Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis

Kim, Neill; Estrada, Olga; Chavez, Benjamin G; Stewart, Charles; D’Auria, John C.

doi:10.3390/molecules21111510

Cited by 56 publications

(54 citation statements)

References 152 publications

(263 reference statements)

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“…The bicyclic ring of tropane [(1R,5S)-8-methyl-8-azabicyclo-[3.2.1]octane] is the fuctional core of pharmaceutically important alkaloids, such as atropine, hyoscyamine, scopolamine, cocaine and their semisynthetic derivatives (Pollini et al, 2006;Kim et al, 2016). As a consequence, there have been a large number of structural studies devoted to tropane-based compounds.…”

Section: Chemical Contextmentioning

confidence: 99%

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Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Britvin

Rumyantsev

2017

Acta Cryst E

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The structure of a salt of diprotonated endo-3-aminotropane crystallized with a copper(II) anionic cluster is reported, viz.Neither ion in the salt has been structurally characterized previously. In the crystal, the ions pack together to form a three-dimensional structure held together by a network of intermolecular N-HÁ Á ÁO, O-HÁ Á ÁCl and N-HÁ Á ÁCl hydrogen-bonding interactions. Selective crystallization of the title compound can be considered as a simple method for the separation of the exo and endo isomers of 3-aminotropane.

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Section: Chemical Contextmentioning

confidence: 99%

“…The endo-3-aminotropane skeleton in the crystal structure of 1. The atomic numbering scheme of the tropane cage is given in accordance with IUPAC nomenclature (Pollini et al, 2006;Kim et al, 2016). Displacement ellipsoids are drawn at the 30% probability level.…”

Section: Figurementioning

confidence: 99%

Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Britvin

Rumyantsev

2017

Acta Cryst E

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“…PAs covalently bind to hydroxylcinnamate to form hyrdroxy-cinnamic acid amides (HCAAs), which drive pollen development and the pollen–pistil interaction during fertilization [ 4 ]. Contrary to mammals and bacteria, plants also utilize PAs for secondary metabolic purposes, such as stress responses [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

“…Due to their sessile nature, plants produce phytoalexins and other specialized metabolites in order to mediate their responses with both the abiotic and biotic forces present in their surrounding environment [ 5 ]. Alkaloids comprise a large class of specialized metabolites that play key roles in these interactions.…”

Section: Introductionmentioning

confidence: 99%

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Improved Synthesis of N-Methylcadaverine

et al. 2018

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Alkaloids compose a large class of natural products, and mono-methylated polyamines are a common intermediate in their biosynthesis. In order to evaluate the role of selectively methylated natural products, synthetic strategies are needed to prepare them. Here, N-methylcadaverine is prepared in 37.3% yield in three steps. The alternative literature two-step strategy resulted in reductive deamination to give N-methylpiperidine as determined by the single crystal structure. A straightforward strategy to obtain the mono-alkylated aliphatic diamine, cadaverine, which avoids potential side-reactions, is demonstrated.

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The rapid identification of chemical constituents in Fufang Xiling Jiedu capsule, a modern Chinese medicine, by ultra‐performance liquid chromatography coupled with quadrupole‐time‐of‐flight tandem mass spectrometry and data mining strategy

Cao

Geng

Luo³

et al. 2021

J of Separation Science

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capsule is an effective Chinese medicine widely used for the treatment of cold and influenza. However, its chemical constituents had not been determined, which entailed a huge obstacle to further pharmacological studies, clinical-safe medication administration, and quality evaluation. To identify the chemical constituents in Fufang Xiling Jiedu capsule, an efficient and systematic approach using ultra-high-performance liquid chromatography coupled with a quadrupole time-of-flight mass spectrometry in conjunction with a data mining strategy was adopted in this study. As a result, 145 compounds were qualitatively identified, including 26 phenolic acids, 46 flavonoids, 39 triterpenes, and 34 other compounds, among which 6 were potentially new and 144 were being reported from Fufang Xiling Jiedu capsule for the first time. This research not only provides useful information for quality control of Fufang Xiling Jiedu capsule and its involved single herbs but also serve as basis data for further study of Fufang Xiling Jiedu capsule in vivo. Moreover, it provides a reference for the characterization of the chemical constituents of other Chinese medicine preparations. K E Y W O R D S chemical constituents, data mining strategy, mass spectrometry, traditional Chinese medicine, quadrupole time of flight 1 INTRODUCTION Traditional Chinese medicines (TCMs) have been used to prevent and cure disease in China and other Asian coun-Article Related Abbreviations: FXJC, Fufang Xiling Jiedu capsule; PSMs, plant secondary metabolites; TCM, traditional Chinese medicine; t R , retention time; Q-TOF-MS, quadrupole time-of-flight mass spectrometry tries for centuries [1]. One characteristic of TCMs is the use of several Chinese medicinal materials in one medicine, mostly of herbal but sometimes also of mineral and animal origin. Therefore, it is necessary to conduct a holistic research on the chemical substances of TCM, which, as a whole, plays a multi-targeted, synergistic therapeutic role in the course of medical treatment [2-4]. UHPLC coupled with quadrupole time-of-flight mass spectrometry (Q-TOF-MS) has been developed and widely

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Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis

Cited by 56 publications

References 152 publications

Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Improved Synthesis of N-Methylcadaverine

The rapid identification of chemical constituents in Fufang Xiling Jiedu capsule, a modern Chinese medicine, by ultra‐performance liquid chromatography coupled with quadrupole‐time‐of‐flight tandem mass spectrometry and data mining strategy

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