Article
Biochemistry & Molecular Biology
Shuo Gao, Xiao Lin, Yeqin Shi, Hu Zhou, Xiao Zheng, Mingyu Li, Ting Lin
Summary: A new prenylated indole alkaloid Penicimutamide CN-oxide (1), a new alkaloid penicimutamine A (2), and six known alkaloids were isolated from the endophytic fungus Pallidocercospora crystallina. A method was used to accurately determine the N-O bond in the N-oxide group of compound 1. Compounds 1, 3, 5, 6, and 8 showed significant hypoglycemic activities in a diabetic zebrafish model. Compounds 1 and 8 were found to lower glucose levels by promoting glucose uptake in zebrafish. Additionally, all eight compounds showed no acute toxicity, teratogenicity, or vascular toxicity in zebrafish, suggesting their potential as lead compounds for antidiabetes strategies.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
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
Qinyu Meng, Xiang Guo, Jingshuai Wu, Dong Liu, Yucheng Gu, Jian Huang, Aili Fan, Wenhan Lin
Summary: The study identified ten undescribed notoamide-type alkaloids from a marine gorgonian-derived fungus. Compound sclerotiamide J showed inhibitory effects against LDH and IL-1 beta expression in cells, and significantly inhibited NLRP3 inflammasome activation.
Article
Limnology
Yanan Wang, Xiaoming Li, Fengyi Lue, Suiqun Yang, Linghong Meng, Bingui Wang
Summary: A new prenylated indole alkaloid 11, 17-epi-mangrovamide A (1), a new natural occurring product, 1,7-dihydroxy-6-methyl-8-hydroxymethyl-xanthone (2), two known alkaloids, mangrovamide A (3) and mangrovamide G (4), and four known polyketide derivatives (5-8) were isolated and identified from the cold-seep sediment derived fungal strain Talaromyces funiculosus SD-523. Their structures were elucidated by combination of nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), quantum chemical electronic circular dichroism (ECD), and DP4+ probability analysis as well as by comparison of the data with literature reports. All isolated compounds were tested for antibacterial activities.
JOURNAL OF OCEANOLOGY AND LIMNOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Fengli Li, Shuyuan Mo, Jie Yin, Sitian Zhang, Saisai Gu, Zi Ye, Jianping Wang, Zhengxi Hu, Yonghui Zhang
Summary: Several novel secondary metabolites were isolated from the fungus Aspergillus calidoustus obtained from wetland soil in Dianchi Lake, Yunnan Province. One of these compounds showed significant cytotoxicity against certain tumor cells.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dong-Lin Zhao, Xue-Yan Huo, Pan-Pan Li, Xiao-Long Yuan, Sheng-Ying Li, Lei Du, Li-Jun Huang, Peng Zhang
Summary: In this study, a novel Prenylated indole alkaloid (PIA) with unique structure was isolated from the endophytic fungus of Nicotiana tabacum. The compound showed significant anti-inflammatory activity.
Article
Chemistry, Multidisciplinary
Yuan-Xing Zhu, Wenxin Ding, Jin-Feng Hu, Juan Xiong, Jiyang Li
Summary: In this study, a structurally unprecedented prenylated indole alkaloid, beshanzuamide A, along with five known analogues, were isolated and identified from the endophytic fungus derived from the critically endangered conifer Abies beshanzuensis. The new structure was determined by extensive spectroscopic methods and quantum chemical calculations, and a plausible biogenetic pathway was proposed.
Article
Chemistry, Medicinal
Li-Hong Yan, Feng-Yu Du, Xiao-Ming Li, Sui-Qun Yang, Bin-Gui Wang, Xin Li
Summary: Five new antibacterial indole diketopiperazine alkaloids were isolated and characterized from a fungal strain of Aspergillus chevalieri derived from a deep-sea cold seep. These compounds showed inhibitory activities against several pathogenic bacteria, with compound 6 potentially being a novel alternative for antibiotic development.
Article
Biochemistry & Molecular Biology
Xin Qi, Weihao Chen, Liurong Chen, Yiwei Hu, Xueni Wang, Wenrong Han, Jiao Xiao, Xiaoyan Pang, Xingang Yao, Shuwen Liu, Yong Li, Jie Yang, Junfeng Wang, Yonghong Liu
Summary: Guided by Global Natural Products Social molecular networking, 14 new p-terphenyl derivatives, asperterphenyls A-N (1-14), together with 20 known p-terphenyl derivatives (15-34), were obtained from a sponge derived fungus Aspergillus sp. SCSIO41315. Among them, new compounds 2-8 and 15-17 were ten pairs of enantiomers. Comprehensive methods such as chiral-phase HPLC analysis, ECD calculations and X-ray diffraction analysis were applied to determine the absolute configurations. Asperterphenyls B (2) and C (3) represented the first reported natural p-terphenyl derivatives possessing a dicarboxylic acid system. Asperterphenyl A (1) displayed neuraminidase inhibitory activity with an IC50 value of 1.77 +/- 0.53 mu M and could efficiently inhibit infection of multiple strains of H1N1 with IC50 values from 0.67 +/- 0.28 to 1.48 +/- 0.60 mu M through decreasing viral plaque formation in a dose-dependent manner, which suggested that asperterphenyl A (1) might be exploited as a potential antiviral compound in the pharmaceutical fields.
BIOORGANIC CHEMISTRY
(2023)
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
Chemistry, Applied
Sharpkate Shaker, Run-Zhu Fan, Hou-Jin Li, Wen-Jian Lan
Summary: Preliminary research on marine fungus Fusarium sp. XBB-9 led to the discovery of a pair of novel bisindole alkaloid enantiomers and 12 diverse compounds. The OSMAC method was used to enhance biosynthetic pathways, with the structures of the compounds elucidated through spectroscopic analysis and X-ray single-crystal diffraction. However, cytotoxicity tests on the compounds showed that they were inactive against HCT-15 and RKO cell lines.
NATURAL PRODUCT RESEARCH
(2021)
Article
Chemistry, Organic
Karen Ichikawa, Jessica C. Neville, Yihan Yu, Jonathan Sperry
Summary: In this study, a synthetic strategy for the marine alkaloid convolutindole A was reported, and an iterative C-H functionalization strategy was found to be more successful. The utility of the iridium-catalyzed C-H borylation methodology in preparing densely functionalized indoles was showcased, providing a foundation for ongoing synthetic efforts.
TETRAHEDRON LETTERS
(2023)
Article
Microbiology
Sha-Sha Liu, Li Yang, Fan-Dong Kong, Jia-Hui Zhao, Li Yao, Zhi-Guang Yuchi, Qing-Yun Ma, Qing-Yi Xie, Li-Man Zhou, Meng-Fei Guo, Hao-Fu Dai, You-Xing Zhao, Du-Qiang Luo
Summary: By feeding tryptophan to the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis, 3 new quinazoline-containing indole alkaloids were obtained, with compound 3 showing a unique structure and promising bioactivities.
FRONTIERS IN MICROBIOLOGY
(2021)
Article
Chemistry, Applied
Xingjie Liu, Ruonan Li, Xiaofei Zhou
Summary: This study investigated the chemical constituents of an endophytic fungus associated with Lonicera Japonica and isolated six structurally diverse indole alkaloids. One of the compounds, peniochroloid A, showed significant cytotoxicity against MCF-7 and THP-1 cell lines.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Applied
Kurnia Nastira Ningsih, Euis Holisotan Hakim
Summary: Six compounds were isolated from the ethyl acetate extract of endophytic fungus Colletotrichum queenslandicum derived from Morus australis Poir. leaf. These compounds, including one new indole alkaloid Morucolletotricin (1), along with two other indole alkaloids, tryptopol (2) and indole-3acetic acid (3), phomopyronol (4), 2-(3-aminophenyl)acetic acid (5), and ergosterol (6), were characterized based on NMR and MS data. Phomopyronol (4) and 2-(3-aminophenyl)acetic acid (5) were reported for the first time from Colletotrichum fungi. The cytotoxic activity of compounds 1-6 was evaluated against murine leukaemia P-388 cells and all compounds showed moderate cytotoxicity. Phomopyronol (4) was the most active compound with an IC50 value of 37.17 μg/mL.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Applied
Masateru Ono, Mizuki Shimode, Shuhei Tsutsumi, Shin Yasuda, Masafumi Okawa, Junei Kinjo, Hiroyuki Miyashita, Tsuyoshi Ikeda, Hitoshi Yoshimitsu, Toshihiro Nohara
Summary: A new cholestane-type steroidal glycoside, solamyriaside A, was isolated from the fruits of Solanum myriacanthum Dunal, along with other known steroidal glycosides. Some of the compounds showed cytotoxic activity against HL-60 human promyelocytic leukaemia cells. Compound 4 exhibited the strongest activity, similar to cisplatin.
NATURAL PRODUCT RESEARCH
(2022)
Article
Biochemistry & Molecular Biology
Yuki Hitora, Ai Sejiyama, Koyo Honda, Yuji Ise, Fitje Losung, Remy E. P. Mangindaan, Sachiko Tsukamoto
Summary: Natural products play important roles in drug development, specifically in cancer biology and the development of antitumor agents. In this study, a new sesquiterpene quinone, neoisosmenospongine, was isolated from a marine sponge extract, along with four known compounds. These compounds were found to inhibit cell cycle progression at S/G2/M phases, demonstrating the effectiveness of fluorescent image-based high-content screening for isolating cell cycle inhibitors from natural resources.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Ahmed H. H. El-Desoky, Keisuke Eguchi, Naoki Kishimoto, Toshifumi Asano, Hikaru Kato, Yuki Hitora, Shunsuke Kotani, Teruya Nakamura, Soken Tsuchiya, Teppei Kawahara, Masato Watanabe, Mikiyo Wada, Makoto Nakajima, Takashi Watanabe, Shogo Misumi, Sachiko Tsukamoto
Summary: Three new diterpenes were isolated from the roots of Stellera chamaejasme L., and their structures were determined through NMR and mass spectroscopic analyses. Compounds 1 and 2 are the first derivatives containing a hydroxy group at C-2 in the family of daphnane and tigliane diterpenes. Compound 1, with a chlorine atom, and compound 3, with an odd-number acyl group, are unique plant metabolites.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Soichiro Nishimura, Yuki Hitora, Teppei Kawahara, Mika Tanabe, Eisuke Ogata, Hikaru Kato, Pattaravadee Srikoon, Takashi Watanabe, Sachiko Tsukamoto
Summary: This study developed a cell-based luminescent assay to screen natural products that inhibit protein degradation. The culture extract of the fungus Remotididymella sp. was found to contain polyketides that inhibit proteasomal degradation, showing potential as anti-tumor agents.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Review
Chemistry, Medicinal
Ahmed H. H. El-Desoky, Sachiko Tsukamoto
Summary: Osteoporosis, a disease that affects the quality of life of elderly people, can be treated by promoting osteoblast differentiation and suppressing osteoclastogenesis. Marine organisms are a promising source for finding new drugs, and some of their secondary metabolites can inhibit osteoporosis.
JOURNAL OF NATURAL MEDICINES
(2022)
Article
Microbiology
Nanami Yoshino, Tsuyoshi Ikeda, Ryoma Nakao
Summary: The study found that fennel has significant activity against Porphyromonas gingivalis, a major pathogen in periodontitis. Fennel extracts showed rapid lethal action against P. gingivalis and minimal effects on other oral bacteria. The extracts formed protruding nanostructures and induced overproduction of outer membrane vesicles. Fennel also inhibited the activity of gingipain enzymes produced by P. gingivalis, preventing damage to oral epithelial cells. Petroselinic acid was identified as the major bactericidal and gingipain-inhibiting component of fennel.
FRONTIERS IN MICROBIOLOGY
(2022)
Article
Chemistry, Medicinal
Yusaku Sadahiro, Yuki Hitora, Ichiro Kimura, Natsuko Hitora-Imamura, Risako Onodera, Keiichi Motoyama, Sachiko Tsukamoto
Summary: Mutant p53 loses its tumor suppressor function and gains new abilities for oncogenic progression. A compound called CF isolated from a fungus was found to decrease mutant p53 levels and inhibit tumor cell growth.
CHEMICAL RESEARCH IN TOXICOLOGY
(2022)
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
Chemistry, Organic
Akiho Yoshidome, Jukiya Sakamoto, Mizuki Kohara, Shinya Shiomi, Mako Hokaguchi, Yuki Hitora, Mariko Kitajima, Sachiko Tsukamoto, Hayato Ishikawa
Summary: Divergent total syntheses of hetero-oligomeric iridoid glycosides were achieved using efficient synthetic methods. The monomer unit loganin was stereoselectively synthesized through reductive cyclization of secologanin. Sequential condensation reactions of derivatives of loganin and secologanin led to the synthesis of heterooligomers cantleyoside, (E)-aldosecologa-nin, dipsaperine, (3R, 5S)-5-carboxyvincosidic acid 22-loganin ester, and dipsanoside A.
Article
Biochemistry & Molecular Biology
Ahmed H. El-Desoky, Toshifumi Asano, Yuka Maeyama, Hikaru Kato, Yuki Hitora, Eishu Goto, Shunsuke Kotani, Makoto Nakajima, Sachiko Tsukamoto
Summary: Antiosteoclastogenic activity-guided screening led to the identification of three undescribed davanone-related terpenoids, arteperoxides A-C, from the extract of Artemisia judaica L. The structural analysis revealed that arteperoxides A-C contained peroxide bridges, which is a previously unobserved variation among terpene-derived compounds. The antiosteoclastogenic activity of the natural and synthetic compounds showed that arteperoxide C and hydroxydavanone exhibited higher potency compared to other compounds at a concentration of 20 μM.
Article
Chemistry, Medicinal
Ichiro Kimura, Yuki Hitora, Yusaku Sadahiro, Teppei Kawahara, Sachiko Tsukamoto
Summary: A new compound, 21F121-A, was isolated from the culture of Penicillium glaucoroseum by LCMS-guided purification and its structure was elucidated. The analysis of its spectroscopy and derivatives revealed the configuration of its components. This study provides more insights into monoacylglyceryltrimethylhomoserine, which is less studied compared to its diacyl counterparts. The new compound also showed inhibitory effects on the growth of HCT116 cells.
JOURNAL OF NATURAL MEDICINES
(2023)
Article
Urology & Nephrology
Jun Kuwazuru, Mary Ann Suico, Kohei Omachi, Haruka Kojima, Misato Kamura, Shota Kaseda, Teppei Kawahara, Yuki Hitora, Hikaru Kato, Sachiko Tsukamoto, Mikiyo Wada, Toshifumi Asano, Shunsuke Kotani, Makoto Nakajima, Shogo Misumi, Yuya Sannomiya, Jun Horizono, Yuimi Koyama, Aimi Owaki, Tsuyoshi Shuto, Hirofumi Kai
Summary: This study provides a novel therapeutic candidate, alisporivir, for Alport syndrome (AS) by enhancing the secretion of mutant 345(IV) and reveals the importance of cyclophilin D in this process. It suggests that alisporivir could be a safer option than cyclosporin A for AS treatment.
Article
Biochemistry & Molecular Biology
Koyo Honda, Yuki Hitora, Sachiko Tsukamoto
Summary: This study demonstrates that a fungal extract and its derivatives can inhibit cell cycle progression, potentially serving as anticancer agents.
Article
Biochemistry & Molecular Biology
Ahmed H. El-Desoky, Keisuke Eguchi, Ippei Kagiyama, Yuki Hitora, Hikaru Kato, Yuji Ise, Fitje Losung, Remy E. P. Mangindaan, Sachiko Tsukamoto
Summary: Seven chlorinated sesquiterpene carbamates have been isolated from a marine sponge collected in Indonesia, and their structures have been determined. Some of these compounds showed inhibitory effects on the formation of multinucleated osteoclasts.
Article
Chemistry, Organic
Yuhei Koyanagi, Yuki Hitora, Teppei Kawahara, Sachiko Tsukamoto
Summary: Two new azaphilone alkaloids, peniphilones A and B, were isolated from the endophytic fungus Penicillium maximae using UPLC-HRMS screening and a natural sources extract library. The structures of these compounds were elucidated based on NMR and HRESI-MS spectroscopic data.
