Secondary metabolite uptake by the Aristolochia-feeding papilionoid butterfly Battus polydamas

Priestap, Horacio A.; Velandia, Alvaro; Johnson, Jodie V.; Barbieri, M. Alejandro

doi:10.1016/j.bse.2011.10.006

Cited by 18 publications

(20 citation statements)

References 23 publications

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“…(Table 1) suggested that the structure of 2 was similar to that of 1 except for the addition of a methoxy group at C-6. This was further confirmed by the HMBC correlation between the methoxy protons (δ H 3.99) and C-6 (δ C 162.9) ( Compounds 1 and 2 were expected to be metabolic products of the related aristolochic acid uptake by the butterfly Battus polydamas, using HPLC-MS analysis [10]. However, to the best of our knowledge, this is the first report in which the chemical structure and NMR data of 1 and 2 are clearly provided.…”

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confidence: 58%

New Alkaloids and Anti-inflammatory Constituents from the Leaves of Antidesma ghaesembilla

Kiệm

Cuong

Trang

et al. 2017

Natural Product Communications

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Using various chromatographic methods, two new alkaloids, antidesoic acids A (1) and B (2) along with fourteen known compounds (3-16) were isolated from the leaves of Antidesma ghaesembilla Gaertn. Their chemical structures were elucidated by physical and chemical methods. All the isolated compounds were evaluated for their inhibitory activity on LPS-stimulated nitric oxide (NO) production in BV2 cells and RAW 264.7 macrophages. Bisflavone 8 significantly inhibited LPSstimulated NO production in BV2 cells and RAW 264.7 macrophages with IC 50 values of 5.4 and 8.0 µM, respectively. Compounds 1-3, 7, 10, 12, 14, and 16 showed moderate inhibitory activities with IC 50 values ranging from 11.7 to 77.4 µM.

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mentioning

confidence: 58%

New Alkaloids and Anti-inflammatory Constituents from the Leaves of Antidesma ghaesembilla

Kiệm

Cuong

Trang

et al. 2017

Natural Product Communications

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“…The identification of AA metabolites in the environment, whether in soil or water systems, has not previously been reported. Interestingly, such metabolites have recently been found, for the first time, in the larva, pupa, and imago of Battus feeding on Aristolochia [34]. Some sequestered AAs in the Battus body (AA-Ia, AA-IIIa, AA-IVa, and AA-IVb) are converted to AA O -glucosides (AA-IaG, AA-IIIaG, AA-IVaG, and AA-IVbG) through insect-mediated O -glucosylation, in which the glucosyl group links to those acids, and is known to be the main detoxification pathway for the insects [34,35].…”

Section: Possible Metabolites In the Environmentmentioning

confidence: 99%

“…Interestingly, such metabolites have recently been found, for the first time, in the larva, pupa, and imago of Battus feeding on Aristolochia [34]. Some sequestered AAs in the Battus body (AA-Ia, AA-IIIa, AA-IVa, and AA-IVb) are converted to AA O -glucosides (AA-IaG, AA-IIIaG, AA-IVaG, and AA-IVbG) through insect-mediated O -glucosylation, in which the glucosyl group links to those acids, and is known to be the main detoxification pathway for the insects [34,35]. Notably, the larval integument contains a high concentration of AAs, while the adult contains a lower level than the larva, which indicates that molting is another method of detoxification.…”

Section: Possible Metabolites In the Environmentmentioning

confidence: 99%

Aristolochic Acids: Newly Identified Exposure Pathways of this Class of Environmental and Food-Borne Contaminants and its Potential Link to Chronic Kidney Diseases

Chan

Liu

Pavlović

et al. 2019

Toxics

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Aristolochic acids (AAs) are nitrophenanthrene carboxylic acids naturally produced by Aristolochia plants. These plants were widely used to prepare herbal remedies until AAs were observed to be highly nephrotoxic and carcinogenic to humans. Although the use of AA-containing Aristolochia plants in herbal medicine is prohibited in countries worldwide, emerging evidence nevertheless has indicated that AAs are the causative agents of Balkan endemic nephropathy (BEN), an environmentally derived disease threatening numerous residents of rural farming villages along the Danube River in countries of the Balkan Peninsula. This perspective updates recent findings on the identification of AAs in food as a result of the root uptake of free AAs released from the decayed seeds of Aristolochia clematitis L., in combination with their presence and fate in the environment. The potential link between AAs and the high prevalence of chronic kidney diseases in China is also discussed.

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“…The ecological functions of magnoflorine also appear to include plant-insect interactions. The larvae of the Battus polydamus butterfly were shown to accumulate magnoflorine after feeding on Aristolochia in manner similar to the defensive sequestration of anti-feedant compounds, such as the aristolochic acids (9).…”

Section: Benzylisoquinoline Alkaloids Are a Large Group Of Plant-specmentioning

confidence: 99%

Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy

Morris

Facchini

2016

Journal of Biological Chemistry

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Benzylisoquinoline alkaloids are a large group of plant-specialized metabolites displaying an array of biological and pharmacological properties associated with numerous structural scaffolds and diverse functional group modification. N-Methylation is one of the most common tailoring reactions, yielding tertiary and quaternary pathway intermediates and products. Two N-methyltransferases accepting (i) early 1-benzylisoquinoline intermediates possessing a secondary amine and leading to the key branch-point intermediate (S)-reticuline and (ii) downstream protoberberines containing a tertiary amine and forming quaternary intermediates destined for phthalideisoquinolines and antimicrobial benzo[c]phenanthridines were previously characterized. We report the isolation and characterization of a phylogenetically related yet functionally distinct N-methyltransferase (NMT) from opium poppy (Papaver somniferum) that primarily accepts 1-benzylisoquinoline and aporphine substrates possessing a tertiary amine. The preferred substrates were the R and S conformers of reticuline and the aporphine (S)-corytuberine, which are proposed intermediates in the biosynthesis of magnoflorine, a quaternary aporphine alkaloid common in plants. Suppression of the gene encoding reticuline N-methyltransferase (RNMT) using virus-induced gene silencing in opium poppy resulted in a significant decrease in magnoflorine accumulation and a concomitant increase in corytuberine levels in roots. RNMT transcript levels were also most abundant in roots, in contrast to the distribution of transcripts encoding other NMTs, which occur predominantly in aerial plant organs. The characterization of a third functionally unique NMT involved in benzylisoquinoline alkaloid metabolism will facilitate the establishment of structure-function relationships among a large group of related enzymes.

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Secondary metabolite uptake by the Aristolochia-feeding papilionoid butterfly Battus polydamas

Cited by 18 publications

References 23 publications

New Alkaloids and Anti-inflammatory Constituents from the Leaves of Antidesma ghaesembilla

New Alkaloids and Anti-inflammatory Constituents from the Leaves of Antidesma ghaesembilla

Aristolochic Acids: Newly Identified Exposure Pathways of this Class of Environmental and Food-Borne Contaminants and its Potential Link to Chronic Kidney Diseases

Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy

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