Tissue-specific metabolite profiling of Cyperus rotundus L. rhizomes and (+)-nootkatone quantitation by laser microdissection, ultra-high-performance liquid chromatography-quadrupole time-of-flight mass spectrometry, and gas chromatography-mass spectrometry techniques

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 29, 2014, Pages 7302-7316

  Jaiswal, Yogini ^a   Liang, Zhitao ^a   Guo, Ping ^a   Ho, Hing Man ^a   Chen, Hubiao ^a   Zhao, Zhongzhen ^a  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

Cyperus rotundus L. (purple nut sedge); GC MS; laser micro dissection; metabolite analysis; UHPLC QTOF MS

Indexed keywords

BIOMOLECULES; ESSENTIAL OILS; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; MICRODISSECTION; OILS AND FATS; TISSUE; CHROMATOGRAPHY; DISSECTION; LIQUID CHROMATOGRAPHY; LIQUIDS; QUALITY CONTROL; SPECTROMETRY; TISSUE ENGINEERING;

CYPERUS ROTUNDUS; GC-MS; LASER MICRO DISSECTIONS; METABOLITE ANALYSIS; NOOTKATONE; UHPLC-QTOF MS;

TISSUE ENGINEERING; GAS CHROMATOGRAPHY;

NOOTKATONE; SESQUITERPENE;

CYPERUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LASER; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; METABOLISM; PROCEDURES;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYPERUS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LASERS; MASS SPECTROMETRY; SESQUITERPENES;

CYPERUS ROTUNDUS;

EID: 84905583404     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf502494z     Document Type: Article

References (50)

1. Bendixen, L. E.; Nandihalli, V. B. Worldwide distribution of purple and yellow nutsedge (Cyperus rotundus and C. esculentus) Weed Technol. 1987, 1, 61-65
2. Bryson, C. T.; Hanks, J. E.; Wills, G. D. Purple nutsedge (Cyperus rotundus) control in reduced-tillage cotton (Gossypium hirsutum L.) with low volume technology Weed Technol. 1994, 8, 28-31
3. Seethapathy, G. S.; Balasubramani, S. P.; Venkatasubramanian, P. nrDNA ITS sequence based SCAR marker to authenticate Aconitum heterophyllum and Cyperus rotundus in Ayurvedic raw drug source and prepared herbal products Food Chem. 2014, 145, 1015-1020
4. Chen, H. Y.; Lin, Y. H.; Su, I. H.; Chen, Y. C.; Yang, S. H.; Chen, J. L. Investigation on Chinese herbal medicine for primary dysmenorrhea: implication from a nationwide prescription database in Taiwan Complementary Ther. Med. 2014, 22, 116-125
5. Imam, M. Z.; Sumi, C. D. Evaluation of antinociceptive activity of hydromethanol extract of Cyperus rotundus in mice BMC Complementary Altern. Med. 2014, 14, 83
6. Kumar, K. H.; Razack, S.; Nallamuthu, I.; Khanum, F. Phytochemical analysis and biological properties of Cyperus rotundus L Ind. Crops Prod. 2014, 815-826
7. Wriessnegger, T.; Augustin, P.; Engleder, M.; Leitner, E.; Müller, M.; Kaluzna, I.; Schürmann, M.; Mink, D.; Zellnig, G.; Schwab, H.; Pichler, H. Production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris Metab. Eng. 2014, 24, 18-29
8. Choi, H.; Lee, J.; Jung, Y. (+)-Nootkatone inhibits tumor necrosis factor α/interferon γ-induced production of chemokines in HaCaT cells Biochem. Biophys. Res. Commun. 2014, 447, 278-284
9. Davies, K. M.; Deroles, S. C. Prospects for the use of plant cell cultures in food biotechnology Curr. Opin. Chem. Biol. 2014, 26, 133-140
10. Handore, K. L.; Seetharamsingh, B.; Reddy, D. S. Ready access to functionally embellished cis -hydrindanes and cis -decalins: protecting group-free total syntheses of (+)-nootkatone and (+)-noreremophilane J. Org. Chem. 2013, 78, 8149-8154
11. Choi, H. J.; Lee, J. H.; Jung, Y. S. (+)-Nootkatone inhibits tumor necrosis factor α/interferon γ-induced production of chemokines in HaCaT cells Biochem. Biophys. Res. Commun. 2014, 447, 278-284
12. Schreier, P. Enzymes and flavour biotechnology. In Biotechnology of Aroma Compounds. Berger, R. G., Ed.; Springer: Berlin, Heidelberg, and New York, 1997; p 51.
13. Meena, A.; Yadav, A.; Niranjan, U.; Singh, B.; Nagariya, A.; Verma, M. Review on Cyperus rotundus-A potential herb Int. J. Pharm. Clin. Res. 2010, 2, 20-22
14. Sharma, P.; Yelne, M.; Dennis, T. In Database on Medicinal Plants Used in Ayurveda; Central Council for Research in Ayurveda and Siddha: Delhi, India, 2001; pp 404-424.
15. Eun, J. S.; Dong-Ung, L.; Jong, H. W.; Sun-Mee, L.; Yeong, S. K.; Yi-Sook, J. Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone J. Ethnophamacol. 2011, 135, 48-54
16. Hemanth, K. K.; Tamatam, A.; Pal, A.; Khanum, F. Neuroprotective effects of Cyperus rotundus on SIN-1 induced nitric oxide generation and protein nitration: Ameliorative effect against apoptosis mediated neuronal cell damage Neurotoxicology. 2013, 34, 150-159
17. Ladd, W. Fragrance raw material monographs Food Chem. Toxicol. 2000, 38, s165-s167
18. Oladunni, O. M.; Abass, O. O.; Adisa, A. I. Studies on the physiochemical properties of the oil, minerals and nutritional composition of nut of nut grass (Cyperus rotundus) Am. J. Food Technol. 2011, 6, 1061-1064
19. Sánchez-Zapata, E.; Fuentes-Zaragoza, E.; Fernández- López, J.; Sendra, E.; Sayas, E.; Navarro, C.; Pérez-Alvarez, J. A. Preparation of dietary fiber powder from tiger nut (Cyperus esculentus) milk ("Horchata") byproducts and its physicochemical properties J. Agric. Food Chem. 2009, 57, 7719-7725
20. Cantalejo, M. J. Development of new products from earth almond Fruit Process. 1996, 3, 87-91
21. Chopra, R. N.; Nayar, S. L.; Chopra, I. C. Glossary of Indian Medicinal Plants; Publications and Information Directorate: New Delhi, India, 1956.
22. Messiaen, C. M. The Tropical Vegetable Garden: Principles for Improvement and Increased Production with Applications to Main Vegetable Types; Macmillan Press: London, 1992; p 514.
23. Umerie, S. C.; Ezeuzo, H. O. Physicochemical characterization and utilization of Cyperus rotundus starch Bioresour. Technol. 2000, 72, 193-196
24. Bamgbose, A. M.; Eruvbetine, D.; Dada, W. Utilization of tigernut (Cyperus rotundus L.) meal in diets for cockerel starters Bioresour. Technol. 2003, 89, 245-248
25. Sebastia, N.; Soler, C.; Soriano, J. M.; Manes, J. Occurrence of aflatoxins in tigernuts and their beverages commercialized in Spain J. Agric. Food Chem. 2010, 58, 2609-2612
26. The Ayurvedic Pharmacopoeia of India, 1 st ed.; Controller of Publication: Delhi, India, 2001; Vol. 3, p 129.
27. Jiangsu New Medical College. Dictionary of Chinese Materia Medica; Shanghai People's Publishing House: Shanghai, China, 1971; pp 3441-3443.
28. Chinese Pharmacopoeia Commission. The Pharmacopoeia of the People's Republic of China, English ed.; China Medical Science Press: Beijing, China, 2010; Vol. 1, p 147.
29. Weehen, H.; Nkunya, M. H. H.; Bray, D. H.; Mwasumbi, L. B.; Kinabo, L. S.; Kilimali, A. E.; Wijnberg, B. P.A. Antimalarial activity of Tanzanian plants. Part 2. Antimalarial compounds containing an α,β-unsaturated carbonyl moiety from Tanzanian medicinal plants Planta Med. 1990, 56, 371-373
30. Sayed, H. M.; Mohamed, M. H.; Farag, S. F.; Mohamed, G. A.; Proksch, P. A new steroid glycoside and furochromones from Cyperus rotundus L Nat. Prod. Res. 2007, 21, 343-350
31. Lawal, O. A.; Oyedeji, A. O. Chemical composition of the essential oils of Cyperus rotundus L. from South Africa Molecules 2009, 14, 2909-2917
32. Kilani-Jaziri, S.; Neffati, A.; Limem, I.; Boubaker, J.; Skandrani, I.; Sghair, M. B.; Bouhlel, I.; Bhouri, W.; Mariotte, A. M.; Ghedira, K.; Dijoux Franca, M. G.; Chekir-Ghedira, L. Relationship correlation of antioxidant and antiproliferative capacity of Cyperus rotundus products towards K562 erythroleukemia cells Chem.-Biol. Interact. 2009, 181, 85-94
33. Natarajan, K. S.; Narasimhan, M.; Shanmugasundaran, K. R.; Shanmugasundaram, E. R. Antioxidant activity of salt-spice-herbal mixture against free radical induction J. Ethnophamacol. 2006, 105, 76-83
34. Nagulendran, K. R.; Velavan, S.; Mahesh, R.; Begum, H. V. In vitro antioxidant activity and total polyphenolic content of Cyperus rotundus rhizomes e-J. Chem. 2007, 4, 440-449
35. Jaiswal, Y.; Liang, Z.; Yong, P.; Chen, H.; Zhao, Z. A comparative study on the traditional Indian shodhana and Chinese processing methods for aconite roots by characterization and determination of the major components Chem. Cent. J. 2013, 7, 169
36. Jaiswal, Y.; Liang, Z.; Ho, A.; Chen, H.; Zhao, Z. A comparative tissue-specific metabolite analysis and determination of protodioscin content in asparagus species used in traditional chinese medicine and ayurveda by use of laser micro-dissection, UHPLC-QTOF MS and LC-MS/MS Phytochem. Anal. 2014, 10.1002/pca.2522
37. Zhao, Z.; Liang, Z.; Ping, G. Macroscopic identification of Chinese medicinal materials: Traditional experiences and modern understanding J. Ethnopharmacol. 2011, 134, 556-564
38. Farnham, M.; Wilson, P.; Stephenson, K.; Fahey, J. Genetic and environmental effects on glucosinolate content and chemoprotective potency of broccoli Plant Breed. 2004, 123, 60-65
39. Charron, C.; Saxton, A.; Sams, C. Relationship of climate and genotype to seasonal variation in the glucosinolate-myrosinase system. II. Myrosinase activity in ten cultivars of Brassica oleracea grown in fall and spring seasons J. Sci. Food Agric. 2005, 85, 682-690
40. Jain, N.; Shasany, A.; Sundaresan, V.; Rajkumar, S.; Darokar, M.; Bagchi, G.; Gupta, A.; Kumar, S.; Khanjua, S. Molecular diversity in Phyllanthus amarus assessed through RAPD analysis Curr. Sci. 2003, 10, 1454-1458
41. Williams, H. J.; Sattler, I.; Moyna, G.; Scott, A. L.; Bell, A. A.; Vinson, S. B. Diversity in cyclic sesquiterpene production by Gossypium hirsutum Phytochemistry 1995, 40, 1633-1636
42. ICH, International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use. Validation of Analytical Procedures: Text and Methodology (Q2 R1); ICH Harmonised Tripartite Guidelines, Geneva, 2005; pp 6-13.
43. Khan, S.; Choi, R. J.; Lee, D. U.; Kim, Y. S. Sesquiterpene derivatives isolated from Cyperus rotundus L. inhibit inflammatory signalling mediated by NF-κB Nat. Prod. Sci. 2011, 17, 250-255
44. Bisht, A.; Bisht, G.; Singh, M.; Gupta, R.; Singh, V. Chemical composition and antimicrobial activity of essential oil of tubers of Cyperus rotundus Linn. collected from Dehradun (Uttarakhand) Int. J. Res. Pharm. Biomed. Sci. 2011, 2, 661-665
45. Kim, S. J.; Kim, H. J.; Kim, H. J.; Jang, Y. P.; Oh, M. S.; Jang, D. S. New patchoulane-type sesquiterpenes from the rhizomes of Cyperus rotundus Bull. Korean Chem. Soc. 2012, 33, 3115-3118
46. Yang, J. L.; Shi, Y. P. Structurally diverse terpenoids from the rhizomes of Cyperus rotundus L Planta Med. 2012, 78, 59-64
47. Anderson, J.; Coats, J. Acetylcholinesterase inhibition by nootkatone and carvacrol in arthropods Pestic. Biochem. Physiol. 2012, 102, 124-128
48. Krugener, S.; Krings, U.; Zorn, H.; Berger, R. G. A dioxygenase of Pleurotus sapidus transforms (+)-valencene regio-specifically to (+)-nootkatone via a stereo-specific allylic hydroperoxidation Bioresour. Technol. 2010, 101, 457-462
49. Gliszczyńska, A.; Łysek, A.; Janeczko, T.; Świtalska, M.; Wietrzyk, J.; Wawrzeńczyk, C. Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites Bioorg. Med. Chem. 2011, 19, 2464-2469
50. Tsoyi, K.; Jang, H. J.; Lee, Y. S.; Kim, Y. M.; Kim, H. J.; Seo, H. G.; Lee, J. H.; Kwak, J. H.; Lee, D. U.; Chang, K. C. (+)-Nootkatone and (+)-valencene from rhizomes of Cyperus rotundus increase survival rates in septic mice due to heme oxygenase-1 induction J. Ethnopharmacol. 2011, 137, 1311-1317