Medicinal Mushrooms

The club-footed clitocybe, Ampulloclitocybe clavipes (Pers.) Redhead.
  Credit: Douglas Smith
  Source: Mushroom Observer, Creative Commons

Classification

Kingdom Fungi
Phylum Basidiomycota
Class Basidiomycetes
Order Agaricales
Family Tricholomataceae
Genus Clitocybe

Synonyms

Agaricus clavipes Pers.
  Syn. meth. fung. (Göttingen) 2: 353 (1801)
Clavicybe clavipes (Pers.) Harmaja
  Karstenia 42(2): 42 (2002)
Clitocybe clavipes (Pers.) P. Kumm.
  Führ. Pilzk. (Zwickau): 124 (1871)

Club-footed clitocybe
Club foot
Clavate-stalked clitocybe
Clitocybe à pied en massue (French)
Hoteishimeji (Japanese)
Keulen-Trichterling (German)
Knotsvoettrechterzwam (Dutch)

Cap: 3-7 cm, applanate to slightly depressed, often slightly umbonate, grayish-brown to dark brown, lighter in color towards the margin, smooth to minutely subtomentose, somewhat greasy when moist, marginal zone somewhat decurved with an involute margin.
Gills: deeply decurrent, thin, crowded to subdistant, 3-6 mm broad, segmentiform, whitish, soon pale-cream to lemon-yellow, with entire, concolorous edge.
Stem: 3-6cm tall x 0.5-1.4 cm diameter, usually clavate towards base, but sometimes cylindrical to subclavate, stuffed, pale greyish cream, slightly to rather coarsely fibrillose-striate; context whitish, spongy in base of stem.
Smell: pleasant, sweet - similar to Iris flowers, even more so in dried specimens.
Taste: mild, indistinct.
Spore print: white.
Spores: sub-spherical to ellipsoid, smooth, hyaline, non-amyloid, with droplets, 6.0-9.5 x 4.0-5.0 µm.
Habitat: alone, in groups or gregariously under deciduous and coniferous trees (especially pine and spruce); common, widespread in the Northern hemisphere; summer-fall.
Edibility: some guide books say 'edible with caution'. However, this mushroom is toxic in combination with alcohol due to presence of Type 6 toxins, similar to disulfram (Cochran and Cochran, 1978). [see also Coprinus atramentaria for a similar reaction caused by coprine] Furthermore, a toxicity text of this species showed that the crude extract was fatally toxic to albino mice 4 hours after consumption (Natour et al., 1993).

Drawings of Ampulloclitocybe (formerly Agaricus) clavipes from Saunders et al., 1871, plate 31.

Fatty acid composition

(E)-8-oxo-9-octadecenoic acid (and the corresponding ethyl ester, not shown)

(E,E)-9-oxooctadeca-10,12-dienoic acid

Novel C18 fatty acid derivative with α,β,γ,δ-dienone moiety

Novel C16 fatty acid ethyl ester

Clavilactones A=1, B=4, C=5, benzoquinoid macrolidic fungal metabolites with antibacterial and antifungal activity.

Clavilactone D

Clavilactone E

Clavilactone D potently inhibited epidermal growth factor receptor (EGFR) (IC₅₀ = 5.5 µM) in a kinase assay (Merlini et al., 2000). The clavilactones represent a novel class of tyrosine kinase inhibitory activity and may hold promise as an anti-tumor therapy (Cassinelli et al., 2000).

Medicinal Properties
Antibacterial activity

Clavilactone B had antibacterial activity against Bacillus subtilis, B. cereus, Sarcina lutea (50 µg/disc); clavilactone A was only active against B. subtilis at 100 µg/disc (Arnone et al., 1994).

All clavilactones had antifungal activity, as determined using bioautography on Cladosporium cladosporioides and C. cucumerinum with amounts as low as 50 µg per plate (Arnone et al., 1994).

Antitumor activity

Polysaccharides extracted from the mycelial culture of A. clavipes and administered intraperitoneally into white mice at a dosage of 300 mg/kg inhibited the growth of Sarcoma 180 and Ehrlich solid cancers by 70% and 60%, respectively (Ohtsuka et al., 1973).

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References

Arnone A, Cardillo R, Meille SV, Nasini G, Tolazzi M.
Secondary mold metabolites. 47. Isolation and structure elucidation of clavilactones AC, new metabolites from the fungus Clitocybe clavipes.
J Chem Soc-Perk Trans 1. 1994 15: 2165-8.

Bousset M.
Sur la presence d'acide cyanhydrique chez Clitocybe clavipes et Rhodopaxillus nudus.
Bull Mens Soc Linn Lyon. 1941 10(10):154-5.

Cassinelli G, Lanzi C, Pensa T, Gambetta RA, Nasini G, Cuccuru G, Cassinis M, Pratesi G, Polizzi D, Tortoreto M, Zunino F.
Clavilactones, a novel class of tyrosine kinase inhibitors of fungal origin.
Biochem Pharmacol. 2000 59(12):1539-47.

Cochran KW, Cochran MW.
Clitocybe clavipes - Antabuse-like reaction to alcohol.
Mycologia. 1978 70(5):1124-5.

Jarvis MC, Miller AM, Sheahan J, Ploetz K, Ploetz J, Watson RR, Palma Ruiz M, Pascario V, Carlos A, Garcia Alvarado J, Lopez Ramirez A, Orr B.
Edible wild mushrooms of the Cofre de Perote region, Veracruz, Mexico: An ethnomycological study of common names and uses.
Economic Botany. 2004 58(Suppl. S):S111-S115.

Kawagishi H, Miyazawa T, Kume H, Arimoto Y, Inakuma T.
Aldehyde dehydrogenase inhibitors from the mushroom Clitocybe clavipes.
J Nat Prod. 2002 65(11):1712-4.

Marekov I, Antonova D, Gyosheva M, Momchilova S, Nikolova-Damyanova B.
Fatty acid composition of lipids from two macrofungal species belonging to genus Clitocybe.
CR Acad Bulg Sci. 2007 60(7):757-762.

Merlini L, Nasini G, Scaglioni L, Cassinelli G, Lanzi C.
Structure elucidation of clavilactone D: an inhibitor of protein tyrosine kinases.
Phytochem. 2000  53(8):1039-41.

Natour RM, Salhab AS, El-Moumani AR, Saba EF.
Wild mushroom in Jordan.
Dirasat Series B Pure and Applied Sciences. 1993 19(2):47-60.

Noordeloos ME, Boekhout T, Vellinga EC, Arnolds EJM. 1995.
Flora agaricina Neerlandica; critical monographs on families of agarics and boleti occurring in the Netherlands, v.3.
CRC Press
Google Books

Ohtsuka S, Ueno S, Yoshikumi C, Hirose F, Ohmura Y, Wada T, Fujii T, Takahashi E.
Polysaccharides having an anticarcinogenic effect and a method of producing them from species of Basidiomycetes.
UK Patent 1331513, 26 September 1973.

Pemberton RT.
Agglutinins (lectins) from some British higher fungi.
Mycol Res. 1994 98(3):277-90.

Saunders WW, Smith WG, Bennett AW. 1871.
Mycological Illustrations: Being Figures and Descriptions of New and Rare Hymenomycetous Fungi.
London: John van Voorst.
Digitized in Google Books

Yamaura Y, Fukuhara M, Kawamata S, Satsumabayashi H, Takabatake E, Hashimoto T.
Effects of Clitocybe clavipes extract on the components and enzymes related to ethanol metabolism in mice.
J Food Hyg Soc Jpn. 1986 27(5):522-7.

Yamaura Y.
Classification of poisonous mushrooms according to their biochemical effects in mice.
Nippon Eiseigaku Zasshi-Japanese Journal of Hygiene. 1988 43(2):669-78.

The wooly gomphus, Gomphus floccosus (Schwein.) Singer.
   Credit: 'leafdesigner'
   Source: UBC Botanical Garden and Centre for Plant Research

Classification

Kingdom Fungi
Phylum Basidiomycota
Class Basidiomycetes
Order Phallales
Family Gomphaceae
Genus Gomphus

Cantharellus canadensis Klotzsch ex Berk.
  Ann. Mag. nat. Hist., Ser. 1 3: 380 (1839)
Cantharellus floccosus Schwein.
  Trans. Am. phil. Soc., Ser. 2 4(2): 153 (1832)
Cantharellus princeps Berk. & M.A. Curtis
  Ann. Mag. nat. Hist., Ser. 3 4(22): 293 (1859)
Chanterel floccosus (Schwein.) Murrill
  N. Amer. Fl. (New York) 9(3): 168 (1910)
Craterellus canadensis (Klotzsch ex Berk.) Sacc.
  in Berkeley, Syll. fung. (Abellini) 6: 519 (1888)
Gomphus canadensis (Klotzsch ex Berk.) Corner
  Ann. Bot. Mem. 2: 116 (1966)
Merulius floccosus (Schwein.) Kuntze
  Revis. gen. pl. (Leipzig) 2: 862 (1891)
Merulius princeps (Berk. & M.A. Curtis) Kuntze
  Revis. gen. pl. (Leipzig) 2: 862 (1891)
Nevrophyllum floccosum (Schwein.) R. Heim
  Revue Mycol., Paris 19: 51 (1954)
Trombetta canadensis (Klotzsch ex Berk.) Kuntze
  Revis. gen. pl. (Leipzig) 2: 873 (1891)
Turbinellus floccosus (Schwein.) Earle
  Bulletin of the New York Botanical Garden 5: 407 (1909) [1906]

Shaggy, scaly, or woolly chanterelle
Woolly gomphus

Fruiting body: 5-15 cm diameter; initially cylindrical with a sunken center, in maturity deeply depressed; cyathiform or infundibuliform; surface dry, covered with flattened, then erect and even recurved, relatively small scales, buff, yellowish to pale orange scales usually darker; flesh fibrous white; margin often undulate.
Hymenium: decurrent, made of narrow, low, blunt ridges and wrinkles that form to give rise to irregular, anastomose veins; yellow to cream.
Stem: not distinct from the hymenium, whole fruiting body stands 8-20 cm tall, width 1-3 cm at base; buff-colored, hollow from the deep trumpet-shaped pileus.
Odor and taste: mild.
Spore print: pale orange-yellow.
Spores: ellipsoid, minutely wrinkled, entire, hyaline, nonamyloid, thick-walled, 11.5-14.5 x 7-8 µm (Bigelow, 1978).
Habitat: solitary or caespitose under conifers; mycorrhizal. Fruits in summer and fall.
Edibility: edible to some, but consumption generally not advisable due to possibility of gastrointestinal upset. The compound norcaperatic acid has been isolated from this species (Miyata et al., 1966; Henry and Sullivan, 1969), and is known to cause similar delayed gastrointestinal effects (Carrano and Malone, 1967).

Apparently oblivious to these reports of toxic effects, the Khasi tribe of Northeast India regularly consume this species, which are found in abundance in the humid Meghalaya forest (Agrahar-Murugkar and Subbulakshmi, 2005). Whether this is possible due to reduced toxicity of a specific regional strain, or perhaps genetic resistance to the mushroom toxin is unclear. Bandala-Gonzalez and Trigos-Landa (1990) list this as an edible species.

The macronutrient content (given in gram %) of G. floccosus is as follows:

• Dry matter: 13.0
• Protein: 21.2
• Fat: 5.3
• Fibre: 9.2
• Ash: 8.0

• Ca: 1.37 g%
• P: 0.34 g%
• Fe: 22.3 mg%
• Mn: 7.04 mg%
• Cu: 3.48 mg%
• Zn: 13.0 mg%
• Na: 0.14 mg%
• K: 18.7 mg%
• Mg: 136 mg%
• Se: negligible
• Vitamin C: 25.8 mg%

Finally, for those brave (or foolish) enough to eat them, the wooly gomphus has an impressive repertoire of essential amino acids (given as µg of amino acid/100g mushroom, dry weight basis): His 12.0, Thr 17.7, Arg 13.9, Val 10.5, Met 57.2, Phe 0.2, Iso 5.0, Leu 22.7, Lys 14.3. All nutritional data is from Agrahar-Murugkar and Subbulakshmi, 2005.

This species contains the polyol mannitol (Henry and Sullivan, 1969; Dominguez 1981), an interesting compound which has seen several uses.

Bandala-Gonzalez and Trigos-Landa, in their 1990 study on mushroom species from the Cofre de Perote region (Veracruz, Mexico) report that this species tested positive for alkaloids.

Medicinal properties
Antifungal activity

In a search for antifungal components from 32 mushroom species, various extracts from G. floccosus were shown to have antiyeast and antifungal activity. Additionally, the ethanol extract showed an antifungal activity against Microsporum gypseum with a MIC of 1,000 µg/ml (Min et al., 1995). Recently, antifungal compounds known as oxylipins have been isolated and identified from the ethyl acetate fraction (Cantrell et al., 2008). The antifungal activity of the bioactive fatty acids (shown and named below) was tested against a variety of plant pathogens, including Colletotrichum fragariae, C. gloeosporioides, C. acutatum, Botrytis cinerea, Fusarium oxysporum, Phomopsis obscurans, and Phomopsis viticola. In some cases, the antifungal activity was comparable to the well-known fungicide captan.

(9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid

(9E,11Z)-13-oxo-9,11-octadecadienoic acid

(10E,12E)-9-oxo-10,12-octadecadienoic acid

Polysaccharides extracted from the mycelial culture of G. floccosus and administered intraperitoneally into white mice at a dosage of 300 mg/kg inhibited the growth of Sarcoma 180 and Ehrlich solid cancers by 100% and 90%, respectively(Ohtsuka et al., 1973).

Web

Mushroom Expert

References

Agrahar-Murugkar D, Subbulakshmi G.
Nutritional value of edible wild mushrooms collected from the Khasi hills of Meghalaya.
Food Chem. 2005 89(4):599-603.

Bandala-Gonzalez E, Trigos-Landa A.
Determination of alkaloids in some mushroom species from the Cofre de Perote region, Veracruz, Mexico.
[Determinacion de alcaloides en algunas especies de hongos de la region del Cofre de Perote, Veracruz, Mexico.]
Micologia Neotropical Aplicada. 1990 3:41-7.

Bigelow HE.
The cantharelloid fungi of New England and adjacent areas.
Mycologia. 1978 70(4):707-56.

Cantrell CL, Case BP, Mena EE, Kniffin TM, Duke SO, Wedge DE.
Isolation and identification of antifungal fatty acids from the basidiomycete Gomphus floccosus.
J Agric Food Chem. 2008 56(13):5062-8.

Carrano RA, Malone MH.
Pharmacologic study of norcaperatic and agaricic acids.
J Pharm Sci. 1967 56:1611–4.
Abstract

Dominguez XA, Guzman G, Davalos L, Guajardo TE.
Preliminary chemical study of 8 macroscopic fungi.
ReV Latinoam Quim. 1981 12:48–49.

Henry ED, Sullivan G.
Phytochemical evaluation of some cantharelloid fungi.
J Pharm Sci. 1969 58(12):1497-1500.

Homola RH.
Cantharelloid Fungi of Maine.
Maine Naturalist. 1993 1(2):5-12.

Jarvis MC, Miller AM, Sheahan J, Ploetz K, Ploetz J, Watson RR, Ruiz MP, Villapan CAP, Alvarado JG, Ramirez AL, Orr B.
Edible wild mushrooms of the Cofre de Perote region, Veracruz, Mexico: An ethnomycological study of common names and uses.
Econ Bot. 2004 58:S111-S115.

Min TJ, Kim EM, Lee SJ, Bae KG.
Studies on the screening and development of antibiotics in the mushroom: The screening of antifungal components in Basidiomycetes (I).
Korean J Mycol. 1995 23(1):14-27.

Miyata JT, Tyler VE, Brady LR, Malone MH.
The occurrence of norcaperatic acid in Cantharellus floccosus.
Lloydia. 1966 29:43–49.

Montoya A, Hernández-Totomoch O, Estrada-Torres A, Kong A, Caballero J.
Traditional knowledge about mushrooms in a Nahua community in the state of Tlaxcala, México.
Mycologia. 2003 95(5):793-806.

Ohtsuka S, Ueno S, Yoshikumi C, Hirose F, Ohmura Y, Wada T, Fujii T, Takahashi E.
Polysaccharides having an anticarcinogenic effect and a method of producing them from species of Basidiomycetes.
UK Patent 1331513, 26 September 1973.

Petersen RH.
Notes on cantharelloid fungi. Part 3 Gomphus canadensis.
J Elisha Mitchell Sci Soc. 1971 87(2):53-55.

Verma RN, Singh SM, Singh TGB, Bilgrami KS.
Gomphus flocculus - A new record for India.
Curr Sci. 1989 58(24):1370-1.

Last modified: 17-Aug-2008

The rooting shank, Xerula radicata (Relhan) Dörfelt.
  Source: Wikipedia Commons, GFDL license

Agaricus radicatus Relhan
  Fl. cantab., Suppl.: 28 (1786)
Collybia radicans P. Kumm.
  Führer Pilzk. (Zwickau): 117 (1871)
Collybia radicata (Relhan) Quél.
  Mém. Soc. Émul. Montbéliard, Sér. 2 5: 92 (1871)
Gymnopus radicatus (Relhan) Gray
  Nat. Arr. Brit. Pl. (London) 1: 605 (1821)
Mucidula radicata (Relhan) Boursier
 Bull. trimest. Soc. mycol. Fr. 40: 332 (1924)
Mucidula radicata f. marginata Konrad & Maubl.
  Flore d'Algerie, Cryptogamie 2: pl. 199 (1931)
Oudemansiella radicata (Relhan) Singer
 Annls mycol. 34(4/5): 333 (1936)
Oudemansiella radicata var. marginata (Konrad & Maubl.) Bon & Dennis
  in Bon, Docums Mycol. 15(no. 59): 51 (1985)
Xerula radicata var. marginata (Konrad & Maubl.) ined.

Rooting shank
Beech rooter

Description

Cap: 3-10 cm diameter, yellow or olive-brown; convex or campanulate, in age becoming plano-convex with broad umbo; sulcate, surface viscid but drying shiny, sometimes radially wrinkled. Flesh pallid, otherwise concolorous and thin. Margin initially incurved, later uplifted.
Gills: white, adnexed or notched, thick, broad, distant.
Stem: 5-20 cm tall x 0.3-1 cm diameter; white at the apex, becoming tinged cap color below, slender, tapering upwards, deeply rooting; ring absent; flesh white and firm.
Spores: hyaline, smooth, ellipsoid, non-amyloid, with droplets, 12-16 x 9-12 µm. See Peterson (2008) for some detailed views of various Xerula spores using electron microscopy.
Spore print: white
Habitat: typically solitary or trooping; under or near deciduous trees, especially beech, attached to roots or buried wood.
Taste: mild.
Edibility: edible.

The lipid composition of this mushroom has been analyzed (Yilmaz et al., 2006). Of note, the mushroom caps contain 42.7% polyunsaturated fatty acids (percentage of total fatty acids), most of which is linoleic acid, an essential fatty acid in humans.

Medicinal properties
Antihypertensive effects

The molecule oudenone is a fungal metabolite that was first isolated from the culture filtrate of X. radicata (as Oudemansiella radicata) (Umezawa et al., 1970). Shortly after, the structure and synthesis of oudenone were reported (Ohno et al., 1971). Oudenone is a strong inhibitor of catecholamine biosynthesis - specifically, it inhibits the enzymes phenylalanine and tyrosine hydroxylase. The physiological effect of this enzyme inhibition is the reduction of blood pressure, the inhibition of tyrosine hydroxylase in the adrenal glands in vivo, as well as the reduction of tissue catecholamine levels in the adrenal glands, heart and brain in spontaneously hypertensive rats (Nagatsu et al., 1971). The biosynthesis and cyclization mechanism of oudenone have been elaborated using feeding experiments using ¹³C and ²H labeled precursors and NMR analysis (Tsantrizos et al., 1995; Tsantrizos et al., 1999). Various synthetic schemes have been proposed for the molecule (Tsujikawa and Hayashi, 1977; Bates and Farina, 1985; Flynn et al., 1995).

The antihypertensive molecule (S)-2-[4,5-dihydro-5-propyl-2- (3H)-furylidene]- 1,3-cyclopentanedione, commonly known as oudenone.

X. radicata has been shown to contain an antibiotic named oudemansin X (shown below), which lacked antibacterial activity against various organisms tested, but showed good antifungal activity (Anke et al., 1990). Later synthetic work described the chiral total synthesis of three kinds of oudemansin X, (-)-1, (+)-1 and (+)-1; like the parent molecule, the synthetic oudemansin X (-)-1 had strong antifungal activity against several molds and yeasts. (Umezawa et al., 1995). The lack of antibacterial activity corroborates the findings of Bianco et al.  (1996).

The antifungal metabolite E-β-methoxyacrylate oudemansin X.

Antitumor effects

Polysaccharides extracted from the mycelial culture of X. radicata and administered intraperitoneally into white mice at a dosage of 300 mg/kg inhibited the growth of Sarcoma 180 and Ehrlich solid cancers by 100% and 90%, respectively (Ohtsuka et al., 1973).

Web

Mushroom Expert
BioPix
Patent for the production and preparation of oudenone

References

Anke T, Werle A, Bross M, Steglich W.
Antibiotics from basidiomycetes. XXXIII. Oudemansin X, a new antifungal E-β-methoxyacrylate from Oudemansiella radicata (Relhan ex Fr.) Sing.
J Antibiot (Tokyo). 1990 43(8):1010-1.

Bates HA, Farina J.
Oxonium ion electrophiles - synthesis of the hypotensive oudenone.
J Org Chem. 1985 50(20):3843-5.

Bianco C, Ausilia M, Giardino L.
Antibiotic activity in Basidiomycetes. X. Antibiotic activity of mycelia and cultural filtrates of 25 new strains.
Allionia (Turin). 1996 34(0):39-43.

Dörfelt H.
The carpophore development of Xerula radicata (Basidiomycetes, Agaricales)
Flora 1982 172(6):533-61.

Flynn BL, Silveira CC, Demeijere A.
Selective formation of 4-ethoxy-5-methylene-2-cyclopentenones and 3-ethoxy-2-(1'-morpholinoalkenyl)-2-cyclopentenones from (1-ethoxy-3-morpholino-alkenylidene)pentacarbonylchromium complexes and terminal alkynes - a short enantioselective synthesis of the hypotensive oudenone.
Synlett. 1995 (8):812-4.

Koide T, Ozawa H.
Pharmacological analysis upon blood-pressure response to oudenone.
Jap J Pharmacol. 1976 26:P149-P.

Koide T, Ozawa H.
Pharmacological studies on blood-pressure response of oudenone, a tyrosine-hydroxylase inhibitor.
Folia Pharmacologica Japonica. 1976 72(3):P8-P9.

Koizumi S, Nagatsu T, Iinuma H, Ohno M, Takeuchi T, Umezawa H.
Inhibition of phenylalanine-hydroxylase, a pterin-requiring Mono-oxygenase, by oudenone and its derivatives.
Journal of Antibiotics. 1982 35(4):458-62.

Nagatsu T, Nagatsu I, Umezawa H, Takeuchi T.
Effect of oudenone on adrenal tyrosine hydroxylase activity in vivo and on tissue catecholamine concentrations.
Biochem Pharmacol. 1971 20(9):2505-7.

Ohtsuka S, Ueno S, Yoshikumi C, Hirose F, Ohmura Y, Wada T, Fujii T, Takahashi E.
Polysaccharides having an anticarcinogenic effect and a method of producing them from species of Basidiomycetes.
UK Patent 1331513, 26 September 1973.

Petersen RH, Methven AS.
Mating systems in the Xerulaceae - xerula.
Can J Bot-Revue Canadienne de Botanique 1994 72(8):1151-63.

Peterson RH.
Scanning electron microscope images of basidiospores of Xerula (Physalacriaceae, Agaricales).
Mycoscience. 2008 49:19-34.
PDF available from publisher

Ohno M, Okamoto M, Kawabe N, Umezawa H, Takeuchi T, Iinuma H, Takahash S.
Oudenone, a novel tyrosine hydroxylase inhibitor from microbial origin.
J Am Chem Soc. 1971 93(5):1285-&.

Ozawa H, Koide T.
Pharmacodynamic actions of (S)-2-[4,5-dihydro-5-propyl-2 (3h)-furylidene]-1,3-cyclopentanedione (oudenone).
Japanese Journal of Pharmacology. 1976 26(5):581-92.

Redhead SA, Ginns J, Shoemaker RA.
The Xerula (Collybia, Oudemansiella) radicata complex in Canada.
Mycotaxon 1997 30:357-405.

Sawada M, Iinuma H, Ohno M, Takeuchi T, Umezawa H, Nagatsu T.
Kinetic-analysis of the inhibition of tryptophan-hydroxylase, a pteridine-requiring monooxygenase, by oudenone and its derivatives.
Biogenic Amines. 1984 1(2):171-8.

Sakai T, Iwata K, Utaka M, Takeda A.
A convenient synthesis of hypotensive (+/-)-oudenone.
Bull Chem Soc Japan. 1987 60(3):1161-2.

Semerdzieva M, Buchalo AS, Huebsch P, Zakordonec OA, Wassser SP, Musilek V.
Comparative study of cultures of four species of the genus Oudemansiella.
Folia Microbiologica. 1988 33(2):115-120.

Tsantrizos YS, Yang X, McClory A.
Studies on the biosynthesis of the fungal metabolite oudenone. 2. Synthesis and enzymatic cyclization of an α-diketone, open-chain precursor into oudenone in cultures of Oudemansiella radicata.
J Org Chem. 1999 64(18):6609-6614.

Tsantrizos YS, Zhou F, Famili P, Yang XS.
Biosynthesis of the hypotensive metabolite oudenone by Oudemansiella radicata.1. Intact incorporation of a tetraketide chain elongation intermediate.
J Org Chem. 1995 60(21):6922-9.

Tsujikawa T, Hayashi M.
Studies on heterocyclic-compounds .7. Syntheses of oudenone and its related compounds .2.
Chem Pharm Bull. 1977a 25(12):3147-54.
PDF -open source - article here

Tsujikawa T, Nakagawa Y, Tsukamura K, Masuda K.
Studies on heterocyclic-compounds .6. Syntheses of oudenone and its related compounds .1.
Chem Pharm Bull. 1977b 25(10):2775-8.
PDF - open source - article here

Tsujikawa T, Nakagawa Y, Tsukamura K, Masuda K.
Synthesis of oudenone and its related compounds.
Heterocycles. 1977c 6(3):261-6.

Umezawa H, Takeuchi T, Iinuma H, Suzuki K, Ito M, Matsuzak M.
A new microbial product, oudenone, inhibiting tyrosine hydroxylase.
J Antibio. 1970 23(10):514-&.

Umezawa I, Nozawa M, Nagumo S, Akita H.
Total synthesis of (racemic)-, (-)-, and (+)-oudemansin X.
Chem Pharm Bull. 1995 43(7):1111-8.

Yilmaz N, Solmaz M, Turkekul I, Elmastas M.
Fatty acid composition in some wild edible mushrooms growing in the middle Black Sea region of Turkey.
Food Chem. 2006 99(1):168-74.

Zou X.
Optimization of nutritional factors for exopolysaccharide production by submerged cultivation of the medicinal mushroom Oudemansiella radicata.
World J Microbiol Biotech. 2005 21(6-7):1267-71.

Last modified: 15-Aug-2008

The Japanese mushroom Lactarius flavidulus S. Imai.

Common name

Ki hatsu take (Japanese)

Description

As far as I can determine, this species has only been reported from Japan, and descriptive information is sketchy. Nagasawa (1998) suggests that a more correct name is L. tottoriensis.

Spores: 8-9.2 x 6-7 µm (see a photo here)
Taste: bitter.
Edibility: edible.

Bioactive compounds

Three novel geranylphenols, flavidulols A, B and C (structures shown below), were isolated from Lactarius flavidulus while screening for new inhibitors of proliferation of mouse lymphocytes (Takahashi et al., 1988). The original structures determined for these compounds were later revised based on NMR analysis (Takahashi et al., 1993). This paper also reported the isolation of flavidulol D, also shown below.
The IC₅₀ values for the concanavalin A-induced proliferation of mouse lymphocytes were determined to be 8.9 µg/ml, 4.9 µg/ml and 36.6 µg/ml, respectively, while against lipopolysaccharide-stimulated proliferation, the corresponding IC₅₀ values were 6.7, 3.9 and 28.3 μg/ml (Fujimoto et al., 1993)

The flavidulols A, B, and C - inhibitors of lymphocyte proliferation.

Flavidulol D: R¹=CH₃, R²=COC₁₇H₃₅

Medicinal properties

Antimicrobial and antifungal activity

Using the serial two-fold dilution method, flavidulol A demonstrated antimicrobial activity against various pathogenic organisms (minimum inhibitory concentrations in µg/ml given in parentheses): Staphylococcus aureus (6.2), Bacillus subtilis (6.2), Escherichia coli (>100), Candida albicans (25), Trichophyton rubrum (6.2), and T. mentagrophytes (6.2) (Takahashi et al., 1988). The latter two organisms are fungi responsible for various skin ailments such as athletes foot, jock itch, and ringworm.

Antitumor effects

Polysaccharides extracted from the mycelial culture of L. flavidulus and administered intraperitoneally into white mice at a dosage of 300 mg/kg inhibited the growth of Sarcoma 180 and Ehrlich solid cancers by 100% (Ohtsuka et al., 1973).

Links

There is more information at Mushbank, a Korean website.

References

Fujimoto H, Nakayama Y, Yamazaki M.
Identification of immunosuppressive components of a mushroom, Lactarius flavidulus.
Chem Pharm Bull. 1993 41(4):654-8.

Lorenzen K, Anke T, Konetschny-Rapp S, Scheuer W.
5-hydroxy-3-vinyl-2(5H)-furanone–a new inhibitor of human synovial phospholipase A2 and platelet aggregation from fermentations of a Calyptella species (basidiomycetes).
Z Naturforsch-[C]. 1995 50(5-6):403-9.

Nagasawa E.
A preliminary checklist of the Japanese Agaricales. II. The suborder Russulineae
Reports of the Tottori Mycological Institute. 1998 0(36):36-71.

Ohtsuka S, Ueno S, Yoshikumi C, Hirose F, Ohmura Y, Wada T, Fujii T, Takahashi E.
Polysaccharides having an anticarcinogenic effect and a method of producing them from species of Basidiomycetes.
UK Patent 1331513, 26 September 1973.

Takahashi A, Kusano G, Ohta T, Nozoe S.
The constituents of Lactarius flavidulus Imai.
Chem Pharm Bull. 1988 36(7):2366-70.

Takahashi A, Kusano G, Ohta T, Nozoe S.
Revised structures of flavidulols, constituents of Lactarius flavidulus Imai, and the structure of flavidulol-D.
Chem Pharm Bull. 1993 41(11):2032-3.

Last modified: 13-Aug-2008