Skip to main content
SpringerLink
Log in

Mechanism of 2-acetyl-1-pyrroline biosynthesis in Bassia latifolia Roxb. flowers

  • Research Article
  • Published:
Physiology and Molecular Biology of Plants Aims and scope Submit manuscript

Abstract

The flowers of Bassia latifolia are known to contain 2-acetyl-1-pyrroline (2AP), the compound responsible for pleasant aroma in basmati and other scented rice. Four growth stages of Bassia flowers were identified and 2AP contents were analysed in each stage. It was found that 2AP (3.30 ppm) gets synthesized only in fleshy corolla of mature flowers (fourth stage). The activity of γ-aminobutyraldehyde dehydrogenase (AADH); an enzyme responsible for synthesis of γ-aminobutyricacid (GABA) from γ-aminobutyraldehyde (GABald) was assessed in these four stages. The AADH activity was absent in the fourth stage. It was concluded that ceased activity of AADH in fourth stage flowers leads to the accumulation of γ-aminobutyraldehyde which is cyclised spontaneously to Δ1-pyrroline, the key precursor of 2AP. Δ1-pyrroline further reacts unenzymatically with methylglyoxal to form 2AP.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Bradbury LMT, Fitzgerald TL, Henry RJ, Jin Q, Waters DLE (2005) The gene for fragrance in rice. Plant Biotech J 3:363–370

    Article  CAS  Google Scholar 

  • Bradbury LM, Gillies SA, Brushett DJ, Waters DLE, Henry RJ (2008) Inactivation of an aminoaldehyde dehydrogenase is responsible for fragrance in rice. Plant Mol Bio 68:439–449

    Article  CAS  Google Scholar 

  • Buttery RG, Juliano BO, Ling LC (1983a) Identification of rice aroma compound 2-acetyl-1-pyrroline in Pandan leaves. Chemistry and Industry (London), p 478

  • Buttery RG, Ling LC, Juliano BO, Turnbaugh JG (1983b) Cooked rice aroma and 2-acetyl-1-pyrroline. J Agric Food Chem 31:823–826

    Article  CAS  Google Scholar 

  • Chen S, Yang Y, Shi W, Ji Q, He F, Zhang Z, Cheng Z, Liu X, Xu M (2008) Badh2, encoding betaine aldehyde dehydrogenase, inhibits the biosynthesis of 2-acetyl-1-pyrroline, a major component in rice fragrance. Plant Cell 20:1850–1861

    Article  PubMed  CAS  Google Scholar 

  • Costello PJ, Henschke PA (2002) Mousy off-flavor of wine: Precursors and biosynthesis of the causative N-heterocycles 2-ethyltetrahydropyridine, 2-acetyl tetrahydropyridine and 2-acetyl-1-pyrroline by Lactobacillus hilgardii DSM 20176. J Agric Food Chem 50:7079–7087

    Article  PubMed  CAS  Google Scholar 

  • Fogel WA, Bieganski T, Maslinski C (1979) Effects of inhibitors of aldehyde metabolizing enzymes on putrescine metabolism in guinea pig liver homogenates. Inflamm Res 9(1):42–44

    CAS  Google Scholar 

  • Grimm CC, Bergman C, Delgado JT, Bryant R (2001) Screening for 2-acetyl-1-pyrroline in the headspace of rice using SPME/GC-MS. J Agric Food Chem 49:245–249

    Article  PubMed  CAS  Google Scholar 

  • Huang TC, Huang YW, Hung HJ, Ho CT, Wu ML (2007) Δ1-Pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline. J Agric Food Chem 55:5097–5102

    Article  PubMed  CAS  Google Scholar 

  • Huang TC, Teng CS, Chang JL, Chuang HS, Ho CT, Wu ML (2008) Biosynthetic mechanism of 2-acetyl-1-pyrroline and its relationship with Δ1-pyrroline-5-carboxylic acid and methylglyoxal in aromatic rice (Oryza sativa L.) callus. J Agric Food Chem 56:7399–7404

    Article  PubMed  CAS  Google Scholar 

  • Ishitani M, Arakawa K, Mizuno K, Kishitani S, Takabe T (1993) Betaine aldehyde dehydrogenase in the gramineae: levels in leaves both betaine-accumulating and nonaccumulating cereal plants. Plant Cell Physiol 34:493–495

    CAS  Google Scholar 

  • Kapilan N, Reddy R (2008) Evaluation of Methyl esters of Mahua oil (Madhuca Indica) as diesel fuel. J Am Oil Chem Soc 85(2):185–188

    Article  CAS  Google Scholar 

  • Livingstone JR, Maruo T, Yoshida I, Tarui Y, Hirooka K, Yamamoto Y, Tsutui N, Hirasawa E (2003) Purification and properties of betaine aldehyde dehydrogenase from Avena sativa. J Plant Res 116:133–140

    PubMed  CAS  Google Scholar 

  • Lorieux M, Petrov M, Huang N, Guiderdoni E, Ghesquiere A (1996) Aroma in rice: genetic analysis of a quantitative trait. Theor Appl Genet 93:1145–1151

    Article  CAS  Google Scholar 

  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin-Phenol reagents. J Biol Chem 193:265–275

    PubMed  CAS  Google Scholar 

  • Midya S, Brahmachary R (1996) The aroma of Bassia flower. Curr Sci 71:430

    Google Scholar 

  • Phillips SA, Thornalley PJ (1993) The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal. Eur J Biochem 212:101–105

    Article  PubMed  CAS  Google Scholar 

  • Romanczyk LJ Jr, McClelland CA, Post LS, Aitken WM (1995) Formation of 2-acetyl-I-pyrroline by several Bacillus cereus strains isolated from cocoa fermentation boxes. J Agric Food Chem 43:469–475

    Article  CAS  Google Scholar 

  • Schieberle P (1989) Formation of 2-acetyl-1-pyrroline and other important flavor compounds in wheat bread crust. In Thermal generation of aromas pp. 268–275, ACS Symposium series 409. American Chemical Society, Washington

  • Schieberle P (1990) The role of free amino acids present in yeast as precursors the odorants 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine in wheat bread crust. Z Lebensm Unters Forsch 191:206–209

    Article  CAS  Google Scholar 

  • Sebela M, Brauner F, Radova A, Jacobsen S, Havlis J, Galuszka P, Pec P (2000) Characterisation of a homogeneous plant aminoaldehyde dehydrogenase. Biochim Biophys Acta 1480:329–341

    Article  PubMed  CAS  Google Scholar 

  • Srivong P, Wangsomnuk P, Pongdontri P (2007) Characterization of a fragrant gene and enzymatic activity of betaine aldehyde dehydrogenase in aromatic and nonaromatic Thai rice cultivars. KKU Sci J 36(4):290–301

    Google Scholar 

  • Stewart CR (1977) Inhibition of proline oxidation by water stress. Plant Physiol 59:930–932

    Article  PubMed  CAS  Google Scholar 

  • Swain MR, Kar S, Sahoo AK, Ray RC (2007) Ethanol fermentation of mahula (Madhuca latifolia L) flowers using free and immobilized yeast Saccharomyces cerevisiae. Microbiol Res 162:93–98

    Article  PubMed  CAS  Google Scholar 

  • Trossat C, Rathinasabapathi B, Hanson AD (1997) Transgenically expressed betaine aldehyde dehydrogenase efficiently catalyzes oxidation of dimethylsulfoniopropionaldehyde and omega-aminoaldehydes. Plant Physiol 113:1457–1461

    PubMed  CAS  Google Scholar 

  • Wakte KV, Thengane RJ, Jawali N, Nadaf AB (2010) Optimization of HS-SPME conditions for quantification of 2-acetyl-1-pyrroline and study of other volatiles in Pandanus amaryllifolius Roxb. Food Chem 121:595–600

    Article  CAS  Google Scholar 

  • Wongpornchai S, Sriseadka T, Choonvisase S (2003) Identification and quantitation of the rice aroma compound, 2-acetyl-1-pyrroline, in bread flowers (Vallaris glabra Ktze). J Agric Food Chem 51:457–462

    Article  PubMed  CAS  Google Scholar 

  • Yadav SK, Singla-Pareek SL, Reddy MK, Sopory SK (2005) Transgenic tobacco plants overexpressing glyoxalase enzymes resist an increase in methylglyoxal and maintain higher reduced glutathione levels under salinity stress. FEBS Lett 579:6265–71

    Article  PubMed  CAS  Google Scholar 

  • Yoshihashi T, Huong NTT, Inatomi H (2002) Precursors of 2-acetyl-1-pyrroline, a potent flavour compound of an aromatic rice variety. J Agric Food Chem 50:2001–2004

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

Authors are thankful to Dr. P. Srinivas (Central Food and Technology Research Institute, Mysore, India) for generous gift of authentic 2AP.

Author information

Authors and Affiliations

  1. Department of Botany, University of Pune, Pune, 411007, India

    Kantilal V. Wakte, Trupti D. Kad, Rahul L. Zanan & Altafhusain B. Nadaf

Authors
  1. Kantilal V. Wakte
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Trupti D. Kad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rahul L. Zanan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Altafhusain B. Nadaf
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Altafhusain B. Nadaf.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wakte, K.V., Kad, T.D., Zanan, R.L. et al. Mechanism of 2-acetyl-1-pyrroline biosynthesis in Bassia latifolia Roxb. flowers. Physiol Mol Biol Plants 17, 231–237 (2011). https://doi.org/10.1007/s12298-011-0075-5

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12298-011-0075-5

Keywords

Search

Navigation