Characterization, crystal structure and cytotoxic activity of a rare iridoid glycoside from Lonicera saccata

2020 ◽  
Vol 76 (3) ◽  
pp. 269-275
Author(s):  
Zhaoxia Qu ◽  
Li Ma ◽  
Qi Zhang ◽  
Renyong Yang ◽  
Guige Hou ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Iridoid Glycosides ◽  
Three Dimensional ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Iridoid Glycoside ◽  
Membered Ring ◽  
Mtt Method ◽  
Liver Hepatocellular Carcinoma

A new iridoid glycoside, methyl (3R,4R,4aS,7S,7aR)-3-hydroxy-7-methyl-5-oxooctahydrocyclopenta[c]pyran-4-carboxylate-3-O-β-D-(1′S,2′R,3′S,4′S,5′R)-glucopyranoside, named loniceroside A, C17H26O10, (1), was obtained from the aerial parts of Lonicera saccata. Its structure was established based on an analysis of spectroscopic data, including 1D NMR, 2D NMR and HRESIMS, and the configurations of the chiral C atoms were determined by X-ray crystallographic analysis. The single-crystal structure reveals that the cyclopenta[c]pyran scaffold is formed from a five-membered ring and a chair-like six-membered ring connected through two bridgehead chiral C atoms. In the solid state, the glucose group of (1) plays an important role in constructing an unusual supramolecular motif. The structure analysis revealed adjacent molecules linked together through intermolecular O—H...O hydrogen bonds to generate a banded structure. Furthermore, the banded structures are linked into a three-dimensional network by interesting hydrogen bonds. Biogenetically, compound (1) carries a glucopyranosyloxy moiety at the C-3 position, representing a rare structural feature for naturally occurring iridoid glycosides. The growth inhibitory effects against human cervical carcinoma cells (Hela), human lung adenocarcinoma cells (A549), human acute mononuclear granulocyte leukaemia (THP-1) and the human liver hepatocellular carcinoma cell line (HepG2) were evaluated by the MTT method.

scholarly journals Crystal structure of creatininium 5-(2,4-dinitrophenyl)-1,3-dimethylbarbiturate monohydrate: a potential anticonvulsant agent

2016 ◽  
Vol 72 (5) ◽  
pp. 620-623
Author(s):  
Ponnusamy Poornima Devi ◽  
Doraisamyraja Kalaivani
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Three Dimensional ◽  
Pyrimidine Ring ◽  
Membered Ring ◽  
Anticonvulsant Agent ◽  
The Mean ◽  
Anions And Cations ◽  
Molecular Salt

In the anion of the title hydrated molecular salt, C4H8N3O+·C12H9N4O7−·H2O [systematic name: 2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate monohydrate], the 2,4-dinitrophenyl ring is inclined to the mean plane of the pyrimidine ring [r.m.s. deviation = 0.37 Å] by 43.24 (8)°. The five-membered ring of the creatininium cation (2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium) is essentially planar with an r.m.s. deviation of 0.015 Å. In the crystal, the anions and cations are linkedviaN—H...O hydrogen bonds, forming sheets parallel to theabplane. The sheets are linkedviaO—H...O hydrogen bonds involving the water molecule, forming a three-dimensional framework. Within the framework, there are C—H...O hydrogen bonds present. The title molecular salt displays anticonvulsant and hypnotic activities.

scholarly journals Crystal structure of melaminium cyanoacetate monohydrate

2020 ◽  
Vol 76 (10) ◽  
pp. 1645-1648
Author(s):  
Bhawani Sigdel Regmi ◽  
Allen Apblett ◽  
Douglas Powell
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Title Compound ◽  
Three Dimensional ◽  
Membered Ring ◽  
Water Molecules ◽  
Asymmetric Unit ◽  
Dimensional Network

The asymmetric unit of the title compound, 2,4,6-triamino-1,3,5-triazin-1-ium cyanoacetate monohydrate, C3H7N6 +·NCCH2COO−·H2O, consists of a melaminium cation, a cyanoacetate anion and a water molecule, which are connected to each other via N—H...O and O—H...O hydrogen bonds, generating an eight-membered ring. In the crystal, the melaminium cations are connected by two pairs of N—H...N hydrogen bonds, forming tapes along [110]. These tapes develop a three-dimensional network through N—H...O, O—H...O, N—H...N and C—H...O hydrogen bonds between the cations, anions and water molecules.

scholarly journals Crystal structure of 4-(prop-2-ynyloxy)-2,2,6,6-tetramethylpiperidin-1-oxyl

2014 ◽  
Vol 70 (9) ◽  
pp. 130-133 ◽  
Author(s):  
Shailesh K. Goswami ◽  
Lyall R. Hanton ◽  
C. John McAdam ◽  
Stephen C. Moratti ◽  
Jim Simpson
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Chair Conformation ◽  
Membered Ring ◽  
Equatorial Orientation ◽  
Propargyl Bromide ◽  
Compound C ◽  
Dimensional Network

The title compound, C12H20NO2, was synthesized from 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl (hydroxy-TEMPO) and propargyl bromide. The six-membered ring adopts a flattened chair conformation and carries a propynyloxy substituent in an equatorial orientation at the 4-position. The N—O bond length of the piperidin-1-oxyl unit is 1.289 (3) Å. In the crystal, C—H...O hydrogen bonds combine with unusual C—H...π interactions involving the alkyne unit as acceptor to generate a three-dimensional network.

scholarly journals Crystal structure and biological evaluation of 4-methylmorpholin-4-ium 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate

2015 ◽  
Vol 71 (6) ◽  
pp. 723-725 ◽  
Author(s):  
Jeganathan Gomathi ◽  
Doraisamyraja Kalaivani
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Chair Conformation ◽  
Biological Evaluation ◽  
Membered Ring ◽  
Dimensional Network ◽  
Hypnotic Activity ◽  
Molecular Salt

The title molecular salt, C5H12NO+·C12H8N5O9−[common name: 4-methylmorpholin-4-ium 1,3-dimethyl-5-(2,4,6-trinitrophenyl)barbiturate], possesses noticeable anticonvulsant and hypnotic activity. In the anion, the 1,3-dimethylbarbituric acid ring and the symmetrically substituted trinitrophenyl ring, linkedviaa C—C bond, are not coplanar but subtend an angle of 44.88 (7)°. The six-membered ring of the 4-methylmorpholin-4-ium cation has a chair conformation. In the crystal, the cation and anion are linkedviaan N—H...O hydrogen bond. The cation–anion units are linked by a number of C—H...O hydrogen bonds, forming a three-dimensional network.

scholarly journals Crystal structure of 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione: a clinically used anticonvulsant

2014 ◽  
Vol 70 (9) ◽  
pp. o942-o943 ◽  
Author(s):  
Carlos Ordonez ◽  
Ilia M. Pavlovetc ◽  
Victor N. Khrustalev
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Membered Ring ◽  
Framework Structure ◽  
Phenyl Substituent ◽  
Compound C ◽  
Planar Part ◽  
The Mean

In the title compound, C12H13NO2, the five-membered ring has an envelope conformation; the disubstituted C atom lies out of the mean plane through the four other ring atoms (r.m.s. deviation = 0.0038 Å) by 0.1877 (18) Å. The plane of the phenyl substituent is practically perpendicular to that of the planar part of the five-membered ring, with a dihedral angle of 87.01 (5)°. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming inversion dimers. The dimers are linked by further C—H...O hydrogen bonds, as well as carbonyl–carbonyl attractive interactions [O...C = 3.2879 (19) Å], forming a three-dimensional framework structure.

scholarly journals Hydrogen bonds and van der Waals forces as tools for the construction of a herringbone pattern in the crystal structure of hexane-1,6-diaminium hexane-1,6-diyl bis(hydrogen phosphonate)

2017 ◽  
Vol 73 (1) ◽  
pp. 76-80
Author(s):  
Guido J. Reiss ◽  
Martin van Megen ◽  
Walter Frank
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Membered Ring ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Diphosphonic Acid ◽  
Dimensional Network ◽  
Anions And Cations ◽  
Graph Set

The asymmetric unit of the title salt, [H3N(CH2)6NH3][(HO)O2P(CH2)6PO2(OH)], consists of one half of a hexane-1,6-diaminium dication and one half of a hexane-1,6-diyl bis(hydrogen phosphonate) dianion. Both are located around different centres of inversion (Wyckoff sites: 2aand 2d) of the space groupP21/c. The shape of the hexane-1,6-diaminium cation is best described as a double hook. Both aminium groups as well as the two attached CH2groups are turned out from the plane of the central four C atoms. In contrast, all six C atoms of the dianion are almost in a plane. The hydrogen phosphonate (–PO3H) groups of the anions and the aminium groups of the cations form two-dimensional O—H... and O—H...N hydrogen-bonded networks parallel to theacplane, built up from ten-membered and twelve-membered ring motifs with graph-set descriptorsR33(10) andR54(12), respectively. These networks are linked by the alkylene chains of the anions and cations. The resulting three-dimensional network shows a herringbone pattern, which resembles the parent structures 1,6-diaminohexane and hexane-1,6-diphosphonic acid.

scholarly journals Crystal structure and Hirshfeld surface analysis of 4,5-dibromo-2-(4-methoxyphenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,6-epoxy-1H-cyclopenta[c]pyridin-1-one

2021 ◽  
Vol 77 (5) ◽  
pp. 532-536
Author(s):  
Dmitriy F. Mertsalov ◽  
Nataliya S. Surina ◽  
Elena A. Sorokina ◽  
Sevim Türktekin Çelikesir ◽  
Mehmet Akkurt ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Membered Ring ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Double Layers ◽  
Compound C ◽  
Dimensional Network

The molecule of the title compound, C15H15Br2NO3, comprises a fused tricyclic system consisting of two five-membered rings (cyclopentane and tetrahydrofuran) and one six-membered ring (tetrahydropyridinone). Both five-membered rings of the tricyclic system have envelope conformations, and the conformation of the six-membered cycle is intermediate between chair and half-chair. In the crystal, the molecules are linked by C—H...O hydrogen bonds and C—H...π, C—Br...π and C...O interactions into double layers. The layers are connected into a three-dimensional network by van der Waals interactions.

scholarly journals Crystal structure of 2-hydroxy-2-(2-oxocycloheptyl)-2,3-dihydro-1H-indene-1,3-dione

2015 ◽  
Vol 71 (10) ◽  
pp. o715-o716
Author(s):  
P. Kaleel Ahamed ◽  
N. Srinivasan ◽  
R. Ranjith Kumar ◽  
R. V. Krishnakumar
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Chair Conformation ◽  
Membered Ring ◽  
Supramolecular Architecture ◽  
Compound C ◽  
Twist Conformation ◽  
Centroid Distance

In the title compound, C16H16O4, the five-membered ring of the indene-1,3-dione unit adopts a twist conformation, whereas the seven-membered ring adopts a twist–chair conformation. In the crystal, molecules are linked by O—H...O hydrogen bonds, weak C—H...O hydrogen bonds and π–π stacking [centroid-to-centroid distance = 3.7373 (8) Å] into a three-dimensional supramolecular architecture.

scholarly journals 2-Acetonyl-2-hydroxyindan-1,3-dione

2009 ◽  
Vol 65 (6) ◽  
pp. o1209-o1209 ◽  
Author(s):  
Hoong-Kun Fun ◽  
Ching Kheng Quah ◽  
Mehtab Parveen ◽  
Raza Murad Ghalib ◽  
Sayed Hasan Mehdi
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Membered Ring ◽  
Envelope Conformation ◽  
Compound C ◽  
Dimensional Network

In the title compound, C12H10O4, the five-membered ring adopts an envelope conformation, with the Csp3atom at the flap [deviation = 0.145 (2) Å]. In the crystal structure, molecules are linked by intermolecular O—H...O and C—H...O hydrogen bonds, forming a three-dimensional network.

scholarly journals (7R)-6-Methyl-7,9-bis(prop-2-yn-1-yl)-7H,8H,9H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8-one

IUCrData ◽  
2016 ◽  
Vol 1 (8) ◽  
Author(s):  
Youness El Bakri ◽  
Abdallah Harmaoui ◽  
Jihad Sebhaoui ◽  
Youssef Ramli ◽  
El Mokhtar Essassi ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Membered Ring ◽  
Boat Conformation ◽  
Title Molecule ◽  
Dimensional Crystal

In the title molecule, C12H11N5O, the seven-membered ring derived from triazepine adopts a boat conformation. Intermolecular C—H...N hydrogen bonds and C—H...π-ring interactions form columns of molecules parallel to theaaxis, which are further associated into the three-dimensional crystal structure by additional C—H...O hydrogen bonds.

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