本實驗以 LabVIEW 電腦語言程式對層析圖譜與拉曼光譜進行 圖譜比對，用來研究油品安全及摻偽篩的快速判讀。得到的結果如 下：
1. 利用氣相層析質譜儀所得到的層析圖對市售薰衣草精油作比較，
可以發現價位較高的薰衣草精油，經程式比對會有較高的相似度。而 同品種的薰衣草，其精油的相似度也比不同品種的高。由狹葉和寬葉 薰衣草雜交出來的醒目薰衣草，其精油層析圖的相似度也介於兩者之 間。
2. 也可利用頂空固相微萃取配合 GC/MS 對花的香味進行分析，在這 裡取花藥的部分作實驗，並比對其相似度，可以發現百合花的相似度 都有在 75%以上。
3. 利用拉曼光譜對市售食用油做比較，可以發現比較五種橄欖油，
高價格樣品相似度較高，低價格相似度較低，但都在 80% 以上。而 有添加松露的橄欖油其相似度則會低於 65%。新、舊油也可用此程式 進行比較，以此觀察油品有無變質。發現放置一年後的舊油和新油相 比，相似度都在 85% 以下。也可比較經過高溫油炸的油和未使用過 的油，其相似度也都在 85% 以下，可以此作為辨別新、舊油的依據。
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而自行開發的相似度比對程式的優、缺點如下：
優點：
1. 因是自行撰寫的程式，故可隨時修改程式添加所需要的功能，使 之更加方便使用。
2. 可將相似度量化，得到兩圖譜的相似度，並可用相似度的值和其 他對照圖譜進行比較。
3. 只需要輸入想要比較的範圍和圖譜的 txt 檔，即可快速比對得到結 果，不需要繁雜的輸入過程。
缺點：
1. 在開發程式前頇先熟悉 LabVIEW 軟體。
2. 一次只能比對兩張圖譜的相似度，無法像其他分析方法一次比對 全部樣品。
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參考文獻
[1] Cruces, M. P., Pimentel, E., & Zimmering, S. (2009). Evidence that low concentrations of chlorophyllin (CHLN) increase the genetic damage induced by gamma rays in somatic cells of Drosophila. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 679(1), 84-86.
[2] Ferruzzi, M. G., & Schwartz, S. J. (2005). Thermal degradation of commercial grade sodium copper chlorophyllin. Journal of agricultural and food chemistry,53(18), 7098-7102.
[3] Harrisson, J., Levin, S. E., & Trabin, B. (1954). The safety and fate of potassium sodium copper chlorophyllin and other copper compounds. Journal of the American Pharmaceutical Association, 43(12), 722-737.
[4] Nelson, R. L. (1991). Chlorophyllin, an antimutagen, acts as a tumor
promoter in the rat-dimethylhydrazine colon carcinogenesis model. Anticancer research,12(3), 737-739.
[5] Olvera, O., Arceo, C., & Zimmering, S. (2000). Chlorophyllin [CHLN] and the mutagenicity of monofunctional alkylating agents in Drosophila: the action of CHLN need not include an influence on metabolic activation. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 467(2), 113-117.
[6] Pimentel, E., Cruces, M. P., & Zimmering, S. (1999). On the persistence of the radioprotective effect of chlorophyllin (CHLN) in somatic cells of
Drosophila.Mutation Research/Genetic Toxicology and Environmental Mutagenesis,446(2), 189-192.
68
[7] Ferruzzi, M. G., & Schwartz, S. J. (2005). Thermal degradation of commercial grade sodium copper chlorophyllin. Journal of agricultural and food chemistry,53(18), 7098-7102.
[8] ElAbassy, R. M., Donfack, P., & Materny, A. (2009). Visible Raman spectroscopy for the discrimination of olive oils from different vegetable oils and the detection of adulteration. Journal of Raman Spectroscopy, 40(9), 1284-1289.
[9] Bauer, A. J. R. RAMAN SPECTROSCOPIC DETECTION OF OLIVE OIL ADULTERATION.
[10] Jimbo, D., Kimura, Y., Taniguchi, M., Inoue, M., & Urakami, K. (2009).
Effect of aromatherapy on patients with Alzheimer's disease. Psychogeriatrics, 9(4), 173-179.
[11] Lafhal, S., Vanloot, P., Bombarda, I., Valls, R., Kister, J., & Dupuy, N.
(2015). Raman spectroscopy for identification and quantification analysis of essential oil varieties: a multivariate approach applied to lavender and lavandin essential oils. Journal of Raman Spectroscopy, 46(6), 577-585.
[12] Shellie, R., Mondello, L., Marriott, P., & Dugo, G. (2002).
Characterisation of lavender essential oils by using gas chromatography–mass spectrometry with correlation of linear retention indices and comparison with comprehensive two-dimensional gas chromatography. Journal of
Chromatography A, 970(1), 225-234.
[13] Hanamanthagouda, M. S., Kakkalameli, S. B., Naik, P. M., Nagella, P., Seetharamareddy, H. R., & Murthy, H. N. (2010). Essential oils of Lavandula bipinnata and their antimicrobial activities. Food Chemistry, 118(3), 836-839.
[14] Da Porto, C., Decorti, D., & Kikic, I. (2009). Flavour compounds of
69
Lavandula angustifolia L. to use in food manufacturing: Comparison of three different extraction methods. Food Chemistry, 112(4), 1072-1078.
[15] Kim, N. S., & Lee, D. S. (2002). Comparison of different extraction methods for the analysis of fragrances from Lavandula species by gas
chromatography–mass spectrometry. Journal of Chromatography a, 982(1), 31-47.
[16] Cuttle, Leila, et al. "A review of first aid treatments for burn injuries." Burns 35.6 (2009): 768-775.
[17] Gattefossé, R. M. (1928). Aromatherapie. Giradot editeur. Paris.
[18] Valnet, J. (1966). Aromathérapie, traitement des maladies par les essences des plantes.
[19] Fischer-Rizzi, S. (1990). Complete aromatherapy handbook: essential oils for radiant health. Sterling Publishing Company, Inc..
[20] Penfold, A. R., & GRANT, R. (1923). Germicidal Values of Australian Essential Oils and Their Pure Constituents. Journal of the Proceedings of the Society of New South Wales, 57, 211.
[21] Fischer-Rizzi, S. (1990). Complete aromatherapy handbook: essential oils for radiant health. Sterling Publishing Company, Inc..
[22] Lin, P. W. K., Chan, W. C., Ng, B. F. L., & Lam, L. C. W. (2007).
Efficacy of aromatherapy (Lavandula angustifolia) as an intervention for agitated behaviours in Chinese older persons with dementia: a crossover randomized trial. International journal of geriatric psychiatry, 22(5), 405-410.
[23] Verma, R. S., Rahman, L. U., Chanotiya, C. S., Verma, R. K., Chauhan, A., Yadav, A., ... & Yadav, A. K. (2010). Essential oil composition of
Lavandula angustifolia Mill. cultivated in the mid hills of Uttarakhand, India. J.
70
Serb. Chem. Soc, 75(3), 343-348.
[24] Harborne, J. B., & Williams, C. A. (2002). Phytochemistry of the genus Lavandula. In M. Lis-Balchin (Ed.), Lavender: The Genus Lavandula. CRC Press.
[25] Boelens, M. H. (1986). The essential oil of Spike Lavender Lavendula latifolia Vill (L. spica DC). Perfum. Flavor, 11, 43-63.
[26] Bonvehi, J. S., & Coll, F. V. (1993). Physico-chemical properties, composition and pollen spectrum of french lavender (Lavandula stoechas L.) honey produced in Spain. Zeitschrift für Lebensmittel-Untersuchung und Forschung,196(6), 511-517.
[27] Kubota, S., Momose, H., Yoneda, K., & Koshioka, M. (2010). Lavandula*
intermedia is a Vernalization Type Plant. Japan Agricultural Research Quarterly: JARQ, 44(1), 67-72.
[28] Rohloff, J. (2002). Volatiles from rhizomes of Rhodiola rosea L. Phytochemistry,59(6), 655-661.
[29] Picone, J. M., MacTavish, H. S., & Clery, R. A. (2002). Emission of floral volatiles from Mahonia japonica (Berberidaceae). Phytochemistry, 60(6), 611-617.
[30] Himejima, M., Hobson, K. R., Otsuka, T., Wood, D. L., & Kubo, I. (1992).
Antimicrobial terpenes from oleoresin of ponderosa pine treePinus ponderosa:
A defense mechanism against microbial invasion. Journal of Chemical Ecology,18(10), 1809-1818.
[31] Lee, N. H., & Ho, J. W. (2008). Celastrol and terpenes as anti-infective agents.Anti-Infective Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Infective Agents), 7(2), 97-100.
71
[32] Menichini, F., Conforti, F., Rigano, D., Formisano, C., Piozzi, F., &
Senatore, F. (2009). Phytochemical composition, anti-inflammatory and antitumour activities of four Teucrium essential oils from Greece. Food Chemistry, 115(2), 679-686.
[33] Belletti, N., Kamdem, S. S., Tabanelli, G., Lanciotti, R., & Gardini, F.
(2010). Modeling of combined effects of citral, linalool and β-pinene used against Saccharomyces cerevisiae in citrus-based beverages subjected to a mild heat treatment. International Journal of Food Microbiology, 136(3), 283-289.
[34] Sakurada, T., Kuwahata, H., Katsuyama, S., Komatsu, T., Morrone, L. A., Corasaniti, M. T., ... & Sakurada, S. (2009). Intraplantar Injection Of Bergamot Essential Oil Into The Mouse Hindpaw: Effects On CapsaicinInduced
Nociceptive Behaviors. International Review of Neurobiology, 85, 237-248.
[35] Re, L., Barocci, S., Sonnino, S., Mencarelli, A., Vivani, C., Paolucci, G., ...
& Mosca, E. (2000). Linalool modifies the nicotinic receptor–ion channel kinetics at the mouse neuromuscular junction. Pharmacological
Research, 42(2), 177-181.
[36] Peana, A. T., D'Aquila, P. S., Panin, F., Serra, G., Pippia, P., & Moretti, M.
D. L. (2002). Anti-inflammatory activity of linalool and linalyl acetate constituents of essential oils. Phytomedicine, 9(8), 721-726.
[37] Juhás, Š., Bukovská, A., Čikoš, Š., Czikková, S., Fabian, D., & Koppel, J.
(2009). Anti-inflammatory effects of Rosmarinus officinalis essential oil in mice.Acta Veterinaria Brno, 78(1), 121-127.
[38] Santos, F. A., Silva, R. M., Campos, A. R., De Araujo, R. P., Júnior, R. L.,
& Rao, V. S. N. (2004). 1, 8-cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis. Food and
72
chemical toxicology, 42(4), 579-584.
[39] Bedoya, L. M., Bermejo, P., & Abad, M. J. (2009). Anti-infectious activity in the cistaceae family in the Iberian Peninsula. Mini reviews in medicinal chemistry,9(5), 519-525.
[40] Chen, J., Sun, Z., Zhang, Y., Zeng, X., Qing, C., Liu, J., ... & Zhang, H.
(2009). Synthesis of gibberellin derivatives with anti-tumor
bioactivities. Bioorganic & medicinal chemistry letters, 19(18), 5496-5499.
[41] LaLone, C. A., Rizshsky, L., Solco, A., Nikolau, B., Murphy, P., & Birt, D.
F. (2009). Unraveling the complexity of Echinacea fractions to identify alkylamides and ketones important for anti-inflammatory bioactivity. The FASEB Journal,23(1 Supplement), 104-5.
[42] Zhang, H. X., Hu, Z. H., Leng, P. S., Wang, W. H., Xu, F., & Zhao, J.
(2013). Qualitative and quantitative analysis of floral volatile components from different varieties of Lilium spp. Scientia Agri Sin, 46(4), 790-799.
[43] Skoog, D. A., & West, D. M. (1997). Principles of instrumental analysis (5th ed.). Philadelphia: Saunders College. (p. 704.)
[44] Karasek, F. W., & Clement, R. E. (2012). Basic gas chromatography-mass spectrometry: principles and techniques. Elsevier.
[45] Skoog, D. A., & West, D. M. (1997). Principles of instrumental analysis (5th ed.). Philadelphia: Saunders College. (p. 713.)
[46] March, R. E., & Hughes, R. J. (1989). Quadrupole storage mass spectrometry. Wiley.
[47] Skoog, D. A., & West, D. M. (1997). Principles of instrumental analysis (5th ed.). Philadelphia: Saunders College. (p. 503.)
[48] Message, G. M. (1984). In Pratical aspects of chromatography/mass
73
spectrometry. chapter 5.
[49] Watson, J. T., & Sparkman, O. D. (2007). Introduction to mass spectrometry: instrumentation, applications, and strategies for data interpretation. John Wiley & Sons. (p. 247.)
[50] Liu, H. W.; Wu, B. Z.; Lo, J. G. (2004). The. Chinese Chem. Soc, 62, No.3, 377-386.
[51] Van Bramer, S., & Goodrich, K. R. (2015). Determination of plant volatiles using solid phase microextraction GC–MS. Journal of Chemical Education, 92(5), 916-919.
[52] Giorgi, A., Panseri, S., Nanayakkara, N. N. M. C., & Chiesa, L. M. (2012).
HS-SPME-GC/MS analysis of the volatile compounds of Achillea collina:
evaluation of the emissions fingerprint induced by Myzus persicae infestation. Journal of Plant Biology, 55(3), 251-260.
[53] Abolghasemi, M. M., Karimi, B., & Yousefi, V. (2013). Periodic
mesoporous organosilica with ionic liquid framework as a novel fiber coating for headspace solid-phase microextraction of polycyclic aromatic
hydrocarbons. Analytica chimica acta, 804, 280-286.
[54] Soto, V. C., Maldonado, I. B., Jofré, V. P., Galmarini, C. R., & Silva, M. F.
(2015). Direct analysis of nectar and floral volatile organic compounds in hybrid onions by HS-SPME/GC–MS: Relationship with pollination and seed production. Microchemical Journal, 122, 110-118.
[55] Marton, D., Tapparo, A., Di Marco, V. B., Repice, C., Giorio, C., &
Bogialli, S. (2013). Ultratrace determination of total and available cyanides in industrial wastewaters through a rapid headspace-based sample preparation and gas chromatography with nitrogen phosphorous detection analysis. Journal of
74
Chromatography A, 1300, 209-216.
[56] Cai, Y., Yan, Z., Wang, L., NguyenVan, M., & Cai, Q. (2016). Magnetic solid phase extraction and static headspace gas chromatography–mass
spectrometry method for the analysis of polycyclic aromatic hydrocarbons.Journal of Chromatography A, 1429, 97-106.
[57] McCreery, R. L. (2005). Raman spectroscopy for chemical analysis (Vol.
225). John Wiley & Sons.
[58] Nie, Shuming, and Steven R. Emory. "Probing single molecules and single nanoparticles by surface-enhanced Raman scattering." science 275.5303 (1997):
1102-1106.
[59] Kneipp, K., Wang, Y., Kneipp, H., Perelman, L. T., Itzkan, I., Dasari, R.
R., & Feld, M. S. (1997). Single molecule detection using surface-enhanced Raman scattering (SERS). Physical review letters, 78(9), 1667.
[60] Maruyama, Y., Ishikawa, M., & Futamata, M. (2001). Surface-Enhanced Raman Scattering of Single Adenine Molecules on Silver Colloidal
Particles.Chemistry Letters, (8), 834-835.
[61] Gould, R. G. (1959, June). The LASER, light amplification by stimulated emission of radiation. In The Ann Arbor conference on optical pumping, the University of Michigan (Vol. 15, p. 128).
[62] Chu, Steven; Townes, Charles (2003). Biographical Memoirs. National Academy of Sciences. (vol. 83, p. 202)
[63] Janesick, J. R. (2001). Scientific charge-coupled devices (Vol. 117).
Bellingham, Washington: SPIE press..
[64] Tompsett, M. F., Amelio, G. F., Bertram, W. J., Buckley, R. R.,
McNamara, W. J., Mikkelsen, J. C., & Sealer, D. A. (1971). Charge-coupled
75
imaging devices: Experimental results. IEEE Transactions on Electron Devices, 18(11), 992-996.
[65] Vo-Dinh, T. (1998). Surface-enhanced Raman spectroscopy using metallic nanostructures. TrAC Trends in Analytical Chemistry, 17(8), 557-582.
[66] Tu, A. T. (1982). Raman spectroscopy in biology: principles and applications. John Wiley & Sons.
[67] Wells, L. K., & Travis, J. (1996). LabVIEW for everyone: graphical programming made even easier. Prentice-Hall, Inc..
[68] Johnson, G. W. (1997). LabVIEW graphical programming. Tata McGraw-Hill Education.
[69] Travis, J., & Kring, J. (2007). LabVIEW for everyone. Prentice-Hall.
[70] Bitter, R., Mohiuddin, T., & Nawrocki, M. (2006). LabVIEW: Advanced programming techniques. CRC Press.
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研究發表
第二十二屆分析技術交流研討會
發表題目: Rapid screening of oils by pattern recognition of spectral features obtained by GC/MS and Raman spectrometry
時間 : 2016 年 5 月 21 (六)
地點 : 高雄醫學大學-第一教學大樓