Metabolites of the honey mushroom, Armillariamellea

1987 ◽  
Vol 65 (1) ◽  
pp. 7-14 ◽  
Author(s):  
William A. Ayer ◽  
John B. Macaulay
Keyword(s):  
Liquid Culture ◽  
Fruit Production ◽  
Dehydroabietic Acid ◽  
Resin Acids ◽  
Fungal Metabolites ◽  
Isopimaric Acid ◽  
Levopimaric Acid ◽  
Sandaracopimaric Acid

The fungus Armillariamellea (Vahl ex. Fr.) Kummer is responsible for severe losses in timber and fruit production. The metabolites isolated when certain strains of this fungus are grown in liquid culture have been identified as diterpenoid acids possessing the abietane (1) and pimarane (2) skeletons. These compounds, known collectively as resin acids, have not been reported previously from a fungal source. In addition to the resin acids dehydroabietic acid (3), pimaric acid (4), isopimaric acid (5), and sandaracopimaric acid (6), three additional acids, levopimaric acid endo-peroxide (7), 7-oxodehydroabietic acid (9), and 7-oxo-15-hydroxydehydroabietic acid (10) were obtained. On one occasion three orange pigments, austocystin F (11), averufin (12), and averufanin (13), all previously known fungal metabolites, were isolated.

Norway Spruce Balm: Phytochemical Composition and Ability to Enhance Re-epithelialization In Vitro

Planta Medica ◽  
2020 ◽  
Vol 86 (15) ◽  
pp. 1080-1088
Author(s):  
Thomas Goels ◽  
Elisabeth Eichenauer ◽  
Julia Langeder ◽  
Franziska Hoeller ◽  
Christina Sykora ◽  
...  
Keyword(s):  
Norway Spruce ◽  
Wound Closure ◽  
2D Nmr ◽  
Positive Control ◽  
Dehydroabietic Acid ◽  
Resin Acids ◽  
Flash Chromatography ◽  
Isopimaric Acid ◽  
Diterpene Resin Acids

AbstractThe balm of the Norway spruce (Picea abies) is a well-known traditional herbal medicine used to cure wounds. Even though clinical trials have confirmed its empirical use, the active constituents, their mode of action, and the exact composition of this natural product are still unknown. In this study, the balm was subjected to fractionated extraction and further purified employing flash chromatography, HPLC-PDA-ELSD, preparative and analytical TLC. Hydroxycinnamic acids ( 1– 3), the lignan pinoresinol ( 4), four hydroxylated derivatives of dehydroabietic acid (DHAA) ( 5 –  8), and dehydroabietic acid ( 9) were isolated. Their structures were elucidated by LC-MS, 1D- and 2D-NMR. Four extracts, two commercially available resin acids–pimaric acid ( 10) and isopimaric acid ( 11)–and the isolated compounds were tested for increased re-epithelialization of cell-free areas in a human adult low calcium high temperature keratinocytes monolayer. Lysophosphatidic acid (10 µM) served as positive control and ranged between 100% and 150% rise in cell-covered area related to the vehicle control. Two extracts containing carboxylic acids and non-acidic apolar constituents, respectively, boosted wound closure by 47% and 36% at 10 and 3 µg/mL, respectively. Pinoresinol, DHAA, three of its hydroxylated derivatives, and pimaric and isopimaric acid as well as defined combinations of the hydroxylated DHAA derivatives led to a significantly enhanced wound closure by up to 90% at concentrations between 1 and 10 µM. Overall, lignans and diterpene resin acids, main constituents of Norway spruce balm, are able to increase migration or proliferation of keratinocytes in vitro. The presented data link the phytochemistry of this natural wound healing agent with boosted re-epithelialization.

scholarly journals THE SIBERIAN LARCH GROUP COMPOSITION AND ACID NEEDLES AT DIFFERENT VEGETATION PERIODS

2019 ◽  
pp. 207-214
Author(s):  
Dar'ya Sergeyevna Mikson ◽  
Viktor Ivanovich Roshchin
Keyword(s):  
Fatty Acids ◽  
Group Composition ◽  
Siberian Larch ◽  
Dehydroabietic Acid ◽  
Resin Acids ◽  
Hydroxy Acids ◽  
Isopimaric Acid ◽  
Isopropanol Extract ◽  
Extractive Substances ◽  
Higher Fatty Acids

The research results of the Siberian larch needle extractives are presented in paper. The content of extractive substances from green and yellow needles extracted by organic solvents with different polarities is determined. It is found out that the double increase of the yellow needle extractive substances content soluble in hydrocarbon extractant is observed, whereas it is decreased by 30 per cent when extracted with propan-2-ol. The group composition of needle extracts derived from isopropanol extract by petroleum ether is determined. The neutral substances content in both needle collections is practically the same, although the yellow needles contain less acid “bound” in the form of esters. There is a high content of waxes in the needles, which mainly consist of secondary nonacosanol-10 alcohol. The composition of free and “bound” acids in Siberian larch needles of different vegetation periods is established. The needles are dominated by groups of higher unsaturated C-18 fatty acids. Resin acids are represented by isopimaric acid (isopimaric and sandaracopimaric) and abietic acids: abietic, dehydroabietic and levopiric acids. In yellow needles, the content of dehydroabietic acid is increased quadrupled and the hydroxy acids are identified: 15-hydroxyabietic acid and 15-hydroxyhydroabietic acid. The tri- and tetraenic C-20 acids are identified among higher fatty acids.

The resin acids dehydroabietic acid and isopimaric acid release calcium from intracellular stores in rainbow trout hepatocytes

1999 ◽  
Vol 46 (1) ◽  
pp. 55-65 ◽  
Author(s):  
Christina M.I. Råbergh ◽  
Henrik Lilius ◽  
John E. Eriksson ◽  
Boris Isomaa
Keyword(s):  
Rainbow Trout ◽  
Dehydroabietic Acid ◽  
Resin Acids ◽  
Isopimaric Acid ◽  
Acid Release

The Thermal Behavior of Some Resin Acids at 400–500 °C

1972 ◽  
Vol 50 (14) ◽  
pp. 2224-2229 ◽  
Author(s):  
Ray F. Severson ◽  
Walter H. Schuller
Keyword(s):  
Mass Spectrum ◽  
Thermal Behavior ◽  
Abietic Acid ◽  
Dehydroabietic Acid ◽  
Resin Acids ◽  
Levopimaric Acid

The hot tube pyrolysis of dehydroabietic acid (1) at 400–500 °C was found to produce as major products the three possible A-ring olefins (19-norabieta-4,8,11,13-tetraene (2); 19-norabieta-4(18),8,11,13-tetraene (3); and 19-norabieta-3,8,11,13-tetraene (4)) resulting from the elimination of the carboxylate moiety. The i.r., n.m.r., u.v., and mass spectrum of each olefln was obtained and discussed. The pyrolysis of abietic acid (7) and levopimaric acid (8) under identical conditions was found to yield A-ring olefins; to isomerize to yield varying mixtures of palustric, 7, and neoabietic acids; to dehydrogenate to yield 1; and to eliminate propylene to form deisopropyldehydroabietic acid (15). A mechanism to explain the formation of 15 from the dienoic resin acids is given.

Resin Acids. II. Cationic Cyclization of Isopimaric Acid Derivatives. Partial Synthesis of Isohibane*,1

1965 ◽  
Vol 30 (6) ◽  
pp. 1873-1881 ◽  
Author(s):  
Werner Herz ◽  
Dieter Melchior ◽  
R. N. Mirrington ◽  
P. J. S. Pauwels
Keyword(s):  
Resin Acids ◽  
Partial Synthesis ◽  
Isopimaric Acid ◽  
Cationic Cyclization

Trypanocidal Activity of Oleoresin and Terpenoids Isolated from Pinus oocarpa

2005 ◽  
Vol 60 (9-10) ◽  
pp. 711-716 ◽  
Author(s):  
Julieta Rubio ◽  
José S. Calderón ◽  
Angélica Flores ◽  
Clementina Castro ◽  
Carlos L. Céspedes
Keyword(s):  
Methyl Ester ◽  
Trypanosoma Cruzi ◽  
Acute Infection ◽  
Acid Methyl Ester ◽  
Positive Control ◽  
Dehydroabietic Acid ◽  
Isopimaric Acid ◽  
Acid Methyl ◽  
Pinus Oocarpa

Abstract Fractionation with n-hexane/ethyl acetate (1:1 v/v) by open column chromatography of the oleoresin from Pinus oocarpa Schiede yielded two diterpenes, pimaric acid (1) and dehydroabietic acid (5), the sesquiterpene longifolene (3) and a diterpenic mixture containing pimaric acid (1), isopimaric acid (4) and dehydroabietic acid (5). Subsequently, the isolated compounds, the mixture of 1, 4 and 5, the oleoresin and the dehydroabietic acid methyl ester (2), were tested in vitro against epimastigotes of Trypanosoma cruzi, the causative agent of Chagas disease. The most active compounds were 1, 3 and the oleoresin, being as active as nifurtimox, a drug effective in the treatment of acute infection by American trypanosomiasis and used in this work as positive control.

THE STEREOCHEMISTRY OF THE TETRAHYDROPIMARIC ACIDS

1965 ◽  
Vol 43 (10) ◽  
pp. 2793-2801 ◽  
Author(s):  
J. W. ApSimon ◽  
P. V. Demarco ◽  
J. Lemke
Keyword(s):  
Isopimaric Acid ◽  
Derivatives Of ◽  
Sandaracopimaric Acid

Evidence is presented that the fully reduced derivatives of pimaric acid (I), sandaracopimaric acid (II), and isopimaric acid (III) have trans–anti–trans fused skeletons. The implications of this observation are discussed.

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