Red Pyrroloquinoline Alkaloids from the Mushroom <i>Mycena haematopus</i>

Peters, Silke; Jaeger, Robert J. R.; Spiteller, Peter

doi:10.1002/ejoc.200700739

Cited by 27 publications

(43 citation statements)

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“…The 1 H, 13 C, COSY, HSQC, and HMBC NMR spectroscopy data of 2 closely resemble those of 1 . The most significant difference concerns C‐2 and C‐7, which indicates the presence of a quinone instead of an iminoquinone moiety; this is in agreement with the corresponding chemical shifts of 8 and 14 …”

Section: Resultssupporting

confidence: 80%

“…Moreover, four other red pyrroloquinoline alkaloids, named mycenarubins A ( 14 ), D ( 13 ), E ( 5 ), and F ( 6 ), were found in the fruiting bodies . Mycenarubin A ( 14 ) is also present in Mycena rosea and Mycena pelianthina , and 13 in M. pelianthina , whereas 5 and 6 have only been found in M. haematopus , to date . Herein, we describe the isolation and structural elucidation of four new pyrroloquinoline alkaloids, which have been named mycenaflavins A ( 1 ), B ( 2 ), C ( 3 ), and D ( 4 ).…”

Section: Introductionmentioning

confidence: 97%

“…In 1993, the red colour of the latex was linked to the then unknown pyrroloquinoline alkaloid haematopodin ( 8 ) or a closely related precursor . In 2008, this precursor was identified as haematopodin B ( 7 ) . Moreover, four other red pyrroloquinoline alkaloids, named mycenarubins A ( 14 ), D ( 13 ), E ( 5 ), and F ( 6 ), were found in the fruiting bodies .…”

Section: Introductionmentioning

confidence: 99%

“…In 2008, this precursor was identified as haematopodin B ( 7 ) . Moreover, four other red pyrroloquinoline alkaloids, named mycenarubins A ( 14 ), D ( 13 ), E ( 5 ), and F ( 6 ), were found in the fruiting bodies . Mycenarubin A ( 14 ) is also present in Mycena rosea and Mycena pelianthina , and 13 in M. pelianthina , whereas 5 and 6 have only been found in M. haematopus , to date .…”

Section: Introductionmentioning

confidence: 99%

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Mycenaflavin A, B, C, and D: Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena haematopus

Lohmann

Wagner

Nussbaum

et al. 2018

Chemistry A European J

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Four so far unknown pyrroloquinoline alkaloids, yellow mycenaflavins A, B, and C, and the purple mycenaflavin D, have been isolated from the fruiting bodies of Mycena haematopus. The structures of these new alkaloids were elucidated by NMR spectroscopy and HRMS (ESI ). The mycenaflavins are structurally related to mycenarubins and haematopodins, which have been previously identified in M. haematopus. However, compared with other known fungal pyrroloquinoline alkaloids, the mycenaflavins contain an additional double bond within the pyrroloquinoline moiety that accounts for the yellow colour of the monomeric mycenaflavins A, B, and C. The purple mycenaflavin D is the first known dimeric pyrroloquinoline alkaloid with a C-C bridge between the two pyrroloquinoline units. Although the minor pyrroloquinoline alkaloid constituent mycenaflavin A exhibits only moderate bioactivity against the soil bacterium Azoarcus tolulyticus, the major pyrroloquinoline alkaloid constituent haematopodin B is similarly active as the antibiotic gentamicin.

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Section: Resultssupporting

confidence: 80%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Mycenaflavin A, B, C, and D: Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena haematopus

Lohmann

Wagner

Nussbaum

et al. 2018

Chemistry A European J

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“…P. Kumm., Peters et al (2008) found its red pyrroloquinolone alkaloid pigment to be sensitive to colour-altering structural changes, which could be inflicted by drying stress or heating, and according to Spiteller (personal communication) there are indications that this could also apply to the structurally related M. pura pigment. This corresponds with our observations of some M. pura specimens sometimes getting a dingy yellowish tinge increasing with age and/or drying.…”

Section: Differentiation In Colouration Within Calodontes?mentioning

confidence: 95%

A comparison between ITS phylogenetic relationships and morphological species recognition within Mycena sect. Calodontes in Northern Europe

et al. 2010

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The members of Mycena sect. Calodontes (Tricholomataceae s.l., Basidiomycota) are characterised by a collybioid aspect and more or less purplish to reddish colours and a distinct raphanoid odour. In Europe, nine species have been recognised though some of these based on somewhat dubious morphological differences. Historically, most were assigned to Mycena pura. However, since Mycena pura displays one of the most striking colour variabilities within European agarics, many attempts have been made to subdivide it into independent entities, and several forms, varieties and species have been split from Mycena pura s.l. based largely on differences in colouration, gross macromorphology or other phenetic traits. We developed a large sample of ITS sequences of all species of sect. Calodontes known from Europe for which vouchers exist. Furthermore, partial LSU data were developed and additional sequences downloaded from GENBANK to assess the relationship of Calodontes with other Mycena spp. We show that most Calodontes form a monophyletic group including a few North and South American collections, but that this cannot be conclusively shown when an additional North American sequence is added. For all other species than M. pura and M. diosma, we found morphological species recognition to be in agreement with the ITS data. Several significantly different clades can be recognised within the M. pura morphospecies, none of which can be linked to the observed (and described by proxy) colour varieties/forms. Indications of a possible environmental basis of the colour differentiation in the M. pura morphospecies are discussed.

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Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubin C

et al. 2020

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Mycenarubin C, a previously unknown red pyrroloquinoline alkaloid, was isolated from fruiting bodies of the mushroom Mycena rosea and its structure was elucidated mainly by NMR spectroscopy and mass spectrometry. Unlike mycenarubin A, the major pyrroloquinoline alkaloid in fruiting bodies of M. rosea, mycenarubin C, contains an eight‐membered ring with an additional C1 unit that is hitherto unprecedented for pyrroloquinoline alkaloids known in nature. Incubation of mycenarubin A with an excess of formaldehyde revealed that mycenarubin C was generated nearly quantitatively from mycenarubin A. An investigation into the formaldehyde content of fresh fruiting bodies of M. rosea showed the presence of considerable amounts of formaldehyde, with values of 5 μg per gram of fresh weight in fresh fruiting bodies. Although mycenarubin C did not show bioactivity against selected bacteria and fungi, formaldehyde inhibits the growth of the mycoparasite Spinellus fusiger at concentrations present in fruiting bodies of M. rosea. Therefore, formaldehyde might play an ecological role in the chemical defence of M. rosea against S. fusiger. In turn, S. fusiger produces gallic acid—presumably to detoxify formaldehyde by reaction of this aldehyde with amino acids and gallic acid to Mannich adducts.

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Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

Cited by 27 publications

References 10 publications

Mycenaflavin A, B, C, and D: Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena haematopus

Mycenaflavin A, B, C, and D: Pyrroloquinoline Alkaloids from the Fruiting Bodies of the Mushroom Mycena haematopus

A comparison between ITS phylogenetic relationships and morphological species recognition within Mycena sect. Calodontes in Northern Europe

Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubin C

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