Fungus Pigments. V. Degradations of Cinnabarin.

Gripenberg, Jarl; Honkanen, Erkki; Patoharju, Ora; Noer, B.; Reio, L.

doi:10.3891/acta.chem.scand.11-1485

Cited by 31 publications

(11 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is the first unequivocal structural assignment of cinnabarin (1) employing 2D NMR spectroscopy. extracted from the HPLC contour plot, displayed UV maxima (λ max ~435 nm) characteristic of the phenoxazone nucleus [3,6,12,13]. The IR spectrum, which was similar to that of 1, once again supported the presence of hydroxy and amine groups (3420 cm -1 ), together with the presence of carbonyl groups (1690 and 1660 cm -1 , C-8 (δ 129.0) and to C-9a (δ 128.2).…”

Section: Isolation and Purification Strategies For Phenoxazone Alkalomentioning

confidence: 77%

“…It has been reported that Australian Aborigines used species of the fungus to treat sore mouths, oral thrush and sore lips [1]. The constituents responsible for the intense color of the fungus have been previously identified as the phenoxazone alkaloid pigments cinnabarin (1) (also known as polystictin), tramesanguin (2) and cinnabarinic acid (3) [2][3][4], with the distribution of these pigments being dependent on the species and season [4]. Phenoxazone pigments have previously been reported from other variants of similar fungi, including Trametes cinnabarina var.…”

mentioning

confidence: 99%

See 1 more Smart Citation

HPLC and NMR Studies of Phenoxazone Alkaloids from Pycnoporus Cinnabarinus

Dias

Urban

2009

Natural Product Communications

View full text Add to dashboard Cite

Crude extracts of the red-orange, bracket fungus Pycnoporus cinnabarinus, collected from five distinct Australian localities were subjected to a chemical and biological profiling study. Subsequent detailed investigation of two of these specimens resulted in the isolation of the new phenoxazone alkaloid, pycnoporin (8), together with cinnabarin (1), tramesanguin (2), and cinnabarinic acid (3). Ergosterol peroxide (11) was also identified from one of the specimens studied. Compounds 1-3 and 8 were elucidated by detailed spectroscopic analyzes, which included the application of elevated temperature-controlled NMR experiments. In addition to the isolation and characterization of 8, this study describes the first successful HPLC purification strategy and complete 2D NMR spectroscopic characterization of compounds 1-3. Also reported are the antioxidant and antiinflammatory activities of the crude extracts of one of the P. cinnabarinus specimens. Compounds 1-3, 8 and 11 displayed varying degrees of antitumor activity while ergosterol peroxide (11) also showed slight antimicrobial and antiviral activities. This is the first report documenting the significant antitumor activity of cinnabarin (1).

show abstract

Section: Isolation and Purification Strategies For Phenoxazone Alkalomentioning

confidence: 77%

mentioning

confidence: 99%

HPLC and NMR Studies of Phenoxazone Alkaloids from Pycnoporus Cinnabarinus

Dias

Urban

2009

Natural Product Communications

View full text Add to dashboard Cite

show abstract

“…sanguineus (L. ex Fr.) Murr., found in tropical and subtropical regions of the Northern and Southern Hemispheres.Three phenoxazinone-type pigments were isolated from Pycnoporus species and their structures elucidated by Gripenberg et al (2)(3)(4)(5) and Cavill et al (6, 7).The chemical structures for cinnabarinic acid (2-amino-3 -0xo-3 H-phenoxazine-1 ,Pdicarboxylic acid) (I), cinnabarin (2-amino-9-hydroxymethyl-3-oxo-3H-phenoxazine-1-carboxylic acid) (11), and tramesanguin (2-amino-l-formyl-3-oxo-3H-phenoxazine -9 -carboxylic acid) (111) are illustrated here.Gripenberg ( 5 ) stated that three different types of phenoxazinone-producing fungi appeared to exist: one producing only cinnabarin, Trametes cinnabarina (Jacq.) Fr.…”

mentioning

confidence: 99%

“…Three phenoxazinone-type pigments were isolated from Pycnoporus species and their structures elucidated by Gripenberg et al (2)(3)(4)(5) and Cavill et al (6,7).…”

mentioning

confidence: 99%

Occurrence and Distribution of Phenoxazinone Pigments in the Genus Pycnoporus

Sullivan¹,

Henry²

1971

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

“…Isatin was purchased from Sigma Chemical Co., St Louis, MO, USA. The isatin analogues were prepared by Brian L. Goodwin by standard methods [14][15][16], modified where necessary. All structures were confirmed by mass spectral analysis [18].…”

Section: Treatmentsmentioning

confidence: 99%

Antipyretic Action of Isatin and Its Analogues in Mice and Rats

Telegdy

Adamik²,

Glover³

2011

View full text Add to dashboard Cite

The effects of isatin (2,3-dioxo-indole) and isatin analogues (5-methylisatin, 6-hydroxyisatin, 7-ethylisatin, N-acety- lisatin) were tested on prostaglandin E2 (PGE2)-induced fever in mice and rats. Two modes of administration were tested. Isatin or an analogue was injected simultaneously with PGE2 and the development of fever was tested, or the test compound was given 30 min following PGE2 administration and the effects on the already existing fever were measured, in mice and in rats. Isatin in a dose of 3.12 mg/kg ip was found to block the development of PGE2-induced fever in mice, while in a dose of 12.5 mg/kg ip it attenuated the existing fever. In rats isatin in a dose of 12.5 mg/kg ip blocked fever initiation, and at 25.0 mg/kg ip attenuated existing PGE2-induced fever. In mice, 5-methylisatin in a dose of 0.21 mg/kg ip blocked the initiation of fever, and at 6.72 mg/kg ip attenuated the existing fever. In rats in a dose of 3.36 mg/kg ip it blocked the development of fever, and at 13.44 mg/kg ip attenuated existing PGE2-induced fever. In mice 5,6-dimetylisatin in a dose of 0.02 mg/kg ip both blocked fever initiation and attenuated the existing fever in mice, in rats in a dose of 0.42 mg/kg ip it blocked the initiation of fever, and at 0.21 mg/kg ip attenuated the existing PGE2-induced fever. In mice 6-hydroxyisatin in a dose of 5.2 mg/kg blocked the development of fever, and at 10.4 mg/kg attenuated the existing fever. In rats in a dose of 10.40 mg/kg ip it blocked fever development and also attenuated the existing fever. In mice, 7-ethylisatin in a dose of 0.02 mg/kg ip both blocked fever initiation and also attenuated the existing fever. In rats, a dose of 0.11 mg/kg both blocked fever initiation and also attenuated the existing fever. In mice, N-acethylisatin in the dose of 0.005 mg/kg blocked fever initiation, while at 1.024 mg/kg it attenuated existing fever, in rats, in a dose of 0.096 mg/kg it blocked fever initiation, and at 0.384 mg/kg attenuated the existing fever. The results demonstrate that 7-ethyl- and N-acetylisatin are the most effective of these compounds both in blocking the development of PGE2-induced fever and also in attenuating existing the PGE 2-induced fever

show abstract

Fungus Pigments. V. Degradations of Cinnabarin.

Cited by 31 publications

References 0 publications

HPLC and NMR Studies of Phenoxazone Alkaloids from Pycnoporus Cinnabarinus

HPLC and NMR Studies of Phenoxazone Alkaloids from Pycnoporus Cinnabarinus

Occurrence and Distribution of Phenoxazinone Pigments in the Genus Pycnoporus

Antipyretic Action of Isatin and Its Analogues in Mice and Rats

Contact Info

Product

Resources

About