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Article: Development and Essential Oil Content of Secretory Glands of Sage (Salvia officinalis).

Venkatachalam, K V / Kjonaas, R / Croteau, R

2006 Volume 76, Issue 1, Page(s) 148–150

Abstract: Scanning electron microscopy of sage (Salvia officinalis L.) leaves confirmed the presence of two basic types of glandular trichomes consisting of a capitate stalked form containing a multicellular stalk and surmounted by a unicellular secretory head, ... ...

Abstract	Scanning electron microscopy of sage (Salvia officinalis L.) leaves confirmed the presence of two basic types of glandular trichomes consisting of a capitate stalked form containing a multicellular stalk and surmounted by a unicellular secretory head, and a capitate sessile form containing a unicellular stalk and unicellular, or multicellular, secretory head. In the latter type, secretory activity and filling of the subcuticular cavity may begin at virtually any stage of the division cycle affording fully developed glands containing from one to twelve cells in the secretory head. Gas liquid chromatographic analysis of the oil content of the most numerous gland species (capitate stalked, capitate sessile with one and with eight secretory cells) indicated only minor quantitative differences in essential oil composition. Thus, each gland type is capable of producing the four major monoterpene families (p-menthanes, pinanes, bornanes and thujanes) characteristic of sage.
Language	English
Publishing date	2006-04-28
Publishing country	United States
Document type	Journal Article
ZDB-ID	208914-2
ISSN	1532-2548 ; 0032-0889
ISSN (online)	1532-2548
ISSN	0032-0889
DOI	10.1104/pp.76.1.148
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Article: Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.

Kjonaas, R / Martinkus-Taylor, C / Croteau, R

Plant physiology

2006 Volume 69, Issue 5, Page(s) 1013–1017

Abstract: The monoterpene ketone l-menthone is specifically converted to l-menthol and l-menthyl acetate and to d-neomenthol and d-neomenthyl-beta-d-glucoside in mature peppermint (Mentha piperita L. cv. Black Mitcham) leaves. The selectivity of product formation ... ...

Abstract	The monoterpene ketone l-menthone is specifically converted to l-menthol and l-menthyl acetate and to d-neomenthol and d-neomenthyl-beta-d-glucoside in mature peppermint (Mentha piperita L. cv. Black Mitcham) leaves. The selectivity of product formation results from compartmentation of the menthol dehydrogenase with the acetyl transferase and that of the neomenthol dehydrogenase with the glucosyl transferase. Soluble enzyme preparations, but not particulate preparations, from mature peppermint leaves catalyzed the NADPH-dependent reduction of l-menthone to both epimeric alcohols, and the two dehydrogenases responsible for these stereospecific transformations were resolved by affinity chromatography on Mātrex Gel Red A. Both enzymes have a molecular weight of approximately 35,000, possess a K(m) for NADPH of about 2 x 10(-5)m, are very sensitive to inhibition by thiol-directed reagents, and are not readily reversible. The menthol dehydrogenase showed a pH optimum at 7.5, exhibited a K(m) for l-menthone of about 2.5 x 10(-4)m, and also reduced d-isomenthone to d-neoisomenthol. The neomenthol dehydrogenase showed a pH optimum at 7.6, exhibited a K(m) for l-menthone of about 2.2 x 10(-5)m, and also reduced d-isomenthone to d-isomenthol. These stereochemically distinct, but otherwise similar, enzymes are of key importance in determining the metabolic fate of menthone in peppermint, and they are probably typical of the class of dehydrogenases thought to be responsible for the metabolism of monoterpene ketones during plant development.
Language	English
Publishing date	2006-04-28
Publishing country	United States
Document type	Journal Article
ZDB-ID	208914-2
ISSN	1532-2548 ; 0032-0889
ISSN (online)	1532-2548
ISSN	0032-0889
DOI	10.1104/pp.69.5.1013
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Article: Relationship of Camphor Biosynthesis to Leaf Development in Sage (Salvia officinalis).

Croteau, R / Felton, M / Karp, F / Kjonaas, R

Plant physiology

2006 Volume 67, Issue 4, Page(s) 820–824

Abstract: The camphor content of sage (Salvia officinalis L.) leaves increases as the leaves expand, and the increase is roughly proportional to the number of filled peltate oil glands which appear on the leaf surface during the expansion process. (14)CO(2) is ... ...

Abstract	The camphor content of sage (Salvia officinalis L.) leaves increases as the leaves expand, and the increase is roughly proportional to the number of filled peltate oil glands which appear on the leaf surface during the expansion process. (14)CO(2) is more rapidly incorporated into camphor and its direct progenitors in expanding leaves than in mature leaves, and direct in vitro measurement of the key enzymes involved in the conversion of geranyl pyrophosphate to camphor indicates that these enzymes, including the probable rate-limiting cyclization step, are at the highest levels during the period of maximum leaf expansion. These results clearly demonstrate that immature sage leaves synthesize and accumulate camphor most rapidly.
Language	English
Publishing date	2006-04-28
Publishing country	United States
Document type	Journal Article
ZDB-ID	208914-2
ISSN	1532-2548 ; 0032-0889
ISSN (online)	1532-2548
ISSN	0032-0889
DOI	10.1104/pp.67.4.820
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Article: Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species.

Kjonaas, R / Croteau, R

Archives of biochemistry and biophysics

1983 Volume 220, Issue 1, Page(s) 79–89

Abstract: The volatile oil of mature Mentha piperita (peppermint) leaves contains as major components the oxygenated p-menthane monoterpenes l-menthol (47%) and l-menthone (24%) as well as very low levels of the monoterpene olefins limonene (1%) and terpinolene (0. ...

Abstract	The volatile oil of mature Mentha piperita (peppermint) leaves contains as major components the oxygenated p-menthane monoterpenes l-menthol (47%) and l-menthone (24%) as well as very low levels of the monoterpene olefins limonene (1%) and terpinolene (0.1%), which are considered to be probable precursors of the oxygenated derivatives. Immature leaves, which are actively synthesizing monoterpenes, produce an oil with comparatively higher levels of limonene (approximately 3%), and isolation of the pure olefin showed this compound to consist of approximately 80% of the l-(4S)-enantiomer and approximately 20% of the d-(4R)-enantiomer. The time course of incorporation of [U-14C]sucrose into the monoterpenes of M. piperita shoot tips was consistent with the initial formation of limonene and its subsequent conversion to menthone via pulegone. d,l-[9-3H]Limonene and [9,10-3H]terpinolene were prepared and tested directly as precursors of oxygenated p-menthane monoterpenes in M. piperita shoot tips. Limonene was readily incorporated into pulegone, menthone, and other oxygenated derivatives, whereas terpinolene was not appreciably incorporated into these compounds. Similarly, d,l-[9-3H]limonene was specifically incorporated into pulegone in Mentha pulegium and into the C-2-oxygenated derivative carvone in Mentha spicata, confirming the role of this olefin as the essential precursor of oxygenated p-menthane monoterpenes. Soluble enzyme preparations from the epidermis of immature M. piperita leaves converted the acyclic terpenoid precursor [1-3H]geranyl pyrophosphate to limonene as the major cyclic product, providing a further indication that this olefin plays a central role in the formation of oxygenated monoterpenes in Mentha. No free intermediates were detected in the cyclization of geranyl pyrophosphate to limonene, suggesting that the olefin is the first cyclic intermediate to arise in the pathway, and resolution of the biosynthetic limonene, by crystallization of the derived d- and l-carvoximes, indicated an enantiomer mixture nearly identical to that isolated from the leaf oil.
MeSH term(s)	Cell-Free System ; Cyclization ; Cyclohexenes ; Limonene ; Menthol/analogs & derivatives ; Oils/analysis ; Oxidation-Reduction ; Plants, Medicinal/metabolism ; Polyisoprenyl Phosphates/metabolism ; Sucrose/metabolism ; Terpenes/biosynthesis
Chemical Substances	Cyclohexenes ; Oils ; Polyisoprenyl Phosphates ; Terpenes ; Menthol (1490-04-6) ; Sucrose (57-50-1) ; geranyl pyrophosphate (763-10-0) ; Limonene (9MC3I34447)
Language	English
Publishing date	1983-01
Publishing country	United States
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	523-x
ISSN	1096-0384 ; 0003-9861
ISSN (online)	1096-0384
ISSN	0003-9861
DOI	10.1016/0003-9861(83)90389-2
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Article: Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species

Kjonaas, R / Croteau, R

Archives of biochemistry and biophysics. Jan 1983. v. 220 (1)

1983

Title variant	Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane [para-menthane] monoterpenes in Mentha piperita and other Mentha species [Mentha piperita, peppermint].
Keywords	Mentha piperita ; Mentha piperita nothosubsp. piperita
Language	English
Dates of publication	1983-01
Size	p. 79-89., ill.
Document type	Article
ZDB-ID	523-x
ISSN	1096-0384 ; 0003-9861
ISSN (online)	1096-0384
ISSN	0003-9861
Database	NAL-Catalogue (AGRICOLA)

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Article: Does N-hydroxyglycine inhibit plant and fungal laccases?

Zhang, J / Kjonaas, R / Flurkey, W.H

Phytochemistry. Nov 1999. v. 52 (5)

1999

Abstract: The effect of N-hydroxyglycine on the oxidation of substrates, syringaldazine, tolidine, 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) and 2,6-dimethoxyphenol, by fungal and plant laccases was examined. At micromolar concentrations, N- ... ...

Abstract	The effect of N-hydroxyglycine on the oxidation of substrates, syringaldazine, tolidine, 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) and 2,6-dimethoxyphenol, by fungal and plant laccases was examined. At micromolar concentrations, N-hydroxyglycine decolorized solutions of substrates oxidized enzymatically by laccase or chemically by sodium periodate. This discoloration, or bleaching, could be mistaken for inhibition of laccase activity if N-hydroxyglycine was added to assays for laccase that monitored colored products. N-hydroxyglycine also affected oxygen consumption assays when some of these substrates were oxidized enzymatically or chemically. Spectral scans of the products formed during enzymatic or chemical oxidation of the substrates indicated that addition of N-hydroxyglycine caused a general decrease in absorption. Except for 2,6-dimethoxyphenol, no formation of new absorption peaks was noted. These results suggest that N-hydroxyglycine may not be a "classical" enzyme inhibitor of laccase, but that this compound interferes with both spectrophotometric and oxygen uptake enzyme assays for laccase.
Keywords	Coriolus hirsutus ; Magnaporthe grisea ; Agaricus bisporus ; Rhus ; enzyme inhibitors ; laccase ; chemical composition ; oxidation ; color ; oxygen consumption ; amino acid derivatives ; glycine (amino acid)
Language	English
Dates of publication	1999-11
Size	p. 775-783.
Document type	Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
Database	NAL-Catalogue (AGRICOLA)

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Article: Metabolism of monoterpenes: conversion of l-menthone to l-menthol and d-neomenthol by stereospecific dehydrogenases from peppermint (Mentha piperita) leaves

Kjonaas, R / Martinkus-Taylor, C / Croteau, R

Plant physiology. Sept 3, 1981. v. 66 (17)

1982

Keywords	plant physiology ; plant biochemistry
Language	English
Dates of publication	1982-05
Size	p. 1013-1017., ill.
Document type	Article
ZDB-ID	208914-2
ISSN	1532-2548 ; 0032-0889
ISSN (online)	1532-2548
ISSN	0032-0889
Database	NAL-Catalogue (AGRICOLA)

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Article: Development and essential oil content of secretory glands of sage (Salvia officinalis)

Venkatachalam, K.V / Kjonaas, R / Croteau, R

Plant physiology. Sept 1984. v. 76 (1)

1984

Keywords	Salvia officinalis ; essential oils ; plant glands ; plant development ; plant morphology ; chemical constituents of plants
Language	English
Dates of publication	1984-09
Size	p. 148-150., ill.
Document type	Article
ZDB-ID	208914-2
ISSN	1532-2548 ; 0032-0889
ISSN (online)	1532-2548
ISSN	0032-0889
Database	NAL-Catalogue (AGRICOLA)

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Article: Metabolism of monoterpenes: oxidation of isopiperitenol to isopiperitenone, and subsequent isomerization to piperitenone by soluble enzyme preparations from peppermint (Mentha piperita) leaves.

Kjonaas, R B / Venkatachalam, K V / Croteau, R

Archives of biochemistry and biophysics

1985 Volume 238, Issue 1, Page(s) 49–60

Abstract: Soluble enzyme extracts from peppermint leaves, when treated with polystyrene resin to remove endogenous monoterpenes and assayed with unlabeled substrates coupled with capillary gas-liquid chromatographic/mass spectrometric detection methods, were shown ...

Abstract	Soluble enzyme extracts from peppermint leaves, when treated with polystyrene resin to remove endogenous monoterpenes and assayed with unlabeled substrates coupled with capillary gas-liquid chromatographic/mass spectrometric detection methods, were shown to oxidize isopiperitenol to isopiperitenone, and to isomerize isopiperitenone to piperitenone. The enzymes responsible for the monoterpenol dehydrogenation and the subsequent allylic isomerization were separated and partially purified by chromatography on Sephadex G-150, and were shown to have molecular weights of approximately 66,000 and 54,000, respectively. The general properties of the NAD-dependent dehydrogenase were examined, and specificity studies indicated that a double bond adjacent to the carbinol carbon was a required structural feature of the monoterpenol substrate. General properties of the isomerase were also determined, and it was demonstrated that the double bond migration catalyzed by this enzyme involved an intramolecular 1,3-hydrogen transfer. These enzymatic transformations represent two key steps in the metabolic pathway for the conversion of the initially formed cyclic olefin, (+/-)-limonene, to (-)-menthol and related monoterpenes characteristic of peppermint. Some stereochemical features of these reactions, and of the overall biogenetic scheme, are described.
MeSH term(s)	Alcohol Oxidoreductases/isolation & purification ; Alcohol Oxidoreductases/metabolism ; Carbon-Carbon Double Bond Isomerases ; Chemical Phenomena ; Chemistry ; Chromatography, Gel ; Gas Chromatography-Mass Spectrometry ; Hydrogen-Ion Concentration ; Isomerases/isolation & purification ; Isomerases/metabolism ; Isomerism ; Monoterpenes ; NAD (+) and NADP (+) Dependent Alcohol Oxidoreductases ; Oxidation-Reduction ; Plants, Medicinal/enzymology ; Solubility ; Stereoisomerism ; Terpenes/biosynthesis ; Terpenes/metabolism
Chemical Substances	Monoterpenes ; Terpenes ; isopiperitenol (491-05-4) ; isopiperitenone (529-01-1) ; Alcohol Oxidoreductases (EC 1.1.-) ; NAD (+) and NADP (+) Dependent Alcohol Oxidoreductases (EC 1.1.1.-) ; isopiperitenol dehydrogenase (EC 1.1.1.223) ; Isomerases (EC 5.-) ; Carbon-Carbon Double Bond Isomerases (EC 5.3.3.-) ; isopiperitenone delta-isomerase (EC 5.3.3.11) ; piperitenone (IKR841W74D)
Language	English
Publishing date	1985-04
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	523-x
ISSN	1096-0384 ; 0003-9861
ISSN (online)	1096-0384
ISSN	0003-9861
DOI	10.1016/0003-9861(85)90139-0
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Relationship of camphor biosynthesis to leaf development in sage (Salvia officinalis)

Croteau, R / Felton, M / Kjonaas, R

Plant physiology. Apr 1981. v. 67 (4)

1981

Keywords	plant physiology ; plant biochemistry
Language	English
Dates of publication	1981-04
Size	p. 820-824., ill.
Document type	Article
ZDB-ID	208914-2
ISSN	1532-2548 ; 0032-0889
ISSN (online)	1532-2548
ISSN	0032-0889
Database	NAL-Catalogue (AGRICOLA)

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