Article
Chemistry, Organic
Liangguang Yi, Yu-Tao He, Shen Tan, Lorenzo White, Ping Lan, Michael G. Gardiner, Zhipeng Pei, Michelle L. Coote, Martin G. Banwell
Summary: The structures assigned to orthoscuticellines A-E are most likely correct based on the fully consistent spectral data with the synthetically derived compounds and taking variations in pH into account.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Sheng-Ge Li, Xu Hu, Qin Zhang, Yan-Hui Zan, Kai-Bo Wang, Chun-Yu Jiang, Jing-Jing Xue, Yong-Xiang Liu, Bin Lin, Yong-Kui Jing, Da-Hong Li, Hui-Ming Hua
Summary: Two pairs of novel beta-carboline-phenylpropanoid alkaloids with a unique chemical structure and moderate cytotoxic activity were isolated from the roots of Peganum harmala. The structures and configurations were determined by spectroscopic analyses and calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Woong Sub Byun, Hyewon Lim, Junhwa Hong, Eun Seo Bae, Seok Beom Lee, Younggwan Kim, Jeeyeon Lee, Sang Kook Lee, Suckchang Hong
Summary: The compound MC0704, a synthetic STAT3 pathway inhibitor, showed potential antitumor activity in docetaxel-resistant TNBC cells. It effectively inhibited the metastatic potential of the cells in vitro and exhibited strong antitumor activity when combined with docetaxel in a xenograft mouse model. MC0704 could be a potential therapeutic agent for TNBC patients with docetaxel resistance.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Plant Sciences
Rui Ma, Shan Cheng, Jiwen Sun, Weiming Zhu, Peng Fu
Summary: Thirteen gilvocarcin-type aryl -C-glycosides were isolated from Streptomyces sp. OUCMDZ-945, including seven new compounds and six known analogues. Their structures and absolute configurations were determined using spectroscopic analysis, chemical methods, ECD curves, and quantum chemical calculations. One of the new compounds (1) is the first reported bis-gilvocarcin derivative with a novel cyclobutane moiety. Compounds 1, 2, 5-8, and 11 showed antibacterial activity against Staphylococcus aureus strains.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Multidisciplinary Sciences
Jiaming Li, Zhencheng Lai, Weiwei Zhang, Linwei Zeng, Sunliang Cui
Summary: In this study, the authors report a modular assembly method that can synthesize tetrahydrocarboline type of indole alkaloids from simple building blocks in a single step, showing broad compatibility with medicinally relevant functionality.
NATURE COMMUNICATIONS
(2023)
Article
Plant Sciences
Yinhuan Hou, Bangjian Dong, Ying Peng, Chongsheng Peng, Mengyue Wang, Xiaobo Li
Summary: Beta-carboline alkaloids from the roots of P. tunicoides have significant analgesic activity by both central and peripheral mechanisms, which may be mediated by regulating the release of NO, Glu, or GABA alpha 1.
JOURNAL OF ETHNOPHARMACOLOGY
(2022)
Review
Pharmacology & Pharmacy
Yusuf Oloruntoyin Ayipo, Mohd Nizam Mordi, Muzaimi Mustapha, Thenmoly Damodaran
Summary: Neuropsychiatric disorders are complex diseases of the central nervous system, with treatment options remaining challenging. Beta-Carboline alkaloids, with their unique structural features, show promise for potential therapeutic agents against these disorders, although our understanding of their biological mechanisms in treating neuropsychiatric conditions is still limited.
EUROPEAN JOURNAL OF PHARMACOLOGY
(2021)
Article
Chemistry, Applied
Matheus Ardenghi Peixoto, Lucilia Kato, Cecilia Maria Alves de Oliveira, Boniek Gontijo, Cleuza Conceicao da Silva, Armando Mateus Pomini, Luiz C. Klein-Junior, Carolina dos Santos Passos, Amelia T. Henriques, Geanderson Bannwart, Silvana Maria de Oliveira Santin
Summary: Aspidosperma macrocarpon, commonly known as 'guatambu' or 'peroba', is found across North America to South America and in Brazil. Two indole alkaloids, kopsanone (1) and unreported N(4)-oxide-kopsanone (2), were isolated from the leaves of A. macrocarpon.
NATURAL PRODUCT RESEARCH
(2021)
Article
Chemistry, Organic
Philipp Gross, Heiko Ihmels
Summary: A novel azoniahetarene, named benzo[b]-indolonaphthyridinium, was unexpectedly synthesized by a specific reaction condition. The products exhibited high fluorescence intensity in polar solvents and showed high affinity to DNA through intercalation. Additionally, DNA-binding sempervirine derivatives were also synthesized under the same conditions, indicating that the reaction pathway is determined by the substrate structure.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
JiYang Pu, Biao Chen, Wanhua Wu, Cheng Yang, Guoqing Zhang, Jason J. Chruma
Summary: The study synthesized 1,3-diaryl-beta-carboline derivatives with unique optical properties, showing strong emission in the range of 387-409 nm and high photoluminescence quantum yields of up to 74%. Density functional theory calculations were conducted to better understand the geometric, electronic, and optical properties of these novel compounds.
Article
Chemistry, Analytical
Jiranan Chaingam, Thaweesak Juengwatanatrakul, Gorawit Yusakul, Tripetch Kanchanapoom, Waraporn Putalun
Summary: This study developed and validated HPLC methods to analyze bioactive compounds in Eurycoma longifolia (EL) and E. harmandiana (EH). EH exhibited anti-inflammatory activity comparable to EL, with a higher concentration of chaparrinone observed in EH.
JOURNAL OF AOAC INTERNATIONAL
(2021)
Article
Geriatrics & Gerontology
Ning Cao, Shuping Li, Aimin Xu, Manlin Li, Xiaoguang Zou, Zunji Ke, Gang Deng, Xuemei Cheng, Changhong Wang
Summary: The study found that harmine is a main compound found in rats, mice, and humans, which can be detected in the plasma and brain of newborn rats without exogenous consumption. The concentration of harmine in rat plasma decreases with age and growth, showing a high dependence on physiological and pathological status.
FRONTIERS IN AGING NEUROSCIENCE
(2022)
Article
Chemistry, Organic
Sasi Sree Marupalli, Mariyaraj Arockiaraj, Gargi Singh, Venkatachalam Rajeshkumar
Summary: A novel transition metal-free strategy for the synthesis of benzene-fused β-carboline scaffolds has been developed using an efficient catalytic system of I-2/DMSO. This method offers a rapid and direct pathway to access benzene-fused β-carbolines from 2-(1H-indol-3-ylsulfanyl)-phenylamines and arylmethyl ketones. The protocol involves Kornblum oxidation, Pictet-Spengler cyclization, and desulfurization reactions, resulting in excellent product yields up to 99%, with wide substrate tolerance and simplicity in operation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Integrative & Complementary Medicine
Cao Ning, Wang Chang-Hong
Summary: This article reviews the latest research on the biosynthesis of natural compounds TIAs and BCAs, focusing on the role of strictosidine synthase in this process and the sources and substrate specificity of related compounds derived from strictosidine. The presence of six-bladed four-stranded beta-propeller folds in many organisms other than plants may indicate similar functions among different organisms. The expression of the strictosidine synthase gene has a significant impact on the production of various compounds, which are mainly used in plant cell suspension culture for the production of valuable drugs and biosynthesis in other carriers.
CHINESE JOURNAL OF NATURAL MEDICINES
(2021)
Review
Chemistry, Multidisciplinary
Deping Li, Renze Yang, Jun Wu, Bin Zhong, Yan Li
Summary: This paper is the first comprehensive review of alpha-carbolines, including their natural products, updated literature on synthesis, and diverse biological activities. By highlighting their antitumor, antimicrobial, anti-Alzheimer’s disease, anti-atherosclerosis, and antioxidant activities, as well as their targets and structure activity relationships (SARs), this review will contribute to further understanding and exploration of this class of alkaloids.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Takaaki Kubota, Hayato Sato, Takahiro Iwai, Jun'ichi Kobayashi
CHEMICAL & PHARMACEUTICAL BULLETIN
(2016)
Article
Chemistry, Medicinal
Takaaki Kubota, Kenta Nakamura, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi
CHEMICAL & PHARMACEUTICAL BULLETIN
(2016)
Article
Chemistry, Organic
Takaaki Kubota, Kenta Nakamura, Shin-ichiro Kurimoto, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi
Article
Plant Sciences
Takaaki Kubota, Kenta Nakamura, Shin-ichiro Kurimoto, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi
JOURNAL OF NATURAL PRODUCTS
(2017)
Article
Chemistry, Medicinal
Shin-ichiro Kurimoto, Taito Ohno, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Satoshi Omura, Jun'ichi Kobayashi, Takaaki Kubota
Article
Chemistry, Organic
Shin-ichiro Kurimoto, Yurika Iinuma, Jun'ichi Kobayashi, Takaaki Kubota
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Organic
Hideaki Takahashi, Shin-ichiro Kurimoto, Jun'ichi Kobayashi, Takaaki Kubota
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Organic
Shin-ichiro Kurimoto, Satsuki Seino, Jane Fromont, Jun'ichi Kobayashi, Takaaki Kubota
Article
Biology
Girish Beedessee, Takaaki Kubota, Asuka Arimoto, Koki Nishitsuji, Ross F. Waller, Kanako Hisata, Shinichi Yamasaki, Noriyuki Satoh, Jun'ichi Kobayashi, Eiichi Shoguchi
Article
Chemistry, Medicinal
Shin-ichiro Kurimoto, Hiroki Fujita, Satomi Kawaguchi, Yu F. Sasaki, Takanori Nakamura, Takaaki Kubota
Summary: Two new polyacetylene glycosides, kamiohnoyneosides A and B, were isolated from edible Chrysanthemum Kamiohno, showing moderate inhibition of the formation of N-epsilon-(carboxymethyl)lysine, a representative advanced glycation endproduct.
JOURNAL OF NATURAL MEDICINES
(2021)
Article
Chemistry, Medicinal
Hiromi Niwa, Shin-ichiro Kurimoto, Takaaki Kubota, Mitsuhiro Sekiguchi
Summary: This study identified 11 meroterpenoids from brown alga Sargassum macrocarpum, with 3 new compounds showing inhibitory activity against AGEs. Among them, macrocarquinoid C exhibited the strongest activity, surpassing the positive control aminoguanidine.
JOURNAL OF NATURAL MEDICINES
(2021)
Article
Chemistry, Organic
Shin-ichiro Kurimoto, Koji Wakabayashi, Yu F. Sasaki, Takanori Nakamura, Takaaki Kubota
Summary: A new neo-clerodane diterpenoid, named teuchamaedol A (1), was isolated from the aerial parts of Teucrium chamaedrys. The structure of compound 1 was determined based on spectral data, and its absolute configuration was determined using a modified Mosher's method. Teuchamaedol A (1) is the first neo-clerodane diterpenoid to possess a tetrahydrofuran moiety without additional oxygen function.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Shin-ichiro Kurimoto, Ayano Okamoto, Satsuki Seino, Jane Fromont, Jun'ichi Kobayashi, Takaaki Kubota
Summary: Two new bromotyrosine alkaloids were isolated from an Okinawan marine sponge Suberea sp., showing moderate cytotoxicity against L1210 murine leukemia cells in vitro.
TETRAHEDRON LETTERS
(2022)
Article
Plant Sciences
Shin-ichiro Kurimoto, Shoichi Suzuki, Mayumi Ueno, Jane Fromont, Jun'ichi Kobayashi, Takaaki Kubota
Summary: Zamamiphidins B and C, two novel manzamine-related alkaloids with a unique fused diazahexacyclic ring system, were isolated from a marine sponge collected in Okinawa. The structures and relative configurations of these compounds were elucidated based on spectroscopic data.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Medicinal
Hien Minh Nguyen, Takuya Ito, Shin-ichiro Kurimoto, Mika Ogawa, Nwet Nwet Win, Vo Quoc Hung, Hoai Thi Nguyen, Takaaki Kubota, Jun'ichi Kobayashi, Hiroyuki Morita
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan
Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang
Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman
Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li
Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang
Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla
Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)