Article
Chemistry, Organic
Hao-Feng Zhou, Wen-Yan Li, Li-Yan Peng, Xiao-Nian Li, Zhi-Li Zuo, Qin-Shi Zhao
Summary: Five new indole alkaloids, Rhynchines A-E, with a unique skeleton structure were isolated from Uncaria rhynchophylla. Among them, compounds 1 and 2 showed strong inhibitory activities against the Ca-v 3.1 calcium channel.
Article
Chemistry, Organic
Tape Kouame, Guillaume Bernadat, Victor Turpin, Marc Litaudon, Aboua Timothee Okpekon, Jean-Francois Gallard, Karine Leblanc, Somia Rharrabti, Pierre Champy, Erwan Poupon, Mehdi A. Beniddir, Pierre Le Pogam
Summary: Melonine is a basic monoterpene indole alkaloid (MIA) skeleton from Melodinus philliraeoides, with its structure revised into an unprecedented MIA scaffold. Proposed DFT-validated biosynthetic paths to both this new core and the originally reported form suggest the thermodynamic feasibility of the original structure of melonine, indicating its potential existence as a natural product.
Article
Chemistry, Organic
Eunjoon Park, Cheolwoo Bae, Cheon-Gyu Cho, Cheol-Hong Cheon
Summary: The total syntheses of the antirhine alkaloids were achieved through a series of reactions, including the cyanide-catalyzed imino-Stetter reaction and subsequent C-ring formation to generate the key intermediate. The trans-selective installation of the homoallylic alcohol side-chain at C-15 allowed the successful total syntheses of antirhine and its known epimer.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiahang Yan, Yanxia Zhen, Pengyan Wang, Yimeng Han, Huanhuan Zou, Junhan Chen, Weigang He, Weiqing Xie
Summary: In this study, a de novo synthesis of the bisindole alkaloid geissolosimine was accomplished, along with the synthesis of related compounds and the demonstration of an innovative strategy. These findings provide new insights for further research.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Matteo Faltracco, Said Ortega-Rosales, Elwin Janssen, Razvan C. Cioc, Christophe M. L. Vande Velde, Eelco Ruijter
Summary: The unexpected discovery in a seemingly trivial reaction led to the selective formation of a new carbazole product. This reaction, by carefully varying substituents, revealed a complex cascade mechanism with at least 10 elementary steps that could be directed towards different carbazole derivatives.
Article
Chemistry, Organic
Chao Liu, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel gold-catalyzed hydroarylation/Michael addition process has been developed for the efficient construction of benzazepinoindole polycyclic scaffolds from readily accessible multifunctional Ugi adducts. The developed methodology exhibits a broad substrate scope, excellent functional-group tolerance, and high yields of the target benzazepinoindoles.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Plant Sciences
Nelson Jeng-Yeou Chear, Francisco Leon, Abhisheak Sharma, Siva Rama Raju Kanumuri, Grant Zwolinski, Khalil A. Abboud, Darshan Singh, Luis F. Restrepo, Avi Patel, Takato Hiranita, Surash Ramanathan, Aidan J. Hampson, Lance R. McMahon, Christopher R. McCurdy
Summary: This study isolated and characterized ten indole and oxindole alkaloids from Malaysian Kratom leaves, and assessed their binding affinity at opioid receptors. Certain oxindole alkaloids showed high binding affinity and greater analgesic efficacy than morphine in rats, indicating their potential therapeutic activity.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Multidisciplinary
Cheng Li, Bin Zhao, Guojiang Mao, Guo-Jun Deng
Summary: In this study, a Rh(iii)-catalyzed intermolecular regioselective dearomative spirocyclization of 2-aryl-3-nitrosoindoles with alkynes was developed, leading to the redox-neutral and atom-economic construction of spiroindoline-3-one oximes bearing a C2 spirocyclic quaternary carbon center under mild conditions. Both aryl alkyl alkynes and 1,3-diynes generally reacted smoothly in the reaction with moderate to good regioselectivities. DFT calculations provided detailed insights into the reaction mechanism and explained the origins of the regioselectivities.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ying-Ying Si, Wei-Wei Wang, Qing-Mei Feng, Zhen-Zhu Zhao, Gui-Min Xue, Yan-Jun Sun, Wei-Sheng Feng, Jun-Im Young, Xian-Shi Wang
Summary: This study isolated new monoterpene indole alkaloid glycosides and phenolic glycoside esters from Gardneria nutans extract, some of which showed significant inhibitory effects on NO production and inflammatory factor expression in microglial cells. Additionally, one compound exhibited stronger cytotoxicity against cancer cell lines than taxol.
Article
Biochemistry & Molecular Biology
Haicheng Liu, Santosh Panjikar, Xiang Sheng, Yushi Futamura, Chenghua Zhang, Nana Shao, Hiroyuki Osada, Hongbin Zou
Summary: Strictosidine synthase (STR), a key enzyme in the biosynthesis of monoterpenoid indole alkaloids, catalyzes Pictet-Spengler reaction with the assistance of indole sandwich stabilization. A new nonindole sandwich binding mode was discovered and the role of Tyr151 hydroxyl group in the reaction was revealed. Further experiments resulted in the synthesis of compounds with antimalarial activity.
ACS CHEMICAL BIOLOGY
(2022)
Article
Plant Sciences
Elvis Otogo N. Nang, Pierre Le Pogam, Thiery Ndong Mba, Cedric Sima Obiang, Elisabeth Mouray, Philippe Grellier, Brice Kumulungui, Pierre Champy, Mehdi A. Beniddir
Summary: A new sulfur-containing vobasane-type indole alkaloid, hemitheion (1), was isolated from the stems of Mostuea brunonis Didr. (Gelsemiaceae), along with three known compounds. Hemitheion (1) showed moderate antiplasmodial activity and no cytotoxic activity against a specific cell line.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Organic
Hong Qiu, Lingfeng Tong, Zhongren Lin, Zheyao Li, Haosong Ren, Teng Wang, Xinhong Yu
Summary: This study reports a one-pot three-component reaction based on an oxidative dearomatization strategy to synthesize 5-hydroxyindole derivatives via a ZnI2-catalyzed tandem process. The multi-unit reactions for the construction of a new C-C bond and two C-N bonds are simple and efficient under mild conditions, and the yield of the target product is as high as 91%.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Daojiang Yan, Kunya Wang, Songlin Bai, Bingyu Liu, Jian Bai, Xiangbing Qi, Youcai Hu
Summary: This study reports a novel mechanism for the formation of 1,2-oxazine by Meisenheimer rearrangement, providing a new example of rearrangement reactions in the biosynthesis of natural products, and offering a new strategy for the discovery of natural products with N-O tethers through genome mining.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Carsten Schotte, Yindi Jiang, Dagny Grzech, Thu-Thuy T. Dang, Larissa C. Laforest, Francisco Leon, Marco Mottinelli, Satya Swathi Nadakuduti, Christopher R. McCurdy, Sarah E. O'Connor
Summary: The central biosynthetic steps responsible for the formation of mitragynine and related alkaloids in Mitragyna speciosa (kratom) have been identified, shedding light on the mechanistic basis and enabling the enzymatic production of these compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Medicinal
Yuqian Zhu, Jinran Zhao, Longbiao Luo, Yang Gao, He Bao, Pengfei Li, Hailong Zhang
Summary: Indole alkaloids play an important role in natural products due to their versatile biological activities, which are a potential source for novel antidiabetic drugs. The synthesized indole derivatives possess properties similar to natural indole alkaloids. In recent years, more and more indole derivatives have been designed and synthesized for exploring their bioactivities.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Chetan Prakash, Manitosh Pandey, Sakshi Talwar, Yatendra Singh, Sanjeev Kanojiya, Amit Kumar Pandey, Niti Kumar
Article
Chemistry, Multidisciplinary
Anjali Mishra, Yashpal Singh Chhonker, Amol Chhatrapati Bisen, Yarra Durga Prasad, Sachin Laxman Tulsankar, Hardik Chandasana, Tushar Dey, Sarvesh Kumar Verma, Veenu Bala, Sanjeev Kanojiya, Sandeep Ghatak, Rabi Sankar Bhatta
Article
Biochemical Research Methods
Yatendra Singh, Renu Nimoriya, Priyanka Rawat, D. K. Mishra, Sanjeev Kanojiya
Summary: This study utilized UPLC-ESI-MS/MS for the structural analysis of 38 naturally occurring cardiac glycosides in Nerium oleander, revealing the chemical diversity of CGs and differentiating diastereomers based on RRt and reference standards. The in-source fragmentation of CGs and MS/MS of disaccharide daughter ions provided intrinsic structural information on the sugar units, confirming the successful application of UPLC-ESI/TQD system for CG structure characterization in Nerium oleander tissues.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2021)
Article
Medicine, Legal
Madhav Nilakanth Mugale, Shubha Shukla, Manish K. Chourasia, Kashif Hanif, Aamir Nazir, Sarika Singh, Jiaur R. Gayen, Jagavelu Kumaravelu, Raj Kamal Tripathi, Baisakhi Mohrana, Manoj K. Barthwal, Akhilesh Kumar, Deepak Sharma, Divya Mohan, Anurag K. Srivastava, Sheeba Saji Samuel, Navodayam Kaleti, Sachi Bharti, Anupama Srivastava, Divyansh Sharma, Anil Kumar Meena, Ramesh Chandra, Sudhaker Yadav, Bharati Bhushan, Sadan K. Pandey, Promod K. Agnihotri, Himangsu K. Bora, Sanjeev Konojiya, Sharad Sharma, Prabhat Ranjan Mishra, Kamal R. Arya, Naibedya Chattopadhyay, Srikanta Kumar Rath, Smrati Bhadauria
Summary: Cassia occidentalis Linn (CO) has traditional medicinal uses for treating various ailments. The stem extract (CSE) at 250mg/kg dose showed no toxicity in rats and mice. Sub chronic study in rats confirmed the safety of CSE at 2500mg/kg dose.
REGULATORY TOXICOLOGY AND PHARMACOLOGY
(2021)
Article
Plant Sciences
Reena Rai, Sudhir Kumar, Krishna Bhan Singh, Sonu Khanka, Yatendra Singh, K. R. Arya, Sanjeev Kanojiya, Rakesh Maurya, Divya Singh
Summary: The ethanolic extract and butanolic fraction of Musa paradisiaca flower show potential in preventing bone density loss and promoting bone regeneration, improving bone microarchitecture in postmenopausal conditions. Compounds isolated from the extract exhibit significant osteogenic effects.
Article
Biochemistry & Molecular Biology
Shiv Nandan, Sumit K. Singh, Pratibha Singh, Vikas Bajpai, Ashwanee K. Mishra, Trapti Joshi, Rohit Mahar, Sanjeev K. Shukla, Dipak K. Mishra, Sanjeev Kanojiya
Summary: The quantitative evaluation of carbazole alkaloids in different climatic zones of India from Murraya koenigii showed that the highest concentrations were recorded in the humid subtropical and tropical wet & dry zones of India. The established method was simple, rapid, and can be used for commercial purposes and quality control of M. koenigii.
CHEMISTRY & BIODIVERSITY
(2021)
Article
Food Science & Technology
Ratnika Sharma, Priyanka Rawat, Pratibha Singh, Sanjeev Kanojiya, Promila Gupta
Summary: This study extracted and analyzed phenolic acids from finger millet using ultrasound-assisted extraction, and compared the phenolic acid content in seeds and microgreens. The results showed that the ultrasound-assisted extraction method yielded higher levels of phenolic acids with excellent antioxidant and antibacterial activity.
JOURNAL OF FOOD MEASUREMENT AND CHARACTERIZATION
(2022)
Article
Biochemical Research Methods
Yatendra Singh, Renu Nimoriya, Priyanka Rawat, Dipak K. Mishra, Sanjeev Kanojiya
Summary: In this study, UHPLC-ESI-MS/MS techniques were used to quantitatively determine cardiac glycosides (CGs) and their seasonal variation in leaf and stem samples of Nerium oleander. A total of 21 CGs were quantitatively determined, including three chemical markers: odoroside H (244.8 μg/g), odoroside A (231.4 μg/g), and oleandrin (703.9 μg/g). The season-specific accumulation of these chemical markers was observed. Additionally, the remaining 18 CGs were relatively quantified in the same samples. The developed method is simple and reliable for the identification and quantification of multiple CGs in N. oleander.
PHYTOCHEMICAL ANALYSIS
(2022)
Article
Toxicology
Kusum Devi, Yatendra Singh, Sanjeev Kanojiya, Baisakhi Moharana
Summary: This study found that Aurintricarboxylic acid (ATA) can alleviate cigarette smoke extract (CSE)-induced pulmonary inflammation by regulating the TNF-alpha/TNFR1/NF-kappa B/p65 signaling pathway. ATA not only reduced cellular apoptosis in alveolar epithelial cells, but also decreased the expression of inflammatory biomarkers and the level of oxidative stress. Furthermore, ATA also reduced fiber deposition and immune cell infiltration in the lungs.
TOXICOLOGY MECHANISMS AND METHODS
(2023)
Article
Biochemistry & Molecular Biology
Rohit Mahar, Nagarajan Manivel, Sanjeev Kanojiya, Dipak K. Mishra, Sanjeev K. Shukla
Summary: This study investigated the alkaloids in different parts of Alstonia scholaris and found that their composition and production are influenced by tissue-specific metabolism and seasonal variation. The trunk bark was identified as the best part to obtain alkaloids, while fruits showed the highest amount of picrinine, picralinal, akuammidine, 19 S scholaricine, and 19,20 E vallesamine. NMR and statistical methods were deemed helpful in differentiating the profile of alkaloids in A. scholaris.
Article
Biochemistry & Molecular Biology
Alka Raj Pandey, Shadab Ahmad, Suriya Pratap Singh, Anjali Mishra, Amol Chhatrapati Bisen, Gaurav Sharma, Ishbal Ahmad, Sanjeev K. Shukla, Rabi Sankar Bhatta, Sanjeev Kanojiya, Akhilesh Kumar Tamrakar, Koneni V. Sashidhara
Summary: Bioactivity guided phytochemical investigation led to the discovery of six new furostanol saponins from the roots of Asparagus racemosus. Among them, furoasparoside E showed significant potential in reducing blood glucose levels and may serve as a lead compound for the management of type 2 diabetes.
Article
Biochemical Research Methods
Priyanka Rawat, Yatendra Singh, Swati Tiwari, Dipak K. Mishra, Sanjeev Kanojiya
Summary: This study investigated the bioactive ingredients of Cajanus scarabaeoides using mass spectrometry analysis and identified 16 compounds, 12 of which were previously unreported. The results suggest that Cajanus scarabaeoides could be a potential source of bioactive ingredients.
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
(2023)
Article
Chemistry, Analytical
Yatendra Singh, Priyanka Rawat, Akhilesh Kumar, Sumit K. Singh, Dipak K. Mishra, Sanjeev Kanojiya
Summary: This study utilized liquid chromatography-mass spectrometry-based approach to screen and study plants from the Fabaceae family, and identified 10 plant species as new sources of bioflavonoids including catechin, epicatechin, quercetin, etc., and 24 plant species as potential alternative sources. The study also revealed significant variations in the flavonoid content among the plants of the Fabaceae family. This liquid chromatography-mass spectrometry-based approach provides an effective method for discovering new compounds and alternative sources of bioflavonoids in the Fabaceae family.
SEPARATION SCIENCE PLUS
(2023)
Article
Physics, Atomic, Molecular & Chemical
Sajan L. Shyaula, Yatendra Singh, Priyanka Rawat, Sanjeev Kanojiya
Summary: The components of D. hatagirea were analyzed using UPLC-ESI/TQ-MS approach for the first time. Twelve compounds were identified and the structures of five compounds were elucidated through MS/MS fragmentation pattern analysis. The presence of Dactylorhins, Loroglossin, and Sucrose in the plant was confirmed.
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY
(2023)
Article
Plant Sciences
Sumit Kumar Singh, Gaurav Sharma, Pratibha Singh, Sanjeev K. K. Shukla, Sanjeev Kanojiya, Dipak Kumar Mishra
Summary: This study aimed to evaluate the impact of salicylic acid (SA) and methyl jasmonate (MJ) on the enrichment of carbazole alkaloids (CAs) in the leaves of Murraya koenigii. Both elicitors were found to enhance the accumulation of CAs, but the effect varied depending on the type of elicitor, its concentration, and time of exposition.
JOURNAL OF PLANT GROWTH REGULATION
(2023)