Article
Chemistry, Multidisciplinary
Tushar M. Khopade, Kalyani Ajayan, Swapnil S. Joshi, Amy L. Lane, Rajesh Viswanathan
Summary: A regioselective tryptophan isoprenylation strategy promoted by Bronsted acid has been investigated, allowing for the synthesis of complex natural products. This method enables the stereoselective increase of sp(3) centers in bioactive cores through asymmetric prenylation, providing access to bioactive compounds. The approach, performed under ambient conditions without the need for expensive metal catalysts or ligands, shows similarities to biosynthetic pathways.
Article
Biochemistry & Molecular Biology
Hironori Suemune, Doukan Nishimura, Kenjiro Mizutani, Yusuke Sato, Tomoya Hino, Hiroshi Takagi, Yumi Shiozaki-Sato, Shunji Takahashi, Shingo Nagano
Summary: In this study, the crystal structures of IptA were determined, providing insights into the substrate selectivity and prenyl acceptor promiscuity. The study found that IptA can accommodate different L-Trp derivatives by adjusting the position of the substrate indole ring and adjacent side chain, resulting in different prenylation activities.
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Baofu Xu, Zining Li, Tyler A. Alsup, Michelle A. Ehrenberger, Jeffrey D. Rudolf
Summary: This study reveals the ability of terpene synthases to catalyze prenylation on small molecules, supports its physiological relevance in vivo, and proposes a substrate decoy mechanism.
Article
Chemistry, Medicinal
Sherif Ahmed Hamdy, Takeshi Kodama, Yu Nakashima, Xiaojie Han, Takashi Matsui, Hiroyuki Morita
Summary: CdpNPT, a fungal enzyme, exhibits substrate promiscuity and can generate prenylated compounds. This study reveals the catalytic potential of CdpNPT towards a beta-carboline harmol, resulting in the production of 6-(3-dimethylallyl)harmol through prenylation reaction.
JOURNAL OF NATURAL MEDICINES
(2022)
Article
Chemistry, Multidisciplinary
Nagaraju Mupparapu, Lauren Brewster, Katrina F. Ostrom, Sherif I. Elshahawi
Summary: A method for late-stage functionalization of indole- and tryptophan-containing compounds with reactive moieties to alter their biological properties was studied. Two hydroxy-bearing allyl pyrophosphates were synthesized. A chemo-enzymatic approach using a promiscuous indole prenyltransferase enzyme was demonstrated, introducing a dual reactive hydroxy-bearing allyl moiety directly onto the indole ring of tryptophan-containing peptides. This is the first report of late-stage indole modifications with this reactive group.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biotechnology & Applied Microbiology
Yuqiao Zhang, Tingting Yao, Yuechen Jiang, Huayue Li, Weicheng Yuan, Wenli Li
Summary: Cyclodipeptide synthases (CDPSs) catalyze the formation of cyclodipeptides using aminoacylated tRNAs as substrates, with great potential in producing diverse 2,5-diketopiperazines (2,5-DKP5). Genome mining of Streptomyces leeuwenhoekii NRRL B-24963 uncovered a two-gene locus, saz, encoding CDPS SazA and a unique fused enzyme (SazB) with PT and MT domains. Heterologous expression of the saz gene(s) in Streptomyces albus J1074 yielded new prenylated indole alkaloids, showcasing the specificity and flexibility of the enzymes involved in the biosynthesis.
APPLIED AND ENVIRONMENTAL MICROBIOLOGY
(2021)
Article
Biotechnology & Applied Microbiology
Sherif Ahmed Hamdy, Takeshi Kodama, Yu Nakashima, Xiaojie Han, Hiroyuki Morita
Summary: This study investigated the prenylation of naturally occurring β-carbolines and elucidated the prenylation mechanism using enzyme assay, X-ray crystal structure analysis, and docking simulation studies. Moreover, antibacterial assays revealed that specific prenylation enhanced the antimicrobial activities of the compounds.
JOURNAL OF BIOSCIENCE AND BIOENGINEERING
(2022)
Article
Agriculture, Multidisciplinary
Li-Bin Lin, Yu-Qi Gao, Rui Han, Jian Xiao, Yi-Meng Wang, Qiang Zhang, Yi-Jie Zhai, Wen-Bo Han, Wen-Li Li, Jin-Ming Gao
Summary: Sixteen metabolites, including seven C-7-alkylated salicylaldehyde derivatives and nine prenylated indole alkaloids, were isolated from the endolichenic fungus Aspergillus chevalieri SQ-8. Some of these compounds exhibited potent antibacterial, antineuroinflammatory, and antioxidant activities, with asperglaucins A and B showing potential as lead compounds for agrochemical bactericides. Additionally, compounds 6 and 10 demonstrated significant inhibition of nitric oxide production and phenolics 3-5 displayed antioxidative effects, suggesting the strain SQ-8 as a novel resource for bioactive metabolites.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Saad Alrashdi, Federica Casolari, Aziz Alabed, Kwaku Kyeremeh, Hai Deng
Summary: This report presents a pilot study on the biotransformation of indole-containing acyloins. The study utilizes the enzymatic combination of PfTrpB variant, LAAO, and NzsH to produce acyloins with different indole substituents. The results show that NzsH has a broad substrate profile and can be further optimized via directed evolution.
Article
Chemistry, Applied
Shili Guo, Haiming Zhou, Xin Huang, Siyan Peng, Jiayi Li, Bo Ding, Yiwen Tao, Hongbo Huang
Summary: Two new glucosidated indole-containing quinazoline alkaloids, designated fumigatosides G (1) and H (2), were isolated from the mangrove-derived fungus Aspergillus fumigatus SAl12, along with the known analogues fumigatoside B (3) and fumiquinazoline J (4). The planar structures of the new compounds were determined by HR-MS and NMR spectroscopy, and the absolute configurations were determined using electronic circular dichroic (ECD) spectra and comparison with a known compound. All the indole-quinazoline compounds were tested for antibacterial and cytotoxic activities.
NATURAL PRODUCT RESEARCH
(2023)
Article
Agriculture, Multidisciplinary
Hua-Yin Liu, Yue-Yu Ma, Zhen-Jie Li, Xue-Mei Li, Yin-Ke Li, Wei-Guang Wang, Min Zhou, Qiu-Fen Hu, Feng-Xian Yang
Summary: Compounds 1-3 from A. versicolor showed potent antiviral activities against TMV including inactivation, protective and curative effects. Compound 1 can directly destroy the virus particles to achieve the effect of anti-TMV. In addition, compounds 1-3 can bind to TMV-CP protein in molecular docking experiments. The above experimental results show that TMV-CP was an important target for active indole alkaloid and isocoumarin derivatives to fracture TMV particle. The results provided evidence that indole alkaloid and isocoumarin derivatives from A. versicolor have the potential to control TMV.
CHEMICAL AND BIOLOGICAL TECHNOLOGIES IN AGRICULTURE
(2023)
Article
Chemistry, Multidisciplinary
Samantha P. Kelly, Vikram V. Shende, Autumn R. Flynn, Qingyun Dan, Ying Ye, Janet L. Smith, Sachiko Tsukamoto, Matthew S. Sigman, David H. Sherman
Summary: In this study, researchers aimed to develop a unified strategy for biocatalytic construction of prenylated DKP indole alkaloids. By identifying and characterizing a substrate-permissive C2 reverse prenyltransferase (PT) NotF, they found that NotF has a significantly broad substrate scope and strong reaction selectivity. Through the conversion of 30 different structurally differentiated substances, they identified key factors that govern the rate of NotF-catalyzed prenyltransfer and developed an engineering strategy to improve substrate turnover. Finally, they successfully demonstrated the one-pot synthesis of the marine fungal natural product (-)-eurotiumin A using NotF in tandem with BvnB.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Plant Sciences
Cao Duc Tuan, Nguyen Van Hung, Le Thi Hong Minh, Hoang Thi Hong Lien, Jung-Woo Chae, Hwi-yeol Yun, Young-Ho Kim, Pham Van Cuong, Doan Thi Mai Huong
Summary: A new compound and ten known compounds were isolated from marine-derived Aspergillus fumigatus M580. Compound 2, 3, and 7 showed significant antimicrobial activity against Gram-positive Enterococcus faecalis. Compound 4 exhibited significant cytotoxic activities against Huh7 and HT 29 cancer cell lines. Compound 3 and 10 showed the most alpha-glucosidase inhibitory activity.
RECORDS OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Kaiser Hamid, Van H. Tran, Rujee K. Duke, Colin C. Duke
Summary: A series of prenylated and hydroxyprenylated compounds were isolated from resin produced by certain Australian plants, showing strong binding affinity and inhibition activity towards melatonin receptors and enzymes.
Article
Chemistry, Medicinal
Yue-Yu Ma, Wen Xiong, Si-Yu Shen, Shan-Shan Li, Xiao-Shan Liu, Yin-Ke Li, Dong Miao, Min Zhou, Wei-Guang Wang, Gang Du, Qiu-fen Hu, Xiao-Wei Ma
Summary: Two new indole alkaloids, 1-(5-prenyl-1H-indol-3-yl)propan-2-one (1) and 1-(6-methoxy-5-prenyl-1H-indol-3-yl)propan-2-one (2), along with five known ones (3-7), were isolated from the fermentation products of a cigar tobacco-derived endophytic fungus Aspergillus fumigatus. Their structures were determined using spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 exhibited potential anti-tobacco mosaic virus (anti-TMV) activities, with inhibition rates of 26.5% and 28.8%, respectively.
CHEMISTRY OF NATURAL COMPOUNDS
(2023)