Structure of calliterpenone hemihydrate

Wong, W. H.; Chen, Wei; Loke, Steffen; Mak, Thomas C. W.

doi:10.1107/s0108270190010332

Cited by 5 publications

(4 citation statements)

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“…Ultimately, four structures were obtained from this extract. The crystal structure of calliterpenone ( 1 ) (Figure ) was obtained directly from the microarrayed TEM grid . High-quality microcrystals of calliterpenone monoacetate ( 2 ) were obtained after additional recrystallization, which provided the first crystal structure of this complex diterpene natural product.…”

Section: Resultsmentioning

confidence: 99%

“…The crystal structure of calliterpenone ( 1 ) ( Figure 3 ) was obtained directly from the microarrayed TEM grid. 36 High-quality microcrystals of calliterpenone monoacetate ( 2 ) were obtained after additional recrystallization, which provided the first crystal structure of this complex diterpene natural product. The structure of a new polymorph of 5-hydroxy-4′,7-dimethoxy-flavone ( 3 ) was also resolved, as well as a polymorph of a presumed plasticizer phthalate 4 .…”

Section: Resultsmentioning

confidence: 99%

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High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED

Delgadillo,

Burch,

Kim

et al. 2023

ACS Cent. Sci.

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The structural determination of natural products (NPs) can be arduous because of sample heterogeneity. This often demands iterative purification processes and characterization of complex molecules that may be available only in miniscule quantities. Microcrystal electron diffraction (microED) has recently shown promise as a method to solve crystal structures of NPs from nanogram quantities of analyte. However, its implementation in NP discovery remains hampered by sample throughput and purity requirements, akin to traditional NP-discovery workflows. In the methods described herein, we leverage the resolving power of transmission electron microscopy (TEM) and the miniaturization capabilities of deoxyribonucleic acid (DNA) microarray technology to address these challenges through the establishment of an NP screening platform, array electron diffraction (ArrayED). In this workflow, an array of high-performance liquid chromatography (HPLC) fractions taken from crude extracts was deposited onto TEM grids in picoliter-sized droplets. This multiplexing of analytes on TEM grids enables 1200 or more unique samples to be simultaneously inserted into a TEM instrument equipped with an autoloader. Selected area electron diffraction analysis of these microarrayed grids allows for the rapid identification of crystalline metabolites. In this study, ArrayED enabled structural characterization of 14 natural products, including four novel crystal structures and two novel polymorphs, from 20 crude extracts. Moreover, we identify several chemical species that would not be detected by standard mass spectrometry (MS) or ultraviolet− visible (UV/vis) spectroscopy and crystal forms that would not be characterized using traditional methods.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED

Delgadillo,

Burch,

Kim

et al. 2023

ACS Cent. Sci.

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show abstract

“…C.C. Wong introduced inhomogeneities into the textile structure by randomly moving the tow paths and studied influence on the permeability for non-crimp fabric and plain weave models [8]. Long Li showed that the change of the fiber orientation and fiber volume fraction leads to the variety of permeability and, as a consequence, to the resin-rich areas in the composite and mechanical properties decreasing [9].…”

Section: Introductionmentioning

confidence: 99%

An Approach to Modelling the Manufacturing Process of Thermoset Composite Reinforced with 3D Woven

Kiauka¹,

Pudeleva²,

Сергеев³

et al. 2020

Proceedings of the 6th World Congress on Mechanical, Chemical, and Material Engineering

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This paper proposes the general approach to modelling the manufacturing process of thermoset composite reinforced with 3D woven based on the digital twin concept. The focus is on the methodology for determining the permeability of a dry 3D woven. Simulation results in ANSYS CFX are presented. Also, a curing simulation technique in ABAQUS with user subroutines for a thermosetting composite is described. The results of curing simulation for the Kamal-Sourour model are presented in more detail and the prediction of shape distortion for a composite U-shaped part as a result of chemical shrinkage and thermal expansion is performed.

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“…The crystal structure of calliterpenone (1) (Figure 3) was obtained directly from the microarrayed TEM grid. [25] High quality microcrystals of calliterpenone monoacetate…”

mentioning

confidence: 99%

High-throughput identification of crystalline natural products from crude extracts enabled by microarray technology and microED

Delgadillo

Burch

Kim

et al. 2023

Preprint

View full text Add to dashboard Cite

The structural determination of natural products (NPs) can be arduous due to sample heterogeneity. This often demands itera-tive purification processes and characterization of complex molecules that may only be available in miniscule quantities. Microcrystal electron diffraction (microED) has recently shown promise as a method to solve crystal structures of NPs from nanogram quantities of analyte. However, its implementation in NP discovery remains hampered by sample throughput and purity requirements akin to traditional NP-discovery workflows. In the methods described herein, we leverage the resolving power of transmission electron microscopy (TEM) and the miniaturization capabilities of DNA microarray technology to address these challenges through the establishment of an NP screening platform, array electron diffraction (ArrayED). In this workflow, an array of HPLC fractions taken from crude extracts are deposited onto TEM grids in picoliter-sized droplets. This multiplexing of analytes on TEM grids enables 1200 or more unique samples to be simultaneously inserted into a TEM equipped with an autoloader. Selected area electron diffraction analysis of these microarrayed grids allows for rapid identification of crystalline metabolites. In this study, ArrayED enabled structural characterization of 14 natural products, including four novel crystal structures and two novel polymorphs, from 20 crude extracts. Moreover, we identify several chemical species that would not be detected by standard mass spectrometry (MS) or UV/Vis and crystal forms that would not be characterized using traditional methods.

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Structure of calliterpenone hemihydrate

Abstract: 16a, 17-Dihydroxy-13fl-kauran-3-one,

Cited by 5 publications

References 0 publications

High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED

High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED

An Approach to Modelling the Manufacturing Process of Thermoset Composite Reinforced with 3D Woven

High-throughput identification of crystalline natural products from crude extracts enabled by microarray technology and microED

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