Untargeted Metabolite Profiling of Philippine-grown Crescentia cujete and its Commercial Fruit Juice using GC-MS and UPLC-HRMS
Klidel Fae B. Rellin1, Dianne D. Dasmariñas2, and Hiyas A. Junio1*
1Institute of Chemistry, University of the Philippines,
Diliman, Quezon City, Metro Manila 1101 Philippines
2Natural Sciences Research Institute, University of the Philippines, Diliman,
Quezon City, Metro Manila 1101 Philippines
*Corresponding author: This email address is being protected from spambots. You need JavaScript enabled to view it.
ABSTRACT
Calabash fruit (Crescentia cujete L.) juice has gained traction in Southern Philippines for its miraculous effect against stroke, diabetes, and cancer. Metabolite profile of local C. cujete fruit pulp and the commercial fruit juice were established using gas chromatography mass spectrometry (GC-MS) and ultra-high perfromance liquid chromatography high-resolution mass spectrometry (UPLC-HRMS). Putative hits to the NIST Mass Spectral Library included methyl salicylate, (+)-δ-cadinene, benzene and its derivatives such as toluene and o-xylene. Toluene and o-xylene are known air pollutants. Results indicated that the fruit has the potential to bioaccumulate small organic molecules. Volatile organic compounds detected in the fruit pulp were absent from the processed commercial juice. Other benzenoid compounds – thiazole and (+)-δ-cadinene, which are important biosynthetic precursors – were identified from the juice sample. Molecular networking analysis of the tandem MS data of the ethanol extract of the juice putatively identified the presence of 1-kestose and sucrose. 1-Kestose is considered as an essential prebiotic compound associated with boosting metabolism and immunity. Other kestose isomers were also indicated to be present in the juice based on the elution profile and MS/MS data. Preliminary activity tested for both samples yielded positive result against Candida albicans using disc diffusion asay. Only the juice sample yielded significant activity against Escherichia coli.
INTRODUCTION
Crescentia cujete L.(Bignoniaceae) or calabash tree (Figure 1) is a species of flowering plants native to South and Central America, but has become widely distributed in some parts of Africa and Southeast Asia (Arbonier 2004). In these areas, the fruit from the plant has gained an extraordinary repute as a remedy for respiratory ailments such as coughs, colds, and even asthma (Morton 1968). Leaves are also used to reduce blood pressure while decoction from tree bark is consumed for its antiseptic and anti-inflammatory properties (Parvin et al. 2015). . . . . read more
REFERENCES
Ahn I, Kim S, Lee Y. 2005. Vitamin B1 Functions as an Activator of Plant Disease Resistance. Plant Physiology 138(3): 1505–15.
Araji S, Grammer TA, Gertzen R, Anderson S, Mikulic-Petkovsek M, Veberic R, Phu ML, Leslie C, Dandekar AM, Escobar MA. 2014. Novel Roles for the Polyphenol Oxidase Enzyme in Secondary Metabolism and the Regulation of Cell Death in Walnut. Plant Physiology 164: 1191–1203.
Arbonier M. 2004. Trees, Shrubs, and Lianas of West Africa Dry Zones. Grad Margae Publishers GmbH, MNHN. 191p.
CAMPBELL JM, BAUER LL, FAHEY GC, HOGARTH AJ, WOLF BW, HUNTER DE. 1997. Selected Fructooligosaccharide (1-Kestose, Nystose, 1F-β-Fructofuranosylnystose) Composition in Foods and Feeds. Journal of Agricultural and Food Chemistry 45(8): 3076–82.
Chen XY, Chen Y, Heinstein P, Davisson VJ. 1995. Cloning, expression, and characterization of (+)-delta-cadinene synthase a catalyst for cotton phytoalexin biosynthesis. Archives of Biochemistry and Biophysics 324: 255–266.
Clement R, Taguchi VY. 1991. Techniques for the Gas Chromatography – Mass Spectrometry Identification of Organic Compounds in Effluents. Queen’s Printer for Ontario, ON, Canada.
[DOST–PCHRD] Department of Science and Technology – Philippine Council for Health Research and Development. n/d. Retrieved from http://www.pchrd.dost.gov.ph/index.php/news/r-d-updates/3133-calabash-fruit-found-potential-in-lowering-blood-sugar on 28 Jun 2017.
DRAYCOTT G. 2006. World Agriculture Series: Sugar Beet. Garsington Road, Oxford: Blackwell Publishing, Ltd.
Duchesne L, Ellis B, Peterson R. 1989. Disease suppression by ectomycorrhizal fungus Paxillus involutus: Contribution of oxalic acid. Canadian Journal of Botany 67(9): 2726–30.
FLAMINI G, CIONI PL, MORELLI I. 2002. Analysis of the Essential Oil of the aerial parts of Viola etrusca from Monte Labbro (South Tuscany, Italy) and in vivo analysis of flower volatiles using SPME. Flavor and Fragrance Journal 17(2): 147–149.
GÓrna-Binkul A, Keymeulen R, Van Langehove H, Buszewski B. 1996. Determination of monocyclic aromatic hydrocarbons in fruits and vegetables by gas chromatography – mass spectrometry. Journal of Chromatography A 734(2): 297–302.
Grosch W. 2007. Key odorants of food identified by aroma analysis. In: Zeighler H (ed.). Flavorings. 2nd Ed. Wiley-VCH, Weinheim, Germany. p. 704–43.
[IARC] International Agency for Research on Cancer (in preparation). A Review of Human Carcinogens.—Part F: Chemical Agents and Related Occupations. Lyon, International Agency For Research on Cancer. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. 100p. [Summary in Baan R, et al. 2009. A Review of Human Carcinogens—Part F: Chemical Agents and Related Occupations. The Lancet Oncology 10(12): 1143–44. Retrieved from http://www.thelancet.com/journals/lanonc/article/PIIS1470-2045(09)70358-4/fulltext].
Jinno S, Nakamura Y, Nagata M, Takahashi T. 2014. 1-Kestose consumption during pregnancy and lactation increases the levels of IgA in milk of lactating mice. Journal of Bioscience, Biotechnology, and Biochemistry 78(5): 861–866.
Kaneko T, Ohtani K, Kasai R, Kazuo Y, Nguyen MD. 1997. Iridoids and iridoid glycosides from fruit of Crescentia cujete. Phytochemistry 46(5): 907–910.
Kaneko T, Ohtani K, Kasai R, Kazuo Y, Nguyen MD. 1998. n-Alkyl Glycosides and p-Hydroxybenzoyloxy Glucose from Fruits of Crescentia cujete. Phytochemistry 47(2): 259–263.
Kayashima T, Katayama T. 2002. Oxalic acid is available as a natural antioxidant in some systems. Biochimica et Biophysica Acta 1573(1): 1–3.
LEE SM, CHANG JY, WU JS. 2015. Antineoplastic effect of a novel chemopreventive agent, neokestose, on the Caco-2 cell line via inhibition of expression of nuclear factor-κB and cyclooxygenase-2. Molecular Medicine Reports 12(1): 1114–18.
Machado CR, de Oliveira RL, Boiteux S, Praekelt UM, Meacock PA, Menck CF. 1996. Thi1, a thiamine biosynthetic gene in Arabidopsis thaliana, complements bacterial defects in DNA repair. Plant Molecular Biology 31(3): 585–593.
Morton JF. 1968. The Calabash (Crescentia cujete) in Folk Medicine. Economic Botany 22: 273–280.
NikoliĆ M, MarkoviĆ T, MojoviĆ M, Pejin B, SaviĆ A, PeriĆ T, MarkoviĆ D, SteviĆ T, SokoviĆ M. 2013. Chemical composition and biological activity of Gautheria procumbens L. essential oil. Industrial Crops and Products 49: 561–567.
Ogbaugu MN. 2008. The Nutritive and Anti-nutritive Compositions of Calabash (Crescentia cujete) Fruit Pulp. Journal of Food Technology 6: 267–270.
Parvin MS, Das N, Jahan N, Akhter MA, Nahar L, Islam ME. 2015. Evaluation of in vitro anti-inflammatory and antibacterial potential of Crescentia cujete leaves and stem bark. BMC Research Notes 8: 412.
Raschke M, Burkle L, Muller N, Nunes-Nesi A, Fernie AR, Arigoni D, Amrhein N, Fitzpatrick T. 2007. Vitamin B1 biosynthesis in plants requires the essential iron-sulfur cluster protein, THC. Proceedings of the National Academy of Sciences 104(49): 19637–42.
Sayyari M, Valero D, Babalar M, Kalantari S, Zapata P, Serrano M. 2010. Prestorage oxalic acid treatment maintained visual quality, bioactive compounds and antioxidant potential of pomegranate after long-term storage at 2 degrees C. Journal of Agriculture and Food Chemistry 58(11): 6804–08.
SHIOMI N, ABE T, KIKUCHI H, ARITSUKA T, TAKATA Y, FUKUSHI Y, KAWABATA J, UENO K, ONODERA S. 2016. Structural analysis of novel kestose isomers isolated from sugar beet molasses. Carbohydrate Research 424: 1–7.
SIMS IM, POLLOCK CJ, HORGAN R. 1992. Structural analysis of oligomeric fructans from excised leaves of Lolium temulentum. Phytochemistry 31(9): 2989–92.
Tacio H. 2015. Calabash, the Miracle Fruit. Business Mirror. Retrieved from http://www.businessmirror.com.ph/calabash-the-miracle-fruit/ on 28 Jun 2017.
Tochio T, Kitaura Y, Nakamura S, Sugawa C, Takahashi M, Endo A, Shimomura Y. 2016. An Alteration in the Cecal Microbiota Composition by Feeding of 1-Kestose Results in a Marked Increase in the Cecal Butyrate Content in Rats. Plos One 11(11): 1–11.
Ugrekhelidze D, Korte F, Kvesitadze G. 1997. Uptake and Transformation of Benzene and Toluene by Plant Leaves. Ecotoxicology and Environmental Safety 37(1): 24–29.
Vlachojannis C, Chrubasik-Haumann S, Hellwig E, Al-Ahmad A. 2015. A Preliminary Investigation on the Antimicrobial Activity of Listerine®: Its Components, and of Mixture Thereof. Phytotherapy Research 29(10): 1590–94.
Wildermuth MC. 2006. Variations on a theme: Synthesis and Modification of Plant Benzoic Acids. Current Opinion in Plant Biology 9: 288–296.
[WHO] World Health Organization. 2010. Exposure to Benzene: A Major Public Health Concern. Public Health and Environment, World Health Organization, Geneva, Switzerland.
World Ngayon. Calabash fruit could be a cure for diabetic patients? Retrieved from http://www.worldngayon.com/2013/10/calabash-fruit/ on 04 Jul 2017.
World Ngayon. Calabash tree contains active ingredients potential for cancer treatment. Retrieved from http://www.worldngayon.com/2013/09/calabash-for-cancer-treatment/ on 04 Jul 2017.
Yang JY, Sanchez LM, Rath CM, Liu X, Boudreau PD, Bruns N, Glukhov E, Wodtke A, de Felicio R, Fenner A, Wong WR, Linington RG, Zhang L, Debonsi HM, Gerwick W, Dorrestein PC. 2013. Molecular Networking as a Dereplication Strategy. Journal of Natural Products 76(9): 1686–99.
Zheng SJ, Ma, JF, Matsumoto H. 1998. High Aluminum Resistance in Buckwheat: Al-induced specific secretion of oxalic acid from root tips. Plant Physiology 117(3): 745–751.
