Erinacine Q, a New Erinacine from Hericium erinaceum , and its Biosynthetic Route to Erinacine C in the Basidiomycete

The United Graduate School of Agricultural Sciences, Iwate University, Tsuruoka, Yamagata, Japan.
Bioscience Biotechnology and Biochemistry (Impact Factor: 1.06). 04/2002; 66(3):571-5. DOI: 10.1271/bbb.66.571
Source: PubMed


Erinacines as cyathane-xylosides are known to have potent stimulating activity for nerve-growth-factor synthesis. Our search for new cyathane metabolites from a liquid culture of Hericium erinaceum YB4-6237 resulted in the isolation of a new erinacine named erinacine Q (1). NMR spectrometry and a chemical derivation from erinacine P (2) determined the compound to be a derivative in which the formyl group of erinacine P had been reduced to the hydroxymethyl group. To clarify the biosynthetic relationship between erinacine Q and the others, [1'-13C]erinacine Q ([1'-13C]-1) was chemically derived from [1'-13C]erinacine P ([1'-13C]-2) which had been prepared by feeding [1-13C]-D-glucose to the basidiomycete. The biotransformation of labeled erinacine Q into [1'-13C]erinacine C ([1'-13C]-5) via [1'-13C]erinacine P in this basidiomycete was demonstrated by NMR spectrometry.

21 Reads
  • Source
    • "In Asia they also call it " a Natures nutrient for neurons " , because it contains erinacines, which stimulate the biosynthesis of the nerve growth factor and catecholamines in the central nervous system (Kenmoku et al. 2002, Shimbo et al. 2005, Mori et al. 2008, Kawagishi et al. 2011). This species shows a good potential for treating Alzheimer's disease, dementia, multiple sclerosis and even physical damages of nerves (Kolotushkina et al. 2003, Mori et al. 2009). "
    [Show abstract] [Hide abstract]
    ABSTRACT: Abstract: Slovenia with its diverse environment is home to more than 2400 fungal species out of which especially many macromycetes have for millennia been used worldwide as natural remedies. These species of mushrooms were in the past picked from the nature, but today can be cultivated as fruiting bodies or fungal biomass on different substrates. They possess immunomodulating, antiviral, antibacterial and anticancer activities and can be used against allergies, dementia, Alzheimer disease and in many other diseases. They represent a vast potential as natural remedies with no or very little adverse effects and can be processed into food supplement or further developed into medicines. These mushrooms are a natural treasure, which enables us to be more self-sufficient if we cultivate them for medical and certain species for nutritional purposes as well.
  • Source
    • "Hericium erinaceum, a well-known traditional medicinal mushroom, has attracted much attention for its antitumor , nematicidal, and anti-microbial properties (Mizuno et al., 1992; Stadler et al., 1994). Composition analysis showed that H. erinaceum contains various bioactive constituents such as polysaccharides , lectins, proteins, lipids, hericenone, erinacol, erinacine, and terpenoids (Kawagishi et al., 1994; Kenmoku et al., 2002; Lee et al., 2000). Accumulating data suggest that the immunomodulating activity of H. erinaceum is responsible for its medicinal activity. "
    [Show abstract] [Hide abstract]
    ABSTRACT: Hericium erinaceum is a medicinal mushroom that has been traditionally used in Asian countries for the treatment of cancers and infectious diseases. Although the immunomodulating activity of H. erinaceum is considered to be responsible for its medicinal activity, its action mechanisms are poorly understood. In the present study, we investigated the capability of water-extracted H. erinaceum (WEHE) to induce the expression of intercellular adhesion molecule-1 (ICAM-1), which regulates the migration of immune cells. THP-1, a human monocytic cell-line, or human peripheral blood mononuclear cells (PBMC) were stimulated with WEHE (0-30 μg/mL) and subsequently analyzed using flow cytometry to examine the surface expression of ICAM-1 protein. Steady-state levels of ICAM-1 mRNA were estimated using real-time reverse transcription-polymerase chain reaction analysis. Electrophoretic mobility shift assay was conducted to examine transcription factors involved in ICAM-1 transcription. WEHE induced ICAM-1 expression at both protein and mRNA levels in THP-1 cells in a dose- and time-dependent fashion. A similar pattern of ICAM-1 induction was also observed in CD14(+) monocytes in human PBMC that were stimulated with WEHE. The ICAM-1 expression on THP-1 cells stimulated with WEHE was suppressed by specific inhibitors for extracellular signal-regulated kinases (ERK) and reactive oxygen species (ROS). Additionally, exposure of THP-1 cells to WEHE increased the DNA binding activities of NF-κB, AP-1, SP-1 and STAT-1 transcription factors, all of which are known to be required for ICAM-1 gene expression. These results suggest that WEHE induces ICAM-1 expression in human monocytes through ERK- and ROS-dependent signaling pathways, resulting in the subsequent activations of NF-κB, AP-1, SP-1, and STAT-1 transcription factors.
    Journal of ethnopharmacology 01/2011; 133(2):874-80. DOI:10.1016/j.jep.2010.11.027 · 3.00 Impact Factor
  • Source
    • "Hericium erinaceum, a traditional edible mushroom in Asia, is composed of numerous constituents such as polysaccharides, proteins, lectins, hericenone, erinacol, erinacine and terpenoids, in which some of their biological activities have been studied [13] [14]. This mushroom has been used in several Asian countries as an edible folk medicine to treat various human diseases, and thus it has attracted considerable attention to its various bioactive properties [14] [15] [16] [17] [18] [19]. Recently, H. erinaceum has been reported to have cytotoxic effect on cancer cell lines, nematicidal and antimicrobial activities [18] [20] [21]. "
    [Show abstract] [Hide abstract]
    ABSTRACT: Hericium erinaceum is a medicinal and edible mushroom with anti-microbial and anti-cancer activities. To evaluate the immunoregulatory functions of H. erinaceum, we prepared water extract from H. erinaceum (WEHE) and investigated its ability to activate macrophages and to induce nitric oxide (NO) production in macrophages. Rat peritoneal macrophages stimulated with 1 to 100 mug/ml of WEHE for 24, 48, or 72 h produced NO in a time- and dose-dependent manner. Reverse transcription-polymerase chain reaction demonstrated that WEHE augmented the steady-state level of inducible NO synthase (iNOS) mRNA in both the peritoneal macrophages and a murine macrophage cell-line, RAW 264.7. Electrophoretic mobility shift assay showed that WEHE increased DNA binding activity of the transcription factor NF-kappaB, which is responsible for iNOS gene expression. Furthermore, its trans-acting activity was confirmative as determined by in vitro transfection assay using a reporter gene construct, p(NF-kappaB)(3)-CAT, whose expression is solely regulated by the activity of NF-kappaB. Concomitantly with the activation of NF-kappaB, WEHE markedly decreased intracellular IkappaBalpha level as demonstrated by Western blot assay. These results suggested that WEHE induces iNOS gene expression followed by NO production in macrophages via enhancing the activation of transcription factor, NF-kappaB.
    International Immunopharmacology 09/2006; 6(8):1363-9. DOI:10.1016/j.intimp.2006.03.005 · 2.47 Impact Factor
Show more