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.

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 CHEMICAL COMPOSTION OF TAURUS FIR (Abies cilicica subsp. isaurica) OLEORESIN

2018 ◽  
Vol 42 (1) ◽  
Author(s):  
Ayben Kilic Pekgözlü ◽  
Esra Ceylan
Keyword(s):  
Chemical Composition ◽  
Abietic Acid ◽  
Main Group ◽  
Resin Acids ◽  
Unsaponified Fraction

ABSTRACT The main objective of this study was to determine the chemical composition of both turpintine and colophony parts of Abies cilicica subsp. isaurica (Taurus fir) oleoresin collected from Mersin-Turkey. Colophony of taurus fir was not performed before. Hydro-distillation was applied for the separation of turpentine and colophony. Samples were analyzed separately by FID-GC and GC-MS. The yield of oleoresin was 14,3 % turpentine and 82,5 % colophony. Fourty-six compounds were found in the turpentine where α-pinene (81,2 %) was the major compound with β-pinene (12,6 %). However, in the colophony abietane type resin acids were forming the main group (abietic 46,8%, neoabietic 29,5%). Resin hydrocarbons and terpenes were identified in the unsaponified fraction of colophony of Taurus fir. High α-pinene and abietic acid contents make this oleoresin to be used in pharmacy and chemical industries.

HPLC Determination and MS Identification of Dehydroabietic Acid and Abietic Acid in Propolis

2005 ◽  
Vol 28 (11) ◽  
pp. 1725-1735 ◽  
Author(s):  
K. Hroboňová ◽  
J. Lehotay ◽  
I. Skačáni ◽  
J. Čižmárik
Keyword(s):  
Abietic Acid ◽  
Dehydroabietic Acid ◽  
Hplc Determination

Thermal Behavior of Certain Resin Acids.

1966 ◽  
Vol 11 (1) ◽  
pp. 89-91 ◽  
Author(s):  
Walter H. Schuller ◽  
Carl M. Conrad
Keyword(s):  
Thermal Behavior ◽  
Resin Acids
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