Chemistry of Lichen Substances

Asahina, Yasuhiko; Shibata, S.

doi:10.2307/1218225

Cited by 58 publications

(38 citation statements)

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“…The following studies confirm its generality and synthetic usefulness, as seen by the greatly improved preparation of the naturally occurring lichen substance (+)-isousnic acid (1) (4)(5)(6).…”

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confidence: 60%

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Studies in the usnic acid series. IV. The base catalyzed usnic acid – isousnic acid rearrangement. Part II. An improved synthesis of (+)-isousnic acid

Kutney¹,

Sánchez²,

Yee³

1977

Can. J. Chem.

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supporting

confidence: 60%

“…The minor components obtained from the basic treatment of 3 result from both Michael addition of water (solvent) to the C,-C,, double bond and alkali cleavage of the nonenolizable C, carbonyl group producing the C,,-hydroxylated derivative 4 and the unsaturated acid 6 respectively (Fig. 1).…”

mentioning

confidence: 99%

Studies in the usnic acid series. IV. The base catalyzed usnic acid – isousnic acid rearrangement. Part II. An improved synthesis of (+)-isousnic acid

Kutney¹,

Sánchez²,

Yee³

1977

Can. J. Chem.

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“…In previous preliminary investigations (9) it was shown that various microorganisms have the ability to degrade the lichen antibiotic (+)-usnic acid (1) (10)(11)(12) and a more detailed study was now warranted. For this purpose a sample of Pseudomonas was obtained from surface soil samples collected in the Whistler mountain area of British Columbia and further experiments were undertaken.…”

mentioning

confidence: 99%

Studies in the usnic acid series. VII. The biodegradation of (+)-usnic acid by a Pseudomonas species. Isolation, structure determination, and synthesis of (+)-6-desacetylusnic acid

Kutney¹,

Leman²,

Salisbury³

et al. 1977

Can. J. Chem.

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. Can. J. Chem. 55, 2336 (1977). Studies on the biodegradation of (+)-usnic acid (1) by a Pseudomonas species have revealed a novel aromatic deacylation process. The isolated metabolite, (+)-6-desacetylusnic acid (2) is crystalline and its structure is established by means of spectroscopic and chemical methods. The synthesis of 2 from usnic acid (1) is also reported and provides conclusive evidence for the structure of this metabolite.

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“…Chemical structures of secondary metabolites have been previously reported by Culberson (1969) and Asahina and Shibata (1971). …”

Section: Isolation Of Lichen Secondary Metabolitesmentioning

confidence: 96%

In vitroantitumor activities of the lichen compounds olivetoric, physodic and psoromic acid in rat neuron and glioblastoma cells

Emsen

Aslan

Toğar

et al. 2015

Pharmaceutical Biology

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Context Since methods utilised in the treatment of glioblastoma multiforme (GBM) are inadequate and have too many side effects, usage of herbal products in the treatment process comes into prominence. Lichens are symbiotic organisms used for medicinal purposes for many years. There are various anticancer treatments about components of two lichen species used in the present study. Objective Antitumor potential of three lichen secondary metabolites including olivetoric acid (OLA) and physodic acid (PHA) isolated from Pseudevernia furfuracea (L.) Zopf (Parmeliaceae) and psoromic acid (PSA) isolated from Rhizoplaca melanophthalma (DC.) Leuckert (Lecanoraceae) were investigated on human U87MG-GBM cell lines and primary rat cerebral cortex (PRCC) cells for the first time. Materials and methods PRCC cells used as healthy brain cells were obtained from SpragueDawley rats. The treatments were carried out on the cells cultured for 48 h. Cytotoxic effects of different concentrations (2.5, 5, 10, 20 and 40 mg/L) of metabolites on the cells were determined via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) analyses. Total antioxidant capacity (TAC) and total oxidant status (TOS) parameters were used for assessing oxidative alterations. Oxidative DNA damage potentials of metabolites were investigated via evaluating 8-hydroxy-2 0 -deoxyguanosine (8-OH-dG) levels. Results Median inhibitory concentration (IC 50 ) values of OLA, PHA and PSA were 125.71, 698.19 and 79.40 mg/L for PRCC cells and 17.55, 410.72 and 56.22 mg/L for U87MG cells, respectively. It was revealed that cytotoxic effects of these metabolites showed positive correlation with concentration, LDH activity and oxidative DNA damage. Discussion and conclusion The present findings obtained in this study revealed that primarily OLA and then PSA had high potential for use in the treatment of GBM. ARTICLE HISTORY

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Chemistry of Lichen Substances

Cited by 58 publications

References 0 publications

Studies in the usnic acid series. IV. The base catalyzed usnic acid – isousnic acid rearrangement. Part II. An improved synthesis of (+)-isousnic acid

Studies in the usnic acid series. IV. The base catalyzed usnic acid – isousnic acid rearrangement. Part II. An improved synthesis of (+)-isousnic acid

Studies in the usnic acid series. VII. The biodegradation of (+)-usnic acid by a Pseudomonas species. Isolation, structure determination, and synthesis of (+)-6-desacetylusnic acid

In vitroantitumor activities of the lichen compounds olivetoric, physodic and psoromic acid in rat neuron and glioblastoma cells

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