Nine Constituents Including Six Xanthone-Related Compounds Isolated from Two Ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, Found in a Screening Study Focused on Immunomodulatory Activity

Fujimoto, Haruhiro; Asai, Takeshi; Kim, Yong-Pil; Ishibashi, Masami

doi:10.1248/cpb.54.550

Cited by 43 publications

(32 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…S3 and S4) and 13 C (Fig. S5 and S6) NMR data in CDCl 3 or acetone- d 6 were in good agreement with the published data (Fujimoto et al, 2006; Fujimoto et al, 1998). …”

Section: Methodssupporting

confidence: 90%

“…S3 – S6) identified the product as microperfuranone which has been isolated from Anixiella micropertusa and Emericella nidulans var. acristata (Fujimoto et al, 2006; Fujimoto et al, 1998; Kralj et al, 2006). The twelve other strains failed to produce new metabolites suggesting that co-overexpression of additional genes in their pathways might be necessary to elicit detectable and isolatable products.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Molecular genetic analysis reveals that a nonribosomal peptide synthetase-like (NRPS-like) gene in Aspergillus nidulans is responsible for microperfuranone biosynthesis

Yeh

Chiang

Entwistle

et al. 2012

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

Genome sequencing of Aspergillus species including A. nidulans has revealed that there are far more secondary metabolite biosynthetic gene clusters than secondary metabolites isolated from these organisms. This implies that these organisms can produce additional secondary metabolites have not yet been elucidated. The A. nidulans genome contains twelve nonribosomal peptide synthetase (NRPS), one hybrid polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS), and fourteen NRPS-like genes. The only NRPS-like gene in A. nidulans with a known product is tdiA which is involved in terrequinone A biosynthesis. To attempt to identify the products of these NRPS-like genes, we replaced the native promoters of the NRPS-like genes with the inducible alcohol dehydrogenase (alcA) promoter. Our results demonstrated that induction of the single NRPS-like gene AN3396.4 led to the enhanced production of microperfuranone. Furthermore, heterologous expression of AN3396.4 in A. niger confirmed that only one NRPS-like gene, AN3396.4, is necessary for the production of microperfuranone.

show abstract

“…S3 and S4) and 13 C (Fig. S5 and S6) NMR data in CDCl 3 or acetone- d 6 were in good agreement with the published data (Fujimoto et al, 2006; Fujimoto et al, 1998). …”

Section: Methodssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Molecular genetic analysis reveals that a nonribosomal peptide synthetase-like (NRPS-like) gene in Aspergillus nidulans is responsible for microperfuranone biosynthesis

Yeh

Chiang

Entwistle

et al. 2012

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

show abstract

“…Compounds ( 1 – 9 ) were tested for suppressive activity (IC 50 values) against the proliferation of mouse splenic lymphocytes stimulated with Con-A and LPS using a MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide) method according to the literature [20]. This method is based on the formation ratio of 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT)-formazan from exogenous MTT in lymphocytes.…”

Section: Methodsmentioning

confidence: 99%

Polyketides with Immunosuppressive Activities from Mangrove Endophytic Fungus Penicillium sp. ZJ-SY2

et al. 2016

View full text Add to dashboard Cite

Nine polyketides, including two new benzophenone derivatives, peniphenone (1) and methyl peniphenone (2), along with seven known xanthones (3-9) were obtained from mangrove endophytic fungus Penicillium sp. ZJ-SY 2 isolated from the leaves of Sonneratia apetala. Their structures were elucidated on the basis of MS, 1D, and 2D NMR data. Compounds 1, 3, 5, and 7 showed potent immunosuppressive activity with IC 50 values ranging from 5.9 to 9.3 µg/mL.

show abstract

“…3 E. variecolor makes simple cytotoxic quinones, 4 indole alkaloids with radical scavenging activity, 5 neuritogenic and antimicrobial polyketides, 6 sesterterpenes, 7 as well as cytotoxic and antimicrobial xanthones. 8,9 E. quadrilineata has yielded some immunostimulant xanthones 10 and tremorgenic alkaloids, while E. aurantiobrunnea some variecolin analogues which compete with macrophage inflammatory protein (MIP)-1α for binding to human CCR5 in a scintillation proximity assay. 11 E. falconensis and E. fruticulosa produce polyketides that inhibit growth of HL60 human leukemia cells and possess antioxidant properties.…”

Section: Introductionmentioning

confidence: 99%

Calmodulin inhibitors from the fungus Emericella sp.

Figueroa

González

Rodríguez‐Sotres

et al. 2009

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

Two new xanthones identified as 15-chlorotajixanthone hydrate (1) and 14-methoxytajixanthone (2) were isolated from an Emericella sp. strain 25379 along with shamixanthone (3) and tajixanthone hydrate (4). The stereostructures of 1 and 2 were elucidated by spectroscopic and molecular modeling methods. The absolute configuration at the stereogenic centers of 1 was established according to CD measurements. In the case of 2, however, the absolute configuration at C-20 and C-25 was designated as S and R, respectively, by Mosher ester methodology. Thereafter, the configuration at C-14 and C-15 of 2 was established as S and S, respectively by comparing the optical rotation and (1)H-(1)H coupling constant experimental values with those obtained through molecular modeling calculations at DFT B3LYP/DGDZVP level of theory for diasteroisomers 2a-2d. The activation of the calmodulin-sensitive cAMP phosphodiesterase (PDE1) was inhibited in the presence of 1-4 in a concentration-dependent manner. The effect of compounds 2 (IC(50)=5.54 microM) and 4 (IC(50)=5.62 microM) was comparable with that of chlorpromazine (CPZ; IC(50)=7.26 microM), a well known CaM inhibitor used as a positive control. The inhibition mechanism of both compounds was competitive with respect to CaM according to a kinetic study. A docking analysis with 2 and 4 using the AutoDock 4.0 program revealed that they interacted with CaM in the same pocket as trifluoropiperazine (TFP).

show abstract

Nine Constituents Including Six Xanthone-Related Compounds Isolated from Two Ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, Found in a Screening Study Focused on Immunomodulatory Activity

Cited by 43 publications

References 10 publications

Molecular genetic analysis reveals that a nonribosomal peptide synthetase-like (NRPS-like) gene in Aspergillus nidulans is responsible for microperfuranone biosynthesis

Molecular genetic analysis reveals that a nonribosomal peptide synthetase-like (NRPS-like) gene in Aspergillus nidulans is responsible for microperfuranone biosynthesis

Polyketides with Immunosuppressive Activities from Mangrove Endophytic Fungus Penicillium sp. ZJ-SY2

Calmodulin inhibitors from the fungus Emericella sp.

Contact Info

Product

Resources

About