Fusaspirols A-D, novel oxaspirol derivatives isolated from Fusarium solani B-18

Ariefta, Nanang Rudianto; Nikmawahda, Hasna Tazkia; Aboshi, Takako; Murayama, Tetsuya; Tawaraya, Keitaro; Koseki, Takuya; Katagi, Genta; Kakihara, Yoshito; Shiono, Yoshihito

doi:10.1016/j.tet.2019.01.052

Cited by 10 publications

(6 citation statements)

References 16 publications

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“…So far, several secondary metabolites with immunosuppressive activities have been found in endophytic fungi, such as subglutinol A and B, two well-known immunosuppressive agents produced by endophytic Fusarium subglutinans (Lee et al, 1995); peniphenone, conioxanthone A, pinselin and porine B from Penicillium sp. (Liu et al, 2016); rigidiusculamide (−)-oxysporidinone and (−)-4,6′-anhydrooxysporidinone isolated from F. tricinctum (Sun et al, 2018); Fusaspirol A isolated from F. solani (Ariefta et al, 2019); 16-O-deacetylhelvolic acid 21,16-lactone in Aspergillus fumigatus (Xu et al, 2020); diaporchromone A in Phomopsis Asparagi (Wei et al, 2021), as well as (−)-mycousunine enamine from M. nawae in our previously study (Wang et al, 2017). Therefore, endophytic fungi may also be an important source of new immunosuppressants.…”

Section: Discussionmentioning

confidence: 99%

A novel dibenzofuran from endophytic fungus Mycosphaerella nawae preferentially inhibits CD4+ T cell activation and proliferation

Wang

Gao

et al. 2022

Journal of Applied Microbiology

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Aim: To obtain promising immunosuppressants from endophytic fungus. Methods and Results:The endophytic fungus Mycosphaerella nawae (ZJLQ129) was isolated from the plant Smilax china L. and its secondary metabolites extracted and fractionated through column chromatography. The metabolites were further modified by a derivatization reaction with ammonium hydroxide. After isolation and derivatization, a new dibenzofuran named as (+)isomycousnine enamine (iME) was obtained. The structures of the derivatives were determined based on chemical evidences and extensive spectroscopic methods including 2D-NMR, DEPT and HRESI-MS spectra. The immune activities of iME were first evaluated on the proliferation and cytokines (IL-2 and IFN-γ) production of T and B cells by using MTT and ELISA methods respectively. Then, its effects on the proliferation of T-cell subsets (CD4 + and CD8 + T cells), as well as CD25 and CD69 expressions were also determined by flow cytometry. Finally, by using Cytometric Bead Array (CBA), the impacts of iME on the secretion of Th1/Th2/Th17 cytokines from purified CD4 + T cells were assayed. The results showed that iME not only selectively suppressed the immune responses of T cells, but also preferentially inhibited the activation and proliferation of CD4 + T cells. Conclusion: A novel dibenzofuran derived from endophytic fungus Mycosphaerella nawae preferentially inhibits CD4 + T-cell activation and proliferation. Significance and Impact of the Study: This work obtained iME, a new dibenzofuran derived from endophytic fungus. iME has the capacity to inhibit CD4 + T-cell activation and therefore is a novel potential immunosuppressant for development in the future.

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Section: Discussionmentioning

confidence: 99%

A novel dibenzofuran from endophytic fungus Mycosphaerella nawae preferentially inhibits CD4+ T cell activation and proliferation

Wang

Gao

et al. 2022

Journal of Applied Microbiology

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“…Four novel compounds with g-methylidene-spirobutanolide core, fusaspirols A–D 421 – 424 ( Figure 12 ), were isolated from the brown rice culture of Fusarium solani B-18. Compound 422 was found as the regioisomer of 421 [ 139 ]. One new polyacetylene glycoside 425 ( Figure 12 ), one new brasilane-type sesquiterpenoid glycoside 426 ( Figure 12 ), and two novel isobenzofuran-1(3H)-one derivatives 427 – 428 ( Figure 12 ) were isolated from the solid culture of the endolichenic fungus Hypoxylon fuscu [ 86 ].…”

Section: New Metabolites Isolated From Plant Endophytesmentioning

confidence: 99%

“…Compound 421 was tested for osteoclastic differentiation activity using murine macrophage derived RAW264.7 cells. 421 significantly increased the number of mature osteoclasts at the comparable levels to the positive control of kenpaullone, compared to the negative control (DMSO), suggesting that 421 activated a signaling pathway in osteoclastic differentiation [ 139 ].…”

Section: Biological Activitymentioning

confidence: 99%

“…Twelve new polyketides, penicichrysogenins A-L 135-146 (Figure 5), were isolated from the solid substrate fermentation cultures of a Huperzia serrata endophytic fungus Penicillium chrysogenum MT-12. The structures of 135-139 were established as (2R)-6-hydroxy-2,4-dimethoxy-5-methylphthalide ( 135), 4,6-dihydroxy-5-hydroxymethylphthalide9 ( 136), 4,6-dihydroxy-5-methoxymethylphthalide ( 137), (2R)-4,5dihydroxy-2,6-dimethoxy-2-pentylphthalide ( 138), (E)-4,5-dihydroxy-2-(4-hydroxypentylidene)-6-methoxyphthalide (139), respectively [45]. Three new polyketides, cylindrocarpones A-C 147-149 (Figure 5), were isolated from the endophytic fungus, Cylindrocarpon sp., obtained from the tropical plant Sapium ellipticum [46].…”

Section: Ketone Compounds 221 Polyketidesmentioning

confidence: 99%

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Biological Activities of Some New Secondary Metabolites Isolated from Endophytic Fungi: A Review Study

Zheng

Zhang

et al. 2021

IJMS

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Secondary metabolites isolated from plant endophytic fungi have been getting more and more attention. Some secondary metabolites exhibit high biological activities, hence, they have potential to be used for promising lead compounds in drug discovery. In this review, a total of 134 journal articles (from 2017 to 2019) were reviewed and the chemical structures of 449 new metabolites, including polyketides, terpenoids, steroids and so on, were summarized. Besides, various biological activities and structure-activity relationship of some compounds were aslo described.

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“…[69] Four new natural products fusaspirols AÀ D, with spirobutanolide core, were isolated from the culture of Fusarium solani B-18. [70] The structural elucidation was done by extensive spectroscopic studies as well as from chemical derivatization. These isolated compounds were also screened for activity in osteoclastic differentiation.…”

Section: (à )-Rubriflordilactone Bmentioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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Fusaspirols A-D, novel oxaspirol derivatives isolated from Fusarium solani B-18

Cited by 10 publications

References 16 publications

A novel dibenzofuran from endophytic fungus Mycosphaerella nawae preferentially inhibits CD4+ T cell activation and proliferation

A novel dibenzofuran from endophytic fungus Mycosphaerella nawae preferentially inhibits CD4+ T cell activation and proliferation

Biological Activities of Some New Secondary Metabolites Isolated from Endophytic Fungi: A Review Study

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

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