Review
Biochemistry & Molecular Biology
Hidayat Hussain, Jianbo Xiao, Akbar Ali, Ivan R. Green, Bernhard Westermann
Summary: This review categorizes and discusses 180 new unusual cyclized triterpenoids, along with their demonstrated biogenetic pathways, syntheses, and biological effects, published between 2009 and 2021. The research showcases significant advances in the field of triterpenes, with a notable increase in the discovery of cyclized triterpenoids and significant progress in their synthesis and biological activities.
NATURAL PRODUCT REPORTS
(2023)
Review
Chemistry, Multidisciplinary
Min Yang, Chao Wu, Tianxi Zhang, Lei Shi, Jian Li, Hongbao Liang, Xuzhen Lv, Fengtang Jing, Lu Qin, Tianlun Zhao, Chenxi Wang, Guangxu Liu, Shuai Feng, Feng Li
Summary: Chicoric acid is widely used in various commercial products due to its significant pharmacological activities. However, the limited availability of chicoric acid hinders its further development and utilization. Echinacea purpurea is the primary natural source of chicoric acid, while other sources are not well-known. The extraction of chicoric acid from plants is the most common method, but its levels vary in different plants and extraction methods.
FRONTIERS IN CHEMISTRY
(2022)
Review
Medicine, Research & Experimental
Jie Gao, Yifeng Zhang, Xihong Liu, Xiayi Wu, Luqi Huang, Wei Gao
Summary: Triptolide, as a diterpenoid compound isolated from Tripterygium wilfordii Hook. F., has shown significant inhibitory effects on solid tumors and is being considered as a potential blockbuster drug candidate. Researchers have developed synthesis methods for triptolide to meet clinical needs and connect different disciplines efficiently for further study.
Article
Biochemistry & Molecular Biology
Jianwen Wang, Pengqing Wang, Mengmeng Xu, Yudie Chen, Liguo Feng
Summary: In this study, the oxidosqualene cyclase family of Rosa rugosa (RrOSC) was analyzed to identify key genes involved in the triterpenoid pathway. A total of 18 RrOSC members were identified and their gene structure and motifs were characterized. The phylogenetic analysis divided RrOSCs into six groups, and the RrOSCs of GI and GIV were identified as likely candidates for producing active triterpenoids. Among the candidates, RrOSC1, RrOSC10, RrOSC12, and RrOSC18 were considered as key genes based on their high expression or specific-tissue expression. Overall, this study provided important information and candidate genes for further understanding of the triterpenoid pathway in Rosa rugosa.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Fabiola A. Lopez-Huerta, Maria Teresa Ramirez-Apan, Carlos A. Mendez-Cuesta, Antonio Nieto-Camacho, Simon Hernandez-Ortega, Ericka K. P. Almeida-Aguirre, Marco A. Cerbon, Guillermo Delgado
Summary: The semisynthesis of novel derivatives of lupeol palmitate and 3 beta-palmitoyloxy-olean-12-ene was conducted, and their cytotoxic and anti-inflammatory activities were evaluated. Several derivatives showed significant inhibition of tumor cell lines, and the modification of compound structure affected their anti-inflammatory activity. Further investigation revealed that compounds 7, 10, and 11 may exert their effects by binding to the NF-kappa B receptor, and these compounds have potential for further research.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Luke R. Churchman, Lauren J. Salisbury, James J. De Voss
Summary: This study reports the first chemical synthesis of the final endogenous substrate of the sterol 14 alpha-demethylases (CYP51s), obtusifoliol, and demonstrates the potential for further investigation into the derivatisation of the sterol skeleton and the development of CYP51 inhibitors to overcome azole resistance in antifungal agents.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Forestry
Pengqing Wang, Guo Wei, Liguo Feng
Summary: This paper summarizes the research advances of the main members of the OSC family in plants, their structure and function, the biosynthesis of triterpenes, and the molecular evolution of OSC.
Article
Agriculture, Multidisciplinary
Fu-Xing Niu, Zhi-Bo Yan, Yuan-Bin Huang, Jian-Zhong Liu
Summary: A novel cell-free biosynthesis system based on a mixture of chassis cell extracts and purified enzymes was developed for efficient production of natural products like chlorogenic acid (CGA). Through optimization of reaction conditions, the yield was significantly increased, demonstrating the potential of this strategy for high-level production of natural products.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Xianglai Li, Zhao Zhou, Wenna Li, Yajun Yan, Xiaolin Shen, Jia Wang, Xinxiao Sun, Qipeng Yuan
Summary: This study integrates a responsive biosensor into a microbial coculture system to achieve autonomous regulation of product ratios. By using multi-metabolite cross-feeding, a stable coculture system is established. The strategy introduced in this study is generally applicable and provides new possibilities for industrial applications of microbial cocultures.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
HtooTint Wai, Glenn C. Micalizio
Summary: Efforts to establish a concise synthesis of 7,11-dideoxy-Delta 5-lucidadone H have resulted in the successful development of a method utilizing metallacycle-mediated annulative cross-coupling and stereoselective bond formation. Key transformations such as formal inversion of C13 and rearrangement were crucial for this synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Zuzanna Rzepka, Ewa Bebenek, Elwira Chrobak, Dorota Wrzesniok
Summary: The synthesized new 28-indole-betulin derivatives showed promising anticancer activity, particularly against MCF-7 breast cancer cells, possibly through inducing apoptosis.
Article
Chemistry, Organic
HtooTint Wai, Glenn C. Micalizio
Summary: Efforts to establish an asymmetric entry to hexanorlanostanes resulted in a concise synthesis of 7,11-dideoxy-Delta 5-lucidadone H from epichlorohydrin. By utilizing metallacycle-mediated annulative cross-coupling and stereoselective formation, key transformations were achieved, including the inversion of the C13 quaternary center and Lewis acid mediated rearrangement, leading to the generation of a hexanorlanostane system.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Tingyao Liu, Jingjing Liao, Min Shi, Li Li, Qun Liu, Xin Cui, Wei Ning, Guoyin Kai
Summary: In this study, it was discovered that methyl jasmonate (MeJA) can enhance the biosynthesis of triterpenes in dandelion. The transcriptional mechanism underlying this biosynthesis process was previously unexplored. Additionally, a MeJA-induced bHLH transcription factor called TaMYC2 was identified, and overexpression of TaMYC2 was found to increase the content of taraxasterol and taraxerol in dandelion by activating the transcription of the squalene synthase gene (TaSS).
Article
Plant Sciences
Yve Veronica da Silva Magedans, Michael A. Phillips, Arthur Germano Fett-Neto
Summary: Saponins are specialized plant terpenoids with various bioactivities, but natural sources are insufficient for industrial demand. Recent research on saponin metabolism and biotechnological approaches offer potential alternative sources for sustainable production.
PHYTOCHEMISTRY REVIEWS
(2021)
Review
Chemistry, Medicinal
The Son Ninh
Summary: This review provides a comprehensive overview of skimmianine, including its natural occurrence, structural features, biosynthesis, synthesis, pharmacological values, and pharmacokinetic action. Accumulative evidence indicates that skimmianine possesses various pharmacological activities and justifies its usage in drug development.
MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Alberto Galisteo Pretel, Helena Perez del Pulgar, Estela Guerrero de Leon, Jose Luis Lopez-Perez, A. Sonia Olmeda, Azucena Gonzalez-Coloma, Alejandro F. Barrero, Jose Francisco Quilez del Moral
Article
Plant Sciences
Jose Francisco Quilez del Moral, Alvaro Perez, Alejandro F. Barrero
PHYTOCHEMISTRY REVIEWS
(2020)
Article
Chemistry, Organic
Jose F. Quilez del Moral, Victoriano Domingo, Alvaro Perez, Kevin A. Martinez Andrade, Lourdes Enriquez, Martin Jaraiz, Jose Luis Lopez-Perez, Alejandro F. Barrero
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Fabio M. F. Santos, Zoe Dominguez, Joao P. L. Fernandes, Catia Parente Carvalho, Daniel Collado, Ezequiel Perez-Inestrosa, Maria V. Pinto, Adelaide Fernandes, Jesus F. Arteaga, Uwe Pischel, Pedro M. P. Gois
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Jose A. Gonzalez-Delgado, Miguel A. Romero, Francisco Bosca, Jesus F. Arteaga, Uwe Pischel
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Inorganic & Nuclear
Antonio A. Garcia-Valdivia, Andoni Zabala-Lekuona, Ainhoa Goni-Cardenas, Belen Fernandez, Jose A. Garcia, Jose F. Quilez del Moral, Javier Cepeda, Antonio Rodriguez-Dieguez
INORGANICA CHIMICA ACTA
(2020)
Article
Chemistry, Organic
Jose F. Quilez del Moral, Cristina Ruiz Martinez, Helena Perez del Pulgar, Juan Eduardo Martin Gonzalez, Ignacio Fernandez, Jose Luis Lopez-Perez, Alejandro Fernandez-Arteaga, Alejandro F. Barrero
Summary: The study demonstrates that water can be used as a solvent for the biomimetic-like synthesis of cannabinoids, with analysis of additives and reaction modes providing theoretical support. Similar reactions conducted in organic media using catalysts revealed a unique reaction process. Computational studies provided insights into the mechanism and energetics of the process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Alberto Galisteo, Fatin Jannus, Amalia Garcia-Garcia, Houssam Aheget, Sara Rojas, Jose A. Lupianez, Antonio Rodriguez-Dieguez, Fernando J. Reyes-Zurita, Jose F. Quilez del Moral
Summary: A variety of diclofenac N-derivatives were synthesized and tested for their anti-cancer and anti-inflammatory effects, showing significant inhibitory effects on cancer cell lines and inflammatory responses. These compounds have the potential to be effective therapeutic strategies against diseases such as cancer and inflammation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Plant Sciences
Jose Francisco Quilez del Moral, Alvaro Perez, Maria Jose Segura Navarro, Alberto Galisteo, Azucena Gonzalez-Coloma, Maria Fe Andres, Alejandro E. Barrero
Summary: Cardenolide-free extracts from Digitalis obscura exhibited significant antifeedant effects against aphids, with the activity correlated to their phenylethanoid content. The isolation of rengyolone and hallerone from D. obscura was achieved, with their antifeedant and nematicidal activities reported for the first time. This study provides new insights into the bioactivity of phenylethanoids from D. obscura.
Article
Chemistry, Multidisciplinary
Antonio M. Borrero-Lopez, David B. Guzman, Jose Antonio Gonzalez-Delgado, Jesus F. Arteaga, Concepcion Valencia, Uwe Pischel, Jose M. Franco
Summary: The new photocured bioadhesive, using o-nitrobenzyl-protected precursor as a phototrigger for the release of diamine cadaverine, demonstrates faster curing with UV light and superior adhesion performance, reaching lap shear strength values of up to 4600 kPa. Characterization with FTIR spectroscopy reveals a well-balanced urethane/urea composition and in-depth chemical analysis, showing the direct impact on adhesion properties. Additionally, the material bonds a variety of surfaces and has approximately the same viscoelastic properties as a result of the favored fast formation of urea bonds.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Analytical
Amalia Garcia-Garcia, Victor Toral, Jose F. Quilez del Moral, Alberto Galisteo Pretel, Diego P. Morales, Alfonso Salinas-Castillo, Javier Cepeda, Duane Choquesillo-Lazarte, Marco Bobinger, Jose F. Salmeron, Almudena Rivadeneyra, Antonio Rodriguez-Dieguez
Summary: In this study, a novel coordination polymer (CP) based on perylene-3,4,9,10-tetracarboxylate (pery) linkers and sodium metal ions was synthesized. By modifying the properties of the metal ions, we confirmed their role in the functionalization of the material and paved the way for the generation of sensitive and selective chemical sensors.
Article
Chemistry, Medicinal
Silvia Baldo, Patricia Antunes, Joao Falcao Felicidade, Fabio M. F. Santos, Jesus F. Arteaga, Fabio Fernandes, Uwe Pischel, Sandra N. Pinto, Pedro M. P. Gois
Summary: This study demonstrates that fluorescent boronic-acid derived salicylidenehydrazone complexes can be used as fluorescent linkers to monitor the delivery of proteasome inhibitor to cancer cells. The complexes were optimized for stability and sequestered by lipid droplets within cells, limiting hydrolysis and drug release. Conjugation with a cell-penetrating peptide improved cytoplasmic availability and potency against cancer cells.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
David Guzman Rios, Miguel A. Romero, Jose A. Gonzalez-Delgado, Jesus F. Arteaga, Uwe Pischel
Summary: The [Ru(bpy)2(Nor)2]2+ complex is an efficient catalyst for the aldol reaction of acetone with activated benzaldehydes in a buffered aqueous solution. The role of the metal as an activator for nornicotine organocatalyst ligands enhances catalytic activity by about 4.5 times compared to free nornicotine. The study provides insights into the synergistic effect of organic catalysts and metals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Alvaro Perez, Jose F. Quilez del Moral, Alberto Galisteo, Juan M. Amaro, Alejandro F. Barrero
Summary: The antibiotic platensymicyn, which can be used to treat infections caused by multidrug-resistant bacteria, was successfully synthesized using a biomimetic approach. The starting materials used in the synthesis, ent-kaurenoic acid and grandiflorenic acid, can be obtained in large quantities from their natural sources. The key steps in the synthesis include long-distance functionalization of ent-kaurenoic acid at position C11 and an efficient protocol for degrading the A-ring of the diterpene framework.