Review
Chemistry, Multidisciplinary
Mei-Jun Chu, Meng Li, He Ma, Ping-Lin Li, Guo-Qiang Li
Summary: This review highlights the chemical structure and biological activity of 355 compounds isolated and characterized from Agelas sponges over the period of about five decades. These compounds are classified and summarized based on their carbon skeleton and biosynthetic origins. The review underscores Agelas sponges as an intriguing source for the discovery of natural compounds.
Article
Chemistry, Organic
Bao-Bao Shi, Jing-Song Lu, Jing Wu, Mei-Fen Bao, Xiang-Hai Cai
Summary: A symmetric monoterpenoid indole alkaloid trimer, bousangustine A, and dimeric alkaloids bousangustines B and C were isolated from the trunks of Bousigonia angustifolia. Their structures with a symmetric 6/9/5/6 ring system were elucidated via comprehensive spectroscopic analysis and their absolute configurations were determined through X-ray crystal diffraction and computational chemistry. These compounds showed significant cytotoxicity against tumor cells.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Biochemistry & Molecular Biology
Ahmed M. Elissawy, Ebrahim Soleiman Dehkordi, Negin Mehdinezhad, Mohamed L. Ashour, Pardis Mohammadi Pour
Summary: Marine sponges are a rich source of unique bioactive secondary metabolites, with alkaloids standing out for their unprecedented structures and outstanding biological activities. A comprehensive survey of demospongian bioactive alkaloids from 1987 to 2020 revealed that sponges from different genera within the phylum porifera are prolific sources of alkaloidal molecules. The production of alkaloids from sponges is a promising approach that merits more attention in future studies to address constraints related to drug supply from marine organisms.
Article
Chemistry, Medicinal
Dawrin Pech-Puch, Abel M. Forero, Juan Carlos Fuentes-Monteverde, Cristina Lasarte-Monterrubio, Marta Martinez-Guitian, Carlos Gonzalez-Salas, Sergio Guillen-Hernandez, Harold Villegas-Hernandez, Alejandro Beceiro, Christian Griesinger, Jaime Rodriguez, Carlos Jimenez
Summary: Three new diterpene alkaloids and three known compounds were isolated from the sponge Agelas citrina collected on the coasts of the Yucatan Peninsula (Mexico). The chemical structures were identified using various analysis techniques. The compounds showed antimicrobial activity against both Gram-positive and Gram-negative pathogens.
Article
Plant Sciences
Vitor F. Freire, Juliana R. Gubiani, Tara M. Spencer, Eduardo Hajdu, Antonio G. Ferreira, Dayana A. S. Ferreira, Erica de Castro Levatti, Joanna E. Burdette, Carlos Henrique Camargo, Andre G. Tempone, Roberto G. S. Berlinck
Summary: This study investigated the marine sponge Agelas dispar and discovered new bromopyrrole-derived metabolites using feature-based molecular networking, dereplication, and isolation techniques. The compounds were identified by analyzing spectroscopic data and MS/MS fragmentation. The antimicrobial activity of the isolated compounds was evaluated, and dibromoageliferin showed the strongest activity against multi-drug-resistant pathogenic bacteria.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Passakorn Teerapongpisan, Virayu Suthiphasilp, Piyaporn Phukhatmuen, Narawadee Rujanapun, Boonyanoot Chaiyosang, Sarawut Tontapha, Tharakorn Maneerat, Brian O. Patrick, Thidarat Duangyod, Rawiwan Charoensup, Raymond J. Andersen, Surat Laphookhieo
Summary: A phytochemical investigation of the twig extract of Trivalvaria costata has identified ten undescribed dimeric aporphine alkaloids, one undescribed isoquinoline alkaloid, and four known aporphine alkaloids. The structures were determined by NMR, HRESITOFMS, and X-ray diffraction analysis. The dimeric aporphine alkaloids exhibited alpha-glucosidase inhibitory activities.
Article
Biochemistry & Molecular Biology
Passakorn Teerapongpisan, Virayu Suthiphasilp, Pakit Kumboonma, Tharakorn Maneerat, Thidarat Duangyod, Rawiwan Charoensup, Raymond J. Andersen, Surat Laphookhieo
Summary: The first phytochemical investigation of the twigs of Phaeanthus lucidus Oliv. led to the discovery of four previously undescribed alkaloids, including two aporphine dimers, phaeanthuslucidines A and B, a hybrid of aristolactam-aporphine, phaeanthuslucidine C, and a C-N linked aporphine dimer, phaeanthuslucidine D, along with two known compounds. Their structures were determined through extensive spectroscopic analysis and comparison with previous reports. Chiral HPLC analysis of phaeanthuslucidines A-C and bidebiline E yielded the (R-a) and (S-a) atropisomers, whose absolute configurations were determined by ECD calculations. Phaeanthuslucidines A and B, bidebiline E, and lanuginosine exhibited alpha-glucosidase inhibitory activities with IC50 values ranging from 6.7 to 29.2 μM. Molecular docking simulations of the active compounds' inhibition of alpha-glucosidase were also studied.
Article
Chemistry, Organic
Yu-Ting Tang, Jing Wu, Yang Yu, Mei-Fen Bao, Qin-Gang Tan, Johann Schinnerl, Xiang-Hai Cai
Summary: Five dimeric Erythrina alkaloids, erythrivarines J-N, were isolated from the barks of Erythrina variegata L. The compounds had unique ring systems and color characteristics, with one compound showing neuroprotective properties against hearing loss causing antibiotics.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xia Wei, Jun-Cheng Su, Jin-Shan Hu, Xi-Xin He, Shuang-Jun Lin, Dong-Mei Zhang, Wen-Cai Ye, Min-Feng Chen, Hou-Wen Lin, Cui-Xian Zhang
Summary: Comprehensive analysis of the metabolite spectra of Aspergillus sp. EGF 15-0-3 under different culture conditions revealed unique environment-induced metabolites exclusively found in the rice medium. Four unprecedented compounds were isolated, showing selective cytotoxicity against various human cancer cells. The putative biosynthetic pathways for these compounds involve Diels-Alder cycloadditions as key steps.
Article
Plant Sciences
Li Xing, Yimin Chang, Xiaoqian Zhang, Xuewen Hou, Yaxin Han, Mudassir Shah, Tianjiao Zhu, Jixing Peng, Guojian Zhang, Qian Che, Dehai Li
Summary: Bitetracenomycin A and its diastereomers were discovered from Streptomyces sp. HDN154193 cultures, showing potent antibacterial activity especially against drug-resistant strains. The enantiomers were separated and their absolute configurations were determined, indicating potential for further study in combating antibiotic resistance.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Plant Sciences
Xiangrong Tian, Dongdong Wang, Wei Jiang, Heidi R. Bokesch, Brice A. P. Wilson, Barry R. O'Keefe, Kirk R. Gustafson
Summary: The marine ascidian Polyandrocarpa sp. yielded two new caulamidines C (2) and D (4), as well as three isocaulamidines B, C, and D (1, 3, and 5), along with the known compound caulamidine B (6). The structures of these compounds were determined through analysis of nuclear magnetic resonance (NMR) and electronic circular dichroism (ECD) data. Isocaulamidines displayed an altered pattern of N-methyl substitution (N-15 instead of N-13 in caulamidines), accompanied by a double-bond rearrangement, leading to the formation of a new C-14/N-13 imine functionality. Caulamidine C (2) and isocaulamidine C (3) are the first members of this alkaloid family to possess two chlorine substituents in the core 6H-2,6-naphthyridine ring system.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Biochemistry & Molecular Biology
Yu-Ting Tang, Jing Wu, Mei-Fen Bao, Qin-Gang Tan, Xiang-Hai Cai
Summary: A study identified ten dimeric and two monomeric Erythrina alkaloids from the bark of Erythrina variegata L. The structures of these alkaloids were determined through NMR, UV-spectroscopy, and mass spectrometry. The study also proposed a possible biosynthetic pathway and evaluated their effects on preventing hearing loss.
Article
Chemistry, Multidisciplinary
Cui Guo, Pei Wang, Xiaoyan Pang, Xiuping Lin, Shengrong Liao, Bin Yang, Xuefeng Zhou, Junfeng Wang, Yonghong Liu
Summary: Study involved isolation and characterization of structurally novel marine natural products. A compound displayed significant antibacterial and cytotoxic activities, indicating potential as a promising drug lead. This finding could attract attention from both chemists and pharmacists in the field.
Article
Chemistry, Multidisciplinary
Yiqing Zhang, Luyao Luo, Shuaiming Zhu, Shubin Niu, Youzhi Zhang, Yang Zhang
Summary: Five new xanthone derivatives (cladoxanthones C-G) and four known compounds were isolated from Cladosporium sp. The structures were determined by NMR experiments, and the absolute configurations were established using electronic circular dichroism calculations and X-ray crystallography. Compound 5 showed weak cytotoxicity against tumor cell lines, with IC50 values ranging from 30.8 to 51.3 mM. Additionally, compounds 8 and 9 displayed antioxidant activity by scavenging DPPH radicals, with IC50 values of 0.19 and 0.15 mM, respectively.
Article
Pharmacology & Pharmacy
Lingyan Wang, Guiyang Xia, Huan Xia, Xiaohong Wei, Yanan Wang, Sheng Lin
Summary: A chemical investigation on the aqueous extract of Corydalis yanhusuo tubers led to the isolation and structural elucidation of three pairs of trace enantiomeric hetero-dimeric alkaloids. These compounds exhibited potent inhibition of NO production and antinociceptive effects.
ACTA PHARMACEUTICA SINICA B
(2023)
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)