Article
Chemistry, Medicinal
Min Woo Ha, Jonghoon Kim, Seung-Mann Paek
Summary: The discovery of novel marine natural products often leads to efforts in finding new therapeutic ingredients. Due to the complexity and uniqueness of substances produced in the marine environment, there have been cases where the structures were incorrectly assigned despite the use of modern chemical techniques. Organic chemical synthesis and thorough spectroscopic data inspection are crucial in refuting inaccuracies in proposed structures.
Review
Chemistry, Multidisciplinary
Debobrata Paul, Ashis Kundu, Sanu Saha, Rajib Kumar Goswami
Summary: This feature article highlights total synthesis as a reliable tool for confirming the structure of natural products. Despite advances in spectroscopic techniques, structural misassignments of natural products remain common. Recent case studies have shown that chemical synthesis can be used to revise the structures of natural products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Xikang Zheng, Yan Li, Mengtie Guan, Lingyue Wang, Shilong Wei, Yi-Cheng Li, Chin-Yuan Chang, Zhengren Xu
Summary: A unified strategy for the biomimetic total synthesis of the spiroindimicin family of natural products was reported. Key transformations include one-pot two-enzyme-catalyzed oxidative dimerization and regioselective bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Huilin Li, Jing Zhang, Xuegong She
Summary: This MiniReview demonstrates the achievements in the construction of the diquinane ring system in the past decade, discussing the strategic synthesis of the diquinane unit and its impact on the field of natural product total synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Haoran Dong, Dachao Hu, Benke Hong, Jin Wang, Xiaoguang Lei
Summary: The first total syntheses of four natural antibiotics, vermisporin, PF1052/AB4015-A, AB4015-L, AB4015-B, and one hydrogenated natural product derivative, AB4015-A2, featuring a tetramic acid bearing cis-decalin ring, are reported. The functionalized cis-decalin ring was constructed via a diastereoselective intramolecular Diels-Alder (IMDA) reaction, with a rare endo-boat transition state. The efficient installation of the sterically hindered epoxy group in vermisporin, PF1052/AB4015-A, and AB4015-L was achieved through an intramolecular neighboring-group-oriented strategy, and the desired tetramic acid structure was obtained through a one-pot aminolysis/Dieckmann condensation cascade using L-amino acid derivatives. The total synthesis allowed for the unequivocal verification of the absolute configuration of these natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Soumik De, Aritra Kumar Dan, Raghaba Sahu, Sagarika Parida, Debadutta Das
Summary: Gold catalysis is a popular and highly innovative field in catalysis research, providing new approaches for chemical transformations from simple starting materials. The application of gold catalysis in the total synthesis of natural products has successfully addressed complex challenges and achieved significant progress.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Review
Chemistry, Organic
Takaaki Sato, Takahiro Suto, Yoshiyuki Nagashima, Shori Mukai, Noritaka Chida
Summary: Skipped dienes, found in various biologically active natural products, have relatively undeveloped synthesis methods compared to conjugated dienes due to challenges posed by the sp(3)-hybridized carbon between two olefins. Recent advances in the synthesis of skipped dienes for total synthesis of complex natural products are classified into three categories, focusing on methods to achieve both high stereoselectivity and convergency.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lukas Anton Wein, Klaus Wurst, Thomas Magauer
Summary: The study presented the construction of seven novel ent-trachylobane diterpenoids using a bioinspired synthetic strategy. Enantioselective and scalable access to five ent-trachylobanes was achieved in the first phase, with one compound produced on a 300 mg scale. Chemical C-H oxidation methods were then used in the second phase to selectively convert two higher functionalized ent-trachylobanes, revealing the potential and limitations of established protocols for complex molecule synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Zijun Chen, Na Chen, Peng Fu, Weiping Wang, Shilin Bian, Huihui Zhang, Sicheng Shen, Bingnan Han
Summary: Two new derivatives of aplysiatoxin, named neo-debromoaplysiatoxin I and neo-debromoaplysiatoxin J, were isolated from marine cyanobacterium Lyngbya sp. collected from the South China Sea. Their structures and absolute configurations were determined. Both compounds exhibited inhibitory activity against Kv1.5 K+ channel, but showed differential cytotoxic effects.
Article
Chemistry, Multidisciplinary
Sandra A. C. Figueiredo, Marco Preto, Gabriela Moreira, Teresa P. Martins, Kathleen Abt, Andre Melo, Vitor M. Vasconcelos, Pedro N. Leao
Summary: The study utilizes the lack of functional beta-oxidation pathway in cyanobacteria to efficiently stable-isotope-label their fatty acid derived lipidome by supplementing with deuterated fatty acids, enabling easy detection of natural product signatures. This strategy has been successfully demonstrated in two cultured cyanobacteria, leading to the discovery of analogues of the multidrug-resistance reverting hapalosin and novel, cytotoxic lactylate-nocuolin A hybrids - the nocuolactylates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Suman Chakrabarty, Evan O. Romero, Joshua B. Pyser, Jessica A. Yazarians, Alison R. H. Narayan
Summary: The total synthesis of structurally complex natural products remains an exciting area of research, with recent advancements in biocatalysis allowing for the application of enzymes in constructing complex molecules. The utilization of enzymes alongside small molecule-based approaches has enabled concise chemoenzymatic routes to natural products, demonstrating the potential for selective oxidation reactions and late-stage diversification of complex scaffolds.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Chemistry, Medicinal
Diaa T. A. Youssef, Shatha J. Mufti, Abeer A. Badiab, Lamiaa A. Shaala
Summary: Cyanobacteria of the Lyngbya genus are a valuable source of chemically diverse natural products with significant pharmaceutical potential. This comprehensive review summarizes the anti-infective compounds isolated from various species within the Lyngbya morphotype, showcasing their antibacterial, antiparasitic, antifungal, antiviral, and molluscicidal activities.
Article
Plant Sciences
Ma Yadanar Phyo, Jun Xian Goh, Lik Tong Tan
Summary: In this study, a new cyclic depsipeptide, triproamide, was isolated from a marine cyanobacterium along with known and new analogues. Triproamide and the analogues showed potential anti-tumor activity.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Chemistry, Organic
Kevin Rafael Sokol, Thomas Magauer
Summary: This review provides an overview of synthetic methods and strategies for constructing oxepin and dihydrooxepin motifs in the context of natural product synthesis, highlighting key steps of each example.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Yun-Fei Cheng, Hui-Jing Li, Xiao-Bo Wang, Yan-Chao Wu
Summary: A facile synthesis method has been developed for the marine natural product Smenodiol, achieving a high overall yield of 23.2% within 8 steps from easily available starting materials. This method involves a TMSOTf-mediated Friedel-Crafts reaction with a methyl ester in the aryl as the key step, enabling a concise synthesis of the marine natural product (-)-Pelorol.
NATURAL PRODUCT RESEARCH
(2023)
Article
Plant Sciences
Aki Yamano, Yuka Asato, Noriyuki Natsume, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya
Summary: Odookeanynes A and B, two acetylene-containing lipopeptides, were isolated from a marine cyanobacterium collected in Okinawa, Japan. Their structures were elucidated through spectroscopic analysis and Marfey's analysis. These compounds dose-dependently promoted the differentiation of mouse 3T3-L1 preadipocytes in the presence of insulin.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Agronomy
Yuki Matuda, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi
Summary: Metasequoia glyptostroboides, one of the oldest living conifer species, exhibits allelopathic properties. The fallen leaves of this species contain allelopathic substances that inhibit the growth of nearby competing plant species, giving M. glyptostroboides a competitive advantage.
Article
Agronomy
Ramida Krumsri, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi
Summary: The extracts of S. garrettiana leaves, containing vanillic acid and ferulic acid, show significant phytotoxicity against L. sativum, indicating their potential as natural herbicides. The compounds were found to have synergistic inhibitory activity when used in combination, suggesting a promising alternative for weed control.
Article
Agronomy
Ei Han Kyaw, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi
Summary: Research showed that extracts of Dregea volubilis contain two phytotoxic compounds, dehydrovomifoliol and loliolide, which significantly inhibit the seedling growth of Italian ryegrass and cress, and may be key substances responsible for the allelopathy of D. volubilis.
Article
Chemistry, Multidisciplinary
Naoaki Kurisawa, Arihiro Iwasaki, Kazuya Teranuma, Shingo Dan, Chikashi Toyoshima, Masaru Hashimoto, Kiyotake Suenaga
Summary: In this study, a new SERCA inhibitor, iezoside (1), isolated from the marine cyanobacterium Leptochromothrix valpauliae, is reported. Iezoside (1) is the second-strongest SERCA inhibitor known to date, with a structure fundamentally different from any other SERCA inhibitor, and the highest potency among marine natural products (K_i 7.1 nM). The comprehensive analysis of iezoside (1), including its isolation, structural characterization supported by density functional theory (DFT) calculations and statistical analysis, total synthesis, and clarification of the mode of action of its potent antiproliferative activity (IC50 6.7 +/- 0.4 nM against HeLa cells), is described.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Agronomy
Ei Han Kyaw, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi
Summary: The phytotoxic potential of Dregea volubilis leaves against several test plants was investigated, and two growth inhibitory compounds were identified. These findings suggest the possibility of utilizing these extracts and compounds for weed control.
Article
Plant Sciences
Hisashi Kato-Noguchi, Yuri Hamada, Misuzu Kojima, Sanae Kumagai, Arihiro Iwasaki, Kiyotake Suenaga
Summary: Osmanthus fragrans Lour. has been cultivated for more than 2500 years for its fragrance and color. The flowers and roots have multiple uses in various industries. Limited information is available on the allelopathic properties of O. fragrans. This study reveals that the fallen leaves of O. fragrans and its hybrid species O. x fortunei possess allelopathic substances that inhibit the growth of neighboring plants. These findings suggest that the leaves of these Osmanthus species can be utilized for weed management in sustainable agriculture systems.
Article
Biochemistry & Molecular Biology
Fumitaka Kudo, Takuji Chikuma, Mizuki Nambu, Taichi Chisuga, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Akimasa Miyanaga, Tadashi Eguchi
Summary: In this study, we analyzed the genome sequence of Moorena bouillonii, a marine cyanobacterium that produces lyngbyapeptin B, and identified a gene cluster responsible for its biosynthesis. We characterized two unique enzymatic activities: O-methylation by LynB2 and oxidative decarboxylation by LynB7. These findings provide insights into the biosynthetic mechanisms of lyngbyapeptin B.
ACS CHEMICAL BIOLOGY
(2023)
Article
Plant Sciences
Kaori Ozaki, Yuka Asato, Noriyuki Natsume, Shunya Tojo, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya
Summary: The linear lipopeptides okeaniamide A (1) and okeaniamide B (2) were isolated from a marine cyanobacterium called Okeania. Their structures were determined using spectroscopic analyses and their absolute configurations were elucidated through a combination of chemical degradations, Marfey's analysis, and derivatization reactions. Okeaniamide A (1) and okeaniamide B (2) were found to dose-dependently promote the differentiation of mouse 3T3-L1 preadipocytes in the presence of insulin.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Organic
Yuta Miyamoto, Arihiro Iwasaki, Haruka Fujimura, Chihiro Kudo, Naoaki Kurisawa, Osamu Ohno, Kiyotake Suenaga
Summary: Caldorazole, a novel polyketide, was isolated from a marine cyanobacterium in 2022. Despite lacking chiral centers, it exhibits potent inhibitory activity against mitochondrial respiratory chain complex I. To study its structure-activity relationship, we accomplished the first total synthesis of caldorazole using a convergent synthetic route, aiming to establish a method for obtaining caldorazole without relying on biological resources.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hiroki Takahashi, Arihiro Iwasaki, Akira Ebihara, Raimu Taguchi, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga
Summary: Two new natural products obtained from the marine cyanobacterium Rivularia sp. collected in Japan are described. Hennaminal possesses a rare beta,beta-diamino unsaturated ketone functional group, only previously found in bohemamine-type natural products. Hennamide contains a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The isolation and structure determination, supported by computational chemistry, total synthesis, and antitrypanosomal activities of hennaminal and hennamide, are discussed.
Article
Plant Sciences
Thang Lam Lun, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi
Summary: This experiment separated two compounds from the medicinal plant Polygonum chinense that were found to inhibit the growth of cress and lettuce seedlings. These compounds, (-)-3-hydroxy-beta-ionone and (-)-3-hydroxy-7,8-dihydro-beta-ionone, could potentially be used as weed control agents.
Article
Plant Sciences
Seinn Moh Moh, Naoaki Kurisawa, Kiyotake Suenaga, Hisashi Kato-Noguchi
Summary: A study found that a bioactive substance, steroidal glycoside 3, extracted from Marsdenia tenacissima leaves, has significant inhibitory effects on weed growth, suggesting its potential as a natural alternative for weed control in sustainable agriculture.
Article
Chemistry, Organic
Hiroki Takahashi, Arihiro Iwasaki, Akira Ebihara, Raimu Taguchi, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga
Summary: Two new natural products were isolated from the marine cyanobacterium Rivularia sp. collected in Japan. Hennaminal contains a rare functional group, beta,beta-diamino unsaturated ketone, which has only been found in bohemamine-type natural products so far. Hennamide possesses a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The article describes the isolation and structure determination of hennaminal and hennamide, supported by computational chemistry and total synthesis, as well as their antitrypanosomal activities.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
