Article
Chemistry, Organic
Thanh-Hao Huynh, Nan-Fu Chen, Jing-Ru Weng, Su-Ying Chien, Yi-Hung Liu, Yu-Chi Tsai, Ping-Jyun Sung
Summary: Four manzamine-type alkaloids, including a novel compound with a 27 -N-oxide moiety, were isolated from the marine sponge Neopetrosia proxima. The structures and absolute configurations of the compounds were determined using spectroscopic data and single X-ray diffraction analysis. Some of the compounds showed cytotoxicity against tumor cells.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Toshiaki Wayama, Hiroki Oguri
Summary: Previous attempts to perform biomimetic transannular reactions utilizing DHP rings within macrocycles similar to manzamine alkaloids had been unsuccessful. In this study, an efficient regiocontrolled transannular cyclization of a C2-symmetric macrocyclic precursor was achieved through rational modifications of the 3 and 6 positions of the DHP rings, resulting in the synthesis of a halicyclamine-type scaffold. The presence of cis-double bonds in the macrocyclic alkyl loops played a critical role in the success of the biomimetic transannular cyclization.
Article
Chemistry, Organic
Oh-Seok Kwon, Sungjin Ahn, Ju-eun Jeon, In Guk Park, Tae Hyung Won, Chung J. Sim, Hyeung-geun Park, Dong-Chan Oh, Ki-Bong Oh, Minsoo Noh, Jongheon Shin
Summary: Psammocindoles A-C, a new class of indole alkaloids isolated from a Psammocinia vermis sponge, were found to significantly stimulate adiponectin secretion in human bone marrow mesenchymal stem cells.
Article
Chemistry, Medicinal
Qi Wang, Chunhua Gao, Zhun Wei, Xiaowen Tang, Lixia Ji, Xiangchao Luo, Xiaoping Peng, Gang Li, Hongxiang Lou
Summary: Twelve new and four known alkaloids were isolated from the sponge Stylissa massa collected in the South China Sea, and their structures and activities were studied.
Article
Chemistry, Organic
Guoliang Zhou, Chunxiao Sun, Xuewen Hou, Qian Che, Guojian Zhang, Qianqun Gu, Chenguang Liu, Tianjiao Zhu, Dehai Li
Summary: Four new indole diterpenoids, ascandinines A-D (1-4), were isolated from an Antarctic sponge-derived fungus. One of them exhibited anti-influenza virus activity, and another showed cytotoxicity against HL-60 cells.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Plant Sciences
Huynh Nguyen Khanh Tran, Min Jin Kim, A-Young Shin, Le Viet Ha Tran, Jihoon Lee, Yeon-Ju Lee
Summary: Ten new norterpene alkaloids, coscinoderines A-J (1-10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. The structures were determined using NMR and HRMS data, and the absolute stereochemistry of compound 4 was confirmed by comparing calculated and measured ECD spectra. The discovery of these coscinoderines expands the range of pyridinium alkaloids found in marine sponges.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Plant Sciences
Yu-Feng Zhang, Dai-Chun Li, Xiao-Jian Liao, Shi-Hai Xu, Bing-Xin Zhao
Summary: Two new alkaloids, named spongimides A (1) and B (2), along with five known compounds (3-7), were isolated from the marine sponge Spongia sp. The structures of 1 and 2 were determined by spectroscopic methods and X-ray diffraction analysis. Compounds 1, 3, and 4 were the first examples of 2,4-imidazolidinediones isolated from this genus. Furthermore, the cytotoxic and antibacterial activities of compounds 1 and 2 were evaluated.
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
(2023)
Article
Biochemistry & Molecular Biology
Li Xu, Panpan Wang, Shijie Yuan, Liangzhou Yu, Jianping Zhao, Guoqiang Li, Gang Zhang, Lianzhong Luo
Summary: A new pyrrololactam alkaloid, axinellamine E (2), and four known analogs were isolated from the EtOH extract of the sponge Axinella sp. The structures of the compounds were determined using 1D-, 2D-NMR, and HR-ESI-MS analysis. Compound 1 exhibited weak anti-inflammatory activity.
CHEMISTRY & BIODIVERSITY
(2022)
Article
Plant Sciences
Ze-Jie Guo, Hui-Xian Liang, Xiao-Ying Lian, Xiao-Jian Liao, Xi-Wen Xing, Shi-Hai Xu, Bing-Xin Zhao
Summary: New enantiomeric indolone alkaloids, named Tedanine, were isolated from a marine sponge and evaluated for their cytotoxic and antibacterial activities.
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
(2023)
Article
Plant Sciences
Ze-Jie Guo, Hui-Xian Liang, Xiao-Ying Lian, Xiao-Jian Liao, Xi-Wen Xing, Shi-Hai Xu, Bing-Xin Zhao
Summary: A pair of new enantiomeric indolone alkaloids, (+)- and (-)-Tedanine, were isolated from the marine sponge Tedania sp., along with nine other compounds. The structures and absolute configurations of (+)-1 and (-)-1 were determined using spectroscopic analysis and quantum chemical calculation. This is the first time that indolone alkaloids have been isolated from this genus. Additionally, the cytotoxic and antibacterial activities of these compounds were evaluated.
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
(2023)
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, Organic
Philipp Moosmann, Tohru Taniguchi, Kazuo Furihata, Hiroaki Utsumi, Yuji Ise, Yasuhiro Morii, Nobuhiro Yamawaki, Tomohiro Takatani, Osamu Arakawa, Shigeru Okada, Shigeki Matsunaga
Summary: Myrindole A, a bis-indole alkaloid isolated from a deep-sea sponge, had a complex structure that was ultimately determined through a combination of experiments and spectral comparison. It showed antimicrobial activity against both Gram-positive and Gram-negative bacteria.
Article
Chemistry, Medicinal
Jae Sung Park, Eunji Cho, Ji-Yeon Hwang, Sung Chul Park, Beomkoo Chung, Oh-Seok Kwon, Chung J. Sim, Dong-Chan Oh, Ki-Bong Oh, Jongheon Shin
Summary: Six new bis(indole) alkaloids, along with eight known ones, were isolated from a sponge in Korea. These compounds showed moderate inhibition against transpeptidase sortase A and weak inhibition against human pathogenic bacteria and cancer cell lines A549 and K562.
Article
Chemistry, Medicinal
Yuxiu Ye, Jiaqi Liang, Jianglian She, Xiuping Lin, Junfeng Wang, Yonghong Liu, Dehua Yang, Yanhui Tan, Xiaowei Luo, Xuefeng Zhou
Summary: Marine sponge-derived fungi have been found to produce bioactive natural products, including two new alkaloids (polonimides E and D) and a new butenolide derivative (eutypoid F). In addition, thirteen known compounds were also isolated from the fungus Penicillium sp. SCSIO 41413. The inhibitory effects of the butenolide derivatives on the enzyme PI3K were investigated, and two compounds showed significant binding to the PI3K protein. Furthermore, two compounds exhibited inhibitory activity against LPS-induced NF-kappa B activation in cells.
Article
Chemistry, Medicinal
Asadhawut Hiranrat, Darren C. Holland, Wilawan Mahabusarakam, John N. A. Hooper, Vicky M. Avery, Anthony R. Carroll
Summary: Two new fluorescent pteridine alkaloids, tedaniophorbasins A and B, were isolated from the sponge Tedaniophorbas ceratosis. They showed significant Stokes shifts in their fluorescence spectra but were inactive against malaria parasite strains, cancer cell lines, and protozoan parasites.
Article
Chemistry, Medicinal
Takaaki Kubota, Kenta Nakamura, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi
CHEMICAL & PHARMACEUTICAL BULLETIN
(2016)
Article
Chemistry, Multidisciplinary
Koji Ochiai, Sankar Kuppusamy, Yusuke Yasui, Kenji Harada, Nishant R. Gupta, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi, Yujiro Hayashi
CHEMISTRY-A EUROPEAN JOURNAL
(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)