Solubilization Behavior of Phorbol Esters from Jatropha Oil in Surfactant Micellar Solutions
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  • 作者:Naphatsarnan Phasukarratchai ; Seelawut Damrongsiri…
  • 关键词:Phorbol esters ; Jatropha oil ; Surfactant solubilization
  • 刊名:Journal of Surfactants and Detergents
  • 出版年:2016
  • 出版时间:January 2016
  • 年:2016
  • 卷:19
  • 期:1
  • 页码:29-37
  • 全文大小:717 KB
  • 参考文献:1.Jongschaap REE, Corré WJ, Bindraban PS, Brandenburg WA (2007) Claims and facts on Jatropha curcas L. Plant Research International, Wageningen
    2.Heller J (1996) Physic nut. Jatropha curcas L. Institute of Plant Genetics and Crop Plant Research International Plant Genetic Resources Institute, Gatersleben
    3.Adolf W, Opferkuch HJ, Hecker E (1984) Irritant phorbol derivatives from four Jatropha species. Phytochem 23:129–132CrossRef
    4.Goel G, Makkar HP, Francis G, Becker K (2007) Phorbol esters: structure, biological activity, and toxicity in animals. Int J Toxicol 26:279–288CrossRef
    5.Hirota M, Suttajit M, Suguri H, Endo Y, Shudo K et al (1988) A new tumor promoter from the seed oil of Jatropha curcas L., an intramolecular diester of 12-deoxy-16-hydroxyphorbol. Cancer Res 48:5800–5804
    6.Devappa RK, Rajesh SK, Kumar V, Makkar HPS, Becker K (2012) Activities of Jatropha curcas phorbol esters in various bioassays. Ecotoxicol Environ Saf 78:57–62CrossRef
    7.Li C-Y, Devappa RK, Liu J-X, Lv J-M, Makkar HPS, Becker K (2010) Toxicity of Jatropha curcas phorbol esters in mice. Food Chem Toxicol 48:620–625CrossRef
    8.Aregheore EM, Becker K, Makkar HPS (2003) Detoxification of a toxic variety of Jatropha curcas using heat and chemical treatments, and preliminary nutritional evaluation with rats. S Pac J Nat Appl Sci 21:51–56
    9.Katole S, Saha SK, Sastry VRB, Lade MH, Prakash B (2011) Intake, blood metabolites and hormonal profile in sheep fed processed Jatropha (Jatropha curcas) meal. Anim Feed Sci Technol 170:21–26CrossRef
    10.Devappa R, Makkar HS, Becker K (2011) Jatropha diterpenes: a review. J Am Oil Chem Soc 88:301–322CrossRef
    11.Phasukarratchai N, Tontayakom V, Tongcumpou C (2012) Reduction of phorbol esters in Jatropha curcas L. pressed meal by surfactant solutions extraction. Biomass Bioenergy 45:48–56CrossRef
    12.Devappa RK, Makkar HPS, Becker K (2010) Optimization of conditions for the extraction of phorbol esters from Jatropha oil. Biomass Bioenerg 34:1125–1133CrossRef
    13.Martínez-Herrera J, Siddhuraju P, Francis G, Dávila-Ortíz G, Becker K (2006) Chemical composition, toxic/antimetabolic constituents, and effects of different treatments on their levels, in four provenances of Jatropha curcas L. from Mexico. Food Chem 96:80–89CrossRef
    14.Haas W, Mittelbach M (2000) Detoxification experiments with the seed oil from Jatropha curcas L. Ind Crops Prod 12:111–118CrossRef
    15.Guedes RE, Cruz FdA, Lima MCd, Sant’Ana LDO, Castro RN, Mendes MF (2014) Detoxification of Jatropha curcas seed cake using chemical treatment: analysis with a central composite rotatable design. Ind Crops Prod 52:537–543CrossRef
    16.Rakshit KD, Darukeshwara J, Rathina Raj K, Narasimhamurthy K, Saibaba P, Bhagya S (2008) Toxicity studies of detoxified Jatropha meal (Jatropha curcas) in rats. Food Chem Toxicol 46:3621–3625CrossRef
    17.Nokkaew R, Punsuvon V, Vaithanomsat P (2008) Eliminated phorbol esters in seed oil and press cake of Jatropha curcas L. In: Proceedings of pure and applied chemistry international conference 30th Jan–1st Feb 2008. Sofitel Centara Grand Hotel Bangkok: Kasetsart University, pp 202–206
    18.Devappa R, Maes J, Makkar H, Greyt W, Becker K (2010) Quality of biodiesel prepared from phorbol ester extracted Jatropha curcas oil. J Am Oil Chem Soc 87:697–704CrossRef
    19.Rug M, Ruppel A (2000) Toxic activities of the plant Jatropha curcas against intermediate snail hosts and larvae of schistosomes. Trop Med Int Health 5:423–430CrossRef
    20.Verma M, Pradhan S, Sharma S, Naik SN, Prasad R (2011) Efficacy of karanjin and phorbol ester fraction against termites (Odontotermes obesus). Int Biodeterior Biodegradation 65:877–882CrossRef
    21.Devappa RK, Angulo-Escalante MA, Makkar HPS, Becker K (2012) Potential of using phorbol esters as an insecticide against Spodoptera frugiperda. Ind Crops Prod 38:50–53CrossRef
    22.Chang RL, Han ZT (2000) USA Patent No. US6063814 A
    23.Jones RJ, Sharkis SJ, Miller CB, Rowinsky EK, Burke PJ, May WS (1990) Bryostatin 1, a unique biologic response modifier: anti-leukemic activity in vitro. Blood 75:1319–1323
    24.Mihalik R, Farkas G, Kopper L, Benczur M, Farago A (1996) Possible involvement of protein kinase C-epsilon in phorbol ester-induced growth inhibition of human lymphoblastic cells. Int J Biochem Cell Biol 28:925–933CrossRef
    25.Scher W, Eto Y, Ejima D, Den T, Svet-Moldavsky IA (1990) Phorbol ester-treated human acute myeloid leukemia cells secrete G-CSF, GM-CSF and erythroid differentiation factor into serum-free media in primary culture. BBA Mol Cell Res 1055:278–286
    26.Makkar HPS, Francis G, Becker K (2008) Protein concentrate from Jatropha curcas screw-pressed seed cake and toxic and antinutritional factors in protein concentrate. J Sci Food Agric 88:1542–1548CrossRef
    27.Ribeiro BD, Barreto DW, Coelho MAZ (2015) Use of micellar extraction and cloud point preconcentration for valorization of saponins from sisal (Agave sisalana) waste. Food Bioprod Process 94:601–609CrossRef
    28.Ribeiro B, Barreto D, Coelho M (2014) Recovery of saponins from Jua (Ziziphus joazeiro) by micellar extraction and cloud Point preconcentration. J Surfactants Deterg 17:553–561CrossRef
    29.Rosen MJ (2004) Surfactants and interfacial phenomena. Wiley, New JerseyCrossRef
    30.Jafvert CT, Patricia LVH, Heath JK (1994) Solubilization of non-polar compounds by non-ionic surfactant micelles. Water Res 28:1009–1017CrossRef
    31.Masrat R, Maswal M, Dar AA (2013) Competitive solubilization of naphthalene and pyrene in various micellar systems. J Hazard Mater 244–245:662–670CrossRef
    32.Takeuchi E, Matsuoka K, Ishii S, Ishikawa S, Honda C, Endo K (2014) Solubilization of polycyclic aromatic hydrocarbons in C16E7 nonionic surfactant solutions. Colloid Surf A Physicochem Eng Asp 441:133–139CrossRef
    33.Xiarchos I, Doulia D (2006) Effect of nonionic surfactants on the solubilization of alachlor. J Hazard Mater 136:882–888CrossRef
    34.Muherei MA, Junin R (2008) Mixing effect of anionic and nonionic surfactants on micellization, adsorption and partitioning of nonionic surfactant. Mod Appl Sci 2:3–12CrossRef
    35.Guo H, Liu Z, Yang S, Sun C (2009) The feasibility of enhanced soil washing of p-nitrochlorobenzene (pNCB) with SDBS/Tween80 mixed surfactants. J Hazard Mater 170:1236–1241CrossRef
    36.Shi Z, Chen J, Yin X (2013) Effect of anionic–nonionic-mixed surfactant micelles on solubilization of PAHs. J Air Waste Manag Assoc 63:694–701CrossRef
    37.Zhou W, Zhu L (2004) Solubilization of pyrene by anionic–nonionic mixed surfactants. J Hazard Mater 109:213–220CrossRef
    38.Mu’azu K, Mohammed-Dabo IA, Waziri SM, Ahmed AS, Bugaje IM, Ahmad AS (2013) Development of a mathematical model for the esterification of Jatropha curcas seed oil. J Pet Technol Altern Fuel 4:44–52
    39.Charoensaeng A, Sabatini D, Khaodhiar S (2009) Solubilization and adsolubilization of polar and nonpolar organic solutes by linker molecules and extended surfactants. J Surfactants Deterg 12:209–217CrossRef
    40.Alam M, Matsumoto Y, Aramaki K (2014) Effects of surfactant hydrophilicity on the oil solubilization and rheological behavior of a nonionic hexagonal phase. J Surfactants Deterg 17:19–25CrossRef
    41.Holmberg K, Jönsson B, Kronberg B, Lindman B (2003) Surfactants and polymers in aqueous solution. Wiley, England
    42.Damrongsiri S, Tongcumpou C, Weschayanwiwat P, Sabatini DA (2010) Solubilization of dibutyltin dichloride with surfactant solutions in single and mixed oil systems. J Hazard Mater 181:1109–1114CrossRef
    43.Ranganathan R, Peric M, Medina R, Garcia U, Bales BL, Almgren M (2001) Size, hydration, and shape of SDS/heptane micelles investigated by time-resolved fluorescence quenching and electron spin resonance. Langmuir 17:6765–6770CrossRef
    44.Kandori K, McGreevy RJ, Schechter RS (1989) Solubilization of phenol in polyethoxylated nonionic micelles. J Colloid Interface Sci 132:395–402CrossRef
    45.Parekh P, Singh K, Marangoni DG, Aswal VK, Bahadur P (2012) Solubilization and location of phenol and benzene in a nonlinear amphiphilic EO–PO block copolymer micelles: 1H NMR and SANS studies. Colloid Surf A Physicochem Eng Asp 400:1–9CrossRef
    46.Luning Prak DJ, Jahraus WI, Sims JM, MacArthur AHR (2011) An 1H NMR investigation into the loci of solubilization of 4-nitrotoluene, 2,6-dinitrotoluene, and 2,4,6-trinitrotoluene in nonionic surfactant micelles. Colloid Surf A Physicochem Eng Asp 375:12–22CrossRef
    47.Bernardez LA (2008) Investigation on the locus of solubilization of polycyclic aromatic hydrocarbons in non-ionic surfactant micelles with 1H NMR spectroscopy. Colloid Surf A Physicochem Eng Asp 324:71–78CrossRef
  • 作者单位:Naphatsarnan Phasukarratchai (1) (2)
    Seelawut Damrongsiri (3)
    Chantra Tongcumpou (2) (3)

    1. International Program in Hazardous Substance and Environmental Management, Graduate School, Chulalongkorn University, Bangkok, 10330, Thailand
    2. Center of Excellence for Hazardous Substance Management (HSM), Chulalongkorn University, Bangkok, 10330, Thailand
    3. Environmental Research Institute, Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Industrial Chemistry and Chemical Engineering
    Surfaces and Interfaces and Thin Films
    Polymer Sciences
    Waste Water Technology, Water Pollution Control, Water Management and Aquatic Pollution
    Analytical Chemistry
    Physical Chemistry
  • 出版者:Springer Berlin / Heidelberg
  • ISSN:1558-9293
文摘
Phorbol esters (PEs) are important toxic compounds found in Jatropha curcas oil and pressed seeds. These compounds are tumor promoters; thus, their removal prior to further utilization of the pressed seed is important. This work aimed to investigate the solubilization behavior of PEs and Jatropha oil in nonionic [effect of the ethylene oxide number (EON), carbon-chain length and temperature] and anionic (NaCl addition) surfactant systems. The results reveal that an increase in the EON of the nonionic surfactant molecules, rather than an increase in the carbon-chain length, enhances PE solubilization. The hydrophile-lipophile balance (HLB) value was correlated with PE solubilization for nonionic surfactant solutions. The solubilization of PEs decreased slightly with increasing temperature, in contrast to solubilization of the oil. Moreover, the mole fraction of PE solubilized in the micelle decreased with increasing electrolyte concentration in anionic surfactant solutions. The solubilization behavior of PEs in both nonionic and anionic solutions indicates that PE acts more like a polar compound than a nonpolar compound. In addition, the PEs in nonionic micelles are likely located in the palisade region (i.e., between the head group and the first few carbon atoms of the tail), whereas those in anionic micelles are likely near the outer core of the head group. This finding suggests that a nonionic surfactant with a higher EON has a greater potential to extract PE from Jatropha seeds. If an anionic surfactant is combined as co-surfactant, a small amount of electrolyte should be added to increase PE solubilization.

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