Review
Biochemistry & Molecular Biology
Lena Barra, Ikuro Abe
Summary: Fungal meroterpenoid cyclases are a newly discovered family of membrane-integrated enzymes that catalyze the conversion of hybrid isoprenic precursors and are important for the structural diversification in polycyclic meroterpenoid biosynthesis.
NATURAL PRODUCT REPORTS
(2021)
Article
Chemistry, Organic
Bo-wen Qi, Na Li, Bei-bei Zhang, Ze-kun Zhang, Wen-jing Wang, Xiao Liu, Juan Wang, Takayoshi Awakawa, Peng-fei Tu, Ikuro Abe, She-po Shi, Jun Li
Summary: The biosynthetic gene cluster of atlantinone B has been discovered in Penicillium chrysogenum. The cluster encodes a multifunctional cytochrome P450 and a new terpene cyclase, which can synthesize structurally diverse meroterpenoids. This study opens up new possibilities for drug discovery.
Article
Biotechnology & Applied Microbiology
Xuan Hong, Xiaoqing Guan, Qiliang Lai, Dehua Yu, Zhongwei Chen, Xiaoteng Fu, Beibei Zhang, Changkun Chen, Zongze Shao, Jinmei Xia, Jiang-Jiang Qin, Weiyi Wang
Summary: A new meroterpenoid, taladrimanin A (1), was isolated from a marine-derived fungus, and its structure and activity were studied. Compound 1 showed inhibitory activity against gastric cancer cells and certain bacteria.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Organic
Telugu Venkatesh, Prathama S. Mainkar, Srivari Chandrasekhar
Summary: The formal synthesis of (+/-)-cochlearol A was achieved using Suzuki coupling and Friedel-Crafts cyclization as a convergent strategy to functionalize the tetralone ring, and an intramolecular construction of the C/D ring involving sequential epoxide formation/acetal formation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xinyang Li, Takayoshi Awakawa, Takahiro Mori, Meiqi Ling, Dan Hu, Bin Wu, Ikuro Abe
Summary: In this study, the biosynthetic pathway of a group of six-cyclic meroterpenoids isolated from marine fungus was investigated. Through heterologous expression and enzyme assays, a heterodimer of NHI proteins was found to play a key role in catalyzing multiple oxidation steps, shedding light on a novel methodology for oxygenase structures in secondary metabolite biosynthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Tao Chen, Yufeng Liu, Yun Huang, Wencong Yang, Bing Sun, Qi Tan, Tianyu Wei, Bo Wang, Jie Yuan, Zhigang She
Summary: Ten new meroterpenoids and ten known analogues were isolated from a mangrove-associated fungus. Their structures and absolute configurations were determined through various analysis methods. Four compounds exhibited cytotoxicity against multiple cancer cell lines.
Article
Biology
Takayoshi Awakawa, Wei Liu, Tongxuan Bai, Tomo Taniguchi, Ikuro Abe
Summary: In this study, the biosynthetic pathway of the fungal meroterpenoid austalide F, which contains an orthoester functionality, was elucidated through heterologous gene expression in Aspergillus oryzae and in vitro assays. The alpha-ketoglutarate-dependent oxygenase AstB was found to produce the hemiacetal intermediate, and the methyltransferase AstL was responsible for transferring a methyl group to construct the orthoester functionality. These findings highlight the extraordinary biosynthetic machinery of orthoester-containing fungal meroterpenoids and provide valuable insights for the engineered biosynthesis of unnatural bioactive meroterpenoids.
PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY B-BIOLOGICAL SCIENCES
(2023)
Article
Chemistry, Medicinal
Yuting Zhang, Xing Peng, Zhejun Sun, Chen Hu, Huihao Zhou, Jun Xu, Qiong Gu
Summary: Fifteen polyacetylenes and one meroterpenoid were isolated from Atractylodes chinensis and evaluated for their effects on osteoclastogenesis. Polyacetylenes 12-14 showed potent inhibitory activity against osteoclastogenesis.
Article
Biochemistry & Molecular Biology
Zhonghao Sun, Yongben Ma, Jiawen Zhang, Guoxu Ma, Haifeng Wu, Leiling Shi, Zhaocui Sun, Xudong Xu
Summary: Four new meroterpenoids with aminoglycoside moiety and a 10-membered carbocycle fused with an alpha, beta-epoxy-gamma-lactone were isolated from Clitocybe clavipes. Compound 1 and 2 showed significant suppression of cell viability in the Hela cell line.
Article
Biochemistry & Molecular Biology
Yuan-kun Zheng, Ya-qi Wang, Bao-jun Su, Heng-shan Wang, Hai-bing Liao, Dong Liang
Summary: Six new lignans, two new meroterpenoids, and 24 known compounds were isolated from an EtOH extract of Piper puberulum. Compound 1a showed notable anti-neuroinflammatory activity and decreased mRNA levels of proinflammatory cytokines in a dose-dependent manner.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Yuting Zhang, Xing Peng, Zhejun Sun, Chen Hu, Huihao Zhou, Jun Xu, Qiong Gu
Summary: A phytochemical investigation of Atractylodes chinensis led to the discovery of polyacetylenes and meroterpenoids. Some of the polyacetylenes showed inhibitory activity against osteoclastogenesis.
Review
Chemistry, Multidisciplinary
Jonathan H. George
Summary: Natural products are biosynthesized using a limited pool of starting materials, while biomimetic total synthesis attempts to replicate predisposed pathways using chemical reagents. By avoiding the use of protecting groups, researchers aim to explore the innate reactivity of biosynthetic intermediates. Biomimetic synthesis is often concise and efficient, following atom, step, and redox economies of synthesis.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Kenta Tanaka, Yosuke Asada, Yujiro Hoshino
Summary: Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed as a promising tool for the synthesis of natural products and bioactive compounds that contain a benzoxepine structure.
CHEMICAL COMMUNICATIONS
(2022)
Review
Microbiology
Takayoshi Awakawa, Ikuro Abe
Summary: The heterologous gene expression system using Aspergillus oryzae as the host is an effective method for studying fungal secondary metabolite biosynthesis, with potential for creating un-natural molecules through biosynthetic re-design in the future.
Article
Biochemistry & Molecular Biology
Yi Huang, Yun Huang, Ge Zhu, Bingzhi Zhang, Yujia Zhu, Bin Chen, Xiaoxia Gao, Jie Yuan
Summary: A compound named D1399 isolated from Meconopsis grandis Prain has shown strong antitumor activity against lung cancer cells by inducing apoptosis and inhibiting tumor growth, without causing weight loss. This study provides the first evidence for the antitumor activity of D1399 and suggests its potential as a promising candidate for antitumor drug development.
Article
Medicine, Research & Experimental
Pongvit Nugitrangson, Songchan Puthong, Tawin Iempridee, Wittaya Pimtong, Surachai Pornpakakul, Chanpen Chanchao
EXPERIMENTAL BIOLOGY AND MEDICINE
(2016)
Article
Plant Sciences
Suphongphan Srisurichan, Surachai Pornpakakul
PHYTOCHEMISTRY LETTERS
(2015)
Article
Plant Sciences
Suphongphan Srisurichan, Jittra Piapukiew, Songchan Puthong, Surachai Pornpakakul
PHYTOCHEMISTRY LETTERS
(2017)
Article
Crystallography
Srinuan Tansuwan, Porntana Chanaprat, Thapong Teerawatananond, Nongnuj Muangsin, Surachai Pornpakakul
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE
(2010)
Article
Chemistry, Medicinal
Sunisa Suwancharoen, Orawan Chonvanich, Sophon Roengsumran, Surachai Pornpakakul
CHEMISTRY OF NATURAL COMPOUNDS
(2012)
Article
Chemistry, Applied
Jaraslak Pechwang, Prakitsin Sihanonth, Surachai Pornpakakul, Nongnuj Muangsin, Jittra Piapukiew, Alisa Vangnai, Narongsak Chaichit, Siriporn Chuchawankul, Amorn Petsom
NATURAL PRODUCT RESEARCH
(2010)
Article
Biochemistry & Molecular Biology
Suphongphan Srisurichan, Songchan Puthong, Surachai Pornpakakul
Article
Chemistry, Organic
Jatupol Liangsakul, Surachai Pornpakakul, Ek Sangvichien, Nongnuj Muangsin, Prakitsin Sihanonth
TETRAHEDRON LETTERS
(2011)
Article
Chemistry, Organic
Sunisa Suwancharoen, Surachai Pornpakakul, Nongnuj Muangsin
TETRAHEDRON LETTERS
(2012)
Article
Chemistry, Applied
Natta Rattanapanya, Surachai Pornpakakul
Summary: The mixture of p-toluenesulfonic acid and sulfuric acid showed good performance as a catalyst in transesterification and etherification processes, resulting in fast reaction rates and high conversions. The catalyst could be reused for 6 cycles and offers an attractive route for converting biodiesel by-products into valuable fuel additives.
JOURNAL OF OLEO SCIENCE
(2021)
Article
Multidisciplinary Sciences
Thanavadee Kor-arnan, Thanawan Rojpitikul, Preecha Phuwapraisirisan, Surachai Pornpakakul, Pattara Thiraphibundet
MAEJO INTERNATIONAL JOURNAL OF SCIENCE AND TECHNOLOGY
(2019)
Article
Multidisciplinary Sciences
Jeroen Bogie, Cindy Hoeks, Melissa Schepers, Assia Tiane, Ann Cuypers, Frank Leijten, Yupyn Chintapakorn, Thiti Suttiyut, Surachai Pornpakakul, Dicky Struik, Anja Kerksiek, Hong-Bing Liu, Niels Hellings, Pilar Martinez-Martinez, Johan W. Jonker, Ilse Dewachter, Eric Sijbrands, Jochen Walter, Jerome Hendriks, Albert Groen, Bart Staels, Dieter Luetjohann, Tim Vanmierlo, Monique Mulder
SCIENTIFIC REPORTS
(2019)
Article
Multidisciplinary Sciences
Nattachai Kengpipat, Surachai Pornpakakul, Jittra Piapukiew, Thanapat Palaga, Geoff Robson, Anthony J. S. Whalley, Prakitsin Sihanonth
CHIANG MAI JOURNAL OF SCIENCE
(2016)
Article
Chemistry, Medicinal
Wichuta Kuanhut, Thammarat Aree, Surachai Pornpakakul, Pattara Sawasdee
NATURAL PRODUCT COMMUNICATIONS
(2014)
Article
Biochemistry & Molecular Biology
Olexander M. Semenenko, Victoria V. Lipson, Alina O. Sadchenko, Olga V. Vashchenko, Natalia A. Kasian, Liliia Sviechnikova, Longin M. Lisetski, Mykola L. Babak, Volodymyr M. Vakula, Oleksandr Borysov, Yuliia Holota, Sergey O. Zozulya, Petro O. Borysko, Olexander Mazepa
Summary: An efficient protocol for the synthesis of novel methotrexate-betulonic acid hybrids has been developed and their structures and properties have been fully established. The hybrids showed inferior interactions with artificial lipid membranes, possibly due to their increasing lipophilicity.
Article
Biochemistry & Molecular Biology
Mohadese Yaghoobi Anzabi, Piotr Cmoch, Roman Luboradzki, Zbigniew Pakulski
Summary: Friedelin and 3-acetoxyfriedel-3-en-2-one, known as friedelane triterpenoids, have been isolated from cork smoker wash solids and used as starting materials for the synthesis of new friedelane derivatives. Reduction reactions result in the formation of friedelinol and epi-cerin derivatives.
Article
Biochemistry & Molecular Biology
Detlef Thieme, Aniko Krumbholz, Martin Bidlingmaier, Christoph Geffert, Annika Hameder, Andreas Stoever, Matthias Graw, Annekathrin M. Keiler
Summary: Ethanol can affect testosterone metabolism and potentially influence steroid biosynthesis and blood steroid profiles. The study emphasizes the importance of sufficient time interval from food and ethanol intake during blood sampling, particularly for diagnostics in doping control.
Article
Biochemistry & Molecular Biology
Masanobu Murao, Tetsuo Imano, Yoshinobu Sato, Masaaki Nakajima
Article
Biochemistry & Molecular Biology
Jingyuan Wang, Ye Feng, Brian Liu, Wen Xie
Summary: Sulfation and desulfation of steroids are opposing processes that regulate steroid homeostasis and are involved in steroid-related diseases. Cytosolic sulfotransferase and steroid sulfatase modify and regulate steroids to affect hormonal dysregulation, metabolic diseases, and cancer.
Article
Biochemistry & Molecular Biology
Noah K. Babel, Brian J. Feldman
Summary: Our research identified a previously unrecognized ADAMTS1-PTN-Wnt pathway in regulating adipose precursor cell behavior. The non-muscle myosin protein MYH9 was found to be a key target of this pathway for modulating adipogenesis. These findings offer potential for developing novel therapeutics for obesity and related metabolic disorders.
Article
Biochemistry & Molecular Biology
Martiniano Bello
Summary: This study explores the structural and thermodynamic basis of molecular recognition between ERβ and DPN and its derivatives using molecular dynamics simulations and end-point methods. The results show that the MMGBSA approach is able to reproduce experimental trends and identify eight residues that strongly interact with the ligands.
