Six Immunosuppressive Features from an Ascomycete, Zopfiella ion gicaudata, Found in a Screening Study Monitored by Immunomodulatory Activity

Fujimoto, Haruhiro; Nakamura, Etsuko; Okuyama, Emi; Ishibashi, Masami

doi:10.1248/cpb.52.1005

Cited by 84 publications

(46 citation statements)

References 23 publications

(22 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1). Then, in 2000 we reported the isolation and planar structures of TT-1 (1a) and 2 (2), two new immunosuppressive constituents from T. terrophilus. 6) Almost at the same time, Hayakawa et al reported the isolation of rasfonin, a new apoptosis inducer from an Ascomycete, Talaromyces sp.…”

mentioning

confidence: 99%

Eleven New 2-Pyrones from a Fungi Imperfecti, Trichurus terrophilus, Found in a Screening Study Guided by Immunomodulatory Activity

Fujimoto

Okamoto

Sone

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

In our screening program on immunomodulatory constituents from fungi, many immunosuppressive metabolites have already been isolated from various Ascomycetes belonging to Gelasinospora, Diplogelasinospora, Microascus, Emericella, Eupenicillium, Chaetomium, and Zopfiella. 2) The EtOAc extract of a Fungi Imperfecti, Trichurus terrophilus SWIFT & POVAH showed an appreciable suppressive effect on the proliferation (blastogenesis) of mouse splenic lymphocytes stimulated with mitogens, concanavalin A (Con A), and lipopolysaccharide (LPS). Solvent partitions followed by repeated chromatographic fractionations of the extract, guided by immunosuppressive activity, afforded eleven new compounds tentatively named TT-1-11 (1-11). This paper deals with the structures and immunosuppressive activities of these constituents.The EtOAc extract of T. terrophilus IFM4606 3) cultivated on sterilized moistened-rice medium suppressed the Con Ainduced proliferation of mouse splenic lymphocytes by 99.6% at 50 mg/ml. The EtOAc extract was partitioned between n-hexane and water into an n-hexane layer and an aqueous suspension. The aqueous suspension was further partitioned between EtOAc and water into an EtOAc layer and an aqueous layer [yields (%) of the n-hexane, EtOAc, and aqueous layers after evaporation of the solvents from the EtOAc extract: 73.2, 17.4, and 2.3, respectively]. The IC 50 values of the n-hexane, EtOAc, and aqueous layers against the Con A-induced proliferation were 9.7, 2.5, and Ͼ50 mg/ml, respectively. Repeated chromatographic fractionations monitored by the immunosuppressive activity of the EtOAc layer afforded four components tentatively named TT-1-4 (1-4) [yields (%) of 1, 2, 3, and 4 from the EtOAc extract: 0.26, 0.0078, 0.011, and 0.0089, respectively]. It was found out that the other strain of this fungus, T. terrophilus IMI462513) also produced 1 and its homologues in good yields. Repeated chromatographic fractionations of the EtOAc layer, which was obtained from the partition of the EtOAc extract of T. terrophilus IMI46251 in the same way as described for the partition of the EtOAc extract of T. terrophilus IFM4606, gave seven new constituents tentatively named TT-5-11 (5-11) in addition to 1-4 [yields (%) of 1, 2, 3, 4, 5, a mixture of 6 and 7 (6/7), 8, 9, 10, and 11 from the EtOAc extract: 1. C-NMR spectral data of 1 (see Table 1) including the two dimensional 1 H-1 H shift correlation (COSY), 1 H-detected heteronuclear correlation through multiple quantum coherence (HMQC), and 1 H-detected heteronuclear multiple-bond correlation (HMBC) NMR data suggested a planar structure for TT-1. On acetylation with acetic anhydride in pyridine, 1 gave diacetate (12). Comparison of the 1 H-and 13 C-NMR spectral data of 1 with those of 12 (Table 1) in reference to the acetylation shift rule, 4,5) confirmed the planar structure of TT-1 (1a) (see Fig. 1 (Table 1) with those of 1 revealed that the unsaturated CϭC bond at position 3 in 1 was saturated in 2, indicating that the planar structure of TT-2 was expressed as 2 (F...

show abstract

mentioning

confidence: 99%

Eleven New 2-Pyrones from a Fungi Imperfecti, Trichurus terrophilus, Found in a Screening Study Guided by Immunomodulatory Activity

Fujimoto

Okamoto

Sone

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…12,13 Esta é a primeira ocorrência desses esteroides em espécies de Penicillium. Os dados de RMN ¹H e ¹³C de 5 e 6 estão dispostos da Tabela 1.…”

Section: Resultsunclassified

Esteroides produzidos por Penicillium herquei, um fungo endofítico isolado dos frutos de Melia azedarach (Meliaceae)

Marinho¹,

Marinho²,

Filho³

2009

Quím. Nova

View full text Add to dashboard Cite

Recebido em 30/4/08; aceito em 18/3/09; publicado na web em 4/8/09 STEROIDS PRODUCED BY Penicillium herquei, AN ENDOPHYTIC FUNGUS ISOLATED FROM THE FRUITS OF Melia azedarach (MELIACEAE). Six compounds comprising the groups of steroids, the ergosterol, the ergosterol peroxide, the cerevisterol, the neociclocitrinols, the ergosta-4,6,8(14),22-tetraen-3-one, the 25-hydroxy-ergosta-4,6,8(14),22-tetraen-3-one, were isolated from Penicillium herquei fungus obtained from Melia azedarach. The structures were identified by spectral methods of RMN 1D and 2D and MS.Keywords: steroids, endophytic fungus, Penicillium. INTRODUÇÃOMicro-organismos endofíticos estão presentes nos tecidos internos das plantas onde esta associação pode ocorrer em nível celular. É estimado que cerca de 80% das plantas são hospedeiras de fungos. 1-3A natureza dessas interações tem despertado o interesse de químicos, bioquímicos e biólogos na tentativa de entender essas associações, que é um fascinante e amplo campo de pesquisa. A colonização das plantas por endofíticos pode ser mediada pelo seu metabolismo secundário. 4 Em geral esses compostos apresentam atividades antimicrobianas e inseticidas, e sua produção pode ser uma forma de proteção da planta hospedeira contra invasões. 1,4 Nosso grupo tem estudado a química de micro-organismos associados a plantas da família Meliaceae. Uma grande coleção de fungos tem sido isolada das folhas, frutos, raiz e caule de Melia azedarach. 5Algumas espécies de Penicillium isoladas dessa planta têm produzido metabólitos secundários interessantes pela sua química e atividade biológica.6 Este artigo descreve o estudo químico de P. herquei, cultivado em arroz, o isolamento e identificação de esteroides. RESULTADOSAs substâncias 1, 2 e 3 foram obtidas da fase diclorometânica do extrato metanólico da biomassa produzida por P. herquei cultivado em arroz (Uncle Ben's). Essas substâncias são sólidas cristalinas e seus dados de RMN e EM são perfeitamente coincidentes com os descritos na literatura para o ergosterol (1), peróxido de ergosterol (2) e cerevisterol (3).

show abstract

“…As substâncias 1, 2 e 3 foram identificadas por análise dos espectros de RMN 1D e 2D, EM e por comparação com a literatura e mostraram total similaridade para os policetídeos citreoroseina (1), emodina (2) e janthinona (3) [8][9][10].…”

Section: Identificação Dos Policetídeosunclassified

Policetídeos isolados de Penicillium herquei

Marinho

Filho

et al. 2011

Eclet. Quim.

View full text Add to dashboard Cite

POLICETÍDEOS ISOLADOS DE Penicillium herquei. Neste trabalho estamos portando o isolamento dos policetídeos citreoserina (1), emodina (2), janthinona (3), dihidrocitrinona (4) e citrinina H-1 (5). Os compostos foram isolados por procedimentos cromatográficos e identificados por métodos espectrais de RMN 1D e 2D e EM. Os compostos 1, 2 e 3 foram testados sobre promastigotas de Leishmania brasiliensis.

show abstract

Six Immunosuppressive Features from an Ascomycete, Zopfiella ion gicaudata, Found in a Screening Study Monitored by Immunomodulatory Activity

Cited by 84 publications

References 23 publications

Eleven New 2-Pyrones from a Fungi Imperfecti, Trichurus terrophilus, Found in a Screening Study Guided by Immunomodulatory Activity

Eleven New 2-Pyrones from a Fungi Imperfecti, Trichurus terrophilus, Found in a Screening Study Guided by Immunomodulatory Activity

Esteroides produzidos por Penicillium herquei, um fungo endofítico isolado dos frutos de Melia azedarach (Meliaceae)

Policetídeos isolados de Penicillium herquei

Contact Info

Product

Resources

About