New Enantiomers of a Nor-Bisabolane Derivative and Two New Phthalides Produced by the Marine-Derived Fungus Penicillium chrysogenum LD-201810

Ge, Yanqing; Tang, Wen-Li; Huang, Qingrong; Wei, Mao-Lian; Li, Youzhi; Jiang, Linlin; Li, Chenglin; Yu, Xin; Zhu, Hongwei; Chen, Guozhong; Zhang, Jianlong; Zhang, Xingxiao

doi:10.3389/fmicb.2021.727670

Cited by 12 publications

(13 citation statements)

References 20 publications

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“…In addition, eight previously reported compounds ( 3 – 10 ) were also isolated from this fungus. They were finally characterized as 6,7-dihydroxy-3-methoxy-3-methylphthalide ( 3 ) ( Wang et al, 2013 ), chrysoalide B ( 4 ) ( Ge et al, 2021 ), rubralide C ( 5 ) ( Kimura et al, 2007 ), cis -(3 RS ,4 SR )-3,4-dihydro-3,4,8-trihydroxynaphthalen-1(2 H )-one ( 6 ) ( Couché et al, 2009 ), 2,5-dimethyl-7-hydroxychromone ( 7 ) ( Kashiwada et al, 1984 ), (7 R )-(hydroxy(phenyl)methyl)-4 H -pyran-4-one ( 8 ) ( Xu et al, 2019 ), 6-benzyl-4-oxo-1,4-dihydropyridine-3-carboxamide ( 9 ) ( Ye et al, 2005 ), and carbonarone A ( 10 ) ( Zhang et al, 2007 ), respectively, by comparison of their spectroscopic data with literatures.…”

Section: Resultsmentioning

confidence: 99%

Polyketides isolated from an endophyte Penicillium oxalicum 2021CDF-3 inhibit pancreatic tumor growth

Weng

Li²,

Zhang³

et al. 2022

Front. Microbiol.

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Fungal secondary metabolites are inherently considered valuable resources for new drugs discovery. To search for novel fungal secondary metabolites with lead compounds potential, a fungal strain Penicillium oxalicum 2021CDF-3, an endophyte of the marine red algae Rhodomela confervoides, was chemically studied. Cultivation of this fungus on solid rice medium yielded 10 structurally diverse metabolites (1–10), including two new polyketides, namely oxalichroman A (1) and oxalihexane A (2). Their structures were determined by detailed analysis of NMR and HRESIMS spectroscopic data. Oxalihexane A (2) was elucidated as a novel polyketide formed by a cyclohexane and cyclohexanone moiety via an ether bond. The stereochemistry of 2 was successfully assigned by NMR and ECD calculations. In the cytotoxic assay, the new compound 2 showed remarkable inhibitory effect on the human pancreatic cancer PATU8988T cell line. Further pharmacological study demonstrated that the expression level of Cyclin D1 was down-regulated by the treatment with 2, which suggested that cell cyclin abnormity was involved in pancreatic tumor cell apoptosis. Moreover, the activation of Wnt5a/Cyclin D1 signaling pathway might be involved in the mechanism of panreatic tumor cell apoptosis induced by 2.

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Section: Resultsmentioning

confidence: 99%

Polyketides isolated from an endophyte Penicillium oxalicum 2021CDF-3 inhibit pancreatic tumor growth

Weng

Li²,

Zhang³

et al. 2022

Front. Microbiol.

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“…Compound 1 possessed the same planar structure as chrysoalide B, a new phthalide produced by the marine-derived fungus Penicillium chrysogenum LD-201810 ( Ge et al, 2021 ). Surprisingly, the specific rotation value of 1 was found to be zero.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic secondary metabolites isolated from Penicillium sp. YT2019-3321, an endophytic fungus derived from Lonicera Japonica

et al. 2022

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IntroductionEndophytic fungi associated with medicinal plants have proven to possess a high potential to produce structurally diverse metabolites, some of which are valuable for medicinal applications. In this study, Penicillium sp. YT2019-3321, an endophytic fungus derived from traditional Chinese medicine Lonicera japonica, was chemically studied.MethodsThe chemical structures of the isolated compounds were established by a correlative interpretation of HRESIMS and NMR spectroscopic data. The optical resolution of (±)-1 by chiral HPLC yielded individual enantiomers (+)-1 and (–)-1, and their stereochemistry were solved by X-ray diffraction crystallography, respectively.Results and discussionEight structurally diversified secondary metabolites, including two previously unreported polyketides, named (±)-chrysoalide B (1) and penicidone E (2), were isolated and identified from Penicillium sp. YT2019-3321. Compound 2 possessed the γ-pyridone nucleus, which is rarely found in natural products. Cytotoxic assay revealed that the new compound 2 demonstrated a dose-dependent cytotoxicity against the human pancreatic tumor cells PATU8988T with the IC50 value of 11.4 μM. Further studies indicated that 2 significantly induced apoptosis of PATU8988T cell lines, characterized by the morphologies abnormity, the reduction of cell number, the upregulation of proportion of apoptotic cells, and the ratio of Bcl-2 to Bax. Our study demonstrates that fungal secondary metabolites may have important significance in the discovery of drug leads.

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“…Compared to bisabolanes isolated from terrestrial fungi, some of bisabolanes from marine-derived fungi possess unique functionalities. For example, the sulfurated bisabolanes were exclusively isolated from marine fungi, including 25 with a rare methylsulfonyl group isolated from the deep sea sediment-derived fungus A. sydowii MCCC 3A00324 ( Niu et al, 2020 ), 40 and 42 – 43 incorporating with a rare methylsulfinyl group isolated from the marine algal-derived endophytic fungus P. chrysogenum LD-201810 ( Ge et al, 2021 ) and the seawater-derived fungus A. flavipes 297 ( Chen et al, 2021 ), respectively. 52 isolated from a marine red alga-epiphytic isolate of T. asperellum Y6−2, represented a rare example of nor-sesquiterpenes with a spiro system ( Shi et al, 2019 ).…”

Section: Discussionmentioning

confidence: 99%

“…Through chemical epigenetic manipulation strategy, the gorgonian-derived fungus A. versicolor XS-20090066 was found to produce a new bisabolane aspergillusene E ( 39 ) with a benzofuran moiety, by the addition of histone deacetylase inhibitor, suberoylanilide hydroxamic acid, and DNA methyltransferase inhibitor, 5-azacytidine ( Wu et al, 2020 ). A pair of new S-containing norbisabolane enantiomers methylsulfinyl-1-hydroxyboivinianin A [(±)- 40 ] were produced by the marine algal-derived endophytic fungus P. chrysogenum LD-201810 ( Ge et al, 2021 ). 40 was proven to possess a rare methylsulfinyl substituent, and finally afforded individual enantiomers (+)- 40 and (−)- 40 by chiral HPLC.…”

Section: Chemical Diversity Of the Newly-discovered Marine-derived Bi...mentioning

confidence: 99%

“…These compounds incorporate an eight continuous carbons side chain, which cause high structural diversity to generate abundant functionalities including double bond, lactone, furan, pyran, and so on, by oxidation, reduction, esterification, and cyclization ( Niu et al, 2020 ; Chen et al, 2021 ). Moreover, some unique members, such as norbisabolanes ( Jian Li et al, 2015 ; Ge et al, 2021 ), dimers ( Sun et al, 2012 ; Georgantea et al, 2013 ), glycosides ( Lv et al, 2014 ), adducts ( Xiao-Dong Li et al, 2015 ), have also been characterized. Chemically speaking, the findings of these fascinating molecules provide considerable chemical foundation in the course of new drugs and agricultural chemicals discovery.…”

Section: Introductionmentioning

confidence: 99%

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Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Liu

Yang

et al. 2022

Front. Chem.

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Natural products, characterized by intriguing scaffold diversity and structural complexity, as well as significant agricultural and medicinal activities, have been a valuable source of agrochemicals/drugs development and have historically made a huge contribution to pharmacotherapy. Structurally, bisabolanes are a family of naturally occurring sesquiterpenoids that featured a hexatomic ring core incorporating with eight continuous carbons, which cause high structural variability along the alkyl side chain to form abundant functionalities. Moreover, apart from their interesting structures, bisabolanes have shown multitudinous bioactivities. Bisabolanes are distributed in a variety of marine invertebrates, terrestrial plant, and microbial sources. Interestingly, bisabolanes characterized from marine environment possess unique characteristics both structurally and biologically. A total of 296 newly-discovered bisabolanes were searched. Among them, 94 members were isolated from marine organisms. This review particularly focuses on the new bisabolanes characterized from marine organisms (covering from 2000 to 2021), including marine-derived fungi, algae, soft corals, and sponges, with emphasis on the diversity of their chemical structures as well as the novelty and differences between terrestrial and marine sources. Moreover, a wide range of bioactivities of marine-derived bisabolanes, including antimicrobial, anti-inflammatory, enzyme inhibitory, and cytotoxic properties, are presented herein, which is considered to be a promising resource for the discovery of new drug leads and agrochemicals.

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New Enantiomers of a Nor-Bisabolane Derivative and Two New Phthalides Produced by the Marine-Derived Fungus Penicillium chrysogenum LD-201810

Cited by 12 publications

References 20 publications

Polyketides isolated from an endophyte Penicillium oxalicum 2021CDF-3 inhibit pancreatic tumor growth

Polyketides isolated from an endophyte Penicillium oxalicum 2021CDF-3 inhibit pancreatic tumor growth

Cytotoxic secondary metabolites isolated from Penicillium sp. YT2019-3321, an endophytic fungus derived from Lonicera Japonica

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

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