Mycenarubins A and B, Red Pyrroloquinoline Alkaloids from the Mushroom <i>Mycena rosea</i>

Peters, Silke; Spiteller, Peter

doi:10.1002/ejoc.200600826

Cited by 39 publications

(66 citation statements)

References 18 publications

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“…[9] However, the presence of a variety of such alkaloids in M. rosea, [3] M. sanguinolenta [4] and in M. haematopus confirms that the occurrence of pyrroloquinoline alkaloids is not restricted to marine sources, but they also appear to be common, in the very least, in some Mycena species.…”

Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 85%

“…It is also noteworthy that mycenarubins 3 and 5 are more stable towards hydrolysis of the iminoquinone moiety than 1. Interestingly, in mycenarubins A (4), B [3] and F (6), the 6-H proton exchanges within a few hours with the NMR solvent D 2 O, whereas 6-H is not exchanged in mycenarubins D (3) and E (5). Mycenarubins containing an iminoquinone at C-7/C-8 can therefore be distinguished from those containing a quinone moiety at C-7/C-8 by 1 H NMR spectroscopy.…”

Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 99%

“…[2] However, at that time the structure of the native main pigment 1 of intact fruiting bodies remained obscure on account of its low stability, although it was assumed that it is closely related to the stable degradation product haematopodin (2). Recently, we isolated red pyrroloquinoline alkaloids from the fruiting bodies of the related species M. rosea [3] and M. sanguinolenta. [4] These results inspired us to reinvestigate the structure of the precursor of 2 and to investigate whether other pyrroloquinoline pigments occur in M. haematopus.…”

Section: Introductionmentioning

confidence: 99%

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Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

Peters¹,

Jaeger²,

Spiteller³

2007

Eur J Org Chem

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Four so far unknown red alkaloid pigments, haematopodin B (1) and the mycenarubins D (3), E (5) and F (6), were isolated from fruiting bodies of Mycena haematopus. The structures of these pyrroloquinoline alkaloids were established by 2D NMR spectroscopic and MS (ESI) methods. Their absolute configurations were determined by comparison of their CD spectra with that of haematopodin (2) or mycenarubin A (4).

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Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 85%

Section: According To the Hrms (Esi) Of 5 With An [M + H]mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

Peters¹,

Jaeger²,

Spiteller³

2007

Eur J Org Chem

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“…The distinct pinkish colouration in M. rosea has been identified as stemming from pyrroloquinolone alkaloid pigments unique to this species (Peters and Spiteller 2007), named Mycenarubin A and B by the authors. According to Spiteller (unpublished), a blue/bluish pigment, which was structurally distantly related, could be found in M. pura (and separate pigments were found in M. pelianthina, too).…”

Section: Differentiation In Colouration Within Calodontes?mentioning

confidence: 99%

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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“…Likewise, this chemsitry, especially the tandem formation of a diketopiperazine and the N- arylation (not necessarily in that order) could provide access to novel structures from readily available precursors such as dipeptides. In addition this route might facilitate the synthesis of a class of compounds known as mycenarubins14 which carry an epimerizable center next to the amide involved in the arylation.…”

mentioning

confidence: 99%

Annulated Diketopiperazines from Dipeptides or Schöllkopf Reagents via Tandem Cyclization−Intramolecular N-Arylation

2010

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Facile CuI-mediated N-arylation of diketopiperazine using the Fukuyama modification of the Ullmann-Goldberg reaction can be exploited in new approaches to enantio-pure polycyclic diketopiperazines from easily assembled dipeptides or functionalized Schöllkopf reagents.Several molecules containing a 2,5-diketopiperazine (1, DKP) moiety show promising biological activities which are helpful in treating human diseases (e.g., 2, 3). 1 However, there is no general method for the synthesis of enantiopure pyrazino[1,2-a]indole-1,4-diones (2), which have potent immunosuppressive and antimicrobial activities. Reported nonstereoselective methods for this important pharmacophore used a stepwise synthesis starting from indole 2-carboxylic acid derivatives. 2 Our studies in the area had its origin in an approach to lyngbyatoxin A, a potent PKC inhibitor, in which we planned to use a biosynthesisinspired 3 N-arylation to construct the 9-memebered lactam ( Figure 2). While investigating the properties of a dipeptide precursor (4, X = Y = Br) for this intramolecular N-arylation, we have uncovered a number of potentially useful transformations that are relevant to the synthesis of functionalized diketopiperazines, and here we report the details of these investigations.Our studies started with the assembly of the indolyldipeptide 13b (Scheme 1). 4 The starting point for the synthesis is a one-step preparation of 4,7-dibromo-indole 5 via the Bartoli protocol. 5 Reaction of 5 with POCl 3 and DMF gives the carboxaldehyde 6, which after BOCprotection of the nitrogen is converted into the dehydroamino acid derivative 12 via a modified Horner-Emmons reaction using the phosphonate 11. 6 Schmidt's phosphonate 11 was prepared by Rh-catalyzed carbene-insertion into an N-H bond of the amide 9. 7 The Horner-Emmons reaction of the aldehyde 7 with the phosphonate 11 under the prescribed procedure gives 71% of the pure Z-dehydrodipeptide 12 after column chromatography. Installation of the additional chiral center in 12 turned out to be more challenging than we anticipated as even the best Rhcatalysts give only modest diastereoselectivity in the asymmetric hydrogenation reaction. Selected results of Rh-catalyzed hydrogenation of 12 with various catalysts are reported in Table 1 With the appropriately protected substrates 13b and 13c in hand we first examined various intramolecular amination procedures to prepare the 9-membered lactam. Our initial attempts focused on Pd-catalyzed N-arylation reactions [9] of 13c, under conditions remniscent of Buchwald's synthesis of dehydrobufotenine. 10 These experiments (Table 2, Supporting Information) 4 were uniformly unsuccessful and lead to no discernable products. Next we turned our attention to the Fukuyama modification 9f of the Ullmann-Goldberg reaction, which he has used very effectively to prepare highly functionalized nitrogen heterocyles. 11 Studies 4 of various substrates quickily revealed that the the substrate 13b, with both amines deprotected, is compatible with the standard conditions...

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Mycenarubins A and B, Red Pyrroloquinoline Alkaloids from the Mushroom Mycena rosea

Cited by 39 publications

References 18 publications

Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

Red Pyrroloquinoline Alkaloids from the Mushroom Mycena haematopus

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

Annulated Diketopiperazines from Dipeptides or Schöllkopf Reagents via Tandem Cyclization−Intramolecular N-Arylation

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