Occurrence of Atromentin and Thelephoric Acid in Cultures of Clitocybe Subilludens

Sullivan, G.; Garrett, Ronald D.; Lenehan, R.F.

doi:10.1002/jps.2600601134

Cited by 11 publications

(4 citation statements)

References 7 publications

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“…It was also confirmed that l -phenyl[U- 14 C]alanine was incorporated into polyporic acid ( 1 ) in fruiting bodies of Hapalopilus rutilans . In cultures of Omphalotus subilludens (= Clitocybe subilludens ) the relative proportion of atromentin to thelephoric acid ( 3 ) decreases with aging; this provides a strong indication that thelephoric acid is derived from atromentin …”

Section: P-terphenylsmentioning

confidence: 70%

“…10 In cultures of Omphalotus subilludens ()Clitocybe subilludens) the relative proportion of atromentin to thelephoric acid (3) decreases with aging; this provides a strong indication that thelephoric acid is derived from atromentin. 19 The discovery that polyporic acid (1) exhibits antileukemic acitivity 16 prompted the synthesis of numerous analogues. [20][21][22] Similarly, atromentin (2) shows significant smooth muscle stimulant activity 23 and proves to be an effective agent with anticoagulant activity.…”

Section: P-terphenylsmentioning

confidence: 99%

“…The red pigment was shown to be 3,6-diphenyl-4,5-methylenedioxy-1,2-benzoquinone, named phlebiarubrone (18), by spectral evidence and alkaline hydrolysis to polyporic acid and formaldehyde. 34,35 Later, phlebiarubrone (18) and a series of hydroxylated derivatives, 4′-hydroxyphlebiarubrone (19), 4′,4′′-dihydroxy-phlebiarubrone (20), and 3′,4′,4′′-trihydroxy-phlebiarubrone (21), were isolated from cultures of Punctularia atropurpurascens (Scheme 3). 36 The structures of phlebiarubrone (18) and its dihydroxy derivative (20) were confirmed by syntheses involving methylenation of the potassium salts of polyporic acid and atromentin, respectively, with methylene sulfate in the presence of sodium bicarbonate.…”

Section: P-terphenylsmentioning

confidence: 99%

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Natural Terphenyls: Developments since 1877

2006

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Section: P-terphenylsmentioning

confidence: 70%

Section: P-terphenylsmentioning

confidence: 99%

Section: P-terphenylsmentioning

confidence: 99%

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Natural Terphenyls: Developments since 1877

2006

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“…The first natural p -terphenyl, polyporic acid, was described as early as 1877 . Derivatives of terphenyl quinone pigments were isolated from basidomycetes, such as Tapinella atrotomentosa (= Paxillus atrotomentosus ), , Omphalotus subilludens (= Clitocybe subilludens ), and Punctularia atropurpurascens , as well as from ascomycetes, e.g., A scocoryne sarcoides and Aspergillus candidus . In 2009, allantofuranone, a fungistatic secondary metabolite, was isolated from cultures of the ascomycete Allantophomopsis lycopodina IBWF58B-05A .…”

mentioning

confidence: 99%

Terphenyl Derivatives from Allantophomopsis lycopodina

et al. 2016

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Three secondary fungal metabolites 1-3 with a benzo[b]naphtho[2,1-d]furan skeleton were isolated from submerged cultures of the ascomycete Allantophomopsis lycopodina. The NMR-based structure elucidation was challenging due to a low H/C ratio of only 0.64 and 0.68, respectively. NMR measurements in two different solvents and the use of NMR experiments such as HSQC-TOCSY and LR-HSQMBC proved to be helpful in this respect. The proposed structures obtained from the comprehensive analysis of the NMR data were verified by comparison of recorded and computed NMR chemical shifts from quantum chemical calculations of several constitutional isomers and were further analyzed with the aid of the DP4 and DP4+ probabilities.

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A Review of the Chemistry and Biological Activities of Natural Colorants, Dyes, and Pigments: Challenges, and Opportunities for Food, Cosmetics, and Pharmaceutical Application

Pasdaran

Zare

Hamedi

et al. 2023

Chemistry & Biodiversity

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Natural pigments are important sources for the screening of bioactive lead compounds. This article reviewed the chemistry and therapeutic potentials of over 570 colored molecules from plants, fungi, bacteria, insects, algae, and marine sources. Moreover, related biological activities, advanced extraction, and identification approaches were reviewed. A variety of biological activities, including cytotoxicity against cancer cells, antioxidant, anti‐inflammatory, wound healing, anti‐microbial, antiviral, and anti‐protozoal activities, have been reported for different pigments. Considering their structural backbone, they were classified as naphthoquinones, carotenoids, flavonoids, xanthones, anthocyanins, benzotropolones, alkaloids, terpenoids, isoprenoids, and non‐isoprenoids. Alkaloid pigments were mostly isolated from bacteria and marine sources, while flavonoids were mostly found in plants and mushrooms. Colored quinones and xanthones were mostly extracted from plants and fungi, while colored polyketides and terpenoids are often found in marine sources and fungi. Carotenoids are mostly distributed among bacteria, followed by fungi and plants. The pigments isolated from insects have different structures, but among them, carotenoids and quinone/xanthone are the most important. Considering good manufacturing practices, the current permitted natural colorants are: Carotenoids (canthaxanthin, β‐carotene, β‐apo‐8′‐carotenal, annatto, astaxanthin) and their sources, lycopene, anthocyanins, betanin, chlorophyllins, spirulina extract, carmine and cochineal extract, henna, riboflavin, pyrogallol, logwood extract, guaiazulene, turmeric, and soy leghemoglobin.

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Occurrence of Atromentin and Thelephoric Acid in Cultures of Clitocybe Subilludens

Cited by 11 publications

References 7 publications

Natural Terphenyls: Developments since 1877

Natural Terphenyls: Developments since 1877

Terphenyl Derivatives from Allantophomopsis lycopodina

A Review of the Chemistry and Biological Activities of Natural Colorants, Dyes, and Pigments: Challenges, and Opportunities for Food, Cosmetics, and Pharmaceutical Application

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