{"title":"Breviane Spiroditerpenoids with Anti-inflammatory and Antiviral Activities from Deep-Sea-Derived Fungus <i>Penicillium</i> sp. F59.","authors":"Yinghui Lv, Wenping Song, Zongze Shao, Tianlei Ying, Bihong Hong, Wenjing Tian, Siwen Niu","doi":"10.1021/acs.jnatprod.4c00997","DOIUrl":null,"url":null,"abstract":"<p><p>Twelve new breviane spiroditerpenoids, namely, chrysobreviones A-L (<b>1</b>-<b>12</b>), together with seven structurally related analogues (<b>13</b>-<b>19</b>) were isolated from the EtOAc extract of the fermented cultures of deep-sea-derived fungus <i>Penicillium</i> sp. F59. These structures including absolute configurations were resolved on the basis of extensive analysis of NMR spectroscopic data and HRESIMS, in association with experimental and calculated ECD data as well as the modified Mosher's method. Compound <b>1</b> represented the first breviane derivative containing an unusual octahydrodifuro[2,3-b:2',3'-d]furan moiety, while <b>7</b> and <b>9</b> were the first breviones featuring an epoxy ring and an 18-hydroxymethyl group, respectively. The anti-inflammatory and antiviral activities of compounds <b>1</b>-<b>19</b> were evaluated. Compounds <b>1</b>, <b>8</b>, <b>16</b>, and <b>17</b> showed inhibitory effects against NO secretion in LPS-activated Raw264.7 macrophage cells with IC<sub>50</sub> values ranging from 1.4 to 12.9 μM, while <b>1</b> and <b>7</b> exhibited antiviral effects against severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) omicron subvariant BA.2 pseudovirus with IC<sub>50</sub> values of 8.5 and 10.3 μM, respectively.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c00997","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Breviane Spiroditerpenoids with Anti-inflammatory and Antiviral Activities from Deep-Sea-Derived Fungus Penicillium sp. F59.
Twelve new breviane spiroditerpenoids, namely, chrysobreviones A-L (1-12), together with seven structurally related analogues (13-19) were isolated from the EtOAc extract of the fermented cultures of deep-sea-derived fungus Penicillium sp. F59. These structures including absolute configurations were resolved on the basis of extensive analysis of NMR spectroscopic data and HRESIMS, in association with experimental and calculated ECD data as well as the modified Mosher's method. Compound 1 represented the first breviane derivative containing an unusual octahydrodifuro[2,3-b:2',3'-d]furan moiety, while 7 and 9 were the first breviones featuring an epoxy ring and an 18-hydroxymethyl group, respectively. The anti-inflammatory and antiviral activities of compounds 1-19 were evaluated. Compounds 1, 8, 16, and 17 showed inhibitory effects against NO secretion in LPS-activated Raw264.7 macrophage cells with IC50 values ranging from 1.4 to 12.9 μM, while 1 and 7 exhibited antiviral effects against severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) omicron subvariant BA.2 pseudovirus with IC50 values of 8.5 and 10.3 μM, respectively.
期刊介绍：
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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