Medicinal Mushrooms

Bovista lilacina Mont. & Berk.
Globaria lilacina (Mont. & Berk.) Speg.
Lycoperdon lilacinum (Mont. & Berk.) Speg.

"Peridium up to 15 cm. diam., subglobose or pyriform, tapering abruptly into a large, well-developed, strongly crenulate rooting base; exoperidium smooth or more frequently floccose, often areolate, cream to bay brown, thin, fragile, fugacious; endoperidium brown, thin, fragile, breaking away irregularly from the apical portion; sterile base well developed, persistent, cellular at the periphery, hemicompact within, separated from the gleba by a prominent diaphragm.

Gleba some shade of purple, sometimes with a greyish tinge, at first compact, soon pulverulent; capillitium threads long, branched, septate, equal, pallid olivaceous.
Spores: globose, 5.5–7.5 mm. diam., occasionally apiculate; epispore strongly verrucose, violaceous.
Habitat: Solitary on the ground, usually in sandy areas.

Characterized by the prominent sterile base, conspicuous diaphragm, and especially by the strongly verrucose, violaceous spores. The peridium and gleba are fragile, consequently the sterile base is often the only portion of the plant collected; nevertheless even this can be determined readily owing to its structure. It is liable to confusion only with that of C. caelata, but may be separated by its peculiar, partly compact, partly cellular structure.

The peridium is usually stated to be smooth externally, but this is by no means a constant feature; on the contrary, collections frequently show the exterior to be floccose and even areolate."
(Cunningham, 1925)

The structure of an antibacterial and antifungal compound isolated from the culture broth of Calvatia lilacina has been described on the basis of chemical and spectroscopic studies as p-carboxyphenylazoxycyanide (calvatic acid) (Gasco et al., 1974). The antimicrobial activity spectra of this compound was reported by Umezawa et al., (1975), who isolated the compound from a closely related species, Calvatia craniformis. Calvatic acid (see structure below) inhibited the growth of Gram-positive bacteria (3.12-6.25 µg/ml) and some Gram-negative bacteria, while showing no activity against yeasts and fungi at 100 µg/ml.

The antibacterial calvatic acid.

The exact stereoisomerism and position of the oxygen atom in the azoxycyano group were later confirmed by X-ray cystallography (Viterbo et al., 1975). A research group led by Gasco developed a synthetic route for making calvatic acid and also studied both the antimicrobial and antimitotic activities of several chemical analogues of this compound (Calvino et al., 1986).

The Umezawa et al. study (1975) reported that calvatic acid has antitumor activity: it inhibited the growth of Yoshida sarcoma in cell culture (IC₅₀=1.56 µg/ml), and also showed growth inhibition of mouse leukemia 1210.

This site describes a patent for large-scale production of calvatic acid.

Calvino R, Fruttero R, Gasco A.
Chemical and biological studies on calvatic acid and its analogues.
J. Antibiot. 1986 39(6):864-8.
Pubmed

Cunningham GH.
Lycoperdaceae of New Zealand.
Trans Proc Roy Soc New Zealand. 1925 57:190-217

Gasco A, Serafino A, Mortarin V, Menziani E, Bianco MA, Scurti JC.
An antibacterial and antifungal compound from Calvatia lilacina.
Tetra Lett. 1974 (38):3431-2.

Umezawa, H, Takeuchi, T, Iinuma, H, Ishizuka, M, Kurakata, Y, Umeda, Y, Nakanishi, Y, Nakamura, T, Obayashi, A, Tanabe, O.
A new antibiotic, calvatic acid.
J. Antibiot. 1975 38(1):87-90.
Pubmed

Viterbo, D, Gasco, A, Serafino, A, Mortarini, V.
p-Carboxyphenylazoxycyanide-dimethyl sulfoxide - antibacterial and antifungal compound from Calvatia lilacina.
Acta Crys Sec B-Struct Sci. 1975 31:2151-3.

Last modified: 21-Apr-2008

  Source: Wikipedia

  Credit: © Br. Alfred Brousseau, Saint Mary's College. (from Calphotos)

Source: Italian Wikipedia

Agaricus meleagris var. grisea (A. Pearson) Wasser
Agaricus pseudocretaceus Bon
Agaricus xanthodermus var. griseus (A. Pearson) Bon & Cappelli
Agaricus xanthodermus var. lepiotoides Maire
Agaricus xanthodermus Genev.
Pratella xanthoderma (Genev.) Gillet
Psalliota flavescens Richon & Roze
Psalliota xanthoderma (Genev.) Richon & Roze
Psalliota xanthoderma var. grisea A. Pearson
Psalliota xanthoderma var. lepiotoides (Maire) Rea

Yellow stainer
Agaric jaunissant, Psalliote jaunissante (French)
Prataiolo - Falso prataiolo (Italian)
Karbolchampignon (German)
Pieczarka karbolowa (Polish)

Agaricus xanthodermus looks similar to the field mushroom (Agaricus campestris), but when the surface of the cap or stem is scraped it stains a distinct yellow colour. With time, the yellow stain fades to dull brown. Also, it has an 'inky' (phenolic) smell that is stronger at the base of the stem. Upon cooking the odor becomes more pronounced. Treatment of this mushroom with potassium hydroxide (KOH) turns the flesh orange-yellow.

Toxicity  

Agaricus xanthodermus is one of the most commonly ingested poisonous mushrooms (Hender et al., 2000). If eaten, symptoms may include abdominal cramps, nausea, vomiting and diarrhea. Less common symptoms include headache, dizziness, sweating and drowsiness. It should be noted that some people haven eaten this species without apparent ill effects.

Also, A. xanthodermus contains a molecule, 4,4'-dihydroxy-azobenzene, that in high doses, is carcinogenic to mice. At lower concentrations, however, the azo compound does not have tumor-inducing effects (Toth et al., 1989).

Although other edible Agaricus species, such as A. augustus, A. arvensis and A. silvicola, turn yellow to a greater or lesser extent, they do not display such an intense reaction as A. xanthodermus. This species is commonly found in grass under trees or in parks, but seldom in deep forest (Kerrigan et al., 2005). It is found in North America, Europe, and Africa.

Bioactive compounds

A number of chemicals have been extracted from Agaricus xanthodermus, including:

  4,4'-dihydroxy-azobenzene
   p-quinol
  4,4'-dihydroxybiphenyl
  phenol

The concentration of phenol in the fruitbodies was found to be high enough to account for the toxicity of the mushrooms (Gill and Stauch, 1984).

Elemental composition
 
The levels of calcium, magnesium, iron, manganese, lead, chromium and cadmium in Agaricus xanthodermus was determined in a South African study. Agaricus xanthodermus had Ca (204), Mg (660), Fe (306), Mn (30), Cr (16.2), Pb (50.6) and Cd (29.5) mg/kg by dry weight (Jonnalagadda et al., 2006). The relatively high Cadmium concentration corroborates a previous study that reported high Cadmium in this species (Yesil et al., 2004)

Psalliotin, the antibiotic found in A. xanthoderma, is light sensitive (Atkinson, 1954). It was later shown that work-up of the methanolic extract in the presence of sodium sulfite yielded the compound agaricin, which has strong antibiotic and cancerostatic properties (K. Dornberger, W. Gutsche, R. Horschak, A. Zureck, Z. Ally. Mikrubiol. 18 (1978) 647; K. Dornberger, H. Lich, C. Schonfeld, H. Knoll, DDRPat. 132878 (15. Nov. 1978); Chem. Abstr. 91 (1979) P 87622e.). The structures of compounds responsible for the antibiotic activity and the yellow discoloration of the fungus were later determined (Hilbig et al., 1985):

1-agaricone

California fungi
Mushroom Expert
Wikipedia
Bioimages (several pictures)

Atkinson N.
Antibacterial activity in members of the higher fungi .1. Cortinarius rotundisporus and Psalliota xanthoderma Genev.
Aust J Exp Biol Med Sci. 1946 24(3):169-73.

Atkinson N.
Psalliotin, the antibiotic of Psalliota xanthoderma.
Nature. 1954 174(4430):598.
Pubmed

Atkinson N.
Antibacterial activity in members of the higher fungi. II. Psalliotin, the antibiotic of Psalliota xanthoderma.
Aust J Exp Biol Med Sci. 1955 33(2):237-42.
Pubmed

Callac P, Guinberteau, J.
Morphological and molecular characterization of two novel species of Agaricus section Xanthodermatei.
Mycologia. 2005 97(2):416-24.
Pubmed

Dornberger K, Ihn W, Schade W, Tresselt D, Zureck A, Radics L.
Antibiotics from Basidiomycetes - evidence for the occurrence of the 4-hydroxybenzenediazonium ion in the extracts of Agaricus xanthodermus Genevier (Agaricales).
Tetra Lett. 1986 27(5):559-60.

Dornberger K, Ihn W, Schade W, Tresselt D, Zureck A, Radics L.
Antibiotics from basidiomycetes - 4-hydroxybenzenediazonium ion, an antibiotically active metabolite of the basidiomycete Agaricus xanthodermus-Genevier.
Pharmazie. 1987 42(3):212-.

Gill M, Strauch RJ.
Constituents of Agaricus xanthodermus Genevier: the first naturally endogenous azo compound and toxic phenolic metabolites.
Z Naturforsch [C]. 1984 39(11-12):1027-9.
Pubmed

Hender E, May T, Beulke S.
Poisoning due to eating fungi in Victoria.
Aust Fam Physician. 2000 29(10):1000-4.
Pubmed

Hilbig S, Andries T, Steglich W, Anke T.
Antibiotics from Basidiomycetes .22. the chemistry and antibiotic-activity of the toadstool Agaricus xanthoderma (Agaricales).
Angewandte Chemie. 1985 24(12):1063-5.

Hocking CS.
The purification of antibiotic extracts of Psalliota xanthoderma.
Aust J Exp Biol Med Sci. 1950 28(5):585-88.
Pubmed

Jonnalagadda SB, Pienaar DH, Haripersad K.
Elemental distribution in selected Agaricus and Rhizina mushrooms in South Africa.
J Environ Sci Health A Tox Hazard Subst Environ Eng. 2006 41(3):507-14.
Pubmed

Kerrigan RW, Callac P, Guinberteau J, Challen MP, Parra LA.
 Agaricus section Xanthodermatei: a phylogenetic reconstruction with commentary on taxa.
 Mycologia. 2005 97(6):1292-315.
 Pubmed

Mitchell AD, Walter M.
Species of Agaricus occurring in New Zealand.
New Zeal J Bot. 1999 37(4):715-25.

Pope KG.
The toxicity of potassium chloride and of extracts of Psalliota xanthoderma for mice and rabbits.
Aust J Exp Biol Med Sci. 1950 28(3):361-6.
Pubmed

Toth B, Patil K, Taylor J, Stessman C, Gannett P.
Cancer induction in mice by 4-hydroxybenzenediazonium sulfate of the Agaricus xanthodermus mushroom.
In Vivo. 1989 3(5):301-5.
Pubmed

Wood, WF, Watson, RL, Largent, DL.
Phenol, the odour compound from Agaricus praeclaresquamosus.
Biochem System Ecol. 1998 26(7):793-4.

Yesil OF, Yildiz A, Yavuz O.
Level of heavy metals in some edible and poisonous macrofungi from Batman of South East Anatolia, Turkey.
J Environ Biol. 2004 25(3):263-8.
Pubmed

Last updated: 20-Apr-2008

Synonyms

Bjerkandera chionea (Fr.) P. Karst.
Boletus candidus Pers.
Leptoporus albellus (Peck) Bourdot & L. Maire
Leptoporus albellus subsp. chioneus (Fr.) Bourdot & Galzin
Leptoporus chioneus (Fr.) Quél.
Leptoporus lacteus f. albellus (Peck) Pilát
Polyporus albellus Peck
Polyporus chioneus Fr.
Polystictus chioneus (Fr.) Gillot & Lucand
Tyromyces albellus (Peck) Bondartsev & Singer
Ungularia chionea (Fr.) Lázaro Ibiza

Cap: 2-7 x 1-12 x 0.5-3.0 cm, convex or plane, semicircular, surface white, finely tomentose to glabrous, drying yellowish or grayish.
Context: 2-15 mm thick, white, soft and watery when fresh, drying friable.
Tubes: 1.5-5 mm deep.
Pore surface: white to cream; pores 4-5 per mm, round to angular. 
Spores: 3-5 x 1-2 μm, allantoid.
Spore print: white.

This fragrant polypore grows on decaying hardwoods or sometimes on decaying conifers, and causes a lignifying decay of the sapwood. Fruiting bodies are usually found between July-November.

Medicinal properties
Antiviral effects

Cadinane sesquiterpenes are a group of molecules with the cadalane carbon skeleton (shown in the diagram) chemically named 4-isopropyl-1,6-dimethyldecahydronaphthalene.

A novel cadinane sesquiterpene (named 4β,14-dihydroxy-6a,7β H-1(10)-cadinene) was isolated from cultures of Tyromyces chioneus. This molecule was shown to have significant anti-HIV-1 activity with EC₅₀,=3.0 µg/mL (SI=25.4) (Liu et al., 2007).

Google preview of Arora's Mushroom's Demystified has a description of the white cheese polypore.

References

Arora, D. Mushrooms Demystified. 2^nd edition.  Ten Speed Press, Berkeley, California. 1986.

Gilbertson, R.L. and L. Ryvarden.  North American Polypores.  Fungiflora, Oslo. 1986-1988.

Lincoff, G. National Audubon Society Field Guide to North American Mushrooms. 9^th printing.  A.A. Knopf, New York.  1994.

Liu DZ, Wang F, Yang LM, Zheng YT, Liu JK.
A new cadinane sesquiterpene with significant anti-HIV-1 activity from the cultures of the basidiomycete Tyromyces chioneus.
J Antibiot. 2007 60(5):332-4.
Pubmed

Last modified: 31-Mar-2008

Synonyms

Agaricus eburneus Bull.
Gymnopus eburneus (Bull.) Gray
Hygrophorus cossus sensu auct.; fide Checklist of Basidiomycota of Great Britain and Ireland (2005)
Hygrophorus eburneus (Bull.) Fr.
Limacium eburneum (Bull.) P. Kumm.

White hygrophor
White waxy-cap
Ivory woodwax
Ivory wax(y)cap
Cowboy's handerchief
Goat-moth
Elfenbeinschneckling (German)

Cap: 3-7 cm broad, convex with an inrolled margin, expanding to nearly plane with a low umbo or the disc depressed with an upturned margin; surface smooth to silky, slimy-viscid, white, occasionally faintly yellow in age.
Flesh: white, soft, thick at the disc, thin elsewhere, unchanging; odor and taste mild.
Gills: subdecurrent to decurrent, subdistant, moderately broad, waxy, white, sometimes faintly yellow in age.
Stipe: 4-10 cm tall, 0.5-1.5 cm thick, equal to tapering towards the base, often bent, stuffed, becoming hollow at maturity; surface finely scaled at the apex, smooth below, white, viscid; veil absent.
Spores: 6.5-8 x 3.5-5 µm, smooth, elliptical.
Spore print: white.
Habitat: solitary to subgregarious in hardwood and conifer woods; fruiting in Sept.-Oct. Widespread in Europe and North America.

Eight unusual fatty acids with bactericidal and fungicidal activity have been isolated from Hygrophorus eburneus (Teichert et al., 2005). These fatty acids, which all contain a so-called γ-crotonate partial structure, are named as follows:

(2E,9E)-4-oxooctadeca-2,9,17-trienoic acid
(2E 11Z)-4-oxooctadeca-2,11,17-trienoic acid
(E)-4-oxohexadeca-2,15-dienoic acid
(E)-4-oxooctadeca-2,17-dienoic acid
(2E, 9E)-4-oxooetadeca-2,9-dienoic acid
(2E, 11Z)-4-oxooetadeca-2,1 I-dienoic acid
(E)-4-oxollexadec-2-enoic acid
(E)-4-oxooctadec-2-enoic acid

A recent study from Greece analyzed the metal contents of eight indigenous mushroom species, including H. eburneus. The metal concentrations, given as µg/g, dry weight basis, are summarized in the table below (mean ± standard deviation):

To help give these values more significance, the second row of the table gives the daily metal intakes by a normal 60 kg consumer, in mg/serving (assuming a serving size of 30 g, dry weight). The authors conclude that the intake of potentially toxic heavy metals (i.e. Pb, Cd and As) by consumption of 30 grams of H. eburneus (dry weight) poses no risk for the consumer. Furthermore, this mushroom can be used in a well-balanced diet due to the high contents of functional minerals (Ouzouni et al., 2007).

California fungi has links to several more pictures.

Ouzouni PK, Veltsistas, PG, Paleologos, EK,  Riganakos, KA.
Determination of metal content in wild edible mushroom species from regions of Greece.
J Food Comp Anal. 2007 20(6):480-6.

Teichert A, Lubken T, Schmidt J, Porzel A, Arnold N, Wessjohann L.
Unusual bioactive 4-oxo-2-alkenoic fatty acids from Hygrophorus eburneus.
Z. Naturfors B:Chem Sci. 2005 60(1):25-32.

Last modified: 31-Mar-2008

Cap: 2–8 cm across, irregularly funnel-shaped, flesh-colored to reddish-brown.
Stem: 30–70 x 8–15 mm, central or lateral, often rooting, reddish-brown darkening towards the base.
Flesh: pinkish, tough.
Taste: mild, smells of aniseed.
Gills: decurrent, pale flesh-colored.
Spore print: white.
Spores: subglobose, amyloid, 4.5–5 x 3.5–4 µm.
Habitat: grows on stumps of deciduous trees, often densely clustered.
Season: late summer to late autumn; uncommon.
Edibility: edible.
Distribution: America and Europe.

Flavor compounds

As might be deduced from its common name, L. cochleatus has an anise-like odor, a sweet smell similar to licorice. A couple of studies have investigated the identity of the compounds responsible for this fragrance. In one study, the fruiting bodies of L. cochleatus were investigated for volatile compounds using gas chromatography-mass spectrometry analysis. The compounds p-anisaldehyde, methyl p-anisate, methyl (Z)-p-methoxycinnamate and methyl (E)-p-methoxy-cinnamate were responsible for the aniseed smell of L. cochleatus (Rapior et al., 2002).

In another study, the major volatile constituents were identified in L. cochleatus grown on a liquid culture medium containing glucose, the amino acid asparagine and mineral salts. The main constituents of L. cochleatus distillate were trans-nerolidol, fokienol and 6-formyl-2,2-dimethyl chromene (Hanssen and Abraham, 1987).

Bioactive compounds

Three previously identified sesquiterpenoids of the lactarane and secolactarane type, deoxylactarorufin A, blennin A and blennin C, were obtained from cultures of Lentinellus cochleatus. These compounds are known to be potent inhibitors of leukotriene biosynthesis in rat basophilic leukemia (RBL-1) cells and human peripheral blood leukocytes. Additionally, the new metabolites (Z)-2-chloro-3-(4-methoxyphenyl)-2-propen-1-ol and lentinellone (a protoilludane derivative) were identified (Wunder et al., 1996).

Medicinal properties
Antibacterial/fungicidal/molluscicidal activity

Dichloromethane extracts of this fungus were shown to be antibacterial to Bacillus subtilis and Escherichia coli, fungicidal towards Candida albicans and Cladosporium cucumerinum, and molluscicidal towards Biomphalaria glabrata. The methanol extract was antibacterial towards both Bacillus subtilis and Escherichia coli (Keller et al., 2002).

The Italian Wikipedia, from which the image was taken, has an entry (in Italian, unfortunately).
See http://www.svims.ca/council/Lentin.htm for a trial field key to Lentinellus and Neolentinus in the Pacific Northwest.

Hanssen HP, Abraham WR.
Volatiles from liquid cultures of Lentinellus cochleatus (Basidiomycotina).
Z. Naturfors C:Biosci. 1986 41(11-12):959-62.

Hanssen HP, Abraham WR.
Odoriferous compounds from liquid cultures of Gloeophyllum odoratum and Lentinellus cochleatus (Basidiomycotina).
Flavor Fragrance J. 1987 2(4):171-4.

Keller C, Maillard, M Keller J, Hostettmann K.
Screening of European fungi for antibacterial, antifungal, larvicidal, molluscicidal, antioxidant and free-radical scavenging activities and subsequent isolation of bioactive compounds.
Pharm Biol. 2002 40(7):518-25.

Rapior S, Breheret S, Talou T, Pelissier Y, Bessiere JM.
The anise-like odor of Clitocybe odora, Lentinellus cochleatus and Agaricus essettei.
Mycologia. 2002 94(3):373-6.

Wunder A, Anke T, Klostermeyer D, Steglich W.
Lactarane type sesquiterpenoids as inhibitors of leukotriene biosynthesis and other, new metabolites from submerged cultures of Lentinellus cochleatus (Pers ex Fr) Karst.
Z. Naturfors C:Biosci. 1996 51(7-8):493-9.
Pubmed

Last modified: 31-Mar-2008