A new isobenzofuranone from the mangrove endophytic fungus <i>Penicillium</i> sp. (ZH58)

Yang, Jianxiang; Huang, Riming; Qiu, Songbai; She, Zhigang; Lin, Yongcheng

doi:10.1080/14786419.2013.784870

Cited by 27 publications

(17 citation statements)

References 16 publications

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“…Compounds 8 – 11 showed anti-influenza A (H1N1) virus activity with the half maximal inhibitory concentration ( IC 50 ) and selectivity index ( SI ) values of 38.3(±1.2)/25.0(±3.6)/39.7(±5.6)/45.9(±2.1) μg/mL and 3.0/16.1/3.1/11.4, respectively. Pyrazine alkaloids from marine organisms exhibited cytotoxic and antimicrobial activities [17,18,19,20,21], three of which were identified from the mangrove plant [22] and fungi [23,24]. β-Carbolines, as a type of natural indol alkaloids, displayed cytotoxic [25], antiviral [26,27], antimicrobial [28], antiparasitic [29], and antithrombotic activities [30].…”

Section: Introductionmentioning

confidence: 99%

“…β-Carbolines, as a type of natural indol alkaloids, displayed cytotoxic [25], antiviral [26,27], antimicrobial [28], antiparasitic [29], and antithrombotic activities [30]. Apart from the terrestrial organisms, marine organisms, including mangrove fungi [24,31], are also a major source of β-carbolines [32,33,34,35,36,37,38,39,40]. Pyrrololactones that had been reported as the volatile components of the roasted roots of Cichorium intrybus [8] were not identified from the marine organisms.…”

Section: Introductionmentioning

confidence: 99%

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Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111

et al. 2014

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A new alkaloid, 2-(furan-2-yl)-6-(2S,3S,4-trihydroxybutyl)pyrazine (1), along with 12 known compounds, 2-(furan-2-yl)-5-(2S,3S,4-trihydroxybutyl)pyrazine (2), (S)-4-isobutyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (3), (S)-4-isopropyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (4), (4S)-4-(2-methylbutyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (5), (S)-4-benzyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (6), flazin (7), perlolyrine (8), 1-hydroxy-β-carboline (9), lumichrome (10), 1H-indole-3-carboxaldehyde (11), 2-hydroxy-1-(1H-indol-3-yl)ethanone (12), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (13), were isolated and identified from the fermentation broth of an endophytic actinomycetes, Jishengella endophytica 161111. The new structure 1 and the absolute configurations of 2–6 were determined by spectroscopic methods, J-based configuration analysis (JBCA) method, lactone sector rule, and electronic circular dichroism (ECD) calculations. Compounds 8–11 were active against the influenza A virus subtype H1N1 with IC50 and selectivity index (SI) values of 38.3(±1.2)/25.0(±3.6)/39.7(±5.6)/45.9(±2.1) μg/mL and 3.0/16.1/3.1/11.4, respectively. The IC50 and SI values of positive control, ribavirin, were 23.1(±1.7) μg/mL and 32.2, respectively. The results showed that compound 9 could be a promising new hit for anti-H1N1 drugs. The absolute configurations of 2–5, 13C nuclear magnetic resonance (NMR) data and the specific rotations of 3–6 were also reported here for the first time.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111

et al. 2014

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“…The isobenzofurannone derivative ( 232 ) isolated from a mangrove endophytic Penicillium sp. displayed moderate cytotoxicity against KB and KBV200 cells (IC 50 = 6 and 10 μg/mL, respectively) [ 145 ], whereas the penicillic acid ( 233 ), isolated from marine-derived Penicillium strain, exhibited moderate cytotoxicity against POS1, AT6-1(murine prostatic carcinoma), and L929 (murine fibroblasts) cell lines (IC 50 = 7.8, 29.4, and 12.9 μM, respectively) while doxorubicin was used as a positive control with IC 50 values of 0.04~2 μM [ 84 ].…”

Section: Miscellaneous Compoundsmentioning

confidence: 99%

“… Marine alga Other P388 0.2 μg/mL [ 111 ] 232 Penicillium sp. Mangrove Other KB, KBv200 (6, 10) μg/mL [ 145 ] Penicillic acid ( 233 ) Penicillium sp. Sea water Other POS1, AT6-1, L299 (7.8, 29.4, 12.9) μM [ 84 ] …”

Section: Table A1mentioning

confidence: 99%

Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

Liu

Song

et al. 2017

Marine Drugs

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Since the discovery of penicillin, Penicillium has become one of the most attractive fungal genera for the production of bioactive molecules. Marine-derived Penicillium has provided numerous excellent pharmaceutical leads over the past decades. In this review, we focused on the cytotoxic metabolites * (* Cytotoxic potency was referred to five different levels in this review, extraordinary (IC50/LD50: <1 μM or 0.5 μg/mL); significant (IC50/LD50: 1~10 μM or 0.5~5 μg/mL); moderate (IC50/LD50: 10~30 μM or 5~15 μg/mL); mild (IC50/LD50: 30~50 μM or 15~25 μg/mL); weak (IC50/LD50: 50~100 μM or 25~50 μg/mL). The comparative potencies of positive controls were referred when they were available). produced by marine-derived Penicillium species, and on their cytotoxicity mechanisms, biosyntheses, and chemical syntheses.

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“…The study of mangrove-associated microbial natural products is a hotspot (Deng et al 2013;Klaiklay et al 2013;Yang et al 2013;Zhu et al 2013;. 348 biomolecules were discovered until 2011 (Xu 2011), and 464 new notable bioactivities of secondary metabolites were isolated during 2011-2013 (Xu 2015).…”

Section: Introductionmentioning

confidence: 99%

Chemical constituents of the mangrove-associated fungus Capnodium sp. SZ-F22. A new eremophilane sesquiterpene

Wang

et al. 2015

Natural Product Research

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A new eremophilane sesquiterpene, capnodiumone (1), along with five known eremophilane sesquiterpenes (2-6) and eight other compounds (7-14), have been isolated from a mangrove-associated fungus Capnodium sp. SZ-F22. The chemical structures were elucidated on the basis of extensive spectroscopic analysis. The broth extract of the fungus exhibited a good inhibitory effect on the mycelium growth against Fusarium graminearum at 100 μg/mL, however, all the 14 compounds showed no expected antifungal activity. The probable reasons were discussed.

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A new isobenzofuranone from the mangrove endophytic fungus Penicillium sp. (ZH58)

Cited by 27 publications

References 16 publications

Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111

Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111

Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

Chemical constituents of the mangrove-associated fungus Capnodium sp. SZ-F22. A new eremophilane sesquiterpene

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