Analysis of Chaulmoogra Oils. IV. <i>Hydnocarpus anthelmintica</i> Oil. V. <i>Taraktogenos kurzii</i> (Chaulmoogra) Oil

Cole, Howard Irving; Cardoso, Humberto T.

doi:10.1021/ja01267a064

Cited by 17 publications

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“…The product was characterized using FT-IR, NMR, and gas chromatography-mass spectrometry (GC-MS). 1 Synthesis of threo-2(R/S),3(R/S)-dibromo cyclopentane-1(R)-methyl undecanoate. A solution of 2-cyclopentene-1(R)-methyl undecanoate (methyl hydnocarpate, 50 g, 0.19 mmol) in chloroform (200 mL) was cooled to 0-5°C.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of dimer and oligomers from (R)‐methyl hydnocarpate

Malkar

Vaidya

Kumar³

2000

J Americ Oil Chem Soc

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We report synthesis and characterization of dimer and oligomer acids from chaulmoogra oil. (R)-Methyl hydnocarpate (methyl ester of the major fatty acid component of chaulmoogra oil) was brominated to give threo-2,3-dibromocyclopentane-1-methyl undecanoate. Formation of two diastereoisomers, viz., threo-2(R),3(R)-dibromocyclopentane-1(R)-methyl undecanoate and threo-2(S),3(S)-dibromocyclopentane-(R)-1-methyl undecanoate, was observed. Dehydrobromination of bromo derivatives using alcoholic KOH gave a cyclopentadiene derivative as intermediate, which underwent Diels-Alder reaction to give dimer and oligomer fatty acids. The products were characterized by ultraviolet, direct exposure probe-mass spectroscopy, 1 H nuclear magnetic resonance (NMR), and 13 C NMR spectroscopic techniques.

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Section: Methodsmentioning

confidence: 99%

“…The chloroform layer was separated and dried over anhydrous Na 2 SO 4 threo-2(R/S),3(R/S)-dibromo cyclopentane-1(R)-methyl undecanoate (76 g, 95% yield) was obtained by distilling off chloroform. The product was then characterized using FT-IR, NMR, and GC-MS. 1 …”

Section: Methodsmentioning

confidence: 99%

Synthesis of dimer and oligomers from (R)‐methyl hydnocarpate

Malkar

Vaidya

Kumar³

2000

J Americ Oil Chem Soc

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“…The classical method for the isolation of the various cyclopentenyl fatty acids, on a preparative scale, involves fractional distillation of the methyl or ethyl esters derived from the total fatty acids of seed oils and subsequent fractional crystallization of the 'free' fatty acids from acetone [12,13,15,16]. This procedure permits oleic acid to be eliminated, but palmitic acid crystallizes with the cyclopentenyl fatty acids [2].…”

Section: Preparative Methodsmentioning

confidence: 99%

The Cyclopentenyl Fatty Acids

Mangold¹,

Spener²

1977

Lipids and Lipid Polymers in Higher Plants

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“…Sleum, belonging to the genus Hydnocarpus (Flacourtiaceae family), is mainly distributed in tropical and subtropical areas. The Bark, seed, leaf and stem of Hydnocarpus have been used for treating leprosy and other skin disorders for thousands of years in India, China and southeast Asia (Cole and Cardoso, ; Cole and Ht, ; Nayer, ; Chellappandian et al ., ). In recent pharmacological studies, extracts of Hydnocarpus demonstrated a variety of in vitro and in vivo activities including anti‐diabetic (Jong‐Anurakkun et al ., ; Lee et al ., ) anti‐inflammatory (Wang, ), hypolipidemic (Sharma and Hall, ), antimicrobial (Bueno Pérez et al ., ) and antioxidant activities (Shi et al ., ), and this has attracted much attention.…”

Section: Introductionmentioning

confidence: 99%

An efficient in vitro and in vivo HPLC method for hydnocarpin in nanomicelles formulation

Feng

Sun

Omari‐Siaw

et al. 2015

Biomedical Chromatography

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For quantitative and other related bioactive studies of hydnocarpin, there is a need to establish an efficient, specific and sensitive analytical method (in vitro and in vivo). In this paper, an efficient HPLC method has been established and validated to analyze hydnocarpin in a nanomicelle formulation for the first time. Various chromatographic conditions for in vitro and in vivo determinations were investigated, with the application examined by pharmacokinetics and tissue distribution studies. The analysis was carried out using an HPLC system with a Waters symmetry C18 column (4.6 × 150 mm, 5 µm) at 25°C with a detecting wavelength of 342 nm. Eluting at a rate of 1.0 mL/min, a 65% methanol and 35% acetic acid solution (0.1%) served as the mobile phase for the in vitro determinations while a 62% methanol and 38% acetic acid solution (0.1%) was used for in vivo analysis with isoliquiritigenin as internal standard. The established in vitro linearity range for hydnocarpin was 0.2-20 µg/mL (R(2) = 0.9996), with the biological (in vivo) samples following the same trend. The accuracy of the method was >99% (in vitro) and 92.4-105.3% (in vivo). Also, the precision met the acceptance criterion. These results indicate that the established method exhibited high specificity, accuracy, linearity and precision. Additionally, this efficient HPLC method was applied to pharmacokinetics and tissue distribution studies.

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Analysis of Chaulmoogra Oils. IV. Hydnocarpus anthelmintica Oil. V. Taraktogenos kurzii (Chaulmoogra) Oil

Cited by 17 publications

References 0 publications

Synthesis of dimer and oligomers from (R)‐methyl hydnocarpate

Synthesis of dimer and oligomers from (R)‐methyl hydnocarpate

The Cyclopentenyl Fatty Acids

An efficient in vitro and in vivo HPLC method for hydnocarpin in nanomicelles formulation

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