Isolation and Identification of a Naturally Occurring Analog of Methionine<sup>1a</sup>

McRorie, Robert A.; Sutherland, George L.; Lewis, Margaret S.; Barton, Alastair; Glazener, Margaret R.; Shive, William

doi:10.1021/ja01630a032

Cited by 132 publications

(34 citation statements)

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“…SMM has been isolated from several plant tissues (16) and has been shown to be a major metabolite of exogenous "4C-methionine in seedlings of several species (6,22). As the thetin-homocysteine transmethylase-catalyzing reaction 1 has also been identified in plant tissues (23) function in plants like S-adenosylmethionine as a methyl donor.…”

Section: Methodsmentioning

confidence: 99%

Methionine Metabolism and Ethylene Biosynthesis in Senescent Flower Tissue of Morning-Glory

Hanson

Kende²

1976

Plant Physiol.

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In immature rib segments prepared from morning-glory (Ipomoea tricolor) flower buds, the major soluble metabolite formed from tracer amounts of L-methionine-U-'4C was S-methylmethionine (SMM). In segments of senescing ribs, 14C was progressively lost from SMM and appeared in free methionine. Immature segments contained about 4 nmoles of free methionine and about 16 nmoles of SMM per 30 segments. As the segments senesced, the methionine content increased about 10-fold while the SMM content remained unchanged; during this time about 0.8 nmole of ethylene was produced per 30 segments. Tracer experiments with L-methionine-U-'4C, L-methionine-methyl-3H, and Lhomocysteine thiolactone-35S indicated that SMM was capable of acting as a methyl donor, and that in senescent segments the methyl group was utilized for methionine production with homocysteine serving as methyl acceptor. Of the 2 molecules of methionine produced in this reaction, 1 was re-methylated to SMM, and the other contributed to the observed rise in the content of free methionine.Internal pools of methionine and SMM were prelabeled (but not sg ntly expaded) by overnight incubation on 10 JAM L-methionine-U-_4C. The spedfic radioactivity of the ethylene subsequently evolved during the senescence of the segments dosely paralleled the specific radioactivity of carbon atoms 3 plus 4 of free methionine extracted from the tissue, demonstrating that methionine was the major precursor of ethylene in this system. The specific radioactivity of carbon atoms 3 plus 4 of extracted SMM was about twice that of the free methionine.Based on these results, a scheme for methionine biosynthesis in senescent rib tissue is presented. The operation of this pathway in the control of ethylene production is discussed.Methionine has been shown to be a precursor of ethylene in a number of higher plants (for a review, see ref. 24) including climacteric tissues of apple, avocado, banana, and tomato (3, 4,12,14), and the metabolism of methionine in climacteric apple has been investigated (1, 2). Although there is good evidence that the total methionine content does not regulate the onset of ethylene production in ripening avocados and apples (2, 3), differences between immature (preclimacteric) and senescent (climacteric) (7). Buds were harvested either 1 or 2 days before flower opening, usually between 4:00 and 7:00 PM, and were used for preparation of 10-mm rib segments (9).The abbreviations used in the text to describe the age of flower tissues are as follows: day 0, day of flower opening and fading; day -1, 1 day before flower opening; day -2, 2 days before flower opening. General features of the incubation conditions of rib segments are outlined below; specific details are supplied in the text and figure legends. After excision on day -1 or day -2, rib segments were incubated overnight in the growth chamber. Fresh weights for segments on day -2 were 7 to 8 mg, on day -1, 9 to 11 mg, and on day 0, 10 to 12 mg. Up to 60 segments were floated in a 6-cm Petri dish on 2 ml of...

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Section: Methodsmentioning

confidence: 99%

Methionine Metabolism and Ethylene Biosynthesis in Senescent Flower Tissue of Morning-Glory

Hanson

Kende²

1976

Plant Physiol.

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“…Stages in the S cycle include the hydrolysis of dimethylsulfoniopropionate by algae to DMS, the oxidation of the latter atmospherically inter alia to dimethyl sulfoxide (DMSO), and reduction of the latter microbially (43). It has been claimed that DMS is used by seabirds to navigate towards food-rich areas (35) Not only does the highly volatile DMS (boiling point 38 o C) comprise a characteristic odor in marine districts, it also plays a key role in the aromas of a range of foodstuffs, including asparagus (47), beetroot (38), corn (13), cabbage (33), tea (26), cocoa (29), milk (41), wine (30), rum (28) and seafoods (37).…”

Section: Dimethyl Sulfide (Dmsmentioning

confidence: 99%

Dimethyl Sulfide – Significance, Origins, and Control

Bamforth

2014

Journal of the American Society of Brewing Chemists

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Dimethyl sulfide (DMS) is a substantial contributor to the aroma of many lager-style beers.Opinion varies on its desirability. It can be derived in beer from two sources: the thermal decomposition of S-methylmethionine (SMM) produced in the embryo of barley during germination; (b) the reduction of dimethyl sulfoxide (DMSO, derived from the breakdown of SMM during the curing of malt) by yeast.The enzyme that effects DMSO reduction is a reductase whose primary function is the reduction of methionine sulfoxide and which competes for reducing power with several other cellular systems.Control of DMS production from SMM is achieved by specifying precursor levels in malt, by attending to the vigor and duration of the boil and by controlling the length of the whirlpool stand. Control of DMS production from yeast is achieved by specifying yeast strain, wort gravity, free amino nitrogen and pH, the type of fermenter (ergo the extent of volatilization) and the fermentation temperature.

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“…Sulphur metabolism plays an important role in the defence responses of plants to various stress factors. One component of the sulphur metabolism, first identified by McRorie et al [1] and given considerable attention in recent years, is a non-proteinogenic amino acid, S-methylmethionine (SMM), which is synthesised from methionine (Met) using S-adenosyl methionine (AdoMet) as the methyl donor [2]. In the course of the methionine cycle this compound is able to revert to methionine through a transmethylation reaction involving homocysteine.…”

Section: Introductionmentioning

confidence: 99%

Effect of S-methylmethionine on the photosynthesis in maize at different chilling temperatures

et al. 2010

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TheeffectofthenaturalcompoundS-methylmethionine(SMM)onthefunctioningofthephotosyntheticapparatus,theefficiencyof photosynthesis and the synthesis of stress-induced phenoloids and anthocyanins involved in defence was investigated in young maize plantsexposedtomoderateandseverechillingstress.DamagetoPSIIwasobservedasareductioninthevalueofvariablefluorescence (Fv/Fm) which could be detected even after few hours of mild chilling stress. At temperatures below 10°C, the reduction in Fv/Fm was more pronounced. Changes in the value of net photosynthesis exhibited a similar tendency. SMM has a moderating effect on this reduction and itsprotectiveeffectwasmorepronouncedunderlong-lastingchillingstressandatthelowesttemperatures.Monitoringoffluorescence intensitiesandratioscorrelatedwiththelevelsofstressdefencecompounds.Thefluorescenceintensitieswerefoundtoincreaseover the course of chilling stress in response to SMM, with the highest values being recorded in plants exposed to the longest period of stress. Asimilartendencywasobservedforthequantityofanthocyanins.TheresultsconfirmthecomplexroleofSMM,whichismanifestedbothin preserving the ability of the photosynthetic apparatus to function and in stimulating the synthesis of metabolites involved in stress defence.

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Isolation and Identification of a Naturally Occurring Analog of Methionine^1a

Abstract: CsHnONSa 41.17 41.45 4.75 5.07 47 c,h7 90.5-91.5 31' C»H13OXS3 43.69 44.01 5.30 5.47 64 (CH3)2CH 112-112.5 21 c,h13oxs3 4.3.69 44.03 5.30 5.38 49 C,H, 106.5-107.5 44d C10H15ONS3 45.94 46.03 5.78 5.42 15 (CH3)2CH-ch2 112-112.5

Cited by 132 publications

References 1 publication

Methionine Metabolism and Ethylene Biosynthesis in Senescent Flower Tissue of Morning-Glory

Methionine Metabolism and Ethylene Biosynthesis in Senescent Flower Tissue of Morning-Glory

Dimethyl Sulfide – Significance, Origins, and Control

Effect of S-methylmethionine on the photosynthesis in maize at different chilling temperatures

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Isolation and Identification of a Naturally Occurring Analog of Methionine1a

Abstract: CsHnONSa 41.17 41.45 4.75 5.07 47 c,h7 90.5-91.5 31' C»H13OXS3 43.69 44.01 5.30 5.47 64 (CH3)2CH 112-112.5 21 c,h13oxs3 4.3.69 44.03 5.30 5.38 49 C,H, 106.5-107.5 44d C10H15ONS3 45.94 46.03 5.78 5.42 15 (CH3)2CH-ch2 112-112.5

Cited by 132 publications

References 1 publication

Methionine Metabolism and Ethylene Biosynthesis in Senescent Flower Tissue of Morning-Glory

Methionine Metabolism and Ethylene Biosynthesis in Senescent Flower Tissue of Morning-Glory

Dimethyl Sulfide – Significance, Origins, and Control

Effect of S-methylmethionine on the photosynthesis in maize at different chilling temperatures

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Product

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Isolation and Identification of a Naturally Occurring Analog of Methionine^1a