Hirsutane Sesquiterpenes from the Fungus Lentinus connatus BCC 8996

Rukachaisirikul, Vatcharin; Tansakul, Chittreeya; Saithong, Saowanit; Pakawatchai, Chaveng; Isaka, Masahiko; Suvannakad, Rapheephat

doi:10.1021/np0502286

Cited by 46 publications

(37 citation statements)

References 6 publications

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“…Hypnophilin (4) (Kis et al 1970), while panepoxydone was isolated with hypnophilin from cultures of the L. connatus (Rukachaisirikul et al 2005) and L. crinitus (Erkel et al 1996).…”

Section: Discussionmentioning

confidence: 99%

“…Hypnophilin (4) was previously isolated from the culture of Pleurotellus hypnophilus (Gianetti et al 1986), Lentinus critinus (Abate & Abraham 1994) and L. connatus (Rukachaisirikul et al 2005). Dihydrohypnophilin (3) was isolated from a culture of L. crinitus (Abate & Abraham 1994) and L. conatus (Rukachaisirikul et al 2005).…”

Section: Discussionmentioning

confidence: 99%

“…Dihydrohypnophilin (3) was isolated from a culture of L. crinitus (Abate & Abraham 1994) and L. conatus (Rukachaisirikul et al 2005). Panepoxydone and neopanepoxydol were obtained from fermentations of Panus rudis and Panus conchatus (Kis et al 1970), while panepoxydone was isolated with hypnophilin from cultures of the L. connatus (Rukachaisirikul et al 2005) and L. crinitus (Erkel et al 1996).…”

Section: Discussionmentioning

confidence: 99%

“…Most of its 40 species grow in the tropics, although some can be found in the boreal region (Pegler 1983). Previous investigations on the chemical composition of Lentinus species identified several sesquiterpenes from L. lepideus (Hanssen 1982(Hanssen , 1985 and L. connatus (Rukachaisirikul et al 2005) and benzoquinones from L. degener (Anchel et al 1948) and L. adhaerens (Lauer et al 1991). However, to the best of our knowledge, no investigations studying TR inhibitors were performed with any species from this genus, and this is the first study on the species L. strigosus.…”

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confidence: 89%

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A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation

Cota

Rosa

Fagundes

et al. 2008

Mem. Inst. Oswaldo Cruz

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The fungus Lentinus strigosus (Pegler 1983) (Polyporaceae, basidiomycete) was selected in a screen for inhibitory activity on Trypanosoma cruzi trypanothione reductase (TR). The crude extract of L. strigosus was able to completely inhibit TR at 20 µg/ml. Two triquinane sesquiterpenoids (dihydrohypnophilin and hypnophilin), in addition to two panepoxydol derivatives (neopanepoxydol and panepoxydone), were isolated using a bioassay-guided fractionation protocol. Hypnophilin and panepoxydone displayed IC 50 values of 0.8 and 38.9 µM in the TR assay, respectively, while the other two compounds were inactive. The activity of hypnophilin was confirmed in a secondary assay with the intracellular amastigote forms of T. cruzi, in which it presented an IC 50 value of 2.5 µM. Quantitative flow cytometry experiments demonstrated that hypnophilin at 4 µM also reduced the proliferation of human peripheral blood monocluear cells (PBMC) stimulated with phytohemaglutinin, without any apparent interference on the viability of lymphocytes and monocytes. As the host immune response plays a pivotal role in the adverse events triggered by antigen release during treatment with trypanocidal drugs, the ability of hypnophilin to kill the intracellular forms of T. cruzi while modulating human PBMC proliferation suggests that this terpenoid may be a promising prototype for the development of new chemotherapeutical agents for Chagas disease. Key words: fungal natural products -Chagas disease -drug discovery -immunomodulators -BasidiomycotaChagas disease is caused by the protozoan parasite Trypanosoma cruzi and affects millions of people in Latin America, having an enormous economic and social impact in the endemic areas. These patients rely on treatment with nitrofuran (nifurtimox; Bayer) or nitroimidazol (benznidazole; Roche), medicines that display little or no activity in chronic infections, in spite of their beneficial effect during the acute phase of the disease (Cançado 2002, Coura & Castro 2002. However, significant differences in the therapeutic effectiveness are observed between these two drugs, especially when considering distinct geographical areas, which is probably due to the occurrence of naturally resistant and susceptible T. cruzi strains (Filardi & Brener 1987, Toledo et al. 2003. Furthermore, both drugs cause several side effects that contribute to their reduced use in clinical medicine (Cançado 1985). Thus, new compounds are needed to develop more effective medicines to treat Chagas disease, espe- cially in its chronic phase, is needed (Schmidt & KrauthSiegel 2002, Nwaka & Ridley 2003. However, due to low profit prospects, the development of new trypanocidal drugs is not attractive to the pharmaceutical industry (Nwaka & Ridley 2003). Thus, this endeavor is being conducted mainly in academic laboratories (Fairlamb 1999).Among the many different strategies for drug discovery, screening the local biodiversity for bioactive natural products using appropriate bioassays is an interesting alternative for researchers in affec...

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“…Hypnophilin (4) (Kis et al 1970), while panepoxydone was isolated with hypnophilin from cultures of the L. connatus (Rukachaisirikul et al 2005) and L. crinitus (Erkel et al 1996).…”

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 89%

See 2 more Smart Citations

A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation

Cota

Rosa

Fagundes

et al. 2008

Mem. Inst. Oswaldo Cruz

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“…As exemplified by phellodonic acid from Phellodon melaleucus, many of them possess antibacterial and antifungal activites. 6 Moreover, the chondrosterins and hirsutanols showed cytotoxicity, 7 connatusins and dihydrohypnophilin showed antimalarial and cytotoxic activities, 8 whereas coriolin C, xeromphalinones and pleurocybellone also have cytotoxic activities. 3 Several triquinane sesquiterpenes with modifications of the hirsutane scaffold were reported.…”

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confidence: 99%

Lentinulactam, a hirsutane sesquiterpene with an unprecedented lactam modification

Helaly

Richter

Thongbai

et al. 2016

Tetrahedron Letters

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Diversity‐Oriented Synthesis of Oxacyclic Spirooxindole Derivatives through Ring‐Closing Enyne Metathesis and Intramolecular Pauson–Khand (2+2+1) Cyclization of Oxindole Enynes

Kandimalla

Sabitha

2017

Adv Synth Catal

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An efficient approach for a reagent‐based diversity‐oriented synthesis (DOS) of novel fused spirooxindole scaffolds from oxindole enynes has been developed. The reaction involves a metal‐catalyzed C‐3 allylation/vinylation/homoallylation of N‐substituted isatins which gives rise to the corresponding alcohols that can be converted into the required enynes. Further transformation to diverse complex molecular scaffolds proceeds via a subsequent ruthenium‐catalyzed ring‐closing enyne metathesis (RCEYM), or cobalt‐catalyzed intramolecular Pauson–Khand (2+2+1) cyclization reaction (IPKR). This strategy provides a facile approach to various spirooxindole‐vinyldihydropyrans/tetrahydrooxepines and spirocyclic fused cyclopentenones in good to excellent yields.magnified image

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Hirsutane Sesquiterpenes from the Fungus Lentinus connatus BCC 8996

Cited by 46 publications

References 6 publications

A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation

A potent trypanocidal component from the fungus Lentinus strigosus inhibits trypanothione reductase and modulates PBMC proliferation

Lentinulactam, a hirsutane sesquiterpene with an unprecedented lactam modification

Diversity‐Oriented Synthesis of Oxacyclic Spirooxindole Derivatives through Ring‐Closing Enyne Metathesis and Intramolecular Pauson–Khand (2+2+1) Cyclization of Oxindole Enynes

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