Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry of Solanidine, Leptinidine, and Acetylleptinidine. Steroidal Alkaloids from <i>Solanum chacoense</i> Bitter

Lawson, David R.; Green, T. P.; Haynes, LeRoy W.; Miller, Anthony R.

doi:10.1021/jf9702914

Cited by 26 publications

(23 citation statements)

References 30 publications

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“…This was also confirmed by ESI-MS recorded in positive-ion mode. In fact, the spectrum of AG-2 showed a pseudomolecular ion [M þ H] þ at m/z 414, that is the same observed for leptinidine [20], the common aglycone of leptinines [6], and for the 3-O-b-d-glucopyronoside alkaloid found in wild potato species [21]. In the ESI-MS of AG-3, the pseudomolecular ion [M þ H] þ was observed at m/z 416, which is consistent with an aglycone related to solanidine but probably modified in the perhydropyridine ring.…”

supporting

confidence: 59%

Glycoalkaloids as Biomarkers for Recognition of Cultivated, Wild, and Somatic Hybrids of Potato

Savarese

Andolfi²,

Cimmino³

et al. 2009

Chemistry & Biodiversity

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Cultivated and wild potato species synthesize a wide variety of steroidal glycoalkaloids (GAs). During breeding programs, species genomes are often put together through either sexual or somatic hybridization. Therefore, the determination of the GA composition of hybrids is very important in that it may affect either human consumption, or resistance to pathogen and pests. Here, we report the results of GA analysis performed on wild Solanum bulbocastanum, haploids of cultivated potato S. tuberosum and their interspecific somatic hybrids. GAs were extracted from tubers and analyzed by HPLC. HPLC Profile of S. tuberosum haploids showed, as expected, the presence of a-solanine and a-chaconine. The profile of S. bulbocastanum extract showed lack of a-solanine and a-chaconine, and the presence of four GAs. The GA pattern of the somatic hybrids was the sum of their parents profile. This represents a noteworthy tool for their unequivocal recognition. Interestingly, two hybrids produced not only GAs of both parents but also new compounds to be further investigated. This provided evidence that somatic hybridization induced the synthesis of new metabolites. The nature of the probable unidentified GAs associated to S. bulbocastanum and its somatic hybrids was ascertained by chemical degradation and spectroscopic analysis of their aglycones and sugar moieties. Our results suggest their close relation with GAs of both wild and cultivated potato species.

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supporting

confidence: 59%

Glycoalkaloids as Biomarkers for Recognition of Cultivated, Wild, and Somatic Hybrids of Potato

Savarese

Andolfi²,

Cimmino³

et al. 2009

Chemistry & Biodiversity

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“…After concentration of the mother liquor, crystallization of the remaining residue from EtOH (96%) provided solanid-3,5-diene (0.51 g). NMR and mass spectral data of solanidine 92 and solanid-3,5-diene 93 are in accordance with literature data. 3β-Acetoxysolanidine (11).…”

Section: Methodssupporting

confidence: 88%

The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids

Vronen¹,

Koval²,

Groot

2003

Arkivoc

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The use of solanidine as starting material for the synthesis of steroid hormones was strongly stimulated by the possibility to isolate large amounts (ton scale) of potato glycoalkaloids from a waste stream of the potato starch production. A procedure is available to isolate these glycoalkaloids from the potato protein fraction and after hydrolysis solanidine is set free and can be made available as alternative for diosgenine as starting material for the production of dehydropregnenolon acetate (DPA). The conversion of solanidine to DPA was first tried by reinvestigation of several known methods like oxidation with Hg(OAc) 2 , the Cope reaction and the Polonovski reaction but none of these approaches were successful. The best option was to open the E,F-ring system using the Von Braun reaction. Besides the desired major E-ring opened compound also the minor F-ring opened compound was isolated. Alternatives for the hazardous Von Braun reagent BrCN were investigated but not found. Further degradation using the Hofmann reaction was successful in a ∆ 16 derivative, which led to the desired triene intermediate.Finally DPA could be obtained starting from solanidine in 9 reaction steps in 30% overall yield using the known conversion to spirosolane compounds followed by conversion to DPA. Extensive research has been performed on finding shortcuts in this route but despite all our efforts, further shortening of the route from 3-acetoxysolanidine via tomatidenol to DPA could not be accomplished.

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“…In addition, compounds described in the literature to be present in WT tomato fruits (Gómez-Romero et al 2010;Tikunov et al 2010;Vallverdu-Queralt et al 2010), transgenic tomato fruits (Butelli et al 2008), transgenic tomato seedlings (Bovy et al 2002), tomato seeds (Ferreres et al 2010) and tomato leaves (Strack et al 1987;Lawson et al 1997;Schmidt et al 2011) were incorporated into the list of known tomato compounds. New metabolites were putatively annotated based on their elemental formulae calculated from the observed accurate mass and using additional information such as UV absorption spectra and high-mass resolution fragmentation data.…”

Section: Metabolite Annotationmentioning

confidence: 99%

Metabolomics reveals organ-specific metabolic rearrangements during early tomato seedling development

et al. 2014

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• A submitted manuscript is the author's version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication Citation for published version (APA):Gomez-Roldan, M. V., Engel, B., Vos, de, R. C. H., Vereijken, P., Astola, L. J., Groenenboom, M., ... Hall, R. D. (2014). Metabolomics reveals organ-specic metabolic rearrangements during early tomato seedling development. Metabolomics, 10(5), 958-974. DOI: 10.1007/s11306-014-0625-2 General rightsCopyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Abstract Tomato seedlings (Solanum lycopersicum cv. MoneyMaker), grown under strictly controlled conditions, have been used to study alterations occurring in secondary metabolite biosynthetic pathways following developmental and environmental perturbations. Robustness and reproducibility of the system were confirmed using detailed statistical analyses of the metabolome. LCMS profiling was applied using whole germinated seeds as well as cotyledons, hypocotyls and roots from 3 to 9 days old seedlings to generate relative levels of 433 metabolites, of which 62 were annotated. Initial focus was given to the polyphenol pathway and several additional mass signals have been putatively annotated using high mass resolution fragmentation. Clear organ and developmental stage-specific differences were observed. Seeds accumulated saponin-like compounds; roots accumulated mainly alkaloids; cotyledons contained mainly glycosylated flavonols and; hypocotyls contained mainly anthocyanins. For each organ, the developmental changes in metabolite profiles were described by using linear mixed models. Across three independent experiments, 85 % of the metabolites showed similar developmental trends. This tomato seedling system has given us valuable additional insights into the complexity of seedling secondary metabolism. How metabolic profiles refle...

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Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry of Solanidine, Leptinidine, and Acetylleptinidine. Steroidal Alkaloids from Solanum chacoense Bitter

Cited by 26 publications

References 30 publications

Glycoalkaloids as Biomarkers for Recognition of Cultivated, Wild, and Somatic Hybrids of Potato

Glycoalkaloids as Biomarkers for Recognition of Cultivated, Wild, and Somatic Hybrids of Potato

The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids

Metabolomics reveals organ-specific metabolic rearrangements during early tomato seedling development

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