Metabolism of Acyclic Monoterpenes: Partial Purification and Properties of Geraniol Dehydrogenase from Lemongrass (Cymbopogon flexuosus Stapf.) Leaves

Sangwan, Rajender S.; Singh-Sangwan, Neelam; Luthra, Rajesh

doi:10.1016/s0176-1617(11)80952-1

Cited by 46 publications

(43 citation statements)

References 13 publications

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“…The properties of this enzyme resemble those of other monoterpenol dehydrogenases described in the literature. As a group, the monoterpenol dehydrogenases possess a wide range of pH optima, varying from around 8.0 (Croteau and Felton, 1980;Sangwan et al, 1993) to 9.0 to 10.0 (Potty and Bruemmer, 1970;Kjonaas et al, 1985;Hallahan et al, 1995). The trans-carveol dehydrogenase studied here also has a high pH optimum, around 10.0.…”

Section: Discussion the Pathway Of Monoterpene Biosynthesis In Carawaymentioning

confidence: 83%

“…The high pH optimum for caraway (ϩ)-trans-carveol dehydrogenase seems to have little physiological relevance because the enzyme is probably localized in the cytoplasm, where a pH of 7.0 to 7.5 can be assumed. Among other monoterpenol dehydrogenases, some require either NAD ϩ or NADP ϩ , whereas some show substantial catalytic activity with both cofactors (Potty and Bruemmer, 1970;Croteau and Felton, 1980;Kjonaas et al, 1985;Sangwan et al, 1993;Hallahan et al, 1995). Caraway trans-carveol dehydrogenase shares its requirement for NAD ϩ with another ␣,␤-unsaturated monoterpenol dehydrogenase, trans- isopiperitenol dehydrogenase from peppermint (Kjonaas et al, 1985).…”

Section: Discussion the Pathway Of Monoterpene Biosynthesis In Carawaymentioning

confidence: 99%

“…NADP ϩ could not substitute for NAD ϩ , and could not act synergistically with NAD ϩ . At a pH of 10.5, which was routinely used in experiments to characterize this activity, no general alcohol (ethanol) dehydrogenase activity was detected, as determined spectrophotometrically with ethanol as a substrate (290 mm) and a mixture of NAD ϩ and NADP ϩ (at 1 mm each) as cofactors (Sangwan et al, 1993). Substantial ethanol dehydrogenase activity was detected at pH 8.0.…”

Section: Demonstration and Characterization Of Enzyme Activitiesmentioning

confidence: 99%

See 2 more Smart Citations

Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1

Bouwmeester¹,

Gershenzon

Konings³

et al. 1998

Plant Physiology

148

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Section: Discussion the Pathway Of Monoterpene Biosynthesis In Carawaymentioning

confidence: 83%

Section: Discussion the Pathway Of Monoterpene Biosynthesis In Carawaymentioning

confidence: 99%

Section: Demonstration and Characterization Of Enzyme Activitiesmentioning

confidence: 99%

See 1 more Smart Citation

Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1

Bouwmeester¹,

Gershenzon

Konings³

et al. 1998

Plant Physiology

148

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“…1). Geraniol-DH activity has been detected in extracts of Citrus sinensis, 8) Cymbopogon flexuosus Stapf., 9) Zingiber officinale Roscoe, 10) and Ocimum basilicum. 11) To understand the regulation of the geraniol metabolic pathway better, we investigated the enzymes that participate in this monoterpene metabolism pathway in P. minus.…”

mentioning

confidence: 99%

Monoterpene Alcohol Metabolism: Identification, Purification, and Characterization of Two Geraniol Dehydrogenase Isoenzymes fromPolygonum minusLeaves

Hassan

Maarof

Ali

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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“…This compound has not been reported in A. annua shoot essential-oil extracts, but was tentatively identified in the roots (Woerdenbag et al 1993). Subsequently, the alcohol could be oxidized two additional times at C12 by either cytochrome P450 enzymes or dehydrogenases, yielding the corresponding acid, artemisinic acid (Funk and Croteau 1994;De Kraker et al 2001;Sangwan et al 1993b;West 1980 Compounds: 1, -copaene;2, -caryophyllene;3, trans--farnesene;5, selina-4,11-diene;6, germacrene D;9, bicyclogermacrene;10, germacrene A;14, amorpha-4,11-diene. From (Bouwmeester et al 1999b) yielding dihydroartemisinic acid, which was shown by others to be converted non-enzymatically to artemisinin (Abdin et al 2003;Brown and Sy 2004;Wallaart et al 1999a;Wallaart et al 1999b).…”

Section: Biosynthetic Pathway Beyond Amorpha-411-dienementioning

confidence: 99%

Research to Improve Artemisinin Production for use in the Preparation of Anti-Malarial Drugs

Bouwmeester

Bertea²,

Kraker³

et al.

Medicinal and Aromatic Plants

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Abstract. An important group of antimalarial drugs consists of the endoperoxide sesquiterpene lactone artemisinin and its semi-synthetically prepared derivatives. Because of the development of resistance against other malarial drugs, the demand for artemisinin has rapidly increased during the past decade. However, the supply of artemisinin is troublesome as neither total nor semi-synthesis are economically feasible and the only plant species known to produce artemisinin, Artemisia annua L., contains only low amounts of this compound. For a directed strategy to improve artemisinin production, one of the first requirements is to have insight into the regulation of its biosynthesis. Surprisingly, until some years ago hardly anything was known about the biosynthesis of artemisinin, particularly about the early enzymatic steps leading to (dihydro)artemisinic acid. To elucidate this important missing part in the pathway, we have analysed the terpenoids in A. annua leaves and the presence of sesquiterpene synthases, the enzyme class that should theoretically catalyse the first step in the formation of artemisinin. This led to the discovery of amorpha-4,11-diene synthase, which indeed catalyses the first step in artemisinin biosynthesis and for which the corresponding gene was cloned shortly afterwards. A subsequent search for oxidized derivatives of amorpha-4,11-diene -which could be postulated to be intermediates en route to artemisinin -revealed the presence of artemisinic alcohol, dihydroartemisinic alcohol, artemisinic aldehyde, dihydroartemisinic aldehyde and dihydroartemisinic acid. We also demonstrated the presence of the biosynthetic enzymes amorpha-4,11-diene hydroxylase, artemisinic alcohol dehydrogenase, artemisinic aldehyde reductase and dihydroartemisinic aldehyde dehydrogenase in A. annua. From these results, we conclude that the early steps in artemisinin biosynthesis involve: cyclization of farnesyl diphosphate by amorpha-4,11-diene synthase to amorpha-4,11-diene, hydroxylation of amorpha-4,11-diene to artemisinic alcohol, oxidation of artemisinic alcohol to artemisinic aldehyde, reduction of the C11-C13 double bond yielding dihydroartemisinic aldehyde, and oxidation of dihydroartemisinic aldehyde to dihydroartemisinic acid. During this biochemical research we have also managed to develop a trichome isolation protocol which has not only accelerated our biochemical work but also enables us to clone -in a very directed way -the genes that encode the enzymes responsible for artemisinin production. This should in the next few years result in several approaches to boost artemisinin production. 276H. BOUWMEESTER ET AL.

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Metabolism of Acyclic Monoterpenes: Partial Purification and Properties of Geraniol Dehydrogenase from Lemongrass (Cymbopogon flexuosus Stapf.) Leaves

Cited by 46 publications

References 13 publications

Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1

Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1

Monoterpene Alcohol Metabolism: Identification, Purification, and Characterization of Two Geraniol Dehydrogenase Isoenzymes fromPolygonum minusLeaves

Research to Improve Artemisinin Production for use in the Preparation of Anti-Malarial Drugs

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