Okaramines S–U, three new indole diketopiperazine alkaloids from Aspergillus taichungensis ZHN-7-07

Cai, Shengxin; Sun, Shiwei; Peng, Jixing; Kong, Xiangfeng; Zhou, Huinan; Zhu, Tianjiao; Gu, Qianqun; Li, Dehai

doi:10.1016/j.tet.2014.09.019

Cited by 43 publications

(40 citation statements)

References 22 publications

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“…Okaramines A–U ( 129 – 149 ) have been isolated from Aspergillus aculeatus [ 60 ], Aspergillus taichungensis [ 61 ], and Penicillium simplicissimum [ 62 , 63 , 64 , 65 ]. Structure–activity studies indicated the importance of the azetidine and azocine rings to okaramine insecticidal activity [ 66 ].…”

Section: Tryptophan–tryptophan Cyclodipeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Wang

Zhang

et al. 2017

Molecules

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Cyclodipeptides, called 2,5-diketopiperazines (2,5-DKPs), are obtained by the condensation of two amino acids. Fungi have been considered to be a rich source of novel and bioactive cyclodipeptides. This review highlights the occurrence, structures and biological activities of the fungal cyclodipeptides with the literature covered up to July 2017. A total of 635 fungal cyclodipeptides belonging to the groups of tryptophan-proline, tryptophan-tryptophan, tryptophan–Xaa, proline–Xaa, non-tryptophan–non-proline, and thio-analogs have been discussed and reviewed. They were mainly isolated from the genera of Aspergillus and Penicillium. More and more cyclodipeptides have been isolated from marine-derived and plant endophytic fungi. Some of them were screened to have cytotoxic, phytotoxic, antimicrobial, insecticidal, vasodilator, radical scavenging, antioxidant, brine shrimp lethal, antiviral, nematicidal, antituberculosis, and enzyme-inhibitory activities to show their potential applications in agriculture, medicinal, and food industry.

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Section: Tryptophan–tryptophan Cyclodipeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Wang

Zhang

et al. 2017

Molecules

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“…Okaramines S–U ( 418 – 420 ) were produced by Aspergillus taichungensis ZHN-7-07, isolated from the rhizosphere soil of the mangrove plant Acrostichum aureum ( Figure 66 ). Okaramine S ( 418 ) showed cytotoxic activity against HL-60 and K562 cell lines (IC 50 0.78 and 22.4 μM, respectively), but none of them exhibited antibiotic activities [ 175 ].…”

Section: Marine Indole Alkaloidsmentioning

confidence: 99%

Marine Indole Alkaloids

2015

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Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed.

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“…Carneamides A-C (72-74) were isolated from the marine-derived fungus A. carneus KMM 4538, and the antimicrobial and cytotoxic activities were examined, in which these compounds showed no activities (Zhuravleva et al 2012). Cai et al (2012Cai et al ( , 2015 obtained aspergilazine A (75) and okaramines S-U (86-88) from the fungal strain A. taichungensis ZHN-7-07, isolated from the mangrove plant Acrostichum aureum, in 2012 and 2015, respectively. Compound 75 had an inhibition rate of 34.1% against influenza A virus H 1 N 1 at a concentration of 50 μg/mL, while compound 86 showed cytotoxic activities against HL-60 and K562 with IC 50 values of 0.78 and 22.4 μmol/L, respectively.…”

Section: Idps From the Fungal Genus Aspergillusmentioning

confidence: 99%

Chemical diversity and biological function of indolediketopiperazines from marine-derived fungi

Cao

Wang

2020

Mar Life Sci Technol

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Natural products from marine-derived fungi have attracted considerable attention in the recent two decades. Indolediketopiperazines are one of the most important classes of marine natural products, mainly discovered from the fungal genera Penicillium, Aspergillus and Eurotium. These compounds span a wide range of chemical structures and bioactivities. This review summarizes 155 indolediketopiperazines that were discovered from marine-derived fungi from 2000 to early 2019 and primarily focuses on their chemical diversity and biological function.

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Okaramines S–U, three new indole diketopiperazine alkaloids from Aspergillus taichungensis ZHN-7-07

Cited by 43 publications

References 22 publications

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Marine Indole Alkaloids

Chemical diversity and biological function of indolediketopiperazines from marine-derived fungi

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