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Volumn 83, Issue 1, 2009, Pages 35-41

Nootkatone-a biotechnological challenge

Author keywords

Bioconversion; Biosynthesis; Flavour; Valencene

Indexed keywords

ALLYLIC OXIDATIONS; CELL EXTRACTS; CELL SYSTEMS; CHEMICAL SYNTHESIS; FILAMENTOUS FUNGUS; FLAVOUR; HIGH YIELDS; MARKET PULLS; MILD REACTION CONDITIONS; MOLECULAR CHARACTERISTICS; MULTI-FACETED APPROACHES; NOOTKATONE; PHARMACEUTICAL INDUSTRIES; PURIFIED ENZYMES; SEQUENCE DATUM; SPECIALTY CHEMICALS; TRACE AMOUNTS; VALENCENE;

EID: 67349134144     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-1968-x     Document Type: Short Survey
Times cited : (109)

References (66)
  • 1
    • 0000068453 scopus 로고
    • Biogenetic implications of the antipodal sesquiterpenes of vetiver oil
    • NH Andersen 1970 Biogenetic implications of the antipodal sesquiterpenes of vetiver oil Phytochemistry 9 145 151
    • (1970) Phytochemistry , vol.9 , pp. 145-151
    • Andersen, N.H.1
  • 2
    • 33847317321 scopus 로고    scopus 로고
    • Lipoxygenase in fruits and vegetables: A review
    • DOI 10.1016/j.enzmictec.2006.11.025, PII S0141022906005904
    • T Baysal A Demirdöven 2007 Lipoxygenase in fruits and vegetables: a review Enzyme Microb Technol 40 491 496 (Pubitemid 46329096)
    • (2007) Enzyme and Microbial Technology , vol.40 , Issue.4 , pp. 491-496
    • Baysal, T.1    Demirdoven, A.2
  • 4
    • 2642577606 scopus 로고    scopus 로고
    • Valencene synthase - A biochemical magician and harbinger of transgenic aromas
    • DOI 10.1016/j.tplants.2004.03.003, PII S1360138504000573
    • J Chappell 2004 Valencene synthase-a biochemical magician and harbinger of transgenic aromas Trends Plant Sci 9 266 269 (Pubitemid 38708846)
    • (2004) Trends in Plant Science , vol.9 , Issue.6 , pp. 266-269
    • Chappell, J.1
  • 6
    • 33947087302 scopus 로고
    • A stereoselective approach to eremophilane sesquiterpenes. A synthesis of (±)-nootkatone
    • KP Dastur 1973 A stereoselective approach to eremophilane sesquiterpenes. A synthesis of (±)-nootkatone J Am Chem Soc 95 6509 6510
    • (1973) J Am Chem Soc , vol.95 , pp. 6509-6510
    • Dastur, K.P.1
  • 7
    • 0037434018 scopus 로고    scopus 로고
    • Hydroxylation of sesquiterpenes by enzymes from chicory (Cichorium intybus L.) roots
    • DOI 10.1016/S0040-4020(02)01479-5, PII S0040402002014795
    • J-W de Kraker M Schurink MCR Franssen WA König A de Groot HJ Bouwmeester 2003 Hydroxylation of sesquiterpenes by enzymes from chicory (Cichorium intybus L.) roots Tetrahedron 59 409 418 (Pubitemid 36050813)
    • (2003) Tetrahedron , vol.59 , Issue.3 , pp. 409-418
    • De Kraker, J.-W.1    Schurink, M.2    Franssen, M.C.R.3    Konig, W.A.4    De Groot, A.5    Bouwmeester, H.J.6
  • 8
    • 0008532857 scopus 로고
    • Accumulation of the sesquiterpenes nootkatone and valencene by callus cultures of Citrus paradisi, Citrus limonia and Citrus aurantium
    • JA del Río A Ortuño DG Puig JL Iborra F Sabater 1991 Accumulation of the sesquiterpenes nootkatone and valencene by callus cultures of Citrus paradisi, Citrus limonia and Citrus aurantium Plant Cell Rep 10 410 413
    • (1991) Plant Cell Rep , vol.10 , pp. 410-413
    • Río Del, J.A.1    Ortuño, A.2    Puig, D.G.3    Iborra, J.L.4    Sabater, F.5
  • 10
    • 27744596897 scopus 로고
    • Mikrobiologische Umsetzung von Terpenen: Valencen
    • RS Dhavlikar G Albroscheit 1973 Mikrobiologische Umsetzung von Terpenen: Valencen Dragoco Rep 12 251 258
    • (1973) Dragoco Rep , vol.12 , pp. 251-258
    • Dhavlikar, R.S.1    Albroscheit, G.2
  • 11
    • 67349252638 scopus 로고
    • Über die Biogenese von Aromastoffen bei Pflanzen und Früchten
    • F Drawert RG Berger 1982 Über die Biogenese von Aromastoffen bei Pflanzen und Früchten Chem Mikrobiol Technol Lebensm 7 143 147
    • (1982) Chem Mikrobiol Technol Lebensm , vol.7 , pp. 143-147
    • Drawert, F.1    Berger, R.G.2
  • 12
    • 0009437723 scopus 로고
    • Regioselective biotransformation of valencene in cell suspension cultures of Citrus sp
    • F Drawert RG Berger R Godelmann 1984 Regioselective biotransformation of valencene in cell suspension cultures of Citrus sp Plant Cell Rep 3 37 40
    • (1984) Plant Cell Rep , vol.3 , pp. 37-40
    • Drawert, F.1    Berger, R.G.2    Godelmann, R.3
  • 13
    • 0000041948 scopus 로고
    • The chemistry of the natural order Cupressales
    • H Erdtman Y Hirose 1962 The chemistry of the natural order Cupressales Acta Chem Scand 16 1311 1314
    • (1962) Acta Chem Scand , vol.16 , pp. 1311-1314
    • Erdtman, H.1    Hirose, Y.2
  • 15
    • 0037467130 scopus 로고    scopus 로고
    • Volatiles from leaves, fruits, and virgin oil from Olea europaea Cv. Olivastra Seggianese from Italy
    • G Flamini PL Cioni I Morelli 2003 Volatiles from leaves, fruits, and virgin oil from Olea europaea Cv. Olivastra Seggianese from Italy J Agric Food Chem 51 1382 1386
    • (2003) J Agric Food Chem , vol.51 , pp. 1382-1386
    • Flamini, G.1    Cioni, P.L.2    Morelli, I.3
  • 17
    • 27744524131 scopus 로고    scopus 로고
    • Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation
    • DOI 10.1248/cpb.53.1513
    • M Furusawa T Hashimoto Y Noma Y Asakawa 2005 Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation Chem Pharm Bull (Tokyo) 53 1513 1514 (Pubitemid 41634231)
    • (2005) Chemical and Pharmaceutical Bulletin , vol.53 , Issue.11 , pp. 1513-1514
    • Furusawa, M.1    Hashimoto, T.2    Noma, Y.3    Asakawa, Y.4
  • 20
    • 12344321050 scopus 로고
    • Conversion of valencene to nootkatone
    • GLK Hunter WB Brogden Jr 1965a Conversion of valencene to nootkatone J Food Sci 30 876 878
    • (1965) J Food Sci , vol.30 , pp. 876-878
    • Hunter, G.L.K.1    Brogden Jr, W.B.2
  • 21
    • 84981864267 scopus 로고
    • Analysis of the terpene and sesquiterpene hydrocarbons in some citrus oils
    • GLK Hunter WB Brogden Jr 1965b Analysis of the terpene and sesquiterpene hydrocarbons in some citrus oils J Food Sci 30 383 387
    • (1965) J Food Sci , vol.30 , pp. 383-387
    • Hunter, G.L.K.1    Brogden Jr, W.B.2
  • 22
    • 0027264768 scopus 로고
    • Lipoxygenase of thermoactinomyces vulgaris, purification and characterization of reaction products
    • DOI 10.1016/0020-711X(93)90084-R
    • D Iny A Pinsky M Cojocoru S Grossman 1993 Lipoxygenase of Thermoactinomyces vulgaris, purification and characterization of reaction products Int J Biochem 25 1313 1323 (Pubitemid 23263084)
    • (1993) International Journal of Biochemistry , vol.25 , Issue.9 , pp. 1313-1323
    • Iny, D.1    Pinsky, A.2    Cojocoru, M.3    Grossman, S.4
  • 24
    • 21344460013 scopus 로고    scopus 로고
    • Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum
    • DOI 10.1007/s00253-004-1794-0
    • R Kaspera U Krings T Nanzad RG Berger 2005 Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum Appl Microbiol Biotechnol 67 477 483 (Pubitemid 40909593)
    • (2005) Applied Microbiology and Biotechnology , vol.67 , Issue.4 , pp. 477-483
    • Kaspera, R.1    Krings, U.2    Nanzad, T.3    Berger, R.G.4
  • 25
    • 27744562828 scopus 로고    scopus 로고
    • Changes in heartwood chemistry of dead yellow-cedar trees that remain standing for 80 years or more in Southeast Alaska
    • DOI 10.1007/s10886-005-7618-6
    • RG Kelsey PE Hennon M Huso JJ Karchesy 2005 Changes in heartwood chemistry of dead yellow-cedar trees that remain standing for 80 years or more in southeast Alaska J Chem Ecol 31 2653 2670 (Pubitemid 41597340)
    • (2005) Journal of Chemical Ecology , vol.31 , Issue.11 , pp. 2653-2670
    • Kelsey, R.G.1    Hennon, P.E.2    Huso, M.3    Karchesy, J.J.4
  • 26
    • 0242384186 scopus 로고    scopus 로고
    • Efficient production of raspberry ketone via 'green' biocatalytic oxidation
    • DOI 10.1016/j.tet.2003.10.019
    • B Kosjek W Stampfer R van Deursen K Faber W Kroutil 2003 Efficient production of raspberry ketone via 'green' biocatalytic oxidation Tetrahedron 59 9517 9521 (Pubitemid 37357105)
    • (2003) Tetrahedron , vol.59 , Issue.48 , pp. 9517-9521
    • Kosjek, B.1    Stampfer, W.2    Van Deursen, R.3    Faber, K.4    Kroutil, W.5
  • 27
    • 0032911057 scopus 로고    scopus 로고
    • The diversity of the lipoxygenase family. Many sequence data but little information on biological significance
    • DOI 10.1016/S0014-5793(99)00396-8, PII S0014579399003968
    • H Kuhn BJ Thiele 1999 The diversity of the lipoxygenase family: many sequence data but little information on biological significance FEBS Lett 449 7 11 (Pubitemid 29182660)
    • (1999) FEBS Letters , vol.449 , Issue.1 , pp. 7-11
    • Kuhn, H.1    Thiele, B.J.2
  • 29
    • 0014038677 scopus 로고
    • Biosynthetic pathways from acetate to natural products
    • F Lynen 1967 Biosynthetic pathways from acetate to natural products Pure Appl Chem 14 137 167
    • (1967) Pure Appl Chem , vol.14 , pp. 137-167
    • Lynen, F.1
  • 30
    • 84981842630 scopus 로고
    • Sesquiterpenes. I. Nootkatone, a new grapefruit flavor constituent
    • WD MacLeod Jr NM Buigues 1964 Sesquiterpenes. I. Nootkatone, a new grapefruit flavor constituent J Food Sci 29 565 568
    • (1964) J Food Sci , vol.29 , pp. 565-568
    • Buigues, N.M.1
  • 31
    • 0342775864 scopus 로고
    • Volatile aroma constituents of celery
    • AJ MacLeod G MacLeod G Subramanian 1988 Volatile aroma constituents of celery Phytochemistry 27 373 375
    • (1988) Phytochemistry , vol.27 , pp. 373-375
    • Subramanian, G.1
  • 32
    • 0007385877 scopus 로고
    • A stereoselective synthesis of (±)-nootkatone and (±)-valencene via an intramolecular Sakurai reaction
    • G Majetich M Behnke K Hull 1985 A stereoselective synthesis of (±)-nootkatone and (±)-valencene via an intramolecular Sakurai reaction J Org Chem 50 3615 3618
    • (1985) J Org Chem , vol.50 , pp. 3615-3618
    • Majetich, G.1    Behnke, M.2    Hull, K.3
  • 33
    • 33947292332 scopus 로고
    • The stereoselective total synthesis of racemic nootkatone
    • JA Marshall RA Ruden 1971 The stereoselective total synthesis of racemic nootkatone J Org Chem 36 594 596
    • (1971) J Org Chem , vol.36 , pp. 594-596
    • Marshall, J.A.1    Ruden, R.A.2
  • 34
    • 0001715519 scopus 로고    scopus 로고
    • Inhibition of Acetylcholinesterase Activity by Monoterpenoids with a p-Menthane Skeleton
    • M Miyazawa H Watanabe H Kameoka 1997 Inhibition of acetylcholinesterase activity by monoterpenoids with a p-menthane skeleton J Agric Food Chem 45 677 679 (Pubitemid 127483687)
    • (1997) Journal of Agricultural and Food Chemistry , vol.45 , Issue.3 , pp. 677-679
    • Miyazawa, M.1    Watanabe, H.2    Kameoka, H.3
  • 35
    • 0033858087 scopus 로고    scopus 로고
    • Insecticidal sesquiterpene from Alpinia oxyphylla against Drosophila melanogaster
    • M Miyazawa Y Nakamura Y Ishikawa 2000 Insecticidal sesquiterpene from Alpinia oxyphylla against Drosophila melanogaster J Agric Food Chem 48 3639 3641
    • (2000) J Agric Food Chem , vol.48 , pp. 3639-3641
    • Miyazawa, M.1    Nakamura, Y.2    Ishikawa, Y.3
  • 36
    • 0035188650 scopus 로고    scopus 로고
    • Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi
    • M Miyazawa H Tougo M Ishihara 2001 Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi Nat Prod Lett 15 205 210 (Pubitemid 33094487)
    • (2001) Natural Product Letters , vol.15 , Issue.3 , pp. 205-210
    • Miyazawa, M.1    Tougo, H.2    Ishihara, M.3
  • 39
    • 33751220498 scopus 로고    scopus 로고
    • Volatile constituents of mandarin (Citrus reticulata blanco) peel oil from Burundi
    • SM Njoroge HN Mungai H Koaze NTL Phi M Sawamura 2006 Volatile constituents of mandarin (Citrus reticulata blanco) peel oil from Burundi J Essent Oil Res 18 659 662
    • (2006) J Essent Oil Res , vol.18 , pp. 659-662
    • Njoroge, S.M.1    Mungai, H.N.2    Koaze, H.3    Phi, N.T.L.4    Sawamura, M.5
  • 40
    • 67349248730 scopus 로고
    • Präparative Möglichkeiten mit Singulettsauerstoff
    • G Ohloff 1971 Präparative Möglichkeiten mit Singulettsauerstoff Nachr Chem Techn 24 446 448
    • (1971) Nachr Chem Techn , vol.24 , pp. 446-448
    • Ohloff, G.1
  • 46
    • 0030937152 scopus 로고    scopus 로고
    • Variation of chlorophyll and essential oils in photomixotrophic cell cultures of Coleonema album (Thunb.)
    • G Reil RG Berger 1997 Variation of chlorophyll and essential oils in photomixotrophic cell cultures of Coleonema album (Thunb.) J Plant Physiol 150 160 166 (Pubitemid 27132272)
    • (1997) Journal of Plant Physiology , vol.150 , Issue.1-2 , pp. 160-166
    • Reil, G.1    Berger, R.G.2
  • 47
    • 0033213706 scopus 로고    scopus 로고
    • The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants
    • DOI 10.1039/a709175c
    • M Rohmer 1999 The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants Nat Prod Rep 16 565 574 (Pubitemid 29501611)
    • (1999) Natural Product Reports , vol.16 , Issue.5 , pp. 565-574
    • Rohmer, M.1
  • 50
    • 57249085588 scopus 로고    scopus 로고
    • The allylic oxidation of unsaturated steroids by tert-butyl hydroperoxide using surface functionalised silica supported metal catalysts
    • JAR Salvador JH Clark 2002 The allylic oxidation of unsaturated steroids by tert-butyl hydroperoxide using surface functionalised silica supported metal catalysts Green Chem 4 352 356
    • (2002) Green Chem , vol.4 , pp. 352-356
    • Salvador, J.A.R.1    Clark, J.H.2
  • 52
    • 0001102567 scopus 로고
    • Quantitative determination of volatile constituents in the pummelo (Citrus grandis Osbeck forma Tosa-buntan)
    • M Sawamura T Kuriyama 1988 Quantitative determination of volatile constituents in the pummelo (Citrus grandis Osbeck forma Tosa-buntan) J Agric Food Chem 36 567 569
    • (1988) J Agric Food Chem , vol.36 , pp. 567-569
    • Sawamura, M.1    Kuriyama, T.2
  • 55
    • 0344664094 scopus 로고    scopus 로고
    • Citrus fruit flavor and aroma biosynthesis: Isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene
    • DOI 10.1046/j.1365-313X.2003.01910.x
    • L Sharon-Asa M Shalit A Frydman E Bar D Holland E Or U Lavi E Lewinsohn Y Eyal 2003 Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene Plant J 36 664 674 (Pubitemid 37502255)
    • (2003) Plant Journal , vol.36 , Issue.5 , pp. 664-674
    • Sharon-Asa, L.1    Shalit, M.2    Frydman, A.3    Bar, E.4    Holland, D.5    Or, E.6    Lavi, U.7    Lewinsohn, E.8    Eyal, Y.9
  • 56
    • 0021258566 scopus 로고
    • Structural determination of nootkatol, a new sesquiterpene isolated from Alpinia oxyphylla Miquel possessing calcium-antagonistic activity
    • N Shoji A Umeyama Y Asakawa T Takemoto K Nomoto Y Ohizumi 1984 Structural determination of nootkatol, a new sesquiterpene isolated from Alpinia oxyphylla Miquel possessing calcium-antagonistic activity J Pharm Sci 73 843 844
    • (1984) J Pharm Sci , vol.73 , pp. 843-844
    • Shoji, N.1    Umeyama, A.2    Asakawa, Y.3    Takemoto, T.4    Nomoto, K.5    Ohizumi, Y.6
  • 58
    • 35748931196 scopus 로고    scopus 로고
    • Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates
    • DOI 10.1074/jbc.M703378200
    • S Takahashi Y-S Yeo Y Zhao PE O'Maille BT Greenhagen JP Noel RM Coates J Chappell 2007 Functional characterization of premnaspirodiene oxygenase, a cytochrome p450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates J Biol Chem 282 31744 31754 (Pubitemid 350044865)
    • (2007) Journal of Biological Chemistry , vol.282 , Issue.43 , pp. 31744-31754
    • Takahashi, S.1    Yeo, Y.-S.2    Zhao, Y.3    O'Maille, P.E.4    Greenhagen, B.T.5    Noel, J.P.6    Coates, R.M.7    Chappell, J.8
  • 60
    • 0038227587 scopus 로고
    • Functionalization of trans-decalin. V. A synthesis of (±)-nootkatone and (±)-valencene from 4β,4aβ-dimethyl- Δ6,7-octalin-1-one ethylene acetal
    • S Torii T Inokuchi K Handa 1982 Functionalization of trans-decalin. V. A synthesis of (±)-nootkatone and (±)-valencene from 4β,4aβ-dimethyl-Δ6,7-octalin-1-one ethylene acetal Bull Chem Soc Jpn 55 887 890
    • (1982) Bull Chem Soc Jpn , vol.55 , pp. 887-890
    • Torii, S.1    Inokuchi, T.2    Handa, K.3
  • 62
    • 67349224227 scopus 로고
    • Enzymatische Transformation von Valencen zu Nootkaton
    • H Willershausen H Graf 1991 Enzymatische Transformation von Valencen zu Nootkaton Chemiker-Zeitung 115 358 360
    • (1991) Chemiker-Zeitung , vol.115 , pp. 358-360
    • Willershausen, H.1    Graf, H.2
  • 63
    • 0344103872 scopus 로고
    • Synthesis of nootkatone from valencene
    • CWIII Wilson PE Shaw 1978 Synthesis of nootkatone from valencene J Agric Food Chem 26 1430 1432
    • (1978) J Agric Food Chem , vol.26 , pp. 1430-1432
    • Cwiii, W.1    Shaw, P.E.2
  • 65
    • 0001488783 scopus 로고
    • Synthetic study of (+)-nootkatone from (-)-β-pinene
    • T Yanami M Miyashita A Yoshikoshi 1980 Synthetic study of (+)-nootkatone from (-)-β-pinene J Org Chem 45 607 612
    • (1980) J Org Chem , vol.45 , pp. 607-612
    • Yanami, T.1    Miyashita, M.2    Yoshikoshi, A.3
  • 66
    • 0034984281 scopus 로고    scopus 로고
    • Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus)
    • DOI 10.1023/A:1010301308649
    • BCR Zhu G Henderson F Chen L Maistrello RA Laine 2001 Nootkatone is a repellent for Formosan subterranean termite (Coptotermes formosanus) J Chem Ecol 27 523 531 (Pubitemid 32554187)
    • (2001) Journal of Chemical Ecology , vol.27 , Issue.3 , pp. 523-531
    • Zhu, B.C.R.1    Henderson, G.2    Chen, F.3    Maistrello, L.4    Laine, R.A.5


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