The Chemistry and Antibiotic Activity of the Toadstool Agaricus xanthoderma (Agaricales)

Abstract

continues the trend for lead chemistry observed by Huttner et al. for the germanium and tin complexes [(F~-E)(W(CO),),] (W=Ge 250.2, W=Sn 270.2 pmf2"I).Of the possible conformers discussed earlier,[3d' only the anticlinal form is found for the lead complex 2 in the crystal ; the antiperiplanar conformation (trans orientation of the C5Hi ligands) is not observed (Fig. 2).Lead is the heaviest main-group element to be combined with transition metals so far.

Natural Products Containing a Nitrogen–Nitrogen Bond

“…73 The arylhydrazide xanthodermine (75) was isolated in 1985 from extracts of the mushroom Agaricus xanthodermia, alongside leucoagaricone (114) and agaricone (132). 74 Xanthodermine (75) was later reported to inhibit growth in melanoma cancer cells. 75 Roullier and co-workers isolated the novel arylhydrazide 76 in 2009 from Lichina pygmaea, a cyanobacterial lichen collected on the west coast of France.…”

“…105 Leucoagaricone (114) was isolated from Agaricus xanthoderma in 1985, alongside xanthodermine (75) and agaricone (132). 74 In 1991, hydrazone NG-061 (115) was isolated from a fermentation broth of Penicillium minioluteum F-4627 collected in Japan, during a search for naturally occurring nerve growth factor mimics and potentiators. 106 NG-061 induced neurite outgrowth in PC12 cells at low concentrations (1−10 μg/mL), thus establishing the hydrazone as an effective nerve growth potentiator.…”

“…Azines. Agaricone (132) was isolated in 1985 from the mushroom Agaricus xanthoderma, 74 alongside leucoagaricone (114) and xanthodermine (75). Agaricone (132) is formed through oxidation of the hydrazone leucoagaricone (114), which occurs rapidly upon external stress to the mushroom.…”

Combining Both Acceptorless Dehydrogenation and Borrowing Hydrogen Mechanisms in One System as Described by DFT Calculations

“…Several natural products [ 4 ] include N‐substituted hydrazones such as NG‐061, [ 5 ] Leucoagaricone, [ 6 ] or Schaefferal A/B, [ 7 ] and applications range from serving as chromogens and enhancers of the growth of nerves to building blocks for anticancer drugs, or antifungal, antimicrobial, anti‐inflammatory treatments. [ 8 ] The usual way [ 9 ] to obtain N‐substituted hydrazones is the combination of N‐substituted hydrazines with aldehydes/ketones whereas the hydrogenation/reduction of azines in heterogeneous systems is a less selective alternative treatment.…”

“…[2] This reaction is catalyzed by a manganese pincerbased catalyst of type Mn(I)-PNN (see Scheme 1) under mild DOI: 10.1002/adts.202100566 reaction conditions and the reaction pathway was hypothesized as the combination of acceptorless dehydrogenative coupling (ADC) of alcohols and a borrowing hydrogen process (see Scheme 2). [3] Several natural products [4] include Nsubstituted hydrazones such as NG-061, [5] Leucoagaricone, [6] or Schaefferal A/B, [7] and applications range from serving as chromogens and enhancers of the growth of nerves to building blocks for anticancer drugs, or antifungal, antimicrobial, anti-inflammatory treatments. [8] The usual way [9] to obtain N-substituted hydrazones is the combination of N-substituted hydrazines with aldehydes/ketones whereas the hydrogenation/reduction of azines in heterogeneous systems is a less selective alternative treatment.…”