Detection and determination of reticuline and N-methylcoculaurine in the Annonaceae family using liquid chromatography-tandem mass spectrometry

Kotake, Yaichiro; Okuda, Kunio; Kamizono, Machiko; Matsumoto, Naoki; Tanahashi, Takao; Hara, Hiroshi; Caparros-Lefebvre, D.; Ohta, Shigeru

doi:10.1016/j.jchromb.2004.03.017

Cited by 27 publications

(7 citation statements)

References 24 publications

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“…BIAs have been extensively investigated by LC-MS (Budzikiewicz et al, 1964;Sariyar et al, 1990;Fabre et al, 2000;Gioacchini et al, 2000;Raith et al, 2003;Hirata et al, 2004;Kotake et al, 2004;Poeaknapo et al, 2004;Sté vigny et al, 2004;Schmidt et al, 2005Schmidt et al, , 2007Wu and Huang, 2006;Gesell et al, 2009), and characteristic ESI þ -CID fragmentation mechanisms have been described (Schmidt et al, 2005. Several compounds were characterized as BIAs based on generation of certain fragment ions.…”

Section: Compound Characterizationmentioning

confidence: 99%

Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy

Desgagné‐Penix

Facchini²

2012

The Plant Journal

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SUMMARYPapaverine, a major benzylisoquinoline alkaloid in opium poppy (Papaver somniferum), is used as a vasodilator and antispasmodic. Conversion of the initial intermediate (S)-norcoclaurine to papaverine involves 3¢-hydroxylation, four O-methylations and dehydrogenation. However, our understanding of papaverine biosynthesis remains controversial more than a century after an initial scheme was proposed. In vitro assays and in vivo labeling studies have been insufficient to establish the sequence of conversions, the potential role of the intermediate (S)-reticuline, and the enzymes involved. We used virus-induced gene silencing in opium poppy to individually suppress the expression of six genes with putative roles in papaverine biosynthesis. Suppression of the gene encoding coclaurine N-methyltransferase dramatically increased papaverine levels at the expense of N-methylated alkaloids, indicating that the main biosynthetic route to papaverine proceeds via N-desmethylated compounds rather than through (S)-reticuline. Suppression of genes encoding (S)-3¢-hydroxy-N-methylcoclaurine 4-O-methyltransferase and norreticuline 7-O-methyltransferase, which accept certain N-desmethylated alkaloids, reduced papaverine content. In contrast, suppression of genes encoding N-methylcoclaurine 3¢-hydroxylase or reticuline 7-O-methyltransferase, which are specific for N-methylated alkaloids, did not affect papaverine levels. Suppression of norcoclaurine 6-O-methyltransferase transcript levels significantly suppressed total alkaloid accumulation, implicating (S)-coclaurine as a key branch-point intermediate. The differential detection of N-desmethylated compounds in response to suppression of specific genes highlights the primary route to papaverine.

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Section: Compound Characterizationmentioning

confidence: 99%

Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy

Desgagné‐Penix

Facchini²

2012

The Plant Journal

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“…Most benzylisoquinoline derivatives are expected to be complex I inhibitors. We found reticuline and Nmethylcoculaurine in leaves of soursop (Annona muricata) of the Annonaceae family [93]. N-Methylcoculaurine showed neurotoxicity in SH-SY5Y neuroblastoma cells [93].…”

Section: Possible Involvement Of Complex I Inhibitors In Neuro-degenementioning

confidence: 85%

MPP+ Analogs Acting on Mitochondria and Inducing Neuro-Degeneration

Kotake¹,

Ohta²

2003

Current Medicinal Chemistry

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This review focuses on the mechanisms of action and the injurious effect of complex I inhibitors, of which 1-methyl-4-phenylpyridinium ion (MPP(+)) is a well studied example. These compounds can be divided into two groups, i.e. competitive inhibitors with respect to ubiquinone, such as piericidine A, and non-competitive inhibitors such as rotenone. Complex I inhibitors such as MPP(+) have been reported to induce anatomical, behavioral, and biochemical changes similar to those seen in Parkinson's disease, which is characterized by nigrostriatal dopaminergic neuro-degeneration. Spectroscopic analyses and structure-activity relationship studies have indicated that the V-shaped structure of the rotenone molecule is critical for binding to the rotenone binding site on complex I. Many isoquinoline derivatives, some of them endogenous, are also complex I inhibitors. Many lines of evidence show that complex I inhibitors elicit neuronal cell death. Recently, it was reported that chronic and systemic exposure to low-dose rotenone reproduces the features of Parkinson's disease. This work further focused attention on compounds acting on mitochondria, such as MPP(+). In Guadeloupe, the French West Indies, patients with atypical parkinsonism or progressive supranuclear palsy are frequently encountered. These diseases seem to be associated with ingestion of tropical herbal teas or tropical fruits of the Annonaceae family, which contain complex I inhibitors such as benzylisoquinoline derivatives and acetogenins. Complex I inhibitors may not simply result in reactive oxygen species generation or ATP exhaustion, but may influence complex downstream signal transduction processes. An understanding of these changes would throw light on the ways in which complex I inhibitors induce a wide range of abnormalities.

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“…Stepharine, coclaurine, coreximine, annonaine, asimilobine, 2,5-dihydroxymethyl-3,4,dihydroxypyrrolidine, deoxymannojirimycin, deoxynojirmycin, swainsonine, (R)-O,O-dimethylcoclaurine, annonamine, R)-4 O-methylcocaurine, S)-narcorydine, xylopine, N-methylcoclaurine, remerine, isoboldine, isolaureline, liriodenine, reticuline, N-methylcoculaurine [109][110][111][112][113][114] Fruit Nornuciferine, annonaine, asimilobine [111,113,114] Peel Nornuciferin, assimilobin, anonaine, isolaureline…”

Section: Leafmentioning

confidence: 99%

Current Situation and Perspectives of Fruit Annonaceae in Mexico: Biological and Agronomic Importance and Bioactive Properties

Fuentes

Montalvo‐González

Magaña

et al. 2021

Plants

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The Annonaceae family is one of the oldest angiosperms. The genus Annona is the one with the most species and, together with Asimina, the only ones that contain edible fruits. In the last 10 years, interest in these fruit species has increased, mainly due to their nutritional properties and their application in the treatment of human diseases. Mexico is the center of origin for most of them. However, at present much of the basic agronomic information, postharvest handling of the fruits, and their potential as new crops for areas with poor soils in organic matter or semi-dry climates is unknown. It is considered that these custard apple species may be an option to change towards instead of crops that have lost profitability and sustainability. A review of the current state of knowledge in different areas of the species A. muricata, A. macroprophyllata, A. reticulata, A. squamosa, and A. cherimola was carried out and to focus research efforts on the topics of greatest interest and on those where is required to achieve a sustainable production and use of these resources in Mexico. However, knowledge about the cultivation and potential uses of these species is needed to increase their commercialization; the integration of interdisciplinary and interinstitutional groups is required.

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Detection and determination of reticuline and N-methylcoculaurine in the Annonaceae family using liquid chromatography-tandem mass spectrometry

Cited by 27 publications

References 24 publications

Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy

Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy

MPP+ Analogs Acting on Mitochondria and Inducing Neuro-Degeneration

Current Situation and Perspectives of Fruit Annonaceae in Mexico: Biological and Agronomic Importance and Bioactive Properties

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