Isolation and purification of azadirachtin from neem (Azadirachta indica) seeds using flash chromatography and high-performance liquid chromatography

Yamasaki, Ryohei; Klocke, James A.; Lee, S.Mark; Stone, Gregory A.; Darlington, Mark V.

doi:10.1016/s0021-9673(00)91483-3

Cited by 61 publications

(33 citation statements)

References 8 publications

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“…Several publications have dealt with different techniques for the separation and identification of products contained in neem extracts [5,6,7,8,9,10,11,12,13,14,15,16]. Separation in these studies involved reversed-phase liquid chromatography (RP-HPLC) [6,8,9,11,12,13,14,15,16], using octadecylsilane (C 18 ) columns and detection by ultraviolet absorption.…”

Section: Introductionmentioning

confidence: 99%

“…Separation in these studies involved reversed-phase liquid chromatography (RP-HPLC) [6,8,9,11,12,13,14,15,16], using octadecylsilane (C 18 ) columns and detection by ultraviolet absorption. These coupled methods are effective for separation and detection of compounds present in the oil extracted from neem but are insufficient to identify all the compounds in insecticide formulations, because of their chemical complexity.…”

Section: Introductionmentioning

confidence: 99%

“…These coupled methods are effective for separation and detection of compounds present in the oil extracted from neem but are insufficient to identify all the compounds in insecticide formulations, because of their chemical complexity. This work employed liquidliquid extraction procedures before separation [5,6,12,13]. Other liquid chromatography techniques, e.g.…”

Section: Introductionmentioning

confidence: 99%

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Analysis of neem oils by LC?MS and degradation kinetics of azadirachtin-A in a controlled environment

Barrek

Paisse

Grenier‐Loustalot

2004

Analytical and Bioanalytical Chemistry

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Since it was first isolated, the oil extracted from seeds of neem (Azadirachtin indica A juss) has been extensively studied in terms of its efficacy as an insecticide. Several industrial formulations are produced as emulsifiable solutions containing a stated titer of the active ingredient azadirachtin-A (AZ-A). The work reported here is the characterization of a formulation of this insecticide marketed under the name of Neem-azal T/S and kinetic studies of the major active ingredient of this formulation. We initially performed liquid-liquid extraction to isolate the neem oil from other ingredients in the commercial mixture. This was followed by a purification using flash chromatography and semi-preparative chromatography, leading to (13)C NMR identification of structures such as azadirachtin-A, azadirachtin-B, and azadirachtin-H. The neem extract was also characterized by HPLC-MS using two ionization sources, APCI (atmospheric pressure chemical ionization) and ESI (electrospray ionization) in positive and negative ion modes of detection. This led to the identification of other compounds present in the extract-azadirachtin-D, azadirachtin-I, deacetylnimbin, deacetylsalannin, nimbin, and salannin. The comparative study of data gathered by use of the two ionization sources is discussed and shows that the ESI source enables the largest number of structures to be identified. In a second part, kinetic changes in the main product (AZ-A) were studied under precise conditions of pH (2, 4, 6, and 8), temperature (40 to 70 degrees C), and light (UV, dark room and in daylight). This enabled us to determine the degradation kinetics of the product (AZ-A) over time. The activation energy of the molecule (75+/-9 kJ mol(-1)) was determined by examining thermal stability in the range 40 to 70 degrees C. The degradation products of this compound were identified by use of HPLC-MS and HPLC-MS-MS. The results enabled proposal of a chemical degradation reaction route for AZ-A under different conditions of pH and temperature. The data show that at room temperature and pH between 4 and 5 the product degrades into two preferential forms that are hydrolyzed to a single product over time and as a function of pH change.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Analysis of neem oils by LC?MS and degradation kinetics of azadirachtin-A in a controlled environment

Barrek

Paisse

Grenier‐Loustalot

2004

Analytical and Bioanalytical Chemistry

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“…Several methods have been employed for isolating azadirachtin and other triterpenoids from the extracts so obtained, including combinations of column and preparative layer chromatography (Butterworth and Morgan, 1972;Siddiqui et al, 1986;Yamasaki et al, 1986). The major compounds of neem kernel extracts and neem oil have been isolated using preparative high performance liquid chromatography (HPLC) (Govindachari et al, 1990(Govindachari et al, , 1992a(Govindachari et al, , b, 1995, but the columns and equipment required are not available in many laboratories.…”

Section: Introductionmentioning

confidence: 99%

Rapid separation of triterpenoids from Neem seed extracts

Jarvis

Morgan

Edwards³

1999

Phytochem. Anal.

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“…Yamasaki et al ( 1986 ) and Schroeder and Nakanishi ( 1987 ) isolated azadirachtins by fl ash chromatography and reported different concentrations. Jarvis et al ( 1999 ) isolated 11 triterpenoids including azadirachtins by supercritical fl uid chromatography.…”

Section: Azadirachtin and Related Compoundsmentioning

confidence: 99%

Efficacy of Major Plant Extracts/Molecules on Field Insect Pests

Gopalakrishnan

Kumari

Vijayabharathi

et al. 2014

Advances in Plant Biopesticides

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Insect pests are considered the major hurdle in enhancing the production and productivity of any farming system. The use of conventional synthetic pesticides has led to the emergence of pesticide-resistant insects, environmental pollution, and negative effects on natural enemies, which have caused an ecological imbalance of the predator-prey ratio and human health hazards; therefore, eco-friendly alternative strategies are required. The plant kingdom, a rich repertoire of secondary metabolites, can be tapped as an alternative for insect pest management strategies. A number of plants have been documented to have insecticidal properties against various orders of insects in vitro by acting as antifeedants, repellents, sterilant and oviposition deterrents, etc. However, only a few plant compounds are applicable at the fi eld level or presently commercialised. Here, we have provided an overview of the broad-spectrum insecticidal activity of plant compounds from neem, Annona , Pongamia , and Jatropha . Additionally, the impact of medicinal plants, herbs, spices, and essential oils has been reviewed briefl y.

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Isolation and purification of azadirachtin from neem (Azadirachta indica) seeds using flash chromatography and high-performance liquid chromatography

Cited by 61 publications

References 8 publications

Analysis of neem oils by LC?MS and degradation kinetics of azadirachtin-A in a controlled environment

Analysis of neem oils by LC?MS and degradation kinetics of azadirachtin-A in a controlled environment

Rapid separation of triterpenoids from Neem seed extracts

Efficacy of Major Plant Extracts/Molecules on Field Insect Pests

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