摘要
茄尼醇(Solanesol)是一种不饱和的九聚异戊二烯醇,主要存在于茄科植物中,其中以烟叶中茄尼醇含量为最高。茄尼醇是合成生物活性的泛醌类物质如辅酶Q_(10)和维生素K_2类的原料,是一种重要的药物中间体。烟叶中化学成分复杂,有许多与茄尼醇结构相近的物质与茄尼醇共同存在,提取与分离茄尼醇具有一定的难度。本文主要研究了以烟叶为原料提取分离纯化茄尼醇的工艺过程。
本文首先研究了烟叶中茄尼醇的分析与检测,建立了以固相萃取技术对茄尼醇样品进行处理,结合HPLC分析检测茄尼醇的方法。采用固相萃取代替传统的多步液-液萃取进行分析样品的制备,减少了样品处理时间,提高了分析效率。采用LC-APCI(+)-MS对烟叶中结合态茄尼醇进行了分析检测,并探讨了结合态茄尼醇在皂化过程中存在形态的变化进行了分析探讨,对其存在的结合态作了初步推断。认为与茄尼醇结合成酯的有机酸的分子量范围在110~170之间。
本文研究了柱浸法浸提烟叶中茄尼醇。经过几种常用试剂的筛选,发现石油醚浸提茄尼醇与其它试剂相比具有提取率高,产物中杂质少的特点。对柱浸法的浸取时间、烟草填充床高径比对茄尼醇的提取效率以及有机溶剂的消耗量进行了考察,采用柱浸提取方法从烟叶粉末中浸提茄尼醇,可以减少浸提单位体积烟叶粉末的石油醚消耗量。同时柱浸法时原料中的粉尘固定在填充床中,不会在过滤过程中产生滤饼,使生产过程变得容易,尤其是采用卷烟厂的烟草粉尘浸提茄尼醇时更加有优势。在制备茄尼醇不皂化物时,采用冷冻处理,使浸膏中的蜡质析出而除去后再皂化,可以使制备茄尼醇不皂化物变得容易,而且茄尼醇损失小。
本文研究了吸附层析分离的过程。在相同溶液浓度和等量吸附介质的条件下,硅胶的穿透点是氧化铝的2倍,表明硅胶对茄尼醇的吸附容量要远高于氧化铝,采用硅胶作为吸附剂,可以增大单位吸附剂的茄尼醇原料处理量。采用硅胶吸附层析从烟叶中分离茄尼醇时,经过TLC分析对洗脱液组成进行初步筛选,然后将筛选得到的吸附剂填料装入不锈钢色谱柱(100mm×6mm..i.d),利用液相色谱系统对溶剂进行系统优化。通过溶剂组成对茄尼醇在硅胶柱上的容量因子、茄尼醇与杂质峰之间的分离度和洗脱剂组成对茄尼醇在硅胶柱上的保留时间进行了考察,发现乙醇/正己烷(1.5/98.5)作为洗脱剂最好。
采用Van Deemter方程考察了在不同洗脱剂流速的情况下,茄尼醇层析分离的理论塔板高度(HETP),确定了最小理论塔板高度和获得最小理论塔板高度时的洗脱剂流速。对两种不同颗粒大小的硅胶填充柱所得到的流速与计算得到的塔板数数据进行拟合,得到Van Deemter方程分别为:粒径200~300目硅胶:H=-19.019+13.191/u+7.46u,当流速为1.3ml/min时,获得最小理论塔板高度0.82mm;粒径300~400目硅胶:H=0.147+0.156/u+0.103u,当流速为1.2ml/min时获得最小理论塔板高度为0.40mm。从理论塔板高度的计算结果可以看出,粒径小的硅胶比粒径大的硅胶理论塔板高度小,即在相同柱高的情况下,采用粒径小的硅胶可以获得更多的理论塔板数,达到更好的分离效果。采用300~400目硅胶对作为吸附剂一次分离得到茄尼醇,纯度为83.0%,得率76.1%。
通过二次层析,采用石油醚洗涤上样后的层析柱,使样品中的色素被洗脱,当色素被去除后,采用丙酮—石油醚(10-90,v/v)将茄尼醇洗脱下来。此方法脱色效果较好,所获得的样品为白色蜡状物质,纯度为91.4%,平均回收率87.4%。
采用自己填装的硅胶色谱柱,在高效液相色谱仪上对茄尼醇的层析过程动力学进行了考察。采用普通速率模型分析了影响茄尼醇分离过程以及茄尼醇分离纯化的因素:1)茄尼醇在硅胶上的吸附采用二次浓度梯度进样获得的色谱图数据,通过计算得到,与静态吸附实验测定物质等温吸附线的方法相比要简单而且容易操作;2)通过模型计算的图谱与实验获得的色谱图进行比较,发现计算与实验结果比较一致。但实验获得的色谱峰有拖尾现象,表明孔内扩散影响比较大;3)通过对色谱峰半峰宽的考察发现,考察发现,当Peclet准数值超过1000时,色谱峰的半峰宽几乎不再随Peclet准数的变化而改变,表明此时轴向扩散系数对色谱峰扩展的影响可以忽略;4)通过分析发现普通速率模型中两个参数Bi和η的乘积在一定的流速下为恒定值,表明物质的液膜传质系数和孔内扩散系数对物质层析过程的贡献的总量是一定的,定义该恒定值为T,其数量级为10~2。并以此考察了Bi和η值的变化对茄尼醇与杂质的色谱峰之间的分离度的影响。当η减小时,Bi增大,孔内扩散成为主要控制因素;当η值增大时则液膜传质系数成为主要影响因素。当孔扩散成为主要控制因素时,物质的色谱峰会出现拖尾,影响物质间的分离;5)采用制备层析一般是在超载的情况下操作的。通过上样量对茄尼醇与杂质色谱峰之间的考察,建立了分离度与上样量之间的线性关系,由此关系可以预测达到理想分离的最大上样量。
以纳滤和亲水膜蒸馏为基础,研究了膜分离过程在茄尼醇提取分离过程中有机溶剂回收中的应用。考察了不同膜材料对茄尼醇制备过程的有机溶剂的通量。发现:1)在0.3MPa的压力条件下,石油醚能够透过聚酰胺纳滤膜,而不能透过聚PAN超滤膜和PVA/PAN复合膜;2)对聚酰胺纳滤膜,通量随压力增加而逐渐增加,当压力增加到0.3MPa时,膜通量达到3.07L/m~2h;3)料液中乙醇的增加减使膜通量减小,而丙酮的含量对膜通量的影响较小;4)对PAN膜和PVA/PAN复合膜,采用膜蒸馏回收有机溶剂,随着铸膜液中PVA浓度的增加,膜的通量逐渐下降。
Solanesol, a polyisoprenoid alcohol, was first isolated from flue-cured tobacco and it is an important source of isoprene units for the synthesis of metabolically active quinones such as coenzyme Q_(10) and vitamin K_2 analogs. Extraction and separation of solanesol from tobacco leaves were studied in this dissertation.
The first part of this dissertation is the summary of bibliographic information of solanesol including the application of solanesol as an important intermediate in the synthesis of medical substances, the form in which solanesol occurred in tobacco, the resource which can be used as materials for extraction solanesol, the technical development in extraction and separation of solanesol. Furthermore, the project of this dissertation was raised and discussed.
In the second part, analysis for solanesol was studied. Including solid-phase extraction (SPE) of solanesol from tobacco leaves coupled high performance liquid chromatography-UV detector (HPLC-UV) for quantitative analysis of solanesol, analysis of solanesol in tobacco leaves. The free and esterified forms of solanesol was studied employed LC-APCI(+)-MS and the bound solanesol was conferred, the molecular weight of fatty acid bounded with solanesol was between 110 and 170.
Extraction of solanesol from tobacco powder employing Column Leaching was studied. The extracting ability of organic solvent, the contact time of solvent with tobacco powder and the ratio of the height of tobacco power column to the diameter were investigated. In the optimized extraction condition, the solvents volume needed to the weight of tobacco was 5:1 (v/v), much smaller than conventional methods.
Enrichment of solanesol from the tobacco extract was studied. The adsorbent was selected through the breakthrough curve of solanesol. The selected adsorbent was put into column and the elution was optimized using HPLC system. Effect of elution consistent on the retention factor, resolution and retention time of solanesol was investigated. Effect of the flow rate of elution on the height equivalent to a theoretical
plate (HETP) was studied to obtain an optimized flow rate during chromatography separation solanesol.
Methods for purifying solanesol was studied. The possibility of using high-speed countercurrent chromatography (HSCCC) was investigated. And solanesol was obtained through rechromatography and crystallization.
Separation process of solanesol on silica gel column was studied using general rate model of chromatography. The range of Peclet number (Pe) was evaluated in which axial dispersion effect could be ignored. Relationship between parameters of
Biot number (Bi ) and η value was studied, and through this relationship the effect
of film mass transfer and pore diffusion was investigated. The sample volume was calculated through the linear relationship between sample and resolution.
The performance of nanofiltration membrane and membrane distillation for organic solvents recovery was investigated. The influence of operation pressure, the consistent of feedstock on the permeation flux of solvent was studied. The results indicated that the permeation flux increased along with the rising of operation pressure. The ascent of ethanol concentration in feedstock decreased the permeation influx . When recovery of organic solvents using membrane distillation, the permeation influx decreased with the concentration increasing of PVA from which the PVA/PAN complex membranes were prepared.
引文
1. Stedman RL, Chemical composition of tobacco and tobacco smoke. Chem Rev, 1968. 68(2): 153-207.
2. Rowland RL, Latimer PH and Giles JA, Flue-cured tobacco. Ⅰ. Isolation of solanesol, and unsaturated alcohol. Journal of the American Chemical Society, 1956. 78: 4680-4683.
3. Carruthers W and Johnstone RAW, Alcohols of tobacco. Solanesol and n-docosanol. Chemistry & Industry (London, United Kingdom), 1960: 867-868.
4. Rowland RL and Giles JA, Flue-cured tobacco. Ⅴ. Polyisoprenoid compounds. Tobacco International, 1960. 4: 29-32.
5. Erickson RE, Shunk CH, Trenner NR, Arison BH and Folkers K, Coenzymes Q. Ⅺ. Structure of solanesol. Journal of the American Chemical Society, 1959. 81: 4999-5000.
6. Wooten JB, Direct detection of solanesol in tobacco by proton and carbon-13 magic angle spinning NMR. Journal of Agricultural and Food Chemistry, 1985. 33(3): 419-425.
7.彭靖里,马敏象等,论烟草废弃物的综合利用技术及其发展前景.中国资源综合利用,2001(8):18-20.
8. Ivanov I and Ognyanov I, Solanesol and its esters on neutral extractive fraction of Bulgarian oriental tobacco. Doklady Bolgarskoi Akademii Nauk, 1965. 18(12): 1123-1126.
9. Rodgman A, Cook LC and Latimer PH, Jr., The composition of cigarette smoke. Ⅱ. Solanesyl and phytosteryl esters. Tobacco International, 1959. 3: 125-128.
10. Rodgman A and Cook LC, The composition of cigaret smoke. Ⅰ. Solanesyl acetate. Tobacco International, 1959. 3: 86-88.
11. Nagaraj G and Chakraborty MK, Lipophilic constituents of Natu tobacco. Ⅳ: b-Sitosterol, solanesol and their esters. Tobacco Research, 1980. 6(2): 121-123.
12. Ruegg R, Gloor U, Goel RN, Ryser G, Wiss O and Isler O, Synthesis of ubiquinone (45) and ubiquinone (50). Helvetica Chimica Acta, 1959. 42: 2616-2621.
13. Grossman JD, Deszyck EJ, Ikeda RM and Bavley A, A study of pyrolysis of solanesol. Chemistry & Industry (London, United Kingdom), 1962: 1950-1951.
14. Britt PF, Buchanan AC, Ⅲ and Owens CV, Jr., Mechanistic investigation into the formation of polycyclic aromatic hydrocarbons from the pyrolysis of terpenes. Preprints of Symposia-American Chemical Society, Division of Fuel Chemistry, 2004. 49(2): 868-871.
15. Ammann JR, Britt PF and Buchanan AC, Ⅲ, Mechanistic investigation into the formation of polycyclic aromatic hydrocarbons from pyrolysis of biomass model compounds. Book of Abstracts, 218th ACS National Meeting, New Orleans, Aug 22-26, 1999: ORGN-494.
16. Lam J, Pedersen BO and Thomasen T, Pyrolytic disintegration of selected tobacco constituents and pyrosynthetic formation of aromatic hydrocarbons from cleavage products formed by pyrolysis. Beitraege zur Tabakforschung International, 1985. 13(1): 1-9.
17. Scholtzhauer WS, Severson RF, Chortyk OT, Arrendale RF and Higman HC, Pyrolytic formation of polynuclear aromatic hydrocarbons from petroleum ether extractable constituents of flue-cured tobacco leaf. Journal of Agricultural and Food Chemistry, 1976. 24(5): 992-997.
18. Watson C, McCraw J, Polzin G and Ashley D, Development of a method to assess cigarette smoke intake. Environmental Science and Technology, 2004. 38(1): 248-253.
19. Ogden MW and Maiolo KC, Collection and determination of solanesol as a tracer of environmental tobacco smoke in indoor air. Environmental Science and Technology, 1989. 23(9): 1148-1154.
20. Benner CL, Bayona JM, Caka FM, Tang H, Lewis L, Crawford J, Lamb JD, Lee ML, Lewis EA et al., Chemical composition of environmental tobacco smoke. 2. Particulate-phase compounds. Environmental Science and Technology, 1989. 23(6): 688-699.
21. Nelson PR, Conrad FW, Kelly SP, Maiolo KC, Richardson JD and Ogden MW, Composition of environmental tobacco smoke (ETS) from international cigarettes and determination of ETS-RSP: particulate marker ratios. Environment International, 1997. 23(1): 47-52.
22. Saint-Jalm Y, Methods for the evaluation of ETS (environmental tobacco smoke). Annales des Falsifications de l'Expertise Chimique et Toxicologique, 1998. 91 (943): 203-213.
23. Bohanon HR, Piade JJ, Schorp MK and Saint-Jalm Y, An international survey of indoor air quality, ventilation, and smoking activity in restaurants: a pilot study. Journal of Exposure Analysis and Environmental Epidemiology, 2003. 13(5): 378-392.
24. Ehmann L, Heusler K, Meystre C, Wieland P, Anner G and Wettstein A, Uber 9. 11-Ungesattigte 16-Methylallopregnene. Uber Steroide 160. Mitt. Helvetica Chimica Acta, 1959. 42(7): 2548-2557.
25. Noll H, Ruegg R, Gloor U, Ryser G and Isler O, Structure of a vitamin K_2 compound from tubercle bacilli and synthesis of higher isoprenologs of the vitamin K_2 series. Helvetica Chimica Acta, 1960. 43: 433-438.
26. Shunk CH, Erickson RE, Wong EL and Folkers K, Coenzymes Q. X. Synthesis of coenzyme Q9, 2,3-dimethyl-5-solanesylbenzoquinone, and a vitamin K analog. Journal of the American Chemical Society, 1959. 81: 5000.
27. Min JH, Lee JS, Yang JD and Koo S, The Friedel-Crafts Allylation of a Prenyl Group Stabilized by a Sulfone Moiety: Expeditious Syntheses of Ubiquinones and Menaquinones. Journal of Organic Chemistry, 2003. 68(20): 7925-7927.
28. Lipshutz BH, Devising an especially efficient route to the 'miracle' nutrient coenzyme Q_(10). Strategies and Tactics in Organic Synthesis, 2004. 4: 269-292.
29.邹志强,符诗聪and刘忠厚,维生素K_2的研究进展.中国骨质疏松杂志,2005.11(3):389-343.
30. Weber P, Vitamin K and bone health, nutrition, 2001. 17(10): 880-887.
31. Chamberlain WJ, Snook ME and Haeberer AF, Analysis of a tumor-inhibiting fraction of tobacco smoke condensate. Journal of Analytical Toxicology, 1978. 2(July-Aug.): 138-140.
32. Ogawa O, Kishi I, Tahara Y and Sugita M, N-solanesyl-N, N'-bis (3,4-dimethoxybenzyl) ethylenediamine malate as anticancer activity potentiator. EP355604, 1990.
33. Suzuki H, Tomida A and Nishimura T, Cytocidal activity of a synthetic isoprenoid, N-solanesyl-N,N'-bis(3,4-dimethoxybenzyl)ethylenediamine, and its potentiation of antitumor drugs against multidrug-resistant and sensitive cells in vitro. Japanese Journal of Cancer Research, 1990. 81(3): 298-303.
34. Tomida A and Suzuki H, Synergistic effect in culture of bleomycin-group antibiotics and N-solanesyl-N,N'-bis(3,4-dimethoxybenzyl)ethylenediamine, a synthetic isoprenoid. Japanese Journal of Cancer Research, 1990. 81(11): 1184-1190.
35. Okamoto Y, Tsuji M and Yamazaki H, (S)-2,3-dihydropolyprenols and, (S)-2,3-dihydropolyprenyl monophosphates, method of preparation and use in inhibiting the metastasis of cancers. EP583572, 1994.
36. Tsuji M and Fukutomi R, Preparation of (2Z)-solanesol as antihypertensive, antihyperlipidemic, and antitumor agent. JP06065128, 1994.
37. Ishihara M, Takayama F, Toguchi M, Nakano K, Yasumoto E, Nakayachi T, Satoh K and Sakagami H, Cytotoxic activity of polyprenylalcohols and vitamin K_2 derivatives. Anticancer Research, 2000. 20(6B): 4307-4313.
38.赵瑾,卜站伟,刘洋,王超杰,茄呢基氮芥衍生物的合成及生理活性.应用化学,2006.23(5).
39.王超杰,宋金勇,赵瑾,二元酸茄呢醇乳糖和麦芽糖糖酯合成及生理活性测试研究.有机化学,2003.23(10):1102-1106.
40.王超杰,王玉霞,赵瑾,孙剑,酰胺型茄呢醇衍生物的合成与生理活性.应用化学,2005.22(1):50-54.
41.王超杰,宋金勇,赵瑾,孙心齐,二元酸茄呢醇乙酰葡萄糖二酯的合成及其生物活性.应用化学,2003.20(8):754-759.
42. Tahara Y, Nagai M, Kogure K, Kawase S and Yamaguchi T, Anti-ulcer agent. DE2812978, 1979.
43. Yamada K, Tahara Y, Toyoda M, Irino O and Misaki N, Preparation of antiulcer isoprenoid derivatives and pharmaceutical compositions containing them. EP304842, 1989.
44. Tawara Y, Takahashi T, Koyama H, Suzuki Y and Hagiwara K, Isoprenyl benzoates. JP62016450, 1987.
45. Yamamoto H and Shiraki K, Preparation of poly(prenyl)phenyl sulfates as reverse transcriptase inhibitors for treatment of AIDS. JP01294660, 1989.
46. Stevenson J, Hemming FW and Morton RA, Intracellular distribution of solanesol and plastoquinone in green leaves of the tobacco plant. Biochemical Journal, 1963. 88(1): 52-56.
47. Ellington JJ, Schlotzhauer PF and Schepartz AI, Lipid distribution in flue-cured tobacco plants. Journal of Agricultural and Food Chemistry, 1978. 26(2): 407-410.
48. Ran CVN, Prabhu SR, Raju KS and Kumar DG, Influence of plant growth on the distribution of solanesol in tobacco green leaf. Tobacco Research, 2000. 26(1): 47-50.
49. Vidal B and Tancogne J, Total solanesol in contents of different types of tobacco: effect of some cultural practices on solanesol content in P.B. tobacco. Annales du Tabac, Section 2, 1982. 17: 93-103.
50. Burton HR, Leggett E and Phillips RE, Factors influencing the concentration of solanesol in Burley tobacco. Beitraege zur Tabakforschung International, 1989. 14(5): 313-320.
51. Schepartz AI, Ellington JJ and Burk LG, Catalase activity and lipid content of leaves from normal and sterile-flowered tobacco plants. Phytochemistry, 1978. 17(10): 1787-1788.
52. Rao CVN and Chakraborthy MK, Variations in solanesol levels among tobacco stalk positions, growth stages and air curing. Tobacco International, 1986. 188(12): 142-143.
53. Chotinuchit P and Puangnak W, Major chemical changes during flue-curing of Thai flue-cured tobacco. Thai Journal of Agricultural Science, 1987. 20(2): 121-130.
54. Rao CVN and Chakraborty MK, Phytochemicals from tobacco wastes. 1. Survey of raw materials. Tobacco Research, 1978. 4(1): 52-58.
55.赵春建,李春英,付玉杰,祖元刚,废次烟叶中茄尼醇的超声提取及HPLC分析测定.应用化学,2005.22(11):1265-1267.
56.岑波,段文贵,从废次烟草中提取茄尼醇的新工艺研究.广西大学学报:自然科学版,2002.27(3):240-242.
57.郑松明,高勇,从废次烟叶中分离茄尼醇、烟草提取物和萃余物的综合利用工艺.CN1843230,2006.
58.俞晓慧,邱运仁,废次烟叶中茄尼醇萃取技术.中国烟草科学,2006.27(2):10-11.
59. Mold JD and Booth JS, Isolation of solanesol from cigaret smoke. Tobacco Sci, 1957. 1: 38-39.
60. Toyoda M, Fukawa H and Shimizu T, Plant polyisoprenoids. Ⅰ. Polyisoprenols of silkworm feces and mulberry leaf. Nippon Nogei Kagaku Kaishi, 1969. 43(10): 688-693.
61.周长新,莫建霞,张相宜,肖昌钱,翁林佳,一种高纯度茄尼醇的制备方法[P]2007.
62. Asahina, Kato M, Fukawa H and Hideaki, Process for the manufacture of solanesol. US4013731, 1975..
63. Toyoda M, Asahina M, Fukawa H and Shimizu T, Isolation of new acyclic C25-isoprenyl alcohol frompotato leaves. Tetrahedron Letters, 1969(55): 4879-4882.
64.扈建民,一种从马铃薯叶中提取茄尼醇的方法.CN1712392,2005.
65.赵瑾,王超杰,孙心齐,高效液相色谱法测定烟叶中茄尼醇的含量.色谱,1997.15(6):544-545.
66.王幼君,李淑芬,茄尼醇和尼古丁的提取与工艺研究.天津化工 2003.17(3):37-40.
67.孙心齐,赵瑾等,从废次烟叶中提取茄尼醇的研究.河南大学学报:自然科学版,1995.25(2):37-40.
68.郑奎玲,余丹梅,废弃烟叶的综合利用现状.重庆大学学报:自然科学版,2004.27(3):61-64.
69. Rowland RL and Latimer PH, Flue-cured tobacco. Ⅳ. Isolation of solanesyl esters. Tobacco International, 1959. 3: 1-3.
70. Nisshin Flour Milling Co. L, Isolation of polyprenoid ketones from plants. JP56025129, 1981.
71. Olmez H and Bekdemir Y, Recovery of phytochemicals from tobacco wastes. Doga: Turk Kimya Dergisi, 1991. 15(2): 140-145.
72. Yamane H, Effective extraction of solanesol from tobacco leaves. JP2006219438, 2006.
73.张德玉,用霉烟或碎烟末制备茄尼醇.CN1056486,1991.
74.夏士朋,一种从马铃薯叶和废弃烟叶中提取纯化茄尼醇的方法.CN1762940,2006.
75.吴井峰,从提取过烟碱的烟草中提取茄呢醇的方法.CN1115751,1996..
76.郑奎玲,张万辉,聂运寿,从废次烟叶中同时提取茄尼醇和烟碱的实验.贵州师范大学学报:自然科学版,2004.22(2):81-83.
77.陶云海,任周阳,云南废次烟叶中茄尼醇的提取及含量测定.云南大学学报:自然科学版,2002.24(2):151-152.
78.张海波,王洪新等,废次烟叶中茄尼醇的提取与测定.河南工业大学学报:自然科学版,2005. 26(2):44-47.
79.祖元刚,杨磊,祖柏实等,一种从烟草中提取茄尼醇的方法.CN1724492,2006.
80. Park OS, Isolation of solanesol from Korean native tobacco. Saengyak Hakhoechi, 1981. 12(4): 211-214.
81. Rao CVN and Chakraborty MK, Solanesol from tobacco waste. Research and Industry, 1979. 24(2): 83-86.
82.张德玉,张海,用霉烟或碎烟末提取茄尼醇的工艺方法.CN1087076,1994.
83.张伟和,史铁军,邢文兰,一种茄尼醇的生产方法.CN1118775,1996.
84.傅强,蒋才良,马世学,一种从烟草中提取茄尼醇的方法及设备.CN1108641,1995.
85.祖元刚,赵春建,付玉杰等,一种从烟叶中提取纯化茄尼醇的方法.CN1534008,2004.
86.张征,武永昆,杨睿,林军,微波辅助萃取废烟叶中茄尼醇工艺研究.云南化工,2005.32(1):7-10.
87. Zhou HY and Liu CZ, Microwave-assisted extraction of solanesol from tobacco leaves. Journal of Chromatography, A, 2006. 1129(1): 135-139.
88. Keca M, Gross S, Malnar I, Kalodera Z and Malojcic R, Isolation of solanesol from tobacco (Nicotiana tabacum L.) by classic extraction and ultrasound extraction. Farmaceutski Glasnik, 1997. 53(6): 173-182.
89.杨群力,吴建华,茄尼醇的提取工艺.CN1294111,2001.
90.王振锟,超临界多元流体萃取精馏烟草的工艺及装置.CN1302568,2001.
91.李烈,马振元,丛晓东,超临界CO2从烟叶中萃取茄呢醇的工艺研究.中国药科大学学报,2002.33(4):351~353.
92.张歆,倪晋仁,黄文,超临界CO2萃取烟草中茄尼醇.精细化工,2006.23(5):480-482,501.
93.张海波,王洪新,烟叶中茄尼醇的超临界CO2萃取.烟草科技,2005(5):29-31.
94.李文松,杨运泉,段正康,刘文英,夹带剂在超临界萃取烟草有效成分中的应用.精细化工中间体,2005.33(6):11-13.
95.位华,宓鹤鸣,柳正良,超临界流体萃取结合柱色谱法从废次烟叶中分离纯化茄尼醇的研究.中草药 2005.36(5):690-692.
96.胡小玲,管萍,赵亚梅,一种提取高纯度茄尼醇的方法.CN1817834,2006.
97.罗波,侯金荣,侯金春等,亚临界DME萃取废弃烟草的方法.CN1682613,2005.
98.薛华欣,陈建民,周新光,一种清洁制备高纯度茄尼醇的方法.CN1626489,2005.
99. Hassam SB, Preparative isolation of [U-14C]solanesol from carbon-14 dioxide-chamber grown tobacco. Journal of Labelled Compounds and Radiopharmaceuticals, 1985. 22(12): 1261-1271.
100. Toyoda M, Asahina M, Fukawa H and Shimizu T, Plant polyisoprenoids. Ⅲ. Polyisoprenols of potato leaves. Nippon Nogei Kagaku Kaishi, 1970. 44(6): 257-261.
101.夏薇,俞迪虎,陈新志,废次烟叶浸膏中茄尼醇的提取.中国医药工业杂志,2003.34(7):328-329.
102. Snook ME, Sverson RF, Arrendale RF, Fortson PJ and Chortyk OT, Behavior of hydrolyzed tobacco leaf lipids during gel chromatography. Tobacco Science, 1979. 23(35-42): 113-117.
103. Cook CE, Twine ME, Tallent CR, Harper I et al., An examination of the hexane extract of flue-cured tobacco involving gel-permeation chromatography. Phytochemistry (Elsevier), 1969. 8(6):1025-1033.
104.胥克亮,马世学,一种提纯茄尼醇的方法.CN1345711,2002.
105.陈恬,一种茄尼醇的纯化方法.CN1772720,2006.
106.徐环昕,江邦和,季华,沈永雷,刘坐镇,一种提取制备茄尼醇的方法.CN1810747 2006.
107. Nisshin Flour Milling Co. L, Isoprenoids. JP56095124, 1981.
108.杨雪峰,一种高纯茄尼醇的生产方法.CN1686988,2005.
109.祖元刚,杨磊,祖柏实,一种连续中压柱层析制备高纯度茄尼醇的方法.CN1724493,2006.
110.孔宁川,唐自文,一种对烟草浸膏深加工制烟草净油及富集茄尼醇的方法.CN1400300,2003..
111. Asahina M, Kato H and Fukawa H, Solanesol from potato leaves. DE2019835, 1970.
112. Koho KT, Substance purification. JP54046733, 1981.
113. Fukawa H, Toyoda M, Shimizu T and Murohashi M, Isolation of new isoprenyl alcohols from silkworm feces. Tetrahedron Letters, 1966(49): 6209-6213.
114.蒋文伟,李晶晶,赖崇伟等,液液两相提取高含量茄尼醇浸膏的方法.CN1742709,2006.
115. Tawara T, Matsushima S, Ninomiya N, Hashimoto T, Terada I and Shimizu Y, Preparation of solanesol from tobacco extracts. JP63190840, 1988.
116. Zhao Y and Du Q, Separation of solanesol in tobacco leaves extract by slow rotary counter-current chromatography using a novel non-aqueous two-phase solvent system. Journal of Chromatography A. 2007, 1151 (1-2): 193-196.
117. Du Q, Wang D and Ito Y, Preparation of solanesol from a tobacco leaf extract using high speed countercurrent chromatography. Journal of Liquid Chromatography & Related Technologies, 2006. 29(17): 2587-2592.
118. Prabhu SR, Mahendra K, Rao CVN, Raj K, Srivastava S and Bhaduri AP, Process for purification of solanesol (95+%) from crude/enriched extracts of tobacco green leaf/tobacco cured leaf/tobacco waste. IN2002-DE1071, 2005.
119.王发森,刘涛,从马铃薯叶中提取高纯茄尼醇的方法.CN1800124,2006.
120.李祥庆,从低含量茄尼醇浸膏中提取高纯茄尼醇的方法.CN1821196,2006.
121. Kim KS, Separation and purification method of solanesol by precipitating solanesol from unsaponifiable product, extracting solanesol extract, and re-precipitating solanesol crystal. KR2006086000, 2006.
122. Takemura M and Amano M, Solanesol from tobacco leaf extracts. JP78-45260, 54138510, 1979.
123.顾正桂,减压蒸馏与液萃取及结晶相结合提取茄尼醇的方法.CN1807374,2006.
124. Toyoda H, Fukawa H, Seo H and Shimizu T, Prenyl alcohols of 9-12 isoprene units. JP45013823, 1970.
125.袁增良,申醒,王国平等,一种纯化茄尼醇的方法.CN1736971,2006.
126.马震,一种高纯茄尼醇的提取方法及异癸异戊二烯醇的合成.CN1629115,2005.
127. Choi WS, Synthesis of solanesol from tobacco leaves by simple solvent extraction. KR2006086000, 2006.
1. Sheen SJ, Davis DL, DeJong DW and Chaplin JF, Gas-liquid chromatographic quantification of solanesol in chlorophyll mutants of tobacco. Journal of Agricultural and Food Chemistry, 1978. 26(1): 259-262.
2.于华忠,龙维珍,饶立群,曹庸,李国章,张爱萍,TLC法测定烟叶中茄尼醇的含量.四川食品与发酵 2006.42(3):58-60.
3.李烈,马振元,钱秋霞,丛晓东,薄层扫描法测定烟叶中茄呢醇的含量.中草药,2002.5:420-421.
4.刘快之,李德亮,薄层分离—库仑滴定法测定茄尼醇.分析化学,1999.27(1):34-37.
5.刘快之,李德亮,陈伯森,孙心齐,赵瑾,库仑滴定法测定烟叶提取物中茄尼醇.化学研究,1997.8(3):56-59.
6.郑奎玲,一种分离提纯和测定烟叶提取物中茄尼醇含量的方法.贵州师范大学学报:自然科学版,2003.21(1):7-9.
7.赵春建,李春英,付玉杰,祖元刚,废次烟叶中茄尼醇的超声提取及HPLC分析测定.应用化学,2005.22(11):1265-1267.
8.郭鹏,李小花,汪选斌,游安,李能丽,反相高效液相色谱法测定烟叶提取物中茄尼醇的含量.中国药房,2006.17(19):1498-1500.
9.陈勇,蔡铭,瞿海斌,程翼宇,RP—HPLC法测定烟叶中茄尼醇的含量.药物分析杂志,2006.26(8):1094-1096.
10.王英娟,李多伟,索志荣,贾敬芬,RP—HPLC法测定烟草愈伤组织中茄尼醇的含量.药物分析杂志,2006.26(8):1091-1093.
11.柳先平,陈军辉,李磊,殷月芬,王小如,黎先春,RP-HPLC-UV法测定不同产地烟叶中茄尼醇的含量.天然产物研究与开发,2006.18(B06):156-159.
12.张明时,黄俊学,高效液相色谱法测定烟叶提取物中茄尼醇的含量.色谱,2001.19(5):470-471.
13.孙心齐,王金中,于丽,张伟,赵飞,高效液相色谱内标法定量测定茄呢醇.化学研究,2002.13(4):27-29.
14.武永昆,张征,苏鹏娟,尹海川,林军,反相高效液相色谱法测定烟叶中茄尼醇的含量.云南民族大学学报:自然科学版,2005.14(3):275-277.
15.姚文,宋爱民,栾和林,废弃烤烟中游离茄尼醇的测定.矿冶,1994.3(3):97-99.
16.张振,茄尼醇提取分离和测定方法.贵州化工 2006.31(2):16-18.
17.边清泉,王秀峰,何志坚,李松,烟草提取物中茄尼醇含量测定方法的研究.绵阳师范学院学报,2006.25(2):30-32,51.
18.李晓露,李宁,张雪霞,王健,刘刚叁,高效液相色谱法测定烟叶提取物中茄尼醇的含量.河北化工,2006.29(6):45-46.
19.赵瑾,王超杰,孙心齐,高效液相色谱法测定烟叶中茄尼醇的含量.色谱,1997.15(6):544-545.
20.李烈,钱秋霞,丛晓东,用高效液相色谱—蒸发光散射检测法测定烟叶中茄呢醇的含量.药物分析杂志,2002.22(2):103-105.
21. Zhou H-Y and Liu C-Z, Rapid determination of solanesol in tobacco by high-performance liquid chromatography with evaporative light scattering detection following microwave-assisted extraction. Journal of Chromatography B, 2006. 835(1-2):119-122.
22. Chen J, Liu X, Xu X, Lee FS-C and Wang X, Rapid determination of total solanesol in tobacco leaf by ultrasound-assisted extraction with RP-HPLC and ESI-TOF/MS. Journal of Pharmaceutical and Biomedical Analysis, 2007. 43(3):879-885.
23. Zhao C, Li C and Zu Y, Rapid and quantitative determination of solanesol in Nicotiana tabacum by liquid chromatography-tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis. In Press, Corrected Proof:885.
24. Huck CW and Bonn GK, Recent developments in polymer-based sorbents for solid-phase extraction. Journal of Chromatography A, 2000. 885(1-2):51-72.
25. Rostagno MA, Palma M and Barroso CG, Solid-phase extraction of soy isoflavones. Journal of Chromatography A, 2005. 1076:110-117.
26. Lin L-q, Zhang J, Fu Q, He L-c and Li Y-c, Concentration and extraction of sinomenine from herb and plasma using a molecularly imprinted polymer as the stationary phase. Analytica Chimica Acta, 2006. 561:178-182.
27. Adahchour M, Wiewel J, Ramon Verdel RJJV and Brinkman UAT, Improved determination of flavour compounds in butter by solid-phase (micro)extraction and comprehensive two-dimensional gas chromatography. Journal of Chromatography A, 2005. 1086:99-106.
28. Azadmard-Damirchi S and Dutta PC, Novel solid-phase extraction method to separate 4-desmethyl-, 4-monomethyl-, and 4,4'-dimethylsterols in vegetable oils. Journal of Chromatography A, 2006. 1108:183-187.
29. Kiss GAC, Forgacs E, Cserhati T, Candeias M, Vilas-Boas L, Bronze R and Spranger I, Solid-phase extraction and high-performance liquid chromatographic separation of pigments of red wines. Journal of Chromatography A, 2000. 889:51-57.
30. Hennion M-C, Solid-phase extration: method development, sorbent, and coupling with liquid chromatography. Journal of Chromatography A, 1999. 856:3-54.
31. Scholtzhauer WS, Severson RF, Chortyk OT, Arrendale RF and Higman HC, Pyrolytic formation of polynuclear aromatic hydrocarbons from petroleum ether extractable constituents of flue-cured tobacco leaf. Journal of Agricultural and Food Chemistry, 1976. 24(5):992-997.
32. Rowland RL and Latimer PH, Flue-cured tobacco. IV. Isolation of solanesyl esters. Tobacco International, 1959. 3:1-3.
1.赵瑾,王超杰,孙心齐,高效液相色谱法测定烟叶中茄尼醇的含量.色谱,1997.15(6):544-545.
2.王幼君,李淑芬,茄尼醇和尼古丁的提取与工艺研究.天津化工 2003.17(3):37-40.
3.孙心齐,赵瑾等,从废次烟叶中提取茄尼醇的研究.河南大学学报:自然科学版,1995.25(2):37-40.
4.郑奎玲,余丹梅,废弃烟叶的综合利用现状.重庆大学学报:自然科学版,2004.27(3):61-64.
5.张德玉,用霉烟或碎烟末制备茄尼醇.CN1056486,1991.
6.岑波,段文贵,从废次烟草中提取茄尼醇的新工艺研究.广西大学学报:自然科学版,2002.27(3):240-242.
7.夏士朋,一种从马铃薯叶和废弃烟叶中提取纯化茄尼醇的方法.CN1762940,2006.
8.姚文,宋爱民,栾和林,废弃烤烟中游离茄尼醇的测定.矿冶,1994.3(3):97-99.
9.姚文,武荣成,SOT溶剂体系从烟渣中萃取茄尼醇的研究.矿冶,1995.4(4):93-96.
10.吴井峰,从提取过烟碱的烟草中提取茄呢醇的方法.CN1115751,1996..
11. Yamane H, Effective extraction of solanesol from tobacco leaves. JP2006219438, 2006.
12.张海波,王洪新等,废次烟叶中茄尼醇的提取与测定.河南工业大学学报:自然科学版,2005.26(2):44-47.
13.陶云海,任周阳,云南废次烟叶中茄尼醇的提取及含量测定.云南大学学报:自然科学版,2002.24(2):151-152.
14.张德玉,张海,用霉烟或碎烟末提取茄尼醇的工艺方法.CN1087076,1994.
15.张伟和,史铁军,邢文兰,一种茄尼醇的生产方法.CN1118775,1996.
16.傅强,蒋才良,马世学,一种从烟草中提取茄尼醇的方法及设备.CN1108641,1995.
17.张征,武永昆,杨睿,林军,微波辅助萃取废烟叶中茄尼醇工艺研究.云南化工.2005.32(1):7-10.
18. Zhou H-Y and Liu C-Z, Microwave-assisted extraction of solanesol from tobacco leaves. Journal of Chromatography, A, 2006. 1129(1): 135-139.
19. Keca M, Gross S, Malnar I, Kalodera Z and Malojcic R, Isolation of solanesol from tobacco (Nicotiana tabacum L.) by classic extraction and ultrasound extraction. Farmaceutski Glasnik, 1997. 53(6): 173-182.
20.杨群力,吴建华,茄尼醇的提取工艺.CN1294111,2001.
21.王振锟,超临界多元流体萃取精馏烟草的工艺及装置.CN1302568,2001.
22.李烈,马振元,丛晓东,超临界CO2从烟叶中萃取茄呢醇的工艺研究.中国药科大学学报,2002.33(4):351~353.
23.张歆,倪晋仁,黄文,超临界CO2萃取烟草中茄尼醇.精细化工,2006.23(5):480-482,501.
24.张海波,王洪新,烟叶中茄尼醇的超临界CO2萃取.烟草科技,2005(5):29-31.
25.李文松,杨运泉,段正康,刘文英,夹带剂在超临界萃取烟草有效成分中的应用.精细化工中间体,2005.33(6):11-13.
26.位华,宓鹤鸣,柳正良,超临界流体萃取结合柱色谱法从废次烟叶中分离纯化茄尼醇的研究.中草药 2005.36(5):690-692.
27.胡小玲,管萍,赵亚梅,一种提取高纯度茄尼醇的方法.CN1817834,2006.
28.罗波,侯金荣,侯金春等,亚临界DME萃取废弃烟草的方法.CN1682613,2005.
29. Sneddon IR, Orueetxebarria M, Hodson ME, Schofield PF and Valsami-Jones E, Use of bone meal amendments to immobilise Pb, Zn and Cd in soil: A leaching column study Environmental Pollution, 2006. 144(3).
30. Stedman RL, Chemical composition of tobacco and tobacco smoke. Chem Rev, 1968. 68(2): 153-207.
31. Ivanov I and Ognyanov I, Solanesol and its esters on neutral extractive fraction of Bulgarian oriental tobacco. Doklady Bolgarskoi Akademii Nauk, 1965. 18(12): 1123-1126.
32. Rodgman A, Cook LC and Latimer PH, Jr., The composition of cigarette smoke. Ⅰ. Solanesyl and phytosteryl esters. Tobacco International, 1959. 3: 125-128.
33. Rodgman A and Cook LC, The composition of cigaret smoke. Ⅰ. Solanesyl acetate. Tobacco International, 1959. 3: 86-88.
34. Nagaraj G and Chakraborty MK, Lipophilic constituents of Natu tobacco. Ⅳ: b-Sitosterol, solanesol and their esters. Tobacco Research, 1980. 6(2): 121-123.
35. Scholtzhauer WS, Severson RF, Chortyk OT, Arrendale RF and Higman HC, Pyrolytic formation of polynuclear aromatic hydrocarbons from petroleum ether extractable constituents of flue-cured tobacco leaf. Journal of Agricultural and Food Chemistry, 1976. 24(5): 992-997.
36.郑奎玲,张万辉,聂运寿,从废次烟叶中同时提取茄尼醇和烟碱的实验.贵州师范大学学报:自然科学版,2004.22(2):81-83.
37.周新光,薛华欣,陆华,陈建民,废弃烟草中茄尼醇和烟碱的提取.中国医药工业杂志,2006.37(7):458-459.
38.胡伟,何洪城,谭利娟,废次烟草中有效成分研究进展.湖南林业科技,2005.32(5):83-85.
1. Delia B. Rodriguez-Amaya, A guide to carotenoid analysis in foods ILSI PRESS, 2001.
2.危凤,纤维素三苯基氨基甲酸酯手性固定相的研制与奥美拉唑的手性色谱分离[D].浙江大学博士学位论文,2003.
3.叶振华等编著,工业色谱基础理论和应用[M].中国石化出版社,1998:59-64.
4.叶振华编著,化工吸附分离过程,中国石化出版社,1992.
5.何华、倪坤仪主编,现代色谱分析,化学工业出版社,2004.
6.叶振华、宋清、朱建华,工业色谱基础理论和应用,中国石化出版社,1998.
1. Ito Y, Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. Journal of chromatography A, 2005. 1065(2): 145-168.
2. Ito Y and Bowman RL, Countercurrent chromatography: liquid-liquid partition chromatography without solid support Science, 1970. 167(916): 281-283.
3. Tanimura T, Pisano JJ, Ito Y and Bowman RL, Droplet countercurrent chromatography. Science, 1970. 169(940): 54-56.
4. Knapp A, [Droplet cotmtercurrent chromatography and related methods]. Pharmazie in unserer Zeit, 1985. 14(3): 77-84.
5. Okamoto K, Yonezawa H and Izumiya N, Preparation of pure peptides from a mixture of gramicidins and of tyrocidines by droplet countercurrent chromatography. Journal of Chromatography A, 1974. 92(1): 147-156.
6. Tani C, Nagakura N and Hattori S, [Studies on the alkaloids of papaveraceous plants. ⅩⅫ. Separation of the alkaloids by droplet countercurrent chromatography. 2. The quaternary bases of Corydalis pallida var. tenuis Yatabe (author's transl)]. Yakugaku zasshi: Journal of the Pharmaceutical Society of Japan, 1975. 95(9): 1103-1107.
7. Tani C, Nagakura N and Kuriyama C, [Studies on the alkaloids of papaveraceous plants. ⅩⅩⅪ. Separation of the alkaloids by droplet countercurrent chromatography. (3). The alkaloids of Corydalis ophiocarpa Hook. et Thoms. (1) (author's transl)]. Yakugaku zasshi: Journal of the Pharmaceutical Society of Japan, 1978. 98(9): 1243-1251.
8. Takahashi N, Utsumi Y, Kato T and Izumiya N, Separation of mono-, di- and tri-1-leucylglylcine by droplet countercurrent chromatography. Journal of Chromatography A, 1975. 109(2): 422-424.
9. Ito Y, Efficient preparative counter-current chromatography with a coil planet centrifuge. Journal of Chromatography A, 1981. 214(1): 122-125.
10. Ito Y, Sandlin J and Bowers WG, High-speed preparative counter-current chromatography with a coil planet centrifuge. Journal of Chromatography A, 1982. 244(2): 247-258.
11. Zhou T, Chen B, Fan G, Chai Y and Wu Y, Application of high-speed counter-current chromatography coupled with high-performance liquid chromatography-diode array. Journal of Chromatography A, 2006. 1116(1): 97-101.
12. Seger C, Eberhart K, Sturm S, Strasser H and Stuppner H, Apolar chromatography on Sephadex LH-20 combined with high-speed counter-current chromatography. Journal of Chromatography A, 2006. 1117(1): 67-73.
13. Tsao R and Yang R, Lutein in selected Canadian crops and agri-food processing by-products and purification by high-speed counter-current chromatography. Journal of chromatography A, 2006. 1112(1-2): 202-208.
14. Remus-Borel W, Shallow N, McNally DJ, Labbe C and Belanger RR, High-speed counter-current chromatography for the study of defense metabolites in wheat. Journal of Chromatography A, 2006. 1121(2): 200-208.
15. Wei Y and Ito Y, Preparative isolation of imperatorin, oxypeucedanin and isoimperatorin from traditional Chinese herb "bai zhi" Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook using multidimensional high-speed counter-current chromatography. Journal of chromatography A, 2006. 1115(1-2): 112-117.
16. Yao S, Li Y and Kong L, Preparative isolation and purification of chemical constituents from the root of Polygonum multiflorurn by high-speed counter-current chromatography. Journal of chromatography A, 2006. 1115(1-2): 64-71.
17. Zhou T, Chen B, Fan G, Chai Y and Wu Y, Application of high-speed counter-current chromatography coupled with high-performance liquid chromatography-diode array detection for the preparative isolation and purification of hyperoside from Hypericum perforatum with online purity monitoring. Journal of chromatography A, 2006. 1116(1-2): 97-101.
18. Seger C, Eberhart K, Sturm S, Strasser H and Stuppner H, Apolar chromatography on Sephadex LH-20 combined with high-speed counter-current chromatography. High yield strategy for structurally closely related analytes-Destrnxin derivatives from Metarhizium anisopliae as a case study. Journal of chromatography A, 2006. 1117(1): 67-73.
19. Du Q, Wang D and Ito Y, Preparation of solanesol from a tobacco leaf extract using high speed countercurrent chromatography. Journal of Liquid Chromatography & Related Technologies, 2006. 29(17): 2587-2592.
20.孙彦,生物分离工程(第二版),化学工业出版社,2005.
21. Li FIB and Chen F, Simultaneous separation and purification of five bioactive coumarins from the Chinese medicinal plant Cnidium monnieri by high-speed countercurrent chromatography. Journal of Separation Science, 2005. 28(3): 268-272.
22. Rowland RL, Latimer PH and Giles JA, Fhie-cured tobacco. Ⅰ. Isolation of solanesol, and unsaturated alcohol. Journal of the American Chemical Society, 1956. 78: 4680-4683.
23. Scholtzhauer WS, Severson RF, Chortyk OT, Arrendale RF and Higman HC, Pyrolytic formation of polynuclear aromatic hydrocarbons from petroleum ether extractable constituents of flue-cured tobacco leaf. Journal of Agricultural and Food Chemistry, 1976. 24(5): 992-997.
1. Gu T and Zheng Y, A study of the scale-up of reversed-phase liquid chromatography. Separation and Purification Technology, 1999. 15(1): 41-58.
2. Kaczmarski K, Antos D, Sajonz H, Sajonz P and Guiochon G, Comparative modeling of breakthrough curves of bovine serum albumin in anion-exchange chromatography. Journal of Chromatography A, 2001. 925(1-2): 1-17.
3. Du X, Yuan Q, Zhao J and Li Y, Comparison of general rote model with a new model—artificial neural network model in describing chromatographic kinetics of solanesol adsorption in packed column by macroporous resins. Journal of Chromatography A. In Press, Corrected Proof: 885.
4. Gu T, Truei Y-H, Tsai G-J and Tsao GT, Modeling of gradient elution in multicomponent nonlinear chromatography. Chemical Engineering Science, 1992. 47(1): 253-262.
5. Gu T, Procedure available on http://wwwentohiouedu/guting/.
6. Marshell AG, Biophysical Chemistry: Principles, Techniques, and Applications, Wiley, New York, 1978.
7.孙彦,生物分离工程(第二版),化学工业出版社,2005.
8. Park YK, Row KH and Chung ST, Adsorption characteristics and separation of taxol from yew tree by NP-HPLC. Separation and Purification Technology, 2000. 19: 27-37.
9.危凤,纤维素三苯基氨基甲酸酯手性固定相的研制与奥美拉唑的手性色谱分离[D].浙江大学博士学位论文,2003.
10. Liu B, Yang Y and Ren Q, Parallel pore and surface diffusion of levulinic acid in basic polymeric adsrbents. journal of chromatography A, 2006. 1132: 190-200.
1.沈秋月,羌宁,有机溶剂回收技术的研究.四川环境,2006.25(6):101-105.
2.史德青,于宏伟,杨金荣,张志华,孔瑛,润滑油酮苯脱蜡溶剂回收用聚酰亚胺纳滤膜分离性能的研究.膜科学与技术,2005.25(3):50-53.
3. White LS and Nitsch AR, Solvent recovery from lube oil filtrates with a polyimide membrane. Journal of Membrane Science, 2000. 179(1): 267-274.
4.李焦丽,倪炳华,聚砜/聚丙烯酰胺合金膜及其在有机溶剂回收中的应用.膜科学与技术,2002.22(5):32-35.
5.康方萍,聚乙烯醇复合纳滤膜的制备.浙江大学硕士学位论文.2006.