Clitocine, a new insecticidal nucleoside from the mushroom clitocybe inversa

Kubo, Isao; Kim, Mujo; Hood, William F.; Naoki, Hideo

doi:10.1016/s0040-4039(00)94251-5

Cited by 64 publications

(50 citation statements)

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confidence: 61%

“…[7] A portion of crude extract I was extracted successively with n-hexane, CHCl 3 ) and was nearly identical to previously reported IR spectra. [7,8] The UV/Vis spectrum was similar to that previously described [8] and was characterized by absorption maxima at l = 212 nm (e = 22962) and l = 332 nm (e = 8611) with a shoulder at l = 230 nm. The 1 H and 13 C NMR spectra indicated the presence of a ribose moiety and were identical to those reported earlier, [7,8] thus confirming the structure of clitocine (Figure 2).…”

supporting

confidence: 61%

“…[7,8] The UV/Vis spectrum was similar to that previously described [8] and was characterized by absorption maxima at l = 212 nm (e = 22962) and l = 332 nm (e = 8611) with a shoulder at l = 230 nm. The 1 H and 13 C NMR spectra indicated the presence of a ribose moiety and were identical to those reported earlier, [7,8] thus confirming the structure of clitocine (Figure 2). The anomeric purity of clitocine given by the b/a ratio was deter- ) for the a anomer, respectively.…”

mentioning

confidence: 68%

“…Clitocine isolates from this mushroom have already been shown to exhibit strong insecticidal activity against the pink bollworm Pectinophora gossypiella and cytotoxic activities against some cancer cell lines (L1210, WI-L2, and CCRF-CEM). [7,8] We report additional data on cell lines 3LL, DU145, K-562, MCF7, and U251. An epimerization of clitocine was also observed, and was dependent on the purification procedure, as discussed herein.…”

mentioning

confidence: 99%

“…In contrast, pure b anomer was isolated from extract I with DCC and C-18 column chromatography as previously described. [7] Clitocine anomerization was examined under various conditions: adsorption on SiO 2 with CH 2 Cl 2 /MeOH 80:20 or MeOH for 30 min or 24 h, or with H 2 O at 378C for 48 h. Dried b anomer appeared to be stable over a period of 48 h, whereas % 15 % converted into the a anomer in aqueous solution at 37 8C or with silica gel. An increase in formation of the a anomer to 30 % was also observed by treatment of mixture B (b/a 80:20) in aqueous conditions.…”

mentioning

confidence: 99%

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In Vivo Antitumor Activity of Clitocine, an Exocyclic Amino Nucleoside Isolated from Lepista inversa

et al. 2006

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A biologically guided fractionation from Lepista inversa (Scop.: Fr.) led to the isolation of clitocine, an exocyclic amino nucleoside. This compound and two mixtures of beta/alpha anomers (mixture A, 40:60 and mixture B, 80:20) were synthesized or isolated depending on the purification procedure. The beta anomer and clitocine mixtures A and B showed similar cytotoxic activities with IC50 values ranging from 20.5 to 42 nM in murine cancer cell lines (3LL and L1210) and from 185 to 578 nM in human cancer cell lines (DU145, K-562, MCF7, and U251). An in vivo study of mixture B was carried out on 3LL- and L1210-tumor-bearing mice. Clitocine solubilized in beta-hydroxypropylcyclodextrin and injected at concentrations of 0.5, 3, and 5 mg kg-1 did not significantly increase the survival rate and lifespan of 3LL-tumor-bearing mice. In contrast, clitocine showed antitumor activity on L1210-tumor-bearing mice with a significant increase in lifespan and a decrease in the development of ascites observed at 3 mg kg-1. The induction of apoptosis may be the basis of the antitumor activity of clitocine against L1210 as suggested by flow-cytometry analysis of cells treated in vitro.

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supporting

confidence: 61%

supporting

confidence: 61%

mentioning

confidence: 68%

mentioning

confidence: 99%

mentioning

confidence: 99%

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In Vivo Antitumor Activity of Clitocine, an Exocyclic Amino Nucleoside Isolated from Lepista inversa

et al. 2006

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Nucleosides and Nucleotides

Suhadolnik¹,

Reichenbach²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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The naturally occurring nucleoside and nucleotide antibiotics exist as either the C ‐ or N ‐glycosides. They include ezomycin A 1 (C 26 H 38 N 8 O 15 S), ezomycin B 1 (C 26 H 39 N 7 O 17 S), ezomycin C 1 (C 26 H 37 N 7 O 16 S), ezomycin A 2 (C 19 H 26 N 6 O 12 ), ezomycin B 2 (C 19 H 25 N 5 O 13 ), ezomycin C 2 (C 19 H 25 N 5 O 13 ), showdomycin (C 9 H 11 NO 6 ), isoshowdomycin (C 9 H 11 NO 6 ), maleimycin (C 7 H 7 NO 3 ), oxazinomycin (C 9 H 11 NO 7 ), pyrazomycin (pyrazofurin) (C 9 H 13 N 3 O 6 ), formycin (C 10 H 13 N 5 O 4 ), formycin B (C 10 H 12 N 4 O 5 ), oxoformycin B (C 10 H 12 N 4 O 6 ). These antibiotics contain a variety of purine and pyrimidine rings. The naturally occurring nucleoside/nucleotide antibiotics, which have been isolated from bacteria, fungi, blue‐green algae, and marine sponges, have proven to be useful biochemical probes in eucaryotic, procaryotic, viral, fungal, and plant systems. The purine nucleosides inhibit protein synthesis, RNA and DNA synthesis, and methyltransferases; they have antimycoplasmal, antiviral, hypotensive, antifungal, antimycobacterial, and antitumor activities and induce sporulation. The pyrimidine nucleosides inhibit protein synthesis, virus replication, RNA and DNA synthesis, and cAMP phosphodiesterase. The imidazole nucleosides inhibit nucleic acid synthesis. The diazepin nucleosides inhibit adenosine deaminase (ADA). The indole nucleosides inhibit bacteria, yeast, fungi, and viruses. The N ‐nucleotide antibiotics include agrocin 84 (C 21 H 34 N 6 O 16 P 2 ), thuringiensin (C 22 H 30 N 5 O 19 P), phosmidosine (C 16 H 24 N 7 O 8 P), fosfadecin (C 13 H 19 N 5 O 10 P 2 ), and fosfocytocin (C 12 H 20 N 4 O 13 P 2 ). Thuringiensin, produced by B. thuringiensis , is a β‐exotoxin that exerts its toxic action on insects and mammals through the inhibition of RNA polymerases. Phosmidosine inhibits pore formation of Botrytis cinerea and Aspergillus niger . Fosfadecin and fosfocytocin inhibit gram‐positive and gram‐negative bacteria.

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Products from Basidiomycetes

Erkel¹,

Anke²

1997

Biotechnology

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Clitocine, a new insecticidal nucleoside from the mushroom clitocybe inversa

Cited by 64 publications

References 5 publications

In Vivo Antitumor Activity of Clitocine, an Exocyclic Amino Nucleoside Isolated from Lepista inversa

In Vivo Antitumor Activity of Clitocine, an Exocyclic Amino Nucleoside Isolated from Lepista inversa

Nucleosides and Nucleotides

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