Juvenile Hormone Mimics in Conifers. I. Isolation of (−)-cis-4-[1′(R)-5′-Dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic Acid from Douglas-fir Wood

1972 ◽  
Vol 50 (14) ◽  
pp. 2380-2382 ◽  
Author(s):  
I. H. Rogers ◽  
J. F. Manville

The petroleum ether extract from the whole-wood meal of a British Columbia Interior variety of Douglas-fir has yielded a new and potentially useful juvenile hormone mimic, (−)-cis-4-[1′(R)-5′-dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic acid (3a). This compound possesses the opposite steric configuration at C-1′ to that of (+)-juvabione (1a), which has been isolated by others from balsam fir. Also, it occurs exclusively as the free acid. Not all Douglas-firs contain this compound and the biological consequences of its formation are being explored.

1974 ◽  
Vol 52 (7) ◽  
pp. 1192-1199 ◽  
Author(s):  
I. H. Rogers ◽  
J. F. Manville ◽  
T. Sahota

The petroleum ether extract from the whole-wood meal of a number of British Columbia Interior-Intermediate variety Douglas-fir trees have yielded two carboxylic acids (+)-todomatuic acid (3b) and cis-dihydrotodomatuic acid (4b) which as their methyl esters are potentially useful juvenile hormone analogs. These compounds possess the R,R and R stereoconfigurations, respectively. The configuration at C-1′ is opposite to that reported by others for "(+)-juvabione" isolated from Abiesbalsamea grown in Czechoslovakia. Whereas (+)-juvabione naturally occurs as and is the methyl ester of (+)-todomatuic acid (4b), in this variety of Douglas-fir these compounds appear as the free acids. Results of biological assays on certain insects indicate that the methyl ester derivatives of these acids are effective ovicides and juvenilizing hormones.


Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
J Slanina ◽  
L Bøezinová ◽  
H Paulová ◽  
O Humpa

2020 ◽  
Vol 13 ◽  
Author(s):  
Fatma Tuğçe Gürağaç Dereli ◽  
Mert Ilhan ◽  
Esra Küpeli Akkol

Background: The fruits with the seeds of Dracunculus vulgaris Schott. (Araceae) are used against inflammatory diseases in Turkey. Objective: Present study was designed to justify this folkloric usage type of the plant. Therefore, the aim of this study is to investigate the anti-inflammatory activity of D. vulgaris. Methods: Petroleum ether, ethyl acetate and methanol extracts were prepared from the fruits, successively. Carrageenan-, serotonin-, and prostaglandin E2-induced hind paw edema; acetic acid–induced capillary permeability and 12-O-tetradecanoyl-phorbol-13-acetate–induced mouse ear edema models were used to assess the antiinflammatory activity of the extracts. The analgesic activity was experienced by using p-benzoquinone-induced abdominal constriction test. Results: The petroleum ether extract displayed the highest activities in all of the used test models compared with the control group. Therefore, the constituents of this extract were determined by using gas chromatography–mass spectroscopy (GC–MS). Linoleic acid was found to be major constituent of the petroleum ether extract of D. vulgaris. Conclusion: This study has provided some justification for the folkloric use of the plant.


1975 ◽  
Vol 21 (2) ◽  
pp. 463-469 ◽  
Author(s):  
Paul Sroka ◽  
Robert H. Barth ◽  
Lawrence I. Gilbert ◽  
Gerardus B. Staal

1975 ◽  
Vol 26 (2-3) ◽  
pp. 105-111 ◽  
Author(s):  
Kazuo BUEI ◽  
Sumiyo ITO ◽  
Takashi YAMADA ◽  
Shinichi GAMO ◽  
Masaaki KATO

2021 ◽  
Author(s):  
Xierenguli Halike ◽  
Jin-Yu Li ◽  
Pengfei Yuan ◽  
Kaimeiliya Yasheng ◽  
Min Chen ◽  
...  

Brassica rapa L. is one of the most popular traditional food with a variety of biological activities. In this study, the petroleum ether extract of B. rapa was separated by...


Author(s):  
Vinodhini Velu ◽  
Swagata Banerjee ◽  
Vidya Rajendran ◽  
Gaurav Gupta ◽  
Dinesh Kumar Chellappan ◽  
...  

Aims: The present investigation was aimed at exploring the phytoconstituents using Gas Chromatography Mass Spectroscopy and to evaluate antioxidant and anti-inflammatory properties of the leaf extracts. Materials and Methods: The extracts were obtained sequentially with petroleum ether, ethyl acetate and water using soxhlet apparatus. The anti-inflammatory property of the identified compounds using GC- MS spectroscopy was evaluated in silico. The antioxidant activity was performed by DPPH and H2O2 method whereas anti-inflammatory study was carried out by HRBC membrane stabilization method. Terpenoids were found to be major constituents in petroleum ether extract while, phenols and flavonoids were predominantly found in ethyl acetate extract. Results and Discussion: The GC-MS analysis of the extract revealed six major molecules including Squalene, 19β, 28- epoxyleanan-3-ol and 2-tu-Butyl-5-chloromethyl-3-methyl-4-oxoimidazolidine-1-carboxylic acid. The ethyl acetate extract showed a significant antioxidant activity (P<0.01) in both DPPH method (70.87 %) and H2O2 method (73.58%) at 200 µg mL-1 . Increased membrane stabilization of petroleum ether extract was observed in the in vitro anti-inflammatory activity study. A strong relationship between the terpenoid content and anti-inflammatory activity was obtained from the correlation (0.971) and docking study. Conclusion: These results justify T. involucrata to be a rich source of terpenoids with potent antiinflammatory property.


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