SIMULTANEOUS DETERMINATION OF IMPORTANT ALKALOIDS IN <i>PAPAVER SOMNIFERUM</i> USING REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY

Singh, Digvijay; Prajapati, Santosh Kumar; Bajpai, S. P.; Verma, Rajesh; Gupta, Madan M.; Kumar, Sushil

doi:10.1081/jlc-100100450

Cited by 25 publications

(6 citation statements)

References 3 publications

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“…According to the literature, bitter-tasting alkaloids, such as morphine, codeine, papaverine, noscapine, thebaine, and narceine, are known to be present in various segments of P. somniferum but their accumulation in the edible, ripe seeds is too low to contribute to the bitterness thereof. , Although several research groups have linked the perceived bitter and rancid off-flavor of poppy seeds to free fatty acids and lipid oxidation and degradation processes, − knowledge about the key molecules imparting the typical bitter off-taste is rather fragmentary. Only Grosch and Laskawy characterized free linoleic acid as a bitter-tasting stimulus in poppy seeds and were able to identify fatty acid oxidation products, such as 9-hydroxy-10,12-octadecadienoic acid (9-HODE), 13-hydroxy-9,11-octadecadienoic acid (13-HODE), or 12,13-dihydroxy-( E )-9-octadecadienoic acid (12,13-DHODE), in a bitter-tasting extract prepared from fresh and stored P.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Bitter-Tasting Oxylipins in Poppy Seeds (Papaver somniferum L.)

Lainer

Dawid

Dunkel

et al. 2019

J. Agric. Food Chem.

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Activity-guided fractionation of poppy seed (Papaver somniferum L.) extracts and analysis of fatty acid oxidation model experiments, followed by liquid chromatography time-of-flight mass spectrometry, tandem mass spectrometry, and one-/two-dimensional nuclear magnetic resonance experiments, revealed the chemical structures of five bitter-tasting fatty acids (1–5), three monoglycerides (6–8), six C18-lipidoxidation products (9–14), and four lipid oxidation degradation products (15 and 17–19) as well as two previously unreported monoglyceride oxidation degradation products, namely, 9-(2′,3′-dihydroxypropyloxy)-9-oxononaic acid (1-azeloyl-rac-glycerol, 16) and 1-(2′,3′-dihydroxypropyl)-8-(5″-oxo-2″,5″-dihydrofruan-2″-yl)-octonoate (1-ODFO-rac-glycerol, 20). Sensory studies exhibited low bitter taste threshold concentrations between 0.08 and 0.29 mmol/L, particularly for the higher oxidated C18-fatty acids trihydroxyoctadecenoic acid (THOE, 12), 12,13-dihydroxy-9-oxo-10-octadecenoic acid (12,13-diOH-9-oxo, 13), and 9,10-dihydroxy-13-oxo-11-octadecenoic acid (9,10-diOH-13-oxo, 14) as well as for the lipidoxidation degradation products 4-hydroxy-2-noneic acid (4-HNA, 17), 4-hydroxy-2-docecendienoic acid (HDdiA, 18), and 8-(5′-oxo-2′,5′-dihydrofuran-2′-yl)-octanoic acid (ODFO, 20).

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Section: Introductionmentioning

confidence: 99%

Characterization of Bitter-Tasting Oxylipins in Poppy Seeds (Papaver somniferum L.)

Lainer

Dawid

Dunkel

et al. 2019

J. Agric. Food Chem.

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“…All of the 291 urine samples of opium users analysed in this laboratory over the last 5-year period of time contained reticuline. In these urine samples, the per cent concentration ratios of reticuline/morphine, which were 2-12 (calculated from peak areas in the TMS-derivative mass spectra of the two com- pounds) was higher than that in opium, 0.01-3 (calculated from reticuline contents [28] and an average morphine content of 10% (w/w)). Based on the foregoing, it can be tentatively concluded that reticuline in the urine of opium users has other potential sources and/or a cumulative effect.…”

Section: Reticuline As a Marker Of Opium Usementioning

confidence: 99%

“…Reticuline is a precursor of the principal opium alkaloids thebaine, morphine and papaverine [27]; and is a minor constituent of opium (0.001-0.3% (w/w) [28]). All of the 291 urine samples of opium users analysed in this laboratory over the last 5-year period of time contained reticuline.…”

Section: Reticuline As a Marker Of Opium Usementioning

confidence: 99%

The GC–MS detection and characterization of reticuline as a marker of opium use

Al-Amri¹,

Smith²,

El‐Haj³

et al. 2004

Forensic Science International

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Reticuline (a precursor of opium alkaloids) was detected and characterised as its trimethylsilyl ethers, acetyl esters and methyl ethers by GC-EIMS and GC-CIMS in opium and the urine of opium users after hydrolysis by acid or beta-glucuronidase as coextractive of morphine. Because this compound cannot be detected in heroin and poppy seeds, it is suggested as a differentiating marker between opium and heroin use, opium and poppy seeds use, or opium and "pharmaceutical" codeine use in cases when opiate use has been confirmed by detection of morphine and codeine in the urine. As well as being a constituent of opium, reticuline in the urine of opium users may also result from the metabolic demethylation of the three other benzyltetrahydroisoquinoline opium alkaloids: codamine, laudanosine and laudanine.

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“…The straw morphinan alkaloid content of opium poppy was analysed using the protocol described by Singh et al (2000). Waters high performance liquid chromatography (HPLC) instrument was used for peak purity, identification and analysis of alkaloids (morphine, codeine and thebaine).…”

Section: Estimation Of Morphinan Alkaloid Content In the Straw (%)mentioning

confidence: 99%

Detection of DNA polymorphism inPapaver somniferumgenotypes differing in straw morphinan alkaloid content

Dubey

Shasany

Dhawan

et al. 2010

Plant Biosystems - An International Journal Dealing with all As

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Thirty-two distinct accessions of Papaver somniferum were screened for morphinan alkaloid content in the straw. The combined content of major morphinan alkaloids (morphine+codeine+thebaine) was found to vary in the range 0.2260-0.0683%. Two genotypes each, were selected as prototypes for low [I-48 (0.0683%) and I-344 (0.0878%)] and high [Pps-1 (0.2260%) and N-3 (0.2074%)] morphinan alkaloid content for studying DNA polymorphism. RAPD analysis of these four genotypes using 80 primers could not detect the polymorphism. However, AFLP analysis of these genotypes with 12 EcoRI/MseI primer pairs could distinctly group the high-and low-morphinan alkaloid genotypes separately. Furthermore, 50 AFLP fragments, specific to high-straw morphinan alkaloid genotypes (Pps-1 and N-3) and 28 DNA fragments specific to low-straw morphinan alkaloid genotypes (I-48 and I-344) could be identified. This investigation is the first report on the polymorphism identified in the genotypes differing in their straw morphinan alkaloid content. This DNA polymorphism could be exploited for defining chemotypes at an early seedling stage in poppy breeding programmes.

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SIMULTANEOUS DETERMINATION OF IMPORTANT ALKALOIDS IN PAPAVER SOMNIFERUM USING REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY

Cited by 25 publications

References 3 publications

Characterization of Bitter-Tasting Oxylipins in Poppy Seeds (Papaver somniferum L.)

Characterization of Bitter-Tasting Oxylipins in Poppy Seeds (Papaver somniferum L.)

The GC–MS detection and characterization of reticuline as a marker of opium use

Detection of DNA polymorphism inPapaver somniferumgenotypes differing in straw morphinan alkaloid content

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