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.

Study on Thermal Isomerization of Isopimaric Acid

2013 ◽  
Vol 634-638 ◽  
pp. 440-444 ◽  
Author(s):  
Yu Xiang Chen ◽  
Zhen Dong Zhao ◽  
Yan Gu ◽  
Yan Ju Lu
Keyword(s):  
Thermal Treatment ◽  
Treatment Time ◽  
Decomposition Reaction ◽  
Thermal Isomerization ◽  
Treatment Temperature ◽  
Isomerization Reaction ◽  
Isopimaric Acid ◽  
Isomerization Rate ◽  
Isomerization Mechanism ◽  
Sandaracopimaric Acid

The thermal isomerization reaction of isopimaric acid was studied by a treatment at different temperature of 250 °C, 260 °C and 270 °C for 1-5 h under the protection of nitrogen. The isomerization mechanism of isopimaric acid was illuminated. Isopimaric acid was remarkably isomerized to 8, 15-isopimaric acid and sandaracopimaric acid, the higher thermal treatment temperature combined with longer thermal treatment time, the faster isomerization rate of isopimaric acid was observed. It was found that the isomerization rate of isopimaric acid towards 8, 15-isopimaric acid was faster than to sandaracopimaric acid. The decomposition reaction of pimaric-type acids occurred slightly in conditions of 250 ~ 270 °C.

scholarly journals New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae)

Antibiotics ◽  
2020 ◽  
Vol 9 (4) ◽  
pp. 173 ◽  
Author(s):  
Nicholas J. Sadgrove ◽  
Haytham Senbill ◽  
Ben-Erik Van Wyk ◽  
Ben W. Greatrex
Keyword(s):  
South Africa ◽  
Essential Oil ◽  
Essential Oils ◽  
South African ◽  
Acaricidal Activity ◽  
Chemical Similarity ◽  
Lower Yield ◽  
Isopimaric Acid ◽  
Diterpene Acids ◽  
Sandaracopimaric Acid

In spite of the evidence for antimicrobial and acaricidal effects in ethnobotanical reports of Callitris and Widdringtonia, the diterpene acids from Widdringtonia have never been described and no comparison to the Australian clade sister genus Callitris has been made. The critically endangered South African Clanwilliam cedar, Widdringtonia wallichii (syn. W. cedarbergensis), of the Cederberg Mountains was once prized for its enduring fragrant timbers and an essential oil that gives an aroma comparable to better known Mediterranean cedars, predominantly comprised by widdrol, cedrol, and thujopsene. In South Africa, two other ‘cedars’ are known, which are called W. nodiflora and W. schwarzii, but, until now, their chemical similarity to W. wallichii has not been investigated. Much like Widdringtonia, Callitris was once prized for its termite resistant timbers and an ‘earthy’ essential oil, but predominantly guaiol. The current study demonstrates that the essential oils were similar across all three species of Widdringtonia and two known non-volatile diterpene acids were identified in leaves: the pimaradiene sandaracopimaric acid (1) and the labdane Z-communic acid (2) with a lower yield of the E-isomer (3). Additionally, in the leaves of the three species, the structures of five new antimicrobial labdanes were assigned: 12-hydroxy-8R,17-epoxy-isocommunic acid (4), 8S-formyl-isocommunic acid (5), 8R,17-epoxy-isocommunic acid (6), 8R-17R-epoxy-E-communic acid (7), and 8R-17-epoxy-E-communic acid (8). Australian Callitris columellaris (syn. C. glaucophylla) also produced 1 and its isomer isopimaric acid, pisiferal (9), and pisiferic acid (10) from its leaves. Callitris endlicheri (Parl.) F.M.Bailey yielded isoozic acid (11) as the only major diterpene. Diterpenes 4–6, pisiferic acid (10), spathulenol, and guaiol (12) demonstrated antimicrobial and acaricidal activity.

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.

Synthesis and biological activity of pyridine acylhydrazone derivatives of isopimaric acid

2020 ◽  
pp. 1-11
Author(s):  
Yan-Ju Lu ◽  
Zhen-Dong Zhao ◽  
Yu-Xiang Chen ◽  
Jing Wang ◽  
Shi-Chao Xu ◽  
...  
Keyword(s):  
Biological Activity ◽  
Isopimaric Acid ◽  
Derivatives Of

Synthetic Transformations of Higher Terpenoids. XXXIV.* Preparation of Carboxyl Derivatives of Isopimaric Acid

2014 ◽  
Vol 50 (4) ◽  
pp. 673-680 ◽  
Author(s):  
M. A. Timoshenko ◽  
A. B. Ayusheev ◽  
Yu. V. Kharitonov ◽  
M. M. Shakirov ◽  
E. E. Shul’ts
Keyword(s):  
Isopimaric Acid ◽  
Derivatives Of ◽  
Synthetic Transformations

Synthesis and biological activity of aldehyde derivatives of isopimaric acid

2021 ◽  
Vol 18 ◽  
Author(s):  
Yanju Lu ◽  
Zhendong Zhao ◽  
Yuxiang Chen ◽  
Jing Wang
Keyword(s):  
Inhibitory Concentration ◽  
Inhibitory Effect ◽  
Positive Control ◽  
Klebsiella Pneumonia ◽  
Hep G2 ◽  
Isopimaric Acid ◽  
Streptococcus Pneumonia ◽  
Derivatives Of ◽  
Better Than

: Four series of acylhydrazone derivatives, including halogenated aryl modified acylhydrazone, thiophene, pyrrole and quinoline, were synthesized and characterized. The minimum inhibitory concentrations of the compounds against five bacteria were determined and most of the compounds displayed some degree of antibacterial activity. Isopimaric acid (pyrrole-3-carboxaldehyde) acylhydrazone (3j) exhibited the most potent activity against Streptococcus pneumonia and Klebsiella Pneumonia, with the minimum inhibitory concentration being 3.91 μg/mL. The antimicrobial activity against S. pneumoniae was improved when the pyrrole structure was introduced into isopimaric acid. All heterocyclic acylhydrazone derivatives of isopimaric acid exhibited a good in vitro antitumorial activity at 100 μM. It is concluded that the inhibitory effect of isopimaric acid (2-fluoro-6-methoxybenzaldehyde) acylhydrazone (3d) on Hep G2 and isopimaric acid (3-bromothiophene-2-carbaldehyde) acylhydrazone (3g) on Hep G2 and MDAMB 231 is better than that of the positive control 5-fluorouracil (5-FU) (76.51%), which is a widely used clinical anticancer agent, at 100 μM.

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