscontrasting

confidence: 70%

Section: Time Course Of Growth Of Hairy Roots In Conical Flasksmentioning

confidence: 97%

Section: Time Course Of Growth Of Hairy Roots In Conical Flasksmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Sotolone Production by Hairy Root Cultures of Trigonella foenum-graecum in Airlift with Mesh Bioreactors

Peraza-Luna

Rodríguez-Mendiola²,

Arias-Castro³

et al. 2001

J. Agric. Food Chem.

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Volatiles responsible for the seasoning‐like flavour of cell cultures of Laetiporus sulphureus

Krings

Grimrath

Linke

et al. 2011

Flavour & Fragrance J

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The basidiomycete Laetiporus sulphureus (the edible 'chicken mushroom') imparted a strong seasoning odour when grown on a substrate containing wheat gluten as the sole carbon and nitrogen source. Secreted fungal peptidases hydrolysed the gluten substrate, and numerous potent heterocyclic flavours, among them sotolon (3-hydroxy-4,5-dimethyl-5H-furan-2-one) and other furanones, emerged in the liquefying hydrolysate. The fungal cells were supplemented with presumed precursors of sotolon, such as acetaldehyde, α-ketobutanoic acid, α-oxopentandioic acid, L-glutamic acid, L-isoleucine, and L-(+)-ascorbic acid. Upon addition of isoleucine and ferrous iron the formation of sotolon became measurable within 2 days. Small amounts of 4-hydroxyisoleucine (HIL) were identified in the culture supernatant of L. sulphureus by HPLC-FD and LC-SIM-MS/MS. An enzymatic formation of sotolon via a presumed isoleucine hydroxylase could not be excluded; however, balancing biochemical vs. chemical pathways, a slow chemical hydroxylation of the isoleucine released during the enzymatic hydrolysis of gluten seemed much more likely because ferric iron was present in the culture medium.

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Resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography

Xie

Han

Sun

et al. 2012

Flavour & Fragrance J

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The resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography was studied. On an analytical scale, the chiral stationary phases of Chiralpak AD‐H, Chiralcel OB‐H, Chiralcel OD‐H, and Chiralcel OJ‐H along with methanol, ethanol, isopropanol and acetonitrile as organic modifiers were tested. The effect on resolution of the modifier content in mobile phase, column temperature, column pressure, and flow rate of mobile phase was investigated through single‐factor experiment and orthogonal experiment. The optimum conditions found were Chiralpak AD‐H, column temperature 28°C, column pressure 8 MPa, 2.5% (v/v) methanol in the mobile phase, and a flow rate of 1.5 ml/min for the mobile phase, whereby the resolution achieved was 2.98. Several milligrams of enantiomers, with an optical purity of S‐100% and R‐93%, were obtained by scaling up the analytical method to preparative separation using Chiralpak AD (250 × 10 mm I.D. 10 µm ps). Copyright © 2012 John Wiley & Sons, Ltd.

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The fenugreek odor ofLactarius helvus

Cited by 7 publications

References 19 publications

Sotolone Production by Hairy Root Cultures of Trigonella foenum-graecum in Airlift with Mesh Bioreactors

Sotolone Production by Hairy Root Cultures of Trigonella foenum-graecum in Airlift with Mesh Bioreactors

Volatiles responsible for the seasoning‐like flavour of cell cultures of Laetiporus sulphureus

Resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography

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