Medicinal Mushrooms

Photos credit: Dr. Robert Thomas and Dorothy B. Orr © 2001 California Academy of Sciences, from CalPhotos.

Synonyms

Calodon suaveolens (Scop.) P. Karst.
Hydnum boreale Banker
Hydnum pullum Fr.
Hydnum suaveolens Scop.
Phaeodon suaveolens (Scop.) J. Schröt.
Sarcodon gravis Coker

Cap: Funnel-shaped, up to 15 cm in diameter; plane when mature; surface uneven; margin thick; white and somewhat woolly, later becoming grayish-brown.
Flesh: Tough, fibrous, discoloring when bruised or cut.
Teeth: up to 0.8 cm; white at first, but soon becoming dark brown basally and gray at tips.
Stem: 3-5 cm long, relatively thick (1-2.5 cm), white at top, shading to bluish-black at base, mycelium blue-violet color, surface tomentose.
Spines: 2-5 mm long, decurrent, pallid, buff to deep brown.
Spore print: Brown.
Spores: Brown,  irregular in shape, tuberculate; 3-3.5 x 4-6µ.
Odor: Strong, sweet, like anise.
Edibility: Inedible.
Habitat: Grows on the ground (often in moss) under coniferous trees, in summer and fall.
Distribution: North America, Europe.

The terphenyl quinone, thelephoric acid was detected in Hydnellum suavolens, as well as various other members of the genus Hydnellum (Sullivan et al., 1967). This fungal pigment, used as a dye for silks and wools, is often used as a defining characteristic of the Thelephoraceae and Bankeraceae.

Coumarin and anisaldehyde seem to contribute to the fragrant anise aroma of H. suaveolens (Wood et al., 1988)

Fractionation of methanol extracts of the fruit bodies Hydnellum suaveolens resulted in isolation of two new p-terphenyl derivatives named hydnellins A and B as well as sarcodonin δ (previously identified in Sarcodon scabrosus) (Hashimoto et al., 2006).

(a)
(b)
(c)

Figure 1. Antioxidant terphenyls from Hydnellum suaveolins. (a) Hydnellin A (R=H) (b) Hydnellin B (R=H) (c) Sarcodonin δ.

The DPPH˙ free-radical scavenging assay was used to assess the antioxidant activity of hydnellin A and sarcodonin δ. Compared to the α-tocopherol standard (IC₅₀=22.8 µM), Hydnellin A and sarcodonin δ showed moderate antioxidant activity with IC₅₀ values of 29.1 and 25.0µM, respectively.

More photos available in the Stridvall fungi gallery.

Hashimoto T, Quang DN, Kuratsune M, Asakawa Y.
Hydnellins A and B, nitrogen-containing terphenyls from the mushrooms Hydnellum suaveolens and Hydnellum geogerirum.
Chem & Pharm Bull. 2006 54(6):912-4.

Sullivan G, Brady LR, Tyler, VE.
Occurrence and distribution of terphenylquinones in Hydnellum species
Lloydia. 1967 30(1):84-90.

Wood WF, Deshazer DA, Largent DL.
The identity and metabolic-fate of volatiles responsible for the odor of Hydnellum suaveolens.
Mycologia. 1988 80(2):252-5.

Picture source: Bulliard, P. 1791. Histoire des champignons de la France. I: 1-368.

Underside view of M. ramealis. Photo Credit: Copyright © Malcolm Storey, 2003, www.bioimages.org.uk.

Synonyms

Agaricus amadelphus Bull.
Agaricus ramealis Bull.
Collybiopsis ramealis (Bull.) Earle
Gymnopus ramealis (Bull.) Gray
Gymnopus ramealis (Bull.) J.L. Mata & R.H. Petersen
Marasmiellus amadelphus (Bull.) Singer
Marasmius amadelphus (Bull.) Fr.
Marasmius ramealis (Bull.) Fr.
Micromphale amadelphum (Bull.) Honrubia [as 'amadelphus']
Micromphale rameale (Bull.) Kühner [as 'ramealis']

Twig Parachute
Twig Mummy-cap
Pinwheel Marasmius
Ast-Schwindling (German)

Cap: 3-10 mm across, convex then flattened or centrally depressed, whitish pink, often darker in the centre, membranous and often wrinkled.
Stem: 3-20 x 1 mm, scurfy, concolorous with cap, darkening towards the curved base.
Flesh: thin, concolorous.
Gills: distant, white or pinkish.
Spore print: white.
Spores: elongate, elliptical, 8.0-10 x 3-4 µm.
Habitat: on old stems.
Season: early summer to autumn. Frequent. Not edible. Found in Europe.

Bendz described the isolation of the antibiotic marasin, shown in figure 1a (Bendz, 1959b).

(a)    (b)
(c)

Soon after (Bendz, 1960), other bioactive substances were identified, including (-)-nona-3,4-diene-6,8-diyne-l-ol. Furthermore, M. ramealis was also shown to produce several other closely related polyacetylenes and an iso-coumarin derivative, identified as 3-methyl-8-hydroxy-isocoumarin (figure 1b).

Using ¹⁴C-labeled precursors, the biosynthetic pathway for the production of the marasin was investigated, suggesting that the diyne-allene moeity in the polyacetylenic marasin is introduced enzymatically, via arrangement of an alkyltriyne moeity (Davies and Hodge, 2005).

The metabolite 3,7-bis(hydroxymethyl)-1-benzoxepin-5(2H)-one (figure 1c), has a benzoxepinone ring structure - at the time of discovery, unknown in natural product chemistry (Holroyde et al., 1976, 1978).

Later work would reveal the presence of the fungal metabolite mellein, as well as pyrrole-2-carboxylic acid and p-hydroxybenzoic acid (Jarrah and Thaller, 1983).

This patent describes the production of 5-substituted picolinic acid derivatives by Marasmiellus species, including M. ramealis.

Bendz G.
8-Hydroxy-3-methylisocoumarin isolated from the culture medium of Marasmius ramealis.
Arkiv for Kemi. 1959a 14(6):511-8.

Bendz G.
Marasin, an antibiotic polyacetylene, isolated from the culture medium of Marasmius ramealis.
Arkiv for Kemi. 1959b 14(4):305-21.

Bendz G.
A study of the chemistry of some Marasmius species.
Arkiv for Kemi. 1960 15(2):131-48.

Bendz G, Wallmark G, Oblom K.
The antibiotic agent from Marasmius ramealis.
Nature. 1948 162(4106):61-2.

Davies DG, Hodge P.
Biosynthesis of the allene (-)-marasin in Marasmius ramealis.
Org Biomol Chem. 2005 3(9):1690-3.
Pubmed

Desjardin DE.
New and noteworthy marasmioid fungi from California.
Mycologia. 1987 79(1):123-34.
First page available online here

Holroyde JK, Orr AF, Thaller V.
3,7-Bis(hydroxymethyl)-1-benzoxepin-5(2h)-one, a novel metabolite from cultures of fungus Marasmiellus ramealis (Bull Ex Fr) Singer.
J Chem Soc-Chem Comm. 1976 (7):242-3.

Holroyde JK, Orr AF, Thaller V.
3,7-Bis(hydroxymethyl)-1-benzoxepin-5(2h)-one, a novel oxygen heterocyclic metabolite from cultures of the fungus Marasmiellus ramealis (Bull Ex Fr) Singer.
J Chem Soc-Perk Trans 1. 1978 (12):1490-3.

Jarrah MY, Thaller V.
Isolation and partial synthesis of 3-methoxycarbonyl- 7-formyl-1-benzoxepin-5(2h)-one the ester of a metabolite from shake cultures of the fungus Marasmiellus ramealis (Bull. Ex Fr.) Singer.
J Chem Soc-Perk Trans 1. 1983 (8):1719-21.

Geotrichum cinnamomeum (Lib.) Sacc.
Malbranchea pulchella var. sulfurea (Miehe) Cooney & R. Emers.
Malbranchea sulfurea (Miehe) Sigler & J.W. Carmich.
Malbranchea sulfurea (Miehe) Pidopl. [as 'sulphurea']
Thermoidium sulphureum Miehe [as 'sulfureum']

Malbranchea cinnamomea is a thermophilic fungi, having a minimum temperature of growth at or above 20°C.  This ascomycete fungi is often isolated from higher-temperature environments such as animal hair, or sun-heated desert soils.

 M. cinnamomea produces a quinone antibiotic (6-(1-acetylethyl)-2-methoxy-2,5-cyclohexadiene-1,4-dione) named malbranicin (Chiung et al., 1993), shown in figure 1.

Figure 1. Malbranicin.

Malbranicin has antimicrobial activities against Gram-positive bacteria. The antimicrobial spectrum is given in table 1.

Table 1. Antimicrobial spectrum of malbranicin, as reported by Chiung et al., 1993. Minimal inhibitory concentration (MIC) was determined using the serial diffusion assay method.

Additionally, the authors report that malbranicin was cytotoxic at 0.7 µg/ml against P388 cells and 2.8 µg/ml to KB cells.

A stereoselective synthesis of (S)-(+)-malbranicin has been reported (Vanderlei et al., 1997).

Other compounds isolated from this fungus include dihydromalbranicin, various novel substituted quinones, including hydroquinone. The compound  2-(7-methoxymalbranicin) at a concentration of 42 µm inhibited by 67% Tax/CREB-mediated expression of β-galactosidase in a recombinant strain of Saccharomyces cerevisiae (Schegel et al., 2003a).

A compound, 7-methoxy-2,3-dimethylbenzofuran-5-ol, isolated from M. cinnamomea, was reported to have antioxidant activity (Schlegel et al., 2003b).

- see the Japan Society for Culture Collections (JSCC) for a culture source.
- see here for details about a patent on polysaccharide extraction from mycelial cultures of this and similar species
- see here for another related patent

Chiung YM, Fujita T, Nakagawa M, Nozaki H, Chen GY, Chen ZC, Nakayama M.
A novel quinone antibiotic from Malbranchea cinnamomea TAIM 13T54.
J Antibiot (Tokyo). 1993 46(12):1819-26.

McKay DJ, Stevenson KJ.
Lipoamide dehydrogenase (E. C. 1.6.4.3) from Malbranchea pulchella var. sulfurea: isolation and characterization.
Biochemistry 1979 18:4702-7.

Schlegel B, Hanel F, Gollmick FA, Saluz HP, Grafe U.
New quinones and hydroquinones from Malbranchea cinnamomea HKI 286 and HKI 296 and interaction with Tax/CREB expression system in yeast.
J Antibiot (Tokyo). 2003a 56(11):917-22.

Schlegel B, Hartl A, Gollmick FA, Grafe U.
7-methoxy-2,3-dimethylbenzofuran-5-ol, a new antioxidant from Malbranchea cinnamomea HKI 0286.
J Antibiot (Tokyo). 2003b 56(9):792-4.

Vanderlei JML, Coelho F, Almeida WP.
A stereoselective synthesis of malbranicin.
Tetrahedron Asymmetry. 1997 8(16): 2781-5.

Aleuria vesiculosa (Bull.) Gillet
Galactinia vesiculosa (Bull.) Le Gal
Helvella vesiculosa (Bull.) Bolton
Pustularia vesiculosa (Bull.) Fuckel
Scodellina vesiculosa (Bull.) Gray

Bladder Cup
Blistered Cup
Common Dung Cup
Orange Fairy-cup

Fruiting body: cupulate at first, expanding, becoming flattened, often irregular in outline, up to 15 cm broad, the upper surface smooth, bright orange, the lower surface white or whitish, attached only to the center. Usually gregarious or densely caespitose.
Flesh: thin, fragile.
Spore print: pale yellow.
Spores: colorless, ellipsoid, smooth; 20-24 x 11-14 µm.
Habitat: On the ground, usually in wet gravely or sandy soils.
Season: Late summer to early winter, less abundantly in the spring.

Vesiculogen, a hot-water extractable mitogen from P. vesiculosa, was shown be a polyclonal B cell activator in mice (Suzuki et al., 1985). This activity was shown earlier to be not due to polysaccharides (Yadomae et al., 1979). The mitogenicity of vesiculogen is due to the presence of anionic groups (such as aspartate and glutamate) (Ohno et al., 1984). Furthermore, the mitogen was determined to be a high-molecular weight, acidic polypeptide, showing charge and weight heterogeneities (Ohno et al., 1986).

The immunomodulatory vesiculogen was shown to have antitumor activity against both solid and ascite forms of sarcoma 180 in mice (Suzuki, 1982). Additionally, an antitumor β-1,3-glucan has been purified and characterized (Mimura et al., 1985). The glucan is branched at position 6 of every fifth 3-substituted β-glucosyl unit. The glucan was assayed against solid form sarcoma 180 tumor cells in mice, and showed growth inhibition of more than 90% at 75, 150, 300 µg/dose x 10 days. A significant difference from the control was observed at all glucan doses.

Mimura H, Ohno N, Suzuki I, Yadomae T.
Purification, antitumor activity, and structural characterization of β-1,3-glucan from Peziza vesiculosa.
Chem Pharm Bull (Tokyo) 1985 33(11):5096-9.
Pubmed

Ohno N, Suzuki I, Miyazaki T, Yadomae T.
Requirement of anionic groups for the mitogenicity of a fungal mitogen, vesiculogen.
Microbiol Immunol. 1984 28(7):821-30.
Pubmed

Ohno N, Mimura H, Suzuki I, Yadomae T.
Antitumor activity and structural characterization of polysaccharide fractions extracted with cold alkali from a fungus, Peziza vesiculosa.
Chem Pharm Bull (Tokyo) 1985 33(6):2564-8.
Pubmed

Ohno N, Mimura H, Suzuki I, Yadomae T.
Chemical characterization of a fungal B-cell mitogen obtained from the fruit body of Peziza vesiculosa.
Chem Pharm Bull (Tokyo) 1986 34(5):2112-7.
Pubmed

Suzuki I, Yadomae T, Yonekubo H, Nishijima M, Miyazaki T.
Antitumor activity of an immunomodulating material extracted from a fungus, Peziza vesiculosa.
Chem Pharm Bull (Tokyo) 1982 30(3):1066-8.
Pubmed

Suzuki I, Yonekubo H, Ohno N, Miyazaki T, Yadomae T.
Effect of a B cell mitogen extracted from a fungus Peziza vesiculosa on antibody production in mice.
J Pharmacobiodyn. 1985 8(7):494-502.
Pubmed

Yadomae T, Suzuki I, Kumazawa Y, Miyazaki T.
A B lymphocyte mitogen extracted from a fungus Peziza vesiculosa.
Microbiol Immunol. 1979 23(10):997-1008.
Pubmed

Amyloporia xantha (Fr.) Bondartsev & Singer ex Bondartsev
Amyloporia xantha f. pachymeres J. Erikss.
Antrodia xantha f. pachymeres (Fr.) J. Erikss.
Chaetoporellus greschikii (Bres.) Bondartsev & Singer ex Bondartsev
Daedalea xantha (Fr.) A. Roy & A.B. De
Physisporus xanthus (Fr.) P. Karst.
Polyporus flavus P. Karst.
Polyporus selectus P. Karst., Not. Sällsk. Fauna et Fl. Fenn. Förh.
Polyporus sulphurellus Peck
Polyporus xanthus Fr.
Poria greschikii Bres.
Poria selecta (P. Karst.) Rodway & Cleland
Poria sulphurella (Peck) Sacc.
Poria xantha (Fr.) Cooke

Spreading, creamy-yellow, partly encrusting, partly hoof-like, the pore-bearing surface exposed as vertical 'lacerations' between individual brackets, annual; in overlapping tiers on vertical surfaces of dead conifer stumps and other timber.

Dimensions: variable diameter overall, individual brackets 1-3 cm diameter x 0.5-1 cm thick.
Fruiting body: upper surface pale cream to pale straw yellow, with slightly iridescent appearance, irregular, lumpy hoof-shaped, margin thinning, undulating.
Flesh: whitish, soft when damp, chalky when dry.
Pores: concolorous, small, sub-circular or angular, lacerate, exposed vertically, 5-7 per mm. Tubes white, 3-5 mm deep.
Spores: hyaline, smooth, allantoid, non-amyloid, thin-walled, 4-5 x 1-1.5 µm.
Basidia: clavate, 10-15 × 4-5 µm, 4-spored. Cystidia absent.
Cystidioles: present, apically pointed, 10-14 × 3-4 µm, thin-walled.
Odor: sweetish.
Taste: bitter.

It is known that during tumor growth, increased reactive oxygen species activate tumor-infiltrating leukocytes to induce an angiogenic response.  Hence, the delay of new blood vessel growth using angiogenesis inhibitors is an important aspect of cancer chemotherapy. In one study, polysaccharides extracted from Antrodia xantha were investigated for its effects on vascular endothelial growth factor (VEGF)-induced tube formation in endothelial cells (ECs). Chemical analysis revealed that the polysaccharides were composed of the neutral sugars myo-inositol, sorbitol, fucose, galactosamine, glucosamine, galactose, glucose, and mannose. However, the monosaccharides fucose, glucose and mannose from A. xantha had the greatest inhibitory effects on endothelial tube formation.  The  results showed that polysaccharides from A. xantha show greater antiangiogenesis than those from commercialized A. murrill (Brazilian mushroom) and A. cinnamomea (Chen et al., 2005).

At the Bioimages site you can see this fungus from various angles.

Chen SC, Lu MK, Cheng JJ, Wang DL.
Antiangiogenic activities of polysaccharides isolated from medicinal fungi.
FEMS Microbiology Letters. 2005 249(2):247-54.
Pubmed

Jordan M.
The Encyclopedia of Fungi of Britain and Europe. 2004. Frances Lincoln Ltd. 384 pp.
Google preview available here.

Wu S-H.
Resupinate polypores (Basidiomycotina) newly recorded from Taiwan.
Bot. Bull. Acad. Sin. 1996 37:151-8.
Text available here.

 
Last updated: 06-Mar-2008