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

Author

Delgadillo, David A., primary, Burch, Jessica E., additional, Kim, Lee Joon, additional, de Moraes, Lygia S., additional, Niwa, Kanji, additional, Williams, Jason, additional, Tang, Melody J., additional, Lavallo, Vincent G., additional, Khatri Chhetri, Bhuwan, additional, Jones, Christopher G., additional, Rodriguez, Isabel Hernandez, additional, Signore, Joshua A., additional, Marquez, Lewis, additional, Bhanushali, Riya, additional, Woo, Sunmin, additional, Kubanek, Julia, additional, Quave, Cassandra, additional, Tang, Yi, additional, and Nelson, Hosea M., additional

Published
2023
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10. High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED.

Author

Delgadillo, David A., Burch, Jessica E., Kim, Lee Joon, de Moraes, Lygia S., Niwa, Kanji, Williams, Jason, Tang, Melody J., Lavallo, Vincent G., Khatri Chhetri, Bhuwan, Jones, Christopher G., Rodriguez, Isabel Hernandez, Signore, Joshua A., Marquez, Lewis, Bhanushali, Riya, Woo, Sunmin, Kubanek, Julia, Quave, Cassandra, Tang, Yi, and Nelson, Hosea M.

Published
2024
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11. High-throughput identification of crystalline natural products from crude extracts enabled by microarray technology and microED

Author

Delgadillo, David A., Burch, Jessica E., Kim, Lee Joon, de Moraes, Lygia, Niwa, Kanji, Williams, Jason, Tang, Melody J., Lavallo, Vincent G., Chhetri, Bhuwan K., Jones, Christopher G., Hernandez Rodriguez, Isabel, Signore, Joshua A., Marquez, Lewis, Bhanushali, Riya, Greene, Madison, Woo, Sunmin, Kubanek, Julia, Quave, Cassandra, Tang, Yi, Nelson, Hosea M., Delgadillo, David A., Burch, Jessica E., Kim, Lee Joon, de Moraes, Lygia, Niwa, Kanji, Williams, Jason, Tang, Melody J., Lavallo, Vincent G., Chhetri, Bhuwan K., Jones, Christopher G., Hernandez Rodriguez, Isabel, Signore, Joshua A., Marquez, Lewis, Bhanushali, Riya, Greene, Madison, Woo, Sunmin, Kubanek, Julia, Quave, Cassandra, Tang, Yi, and Nelson, Hosea M.

Abstract

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.

Published
2023

13. Recent advances in the discovery of plant-derived antimicrobial natural products to combat antimicrobial resistant pathogens: insights from 2018–2022.

Author

Woo, Sunmin, Marquez, Lewis, Crandall, William J., Risener, Caitlin J., and Quave, Cassandra L.

Subjects
*NATURAL products, *BIRTHPARENTS, *ANTI-infective agents, *PLANT products, *DRUG resistance in microorganisms
Abstract

Covering: 2018 to 2022 Antimicrobial resistance (AMR) poses a significant global health threat. There is a rising demand for innovative drug scaffolds and new targets to combat multidrug-resistant bacteria. Before the advent of antibiotics, infections were treated with plants chosen from traditional medicine practices. Of Earth's 374 000 plant species, approximately 9% have been used medicinally, but most species remain to be investigated. This review illuminates discoveries of antimicrobial natural products from plants covering 2018 to 2022. It highlights plant-derived natural products with antibacterial, antivirulence, and antibiofilm activity documented in lab studies. Additionally, this review examines the development of novel derivatives from well-studied parent natural products, as natural product derivatives have often served as scaffolds for anti-infective agents. [ABSTRACT FROM AUTHOR]

Published
2023
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14. Identification of Botanical Viral Entry Inhibitors for SARS‐CoV‐2

Author

Risener, Caitlin J., primary, Woo, Sunmin, additional, Samarakoon, Tharamangala, additional, Caputo, Marco, additional, Edwards, Emily, additional, Zandi, Keivan, additional, Goh, Shu Ling, additional, Downs‐Bowen, Jessica A., additional, Schinazi, Raymond F., additional, and Quave, Cassandra L., additional

Published
2022
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17. Linking a Gene Cluster to Atranorin, a Major Cortical Substance of Lichens, through Genetic Dereplication and Heterologous Expression

Author

Kim, Wonyong, primary, Liu, Rundong, additional, Woo, Sunmin, additional, Kang, Kyo Bin, additional, Park, Hyun, additional, Yu, Young Hyun, additional, Ha, Hyung-Ho, additional, Oh, Seung-Yoon, additional, Yang, Ji Ho, additional, Kim, Hangun, additional, Yun, Sung-Hwan, additional, and Hur, Jae-Seoun, additional

Published
2021
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20. Botanical inhibitors of SARS-CoV-2 viral entry: a phylogenetic perspective.

Author

Risener, Caitlin J., Woo, Sunmin, Samarakoon, Tharanga, Caputo, Marco, Edwards, Emily, Klepzig, Kier, Applequist, Wendy, Zandi, Keivan, Goh, Shu Ling, Downs-Bowen, Jessica A., Schinazi, Raymond F., and Quave, Cassandra L.

Subjects
*CARDIAC glycosides, *COVID-19 pandemic, *SARS-CoV-2, *CELL receptors, *VIRAL proteins
Abstract

Throughout the SARS-CoV-2 pandemic, the use of botanical dietary supplements in the United States has increased, yet their safety and efficacy against COVID-19 remains underexplored. The Quave Natural Product Library is a phylogenetically diverse collection of botanical and fungal natural product extracts including popular supplement ingredients. Evaluation of 1867 extracts and 18 compounds for virus spike protein binding to host cell ACE2 receptors in a SARS-CoV-2 pseudotyped virus system identified 310 extracts derived from 188 species across 76 families (3 fungi, 73 plants) that exhibited ≥ 50% viral entry inhibition activity at 20 µg/mL. Extracts exhibiting mammalian cytotoxicity > 15% and those containing cardiotoxic cardiac glycosides were eliminated. Three extracts were selected for further testing against four pseudotyped variants and infectious SARS-CoV-2 and were then further chemically characterized, revealing the potent (EC50 < 5 µg/mL) antiviral activity of Solidago altissima L. (Asteraceae) flowers and Pteridium aquilinum (L.) Kuhn (Dennstaedtiaceae) rhizomes. [ABSTRACT FROM AUTHOR]

Published
2022
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24. A new phenolic compound from Phedimus middendorffianus with antiproliferative activity.

Author

Lee, Jiho, Woo, Sunmin, Sung, Sang Hyun, and Yang, Heejung

Subjects
PHENOLS, BENZOATES, CELL lines, BENZOIC acid, CANCER cells, GALLIC acid
Abstract

A new phenolic compound (1) and together with 12 known compounds–eight flavonoids (2 ∼ 9), two phenolic compounds (10 and 11) and two benzoic acid (12 and 13)–were isolated from Phedimus middendorffianus (Maxim.). The structures of all compound were determined on the basis of spectroscopic (MS and NMR) analyses. Compounds 4, 5, 7 and 11 ∼ 13 were showed anti-proliferative activities against MCF-7 than PC-3 cell line. Also compound 12 and 13 showed the significant cytotoxic activities against two cancer cell lines, PC-3 and MCF-7. [ABSTRACT FROM AUTHOR]

Published
2020
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25. Selaginellin Derivatives from Selaginella tamariscinaand Their Upregulating Effects on Low-Density Lipoprotein Receptor Expression

Author

Woo, Sunmin, Chae, Hee-Sung, Kim, Jinwoong, and Chin, Young-Won

Abstract

Two new dimeric selaginellins, diselaginellins C and D (1and 2), a new unusual derivative, selapiginellin A (4), a new selaginpulvilin U (5), and a known derivative, diselaginellin A (3), were isolated from Selaginella tamariscina(P. Beauv.) Spring. Among these compounds, selapiginellin A (4) is the first naturally occurring compound comprising an ether-linked dimer of a selaginellin and a selaginpulvilin. The absolute configurations of 1, 2, and 4were elucidated by spectroscopic data analyses. Compound 5was found to regulate mRNA expression of the low-density lipoprotein receptor (LDLR) gene and LDLR-related genes.

Published
2021
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