Triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle Lonicera caerulea var. kamtschatica

Rafał Becker, Cezary Pączkowski, Anna Szakiel

Abstract


Edible honeysuckle (honeyberry) Lonicera caerulea is becoming popular as a novel berry crop with several useful features such as early fruit ripening and exceptional hardiness, particularly resistance to pests and diseases as well as severe frosts in winter and droughts in summer. The triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle (a Russian cultivar Chernichka) was analyzed by GC-MS. The major compounds identified were the tetracyclic triterpenoids campesterol, cholesterol, cycloartanol, cycloart-23-ene-3,25-diol, 24-methylenecycloartanol (only in leaves), sitosterol, stigmasta-3,5-dien-7-one, and stigmasterol; and the pentacyclic triterpenes: α-amyrin, β-amyrin, hop-22(29)-en-3-one, oleanolic acid, and ursolic acid. Several remarkable features of the analyzed triterpenoid contents were revealed, including the relatively low abundance of triterpenoids in fruit waxes (6.5% of wax extract) compared to leaf waxes (22%), and a particularly high proportion of tetracyclic triterpenoids (tetracyclic to pentacyclic compound ratios of 4:1 in fruits and almost 7:1 in leaves). These rare features distinguish the triterpenoid profile of the cuticular waxes of L. caerulea var. kamtschatica from the majority of triterpenoid profiles in plant cuticular waxes investigated to date. To our knowledge, this is the first quantitative compositional study on triterpenoid compounds in the cuticular waxes of edible honeysuckle, supplementing the knowledge of cuticular triterpenoid diversity and distribution.

Keywords


Lonicera caerulea; edible honeysuckle; cuticular wax; sterols; triterpenoids

Full Text:

PDF

References


Shang X, Pan H, Li M, Miao X, Ding H. Lonicera japonica Thunb.: ethnopharmacology, phytochemistry and pharmacology of an important traditional Chinese medicine. J Ethnopharmacol. 2011;138(1):1–21. https://doi.org/10.1016/j.jep.2011.08.016

Plekhanova MN. Blue honeysuckle (Lonicera caerulea L.) – a new commercial berry crop for temperate climate: genetic resources and breeding. Acta Hortic. 2000;538:159–164. https://doi.org/10.17660/ActaHortic.2000.538.25

Hummer KE. Blue honeysuckle: a new berry crop for North America. Journal of the American Pomological Society. 2006;60(1):3–8.

Ochmian I, Skupień K, Grajkowski J, Smolik M, Ostrowska K. Chemical composition and physical characteristics of fruits of two cultivars of blue honeysuckle (Lonicera caerulea L.) in relation to their degree of maturity and harvest date. Not Bot Horti Agrobot Cluj Napoca. 2012;40(1):155–162.

Kula M, Majdan M, Radwańska A, Nasal A, Hałasa R, Głód D, et al. Chemical composition and biological activity of the fruits from Lonicera caerulea var. edulis ‘Wojtek’. Academia Journal of Medicinal Plants. 2013;1(8):141–148.

Ochmian I, Grajkowski J, Skupień K. Field performance, fruit chemical composition and firmness under cold storage and simulated “shelf-life” conditions of three blue honeysuckle cultigens (Lonicera caerulea). Journal of Fruit and Ornamental Plant Research. 2008;16:83–91.

Jurikova T, Rop O, Mlcek J, Sochor J, Balla S, Szekeres L, et al. Phenolic profile of edible honeysuckle berries (genus Lonicera) and their biological effects. Molecules. 2012;17(1):61–79. https://doi.org/10.3390/molecules17010061

Chaovanalikit A, Thompson MM, Wrolstad RE. Characterization and quantification of anthocyanins and polyphenolics in blue honeysuckle (Lonicera caerulea L.). J Agric Food Chem. 2004;52(4):848–852. https://doi.org/10.1021/jf030309o

Wojdyło S, Jáuregui PNN, Oszmiański J, Golis T. Variability of phytochemical properties and content of bioactive compounds in Lonicera cearulea L. var. kamtschatica berries. J Agric Food Chem. 2013;61(49):12072–12084. https://doi.org/10.1021/jf404109t

Mahato SB, Nandy AK, Roy G. Triterpenoids. Phytochemistry. 1992;31(7):2199–2249. https://doi.org/10.1016/0031-9422(92)83257-Y

Phillips DR, Rasbery JM, Bartel B, Matsuda SP Biosynthetic diversity in plant triterpene cyclization. Curr Opin Plant Biol. 2006;9(3):305–314. https://doi.org/10.1016/j.pbi.2006.03.004

Patlolla JM, Rao CV. Triterpenoids for cancer prevention and treatment: current status and future prospects. Curr Pharm Biotechnol. 2012;13(1):147–155. https://doi.org/10.2174/138920112798868719

Podolak I, Janeczko Z. Pharmacological activity of natural non-glycosylated triterpenes. Mini Rev Org Chem. 2014;11(3):280–291. https://doi.org/10.2174/1570193X1103140915105546

Szakiel A, Pączkowski C, Pensec F, Bertsch C. Fruit cuticular waxes as a source of biologically active triterpenoids. Phytochem Rev. 2012;11(2–3):263–284. https://doi.org/10.1007/s11101-012-9241-9

Jetter R, Kunst L, Samuels AL. Composition of plant cuticular waxes. In: Riederer M, Müller C, editors. Biology of the plant cuticle. Oxford: Blackwell Publishing; 2006. p. 155–157. (Annual Plant Reviews; vol 23). https://doi.org/10.1002/9780470988718.ch4

Tsubaki S, Sugimura K, Teramoto Y, Yonemori K, Azuma J. Cuticular membrane of Fuyu persimmon fruit is strengthened by triterpenoid nano-fillers. PLoS One. 2013;8:e75275. http://dx.doi.org/10.1371/journal.pone.0075275

Lara I, Belge B, Goulao LF. The fruit cuticle as a modulator of postharvest quality. Postharvest Biol Technol. 2014;87:103–112. https://doi.org/10.1016/j.postharvbio.2013.08.012

Seeram NP. Berry fruits: compositional elements, biochemical activities, and the impact of their intake on human health, performance, and disease. J Agric Food Chem. 2008;56(3):627–629. https://doi.org/10.1021/jf071988k

Szakiel A, Pączkowski C, Koivuniemi H, Huttunen S. Comparison of the triterpenoid content of berries and leaves of lingonberry Vaccinium vitis-idaea from Finland and Poland. J Agric Food Chem. 2012;60:4994–5002. https://doi.org/10.1021/jf300375b

Szakiel A, Pączkowski C, Huttunen S. Triterpenoid content of berries and leaves of bilberry Vaccinium myrtillus from Finland and Poland. J Agric Food Chem. 2012;60(48):11839–11849. https://doi.org/10.1021/jf3046895

Pensec F, Pączkowski C, Grabarczyk M, Woźniak A, Bénard-Gellon M, Bertsch C, et al. Changes in the triterpenoid content of cuticular waxes during fruit ripening of eight grape (Vitis vinifera) cultivars grown in the Upper Rhine Valley. J Agric Food Chem. 2014;62(32):7998–8007. https://doi.org/10.1021/jf502033s

Pensec F, Szakiel A, Pączkowski C, Woźniak A, Grabarczyk M, Bertsch C, et al. Characterization of triterpenoid profiles and triterpene synthase expression in the leaves of eight Vitis vinifera cultivars grown in the Upper Rhine Valley. J Plant Res. 2016;129(3):499–512. https://doi.org/10.1007/s10265-016-0797-0

Szafranek BM, Synak EE. Cuticular waxes from potato (Solanum tuberosum) leaves. Phytochemistry. 2006;67(1):80–90. https://doi.org/10.1016/j.phytochem.2005.10.012

Szakiel A, Niżyński B, Pączkowski C. Triterpenoid profile of flower and leaf cuticular waxes of heather Calluna vulgaris. Nat Prod Res. 2013;27(15):1404–1407. https://doi.org/10.1080/14786419.2012.742083

Medina E, Aguia G, Gomez M, Aranda, J, Medina JD, Winter K. Taxonomic significance of the epicuticular wax composition in species of the genus Clusia from Panama. Biochem Syst Ecol. 2006;34:319–326. https://doi.org/10.1016/j.bse.2005.10.009

Cordeiro SZ, Simas NK, Arruda RCO, Sato A. Composition of epicuticular wax layer of two species of Mandevilla (Apocynoideae, Apocynaceae) from Rio de Janeiro, Brazil. Biochem Syst Ecol. 2011;39(3):198–202. https://doi.org/10.1016/j.bse.2011.02.009

Medina E, Aguiar G, Gómez M, Medina JD. Patterns of leaf epicuticular waxes in species of Clusia: taxonomical implications. Interciencia. 2004;29:579–582.

Kondo M, MacKinnon SL, Craft CC, Matchett MD, Hurta RAR, Neto CC. Ursolic acid and its esters: occurrence in cranberries and other Vaccinium fruit and effects on matrix metalloproteinase activity in DU145 prostate tumor cells. J Sci Food Agric. 2011;91(5):789–796. https://doi.org/10.1002/jsfa.4330

Szakiel A, Mroczek A. Distribution of triterpene acids and their derivatives in organs of cowberry (Vaccinium vitis-idaea L.) plant. Acta Biochim Pol. 2007;54(4):733–740.

Guinda A, Rada M, Delgado T, Gutiérrez-Adánez P, Castellano JM. Pentacyclic triterpenoids from olive fruit and leaf. J Agric Food Chem. 2010;58(17):9685–9691. https://doi.org/10.1021/jf102039t

Murphy BT, MacKinnon SL, Yan X, Hammond GB, Vaisberg AJ, Neto CC. Identification of triterpene hydroxycinnamates with in vitro antitumor activity from whole cranberry fruit (Vaccinium macrocarpon). J Agric Food Chem. 2003;51(12):3541–3545. https://doi.org/10.1021/jf034114q

Xiang T, Tezuka Y, Wu LJ, Banskota AH, Kadota S. Saponins from Lonicera bournei. Phytochemistry. 2000;54(8):795–799. https://doi.org/10.1016/S0031-9422(00)00194-1




DOI: https://doi.org/10.5586/asbp.3539

Journal ISSN:
  • 2083-9480 (online)
  • 0001-6977 (print; ceased since 2016)
This is an Open Access journal, which distributes its content under the terms of the Creative Commons Attribution License, which permits redistribution, commercial and non-commercial, provided that the content is properly cited.
The journal is a member of the Committee on Publication Ethics (COPE) and aims to follow the COPE’s principles.
The journal publisher is a member of the Open Access Scholarly Publishers Association.
The journal content is indexed in Similarity Check, the Crossref initiative to prevent scholarly and professional plagiarism.
Publisher
Polish Botanical Society