The diterpenes of Dacrydium kirkii

1969 ◽  
Vol 22 (8) ◽  
pp. 1691 ◽  
Author(s):  
RC Cambie ◽  
PK Grant ◽  
C Huntrakul ◽  
RJ Weston
Keyword(s):  
Isopimaric Acid

Examination of the heartwood of Dacrydium kirkii has shown the presence of isopimaradiene, sclarene, cis-biformene, trans-biformene, manoyl oxide, 14,15-bisnorlabd-8(17)-en-13-one, labda-8(17),13-dien-15-ol, manool, isopimaradienol, β-sitosterol, torulosol, sandaracopimaradiene- 3β,19-diol, and isopimaric acid. Two new diterpene alcohols isolated have been shown to be 7α-hydroxymanool (I) and 2β,3β-dihydroxymanoyl oxide (II).

scholarly journals Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives

ChemistryOpen ◽  
2015 ◽  
Vol 5 (1) ◽  
pp. 65-70 ◽  
Author(s):  
Mariya A. Timoshenko ◽  
Yurii V. Kharitonov ◽  
Makhmut M. Shakirov ◽  
Irina Yu. Bagryanskaya ◽  
Elvira E. Shults
Keyword(s):  
Allylic Amination ◽  
Isopimaric Acid ◽  
Amination Reaction ◽  
Synthetic Studies

scholarly journals 1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic acid

2009 ◽  
Vol 65 (6) ◽  
pp. o1429-o1429
Author(s):  
Zhen-Dong Zhao ◽  
Yu-Xiang Chen ◽  
Yu-Min Wang ◽  
Liang-Wu Bi
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Molecular Conformation ◽  
Slash Pine ◽  
Carboxyl Groups ◽  
Isopimaric Acid ◽  
Hydrogen Bonding Interactions ◽  
Cyclohexene Ring

The title compound, also known as isopimaric acid, C20H30O2, was isolated from slash pine rosin. There are two unique molecules in the unit cell. The two cyclohexane rings have classical chair conformations. The cyclohexene ring represents a semi-chair. The molecular conformation is stabilized by weak intramolecular C—H...O hydrogen-bonding interactions. The molecules are dimerized through their carboxyl groups by O—H...O hydrogen bonds, formingR22(8) rings.

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

Synthesis and Cytotoxic Activity of Amides from Isopimaric Acid

2018 ◽  
Vol 54 (4) ◽  
pp. 695-700 ◽  
Author(s):  
Juan-Juan Liu ◽  
Yan-Ju Lu ◽  
Zhen-Dong Zhao ◽  
Shi-Chao Xu ◽  
Liang-Wu Bi
Keyword(s):  
Cytotoxic Activity ◽  
Isopimaric Acid

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.

Diterpenes of Dacrydium bidwillii

1967 ◽  
Vol 20 (5) ◽  
pp. 969 ◽  
Author(s):  
PK Grant ◽  
C Huntrakul ◽  
DRJ Sheppard
Keyword(s):  
Isopimaric Acid

Examination of the heartwood of Dacrydium bidwillii has shown the presence of isopimara-7,15-diene, isopimaradienal, isopimaradienol, manool, torulosol, β-sitosterol, and isopimaric acid. A nor-diterpene isolated was shown to be 18-nor-isopimaradien-4a-ol (I), and this was confirmed by its synthesis from isopimaradienal.

scholarly journals Platelet Antiaggregating Activity and Chemical Constituents of Salvia x Jamensis J. Compton

2008 ◽  
Vol 3 (6) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Angela Bisio ◽  
Giovanni Romussi ◽  
Eleonora Russo ◽  
Nunziatina De Tommasi ◽  
Nicola Mascolo ◽  
...  
Keyword(s):  
Data Analysis ◽  
Platelet Aggregation ◽  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Data ◽  
Chemical Constituents ◽  
Isopimaric Acid ◽  
Phytochemical Study ◽  
Rat Platelets ◽  
Significant Concentration

A phytochemical study has been carried out on the surface exudate of Salvia x jamensis, which showed a significant platelet antiaggregating activity. The known compounds isopimaric acid (2), 14-α-hydroxy-isopimaric acid (3), 3β-hydroxy-isopimaric acid (4), 7,8β-dihydrosalviacoccin (5), betulinic acid (6), and ursolic acid (7) were isolated together with the new diterpene 1. The structure of 1 was determined as 15,16-epoxy-cleroda-3-en-7α,10β-dihydroxy-12,17;19,18-diolide on the basis of spectroscopic data analysis. Among all tested compounds, 2 showed a significant concentration-dependent antiaggregating activity when ADP (3 μM) was used as agonist on rat platelets. Conversely, 1 increased ADP–induced platelet aggregation.

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.

Two New 24-Isopropenyl-lanostanoids from Tillandsia brachycaulos

2003 ◽  
Vol 58 (9-10) ◽  
pp. 649-654 ◽  
Author(s):  
Zulema Cantillo-Ciau ◽  
Gonzalo J. Mena-Rejón ◽  
Esther Quintero-Mármol ◽  
Antonio Jiménez-Díaz ◽  
Leovigildo Quijano
Keyword(s):  
Spectral Analysis ◽  
Chlorogenic Acid ◽  
Significant Activity ◽  
Isopimaric Acid ◽  
Heteronuclear Correlation ◽  
Antifungal Activities ◽  
Antimicrobial And Antifungal Activities

AbstractThe leaves of Tillandsia brachycaulos afforded two novel tetracyclic triterpenoids identified as (24S)-24-isopropenyl-29-nor-5α-lanosta-7-en-3β-ol (1) and (24S)-24-isopropenyl-29-nor- 5α-lanosta-7-en-3-one (2), in addition to the known isopimaric acid (3) and chlorogenic acid (4). Their structures were elucidated on the basis of spectral analysis, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HMQC and HMBC) and by comparison with data in the literature. The antimicrobial and antifungal activities were studied. The compounds did not show significant activity.

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