An LC-ESI-MS/MS method for the simultaneous determination of pronuciferine and roemerine in some Papaver species

Bayazeid, Omer; Eylem, Cemil Can; Reçber, Tuba; Yalçın, Funda Nuray; Kır, Sedef; Nemutlu, Emirhan

doi:10.1016/j.jchromb.2018.08.020

“…Targeted fragmentation of the tentative pronuciferine peak from lotus extract and supernatants of LP626 fed with rac -norcoclaurine yielded identical fragmentation spectra ( Fig. 1e ), which were in agreement with published spectra derived from authentic pronuciferine (8, 9). Collectively, these data demonstrate that Nn CYP80G stereospecifically converts ( R )-armepavine to pronuciferine in the committed step of the sacred lotus aporphine biosynthesis pathway.…”

Section: Resultssupporting

confidence: 85%

“…e, MS/MS fragmentation of pronuciferine from sacred lotus extract and strain LP626 fed with ( R,S )- norcoclaurine. Pronuciferine fragmentation is compared against two prior reports using authentic pronuciferine standard (Bayazeid et al, 2018; Lin et al, 2014). f, Ion-extracted LC-MS chromatograms of strain LP626 and its NnOMT5 Δ derivative (LP627) fed with ( R , S )- norcoclaurine.…”

Section: Resultsmentioning

confidence: 99%

Pathway elucidation and microbial synthesis of proaporphine and bis-benzylisoquinoline alkaloids from sacred lotus (Nelumbo nucifera)

Pyne¹,

Martin²

2022

Preprint

2

0

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Sacred lotus (Nelumbo nucifera) has been utilized as a food, medicine, and spiritual symbol for nearly 3,000 years. The medicinal properties of lotus are largely attributed to its unique profile of benzylisoquinoline alkaloids (BIAs), which includes potential anti-cancer, anti-malarial and anti-arrhythmic compounds. BIA biosynthesis in sacred lotus differs markedly from that of opium poppy and other members of the Ranunculales, most notably in an abundance of BIAs possessing the (R)-stereochemical configuration and the absence of reticuline, a major branchpoint intermediate in most BIA producers. Owing to these unique metabolic features and the pharmacological potential of lotus, we set out to elucidate the BIA biosynthesis network in N. nucifera. Here we show that lotus CYP80G (NnCYP80G) and a superior ortholog from Peruvian nutmeg (Laurelia sempervirens; LsCYP80G) stereospecifically convert (R)-armepavine to pronuciferine, a proaporphine alkaloid and the presumed precursor to nuciferine. While sacred lotus employs a dedicated (R)-route to aporphine alkaloids from (R)-norcoclaurine, we implemented an artificial stereochemical inversion approach to flip the stereochemistry of the core BIA pathway. Exploiting the unique substrate specificity of dehydroreticuline synthase from common poppy (Papaver rhoeas) and pairing it with dehydroreticuline reductase enabled de novo synthesis of (R)-armepavine from (S)-norcoclaurine and its subsequent conversion to pronuciferine. We leveraged our stereochemical inversion approach to also elucidate the role of NnCYP80A in sacred lotus metabolism, which we show catalyzes the stereospecific formation of the bis-BIA nelumboferine. Screening our collection of 66 plant O-methyltransferases enabled conversion of nelumboferine to liensinine, a potential anti-cancer bis-BIA from sacred lotus.

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“…Roemerine is a naturally occurring alkaloid that was reported to facilitate in reducing symptoms of Neurodegenerative diseases [22]. Previous work also detected signi cant amount of Roemerine in P. lacerum and P. syriacum and labeled it as possible strong antidepressant drug [23]. The current study also detected a variety of alkaloids in the plant organs as mentioned in the table 1, which were not discussed in this report.…”

Section: Gc-ms Pro Lementioning

confidence: 44%

Papaver Decaisnei: GC-MS Alkaloids Profiling, in Vitro Antioxidant, and Anticancer Activity

Jabbar

¹

,

Abdullah

²

,

Abdoulrahman

³

et al. 2022

Preprint

0

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The Papaver L. plant have been well known as a source of pharmaceutically valuable alkaloids (noscapine, thebaine, codeine, roemerine, papaverine and morphine). The current study investigates the phytochemical, in-vitro antioxidant, and anticancer activities of papaver decaisnei, an endemic plant species to the flora of Kurdistan-Iraq. The chemical analysis of the methanolic (MeOH) extracts of flowers, leaves, and roots of papaver decaisnei were made by using gas chromatography-mass spectrophotometry (GC-MS), and the antioxidant activity evaluation done by radical scavenging [on 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2j-azino-bis (3- ethylbenzothiazoline-6-sulfonic acid) (ABTS)], and reducing power [cupric reducing antioxidant capacity (CUPRAC), and ferric reducing antioxidant power (FRAP)] assays. The anticancer actions were presented as IC50 (inhibitory concentration at 50%) on human colorectal adenocarcinoma (Caco-2), mammary cancer cells (MCF-7), and human cervical carcinoma (HeLa) cells. The results of the phytochemical analysis showed 17, 19, and 22 chemical compounds for flowers, leaves, and roots of P. decaisnei, respectively. The prevalent organic compounds of P. decaisnei were alkaloids, phenolics, fatty acids, esters, and phytosterols, namely Roemerine (70.44%), Decarbomethoxytabersonine, 9,12,15-Octadecatrien-1-ol, Hexadecanoic acid, 6,8-Dioxa-3-thiabicyclo(3,2,1)octane 3,3-dioxide, and γ-Sitosterol. The antioxidant activity of plant organ extracts was within 39.1-143.5 μg/ml for DPPH and 123.12-276.4 μg/ml for ABTS assays, while, the FRAP and CUPRAC values ranged within 12.4- 34.3 and 42.6-75.8 μg/ml, respectively. The anticancer action of P.decaisnei organ extracts was found against all tested human cell lines (Caco-2, MCF-7, HeLa) with inhibitory concentrations (IC50) values between 125.3-388.4 μg/ml. The presented data on alkaloid contents and biological activity of P. decaisnei can serve a ground knowledge for the future biomedical synthesis and cancer research projects.

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“…Neurodegenerative diseases [22]. Previous work also detected signi cant amount of Roemerine in P. lacerum and P. syriacum and labeled it as possible strong antidepressant drug [23]. The current study also detected a variety of alkaloids in the plant organs as mentioned in the table 1, which were not discussed in this report.…”

Section: Gc-ms Pro Lementioning

confidence: 48%

Papaver decaisnei: GC-MS alkaloids profiling, in vitro antioxidant, and anticancer activity

Jabbar

¹

,

Abdullah

²

,

Abdoulrahman

³

et al. 2022

Preprint

1

0

View full text Add to dashboard Cite

The Papaver L. plant have been well known as a source of pharmaceutically valuable alkaloids (noscapine, thebaine, codeine, roemerine, papaverine and morphine). The current study investigates the phytochemical, in-vitro antioxidant, and anticancer activities of papaver decaisnei, an endemic plant species to the flora of Kurdistan-Iraq. The chemical analysis of the methanolic (MeOH) extracts of flowers, leaves, and roots of papaver decaisnei were made by using gas chromatography-mass spectrophotometry (GC-MS), and the antioxidant activity evaluation done by radical scavenging [on 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2j-azino-bis (3- ethylbenzothiazoline-6-sulfonic acid) (ABTS)], and reducing power [cupric reducing antioxidant capacity (CUPRAC), and ferric reducing antioxidant power (FRAP)] assays. The anticancer actions were presented as IC50 (inhibitory concentration at 50%) on human colorectal adenocarcinoma (Caco-2), mammary cancer cells (MCF-7), and human cervical carcinoma (HeLa) cells. The results of the phytochemical analysis showed 17, 19, and 22 chemical compounds for flowers, leaves, and roots of P. decaisnei, respectively. The prevalent organic compounds of P. decaisnei were alkaloids, phenolics, fatty acids, esters, and phytosterols, namely Roemerine (70.44%), Decarbomethoxytabersonine, 9,12,15-Octadecatrien-1-ol, Hexadecanoic acid, 6,8-Dioxa-3-thiabicyclo(3,2,1)octane 3,3-dioxide, and γ-Sitosterol. The antioxidant activity of plant organ extracts was within 39.1-143.5 μg/ml for DPPH and 123.12-276.4 μg/ml for ABTS assays, while, the FRAP and CUPRAC values ranged within 12.4- 34.3 and 42.6-75.8 μg/ml, respectively. The anticancer action of P.decaisnei organ extracts was found against all tested human cell lines (Caco-2, MCF-7, HeLa) with inhibitory concentrations (IC50) values between 125.3-388.4 μg/ml. The presented data on alkaloid contents and biological activity of P. decaisnei can serve a ground knowledge for the future biomedical synthesis and cancer research projects.

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An LC-ESI-MS/MS method for the simultaneous determination of pronuciferine and roemerine in some Papaver species

Cited by 12 publications

References 5 publications

Pathway elucidation and microbial synthesis of proaporphine and bis-benzylisoquinoline alkaloids from sacred lotus (Nelumbo nucifera)

Pathway elucidation and microbial synthesis of proaporphine and bis-benzylisoquinoline alkaloids from sacred lotus (Nelumbo nucifera)

Papaver Decaisnei: GC-MS Alkaloids Profiling, in Vitro Antioxidant, and Anticancer Activity

Papaver decaisnei: GC-MS alkaloids profiling, in vitro antioxidant, and anticancer activity

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