Indole-Diterpenoids with Protein Tyrosine Phosphatase Inhibitory Activities from the Marine-Derived Fungus <i>Penicillium</i> sp. KFD28

Zhou, Li-Man; Kong, Fan-Dong; Fan, Peng; Ma, Qing‐Yun; Xie, Qing; Li, Jiuhui; Zheng, H.; Zheng, Zhaohui; Yuan, Jing-Zhe; Dai, Hao‐Fu; Luo, Du‐Qiang; Zhao, You‐Xing

doi:10.1021/acs.jnatprod.9b00620

Cited by 48 publications

(38 citation statements)

References 21 publications

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“…Compounds 252 , 253 , and 256 displayed inhibitory effects toward protein tyrosine phosphatase 1B (PTP1B) (IC 50 = 14, 27, and 23 μmol/L, respectively). 120…”

Section: Marine Fungal Indole Alkaloidsmentioning

confidence: 99%

Natural Indole Alkaloids from Marine Fungi: Chemical Diversity and Biological Activities

Zhuang

2021

Pharmaceutical Fronts

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The indole scaffold is one of the most important heterocyclic ring systems for pharmaceutical development, and serves as an active moiety in several clinical drugs. Fungi derived from marine origin are more liable to produce novel indole-containing natural products due to their extreme living environments. The indole alkaloids from marine fungi have drawn considerable attention for their unique chemical structures and significant biological activities. This review attempts to provide a summary of the structural diversity of marine fungal indole alkaloids including prenylated indoles, diketopiperazine indoles, bisindoles or trisindoles, quinazoline-containing indoles, indole-diterpenoids, and other indoles, as well as their known biological activities, mainly focusing on cytotoxic, kinase inhibitory, antiinflammatory, antimicrobial, anti-insecticidal, and brine shrimp lethal effects. A total of 306 indole alkaloids from marine fungi have been summarized, covering the references published from 1995 to early 2021, expecting to be beneficial for drug discovery in the future.

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“…Compounds 252 , 253 , and 256 displayed inhibitory effects toward protein tyrosine phosphatase 1B (PTP1B) (IC 50 = 14, 27, and 23 μmol/L, respectively). 120…”

Section: Marine Fungal Indole Alkaloidsmentioning

confidence: 99%

Natural Indole Alkaloids from Marine Fungi: Chemical Diversity and Biological Activities

Zhuang

2021

Pharmaceutical Fronts

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“…KFD28, which is associated with the bivalve mollusk, Meretrix lusoria (Haikou Bay, China), nine new diverse skeletons of indole terpenoids, penerpenes A−D (437-440) [146] and E-I (441-445) [147], and nine known indole terpenoids, including paxilline, emindole SB, and 7-hydroxypaxilline-13-ene, were isolated. Notably, compound 437 possesses a 1,4-dihydro-2Hbenzo[d] [1,3] oxazine moiety in an unusual spiro indole diterpene; compound 438 has an uncommon heptacyclic scaffold containing pyridine in the indole diterpene; compounds 439, 440, and 442 are norindole diterpenoids with new carbon frameworks possibly derived from paxilline via the loss of 3-5 carbons; compound 441 bears a unique 6/5/5/6/6/5/5 heptacyclic ring system; and compound 443 contains an unusual 6/5/5/6/6/7 hexacyclic motif bearing a 1,3-dioxepane ring rarely found in nature [146,147]. Compounds 437 and 438 and emindole SB are considered to be new potent protein tyrosine phosphatase (PTP1B and TCPTP, IC 50 = 0.7-5.0 µM) inhibitors via PTP inhibition and molecular docking experiments [146].…”

Section: Aspergillus Spmentioning

confidence: 99%

“…Compounds 441, 442, 444, and 7-hydroxypaxilline-13-ene inhibited PTP1B (IC 50 = 13-27 µM). Compound 441 also showed anti-PTPσ activity (IC 50 = 38 µM), while compound 444 and 7-hydroxypaxilline-13-ene inhibited TCPTP (IC 50 = 35 and 37 µM, respectively) [147]. Penicindopene A (446), possessing a 3-hydroxyl-2-indolone moiety rarely found in indole diterpenes, was isolated from the deep-sea fungus Penicillium sp.…”

Section: Aspergillus Spmentioning

confidence: 99%

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

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Marine-derived fungi are a significant source of pharmacologically active metabolites with interesting structural properties, especially terpenoids with biological and chemical diversity. In the past five years, there has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered. In this updated review, we examine the chemical structures and bioactive properties of new terpenes from marine-derived fungi, and the biodiversity of these fungi from 2015 to 2019. A total of 140 research papers describing 471 new terpenoids of six groups (monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and meroterpenes) from 133 marine fungal strains belonging to 34 genera were included. Among them, sesquiterpenes, meroterpenes, and diterpenes comprise the largest proportions of terpenes, and the fungi genera of Penicillium, Aspergillus, and Trichoderma are the dominant producers of terpenoids. The majority of the marine-derived fungi are isolated from live marine matter: marine animals and aquatic plants (including mangrove plants and algae). Moreover, many terpenoids display various bioactivities, including cytotoxicity, antibacterial activity, lethal toxicity, anti-inflammatory activity, enzyme inhibitor activity, etc. In our opinion, the chemical diversity and biological activities of these novel terpenoids will provide medical and chemical researchers with a plenty variety of promising lead compounds for the development of marine drugs.

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“…KFD28 which was obtained from a bivalve mollusc, Meretrix lusoria, collected from Haikou Bay. Compounds 311, 312, 314 and 316 displayed moderate protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC 50 values of 14, 27, 23, and 13 µM, respectively [86].…”

Section: Meroditerpenoidsmentioning

confidence: 99%

Chemical Diversity and Biological Activities of Meroterpenoids from Marine Derived-Fungi: A Comprehensive Update

2020

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Meroterpenoids are a class of hybrid natural products, partially derived from a mixed terpenoid pathway. They possess remarkable structural features and relevant biological and pharmacological activities. Marine-derived fungi are a rich source of meroterpenoids featuring structural diversity varying from simple to complex molecular architectures. A combination of a structural variability and their myriad of bioactivities makes meroterpenoids an interesting class of naturally occurring compounds for chemical and pharmacological investigation. In this review, a comprehensive literature survey covering the period of 2009–2019, with 86 references, is presented focusing on chemistry and biological activities of various classes of meroterpenoids isolated from fungi obtained from different marine hosts and environments.

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Indole-Diterpenoids with Protein Tyrosine Phosphatase Inhibitory Activities from the Marine-Derived Fungus Penicillium sp. KFD28

Cited by 48 publications

References 21 publications

Natural Indole Alkaloids from Marine Fungi: Chemical Diversity and Biological Activities

Natural Indole Alkaloids from Marine Fungi: Chemical Diversity and Biological Activities

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Chemical Diversity and Biological Activities of Meroterpenoids from Marine Derived-Fungi: A Comprehensive Update

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