Crystal and molecular structure of l-hypaphorine hydroiodide

Jones, Gurnos; Tiekink, Edward R. T.

doi:10.1524/zkri.1997.212.12.881

Cited by 4 publications

(2 citation statements)

References 11 publications

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“…The N1-C2 [1.371(4) Å] bond distance is similar to the average values reported for a Csp2-N in imidazole bond (1.370 Å) [16]. All the other relevant structural parameters (bond distances and angles) are as expected and in acceptable agreement with L-hypaphorine hydroiodide analogue [17]. In the crystal the molecules are linked via hydrogen bonds between chloride anions and organic molecules.…”

Section: Commentsupporting

confidence: 81%

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C₁₄H₁₉N₂O₂Cl

García‐Beltrán

Areche

Galdámez

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Commentsupporting

confidence: 81%

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C₁₄H₁₉N₂O₂Cl

García‐Beltrán

Areche

Galdámez

et al. 2020

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Also, two related structures were published in CSD, namely L-6-Bromohypaphorine (BHYPOR) [40] and L-hypaphorine hydroiodide (PAMRUQ) [41].…”

Section: Crystal Structure and Dft Resultsmentioning

confidence: 99%

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

et al. 2020

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This study was aimed at isolating hypaphorine from Erythrina mildbraedii Harms (Fabaceae) and Erythrina addisioniae Hutch. & Datziel (Fabaceae) in order to determine its structural and antibacterial effects. Density functional theory (DFT) calculations and X-ray crystallographic analysis of the isolated hypaphorine was determined. The antibacterial effects of hypaphorine against a number of Gram positive and Gram negative bacterial strains were investigated. The root mean square deviation between the experimental and calculated bond lengths and bond angles of hypaphorine were found to be 0.046 Å and 1.5° respectively. The highest occupied molecular orbital (HOMO) of hypaphorine was delocalised on the indole moiety whereas the lowest occupied molecular orbital (LUMO) was delocalised on the -N(CH 3 ) 3 group and the HOMO-LUMO gap of hypaphorine was 4.65 eV. Hypaphorine inhibited the growth of the Gram-positive bacteria tested, namely Bacillus cereus, B. subtilis, Staphylococcus aureus and S. epidermidis. The lowest minimum inhibitory concentration (MIC) value of 2 mg/mL was exhibited against Mycobacterium smegmatis, Staphylococcus aureus and B. subtilis. The theoretical and experimental results from this study showed that hypaphorine is capable of forming quadrupole moments thus explaining its antibacterial effects on Gram positive bacteria. Graphic abstractroot hair formation and stimulates curling of the roots which aids in these symbiotic relationships [7]. Hypaphorine has thus been detected in a number of ectomycorrhizal fungal species like Pisolithus tinctorius [1,11,12]. In these symbiotic relationships, hypaphorine inhibits the effect of IAA in the fungi by blocking membrane-bound IAA receptors thus inducing abnormal proliferation of hyphae that extend intracellularly into plant tissues.

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Hypaphorine Is Present in Human Milk in Association with Consumption of Legumes

Keller

et al. 2013

J. Agric. Food Chem.

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In metabolomic analysis of human milk amines, we found a previously unidentified compound. This was tentatively identified as hypaphorine, an indole alkaloid composed of tryptophan and three methyls, and with neurological and glucose-lowering effects in rodents. Hypaphorine identity was confirmed by hypaphorine synthesis, and then a fluorometric method was developed to quantify hypaphorine in milk and foods. Using dietary records, we identified peanut products as probable sources of hypaphorine. Milk from 24 lactating women showed widely varying hypaphorine, with a mean ± SD 0.34 ± 0.33 μM, and the highest concentration of 1.24 μM. Peanuts showed high hypaphorine of 70 μg/g compared to 60 and 100 μg/g in dried chickpeas and lentils. Dietary challenge in lactating women with hypaphorine-rich foods demonstrated transfer of hypaphorine into milk with hypaphorine appearance peaking 5-18 h after consumption and prolonged disappearance indicative of slow excretion or metabolism. The potential functional roles of hypaphorine in human nutrition remain to be addressed.

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Crystal and molecular structure of l-hypaphorine hydroiodide

Cited by 4 publications

References 11 publications

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C₁₄H₁₉N₂O₂Cl

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C₁₄H₁₉N₂O₂Cl

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

Hypaphorine Is Present in Human Milk in Association with Consumption of Legumes

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Crystal and molecular structure of l-hypaphorine hydroiodide

Cited by 4 publications

References 11 publications

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C14H19N2O2Cl

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C14H19N2O2Cl

Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties

Hypaphorine Is Present in Human Milk in Association with Consumption of Legumes

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The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C₁₄H₁₉N₂O₂Cl

The crystal structure of 1-carboxy-2-(1H-indol-3-yl)-N,N,N-trimethylethan-1-ammonium chloride, C₁₄H₁₉N₂O₂Cl