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Potentially Bioactive Volatile Compounds of Some FARMACIA, 2020, Vol. 68, 5 https://doi.org/10.31925/farmacia.2020.5.13 ORIGINAL ARTICLE POTENTIALLY BIOACTIVE VOLATILE COMPOUNDS OF SOME EPIPHYLLUM, HYLOCEREUS AND OPUNTIA SPECIES (CACTACEAE FAMILY) CULTIVATED IN CENTRAL EUROPE AND THEIR HS- SPME GC-MS ANALYSIS SZILVIA CZIGLE 1*, MICHAELA BARKOCIOVÁ 1, ÉVA HÉTHELYI B. 2, ANNAMARIA PALLAG 3, ANDREA BӦSZӦRMÉNYI 2, ANTONIOS KOUTSOULAS 1, JAROSLAV TÓTH 1, PAVEL MUČAJI 1 1Comenius University in Bratislava, Faculty of Pharmacy, Department of Pharmacognosy and Botany, 10 Odbojárov Street, SK-832 32, Bratislava, Slovak Republic 2Semmelweiss University, Faculty of Pharmacy, Institute of Pharmacognosy, 26 Üllői út Street, H-1085, Budapest, Hungary 3University of Oradea, Faculty of Medicine and Pharmacy, Department of Pharmacy, 29 Nicolae Jiga Street, RO-410028, Oradea, Romania *corresponding author: [email protected] Manuscript received: December 2019 Abstract The aim of our work was to analyse volatile compounds obtained from the fruits of three plant genera – Epiphyllum, Hylocereus and Opuntia – using HS-SPME GC-MS (headspace solid phase microextraction gas chromatography - mass spectrometry) methods. In violet Epiphyllum fruits, 12 compounds were identified, the most abundant being 2,3-butane-diol and hexanoic acid. In pink Epiphyllum fruits, 13 compounds were identified, the most abundant being (E)-anethol and 1-nonadecene. In green Epiphyllum fruits, 10 compounds were identified, the most abundant being (E)-anethol and methyl eugenol. In white- fleshed Hylocereus fruits, 9 compounds were identified, the most abundant being 1-hexadecanol and nonadecane. In red- fleshed Hylocereus fruits, 11 compounds were identified, the most abundant being 1-hexadecanol and nonadecane. Analysis of violet Opuntia fruits yielded 12 compounds, the most abundant being nonanal and ethyl decanoate. Analysis of orange Opuntia fruits yielded 8 compounds, the most abundant being ethyl decanoate and (3E)-1,3-octadecadiene. Rezumat Scopul lucrării noastre a fost analiza compușilor volatili din fructele obținute de la trei genuri – Epiphyllum, Hylocereus și Opuntia – folosind o metodă HS-SPME GC-MS. În fructele violete de Epiphyllum, au fost identificați 12 compuși, cei mai abundenți fiind 2,3-butan-diolul și acidul hexanoic. În fructele de Epiphyllum roz, au fost identificați 13 compuși, cei mai abundenți fiind (E)-anetolul și 1-nonadecenul. În fructele de Epiphyllum verzi au fost identificați 10 compuși, cei mai abundenți fiind (E)-anetolul și metil eugenolul. În fructele de Hylocereus cu mezocarpul alb, au fost identificați 9 compuși, cei mai abundenți fiind 1-hexadecanolul și nonadecanul. În fructele de Hylocereus cu mezocarpul roșu, au fost identificați 11 compuși, cei mai abundenți fiind 1-hexadecanolul și nonadecanul. Prin analiza fructelor violete de Opuntia am obținut 12 compuși, cei mai abundenți fiind nonanalul și decanoatul de etil. Prin analiza fructelor portocalii de Opuntia am obținut 8 compuși, cei mai abundenți fiind decanoatul de etil și (3E)-1,3-octadecadiena. Keywords: Epiphyllum ssp., Hylocereus ssp., Opuntia ssp., HS-SPME GC-MS Introduction 28, 31, 32]. Current research indicates that these plants possess antioxidant, antiinflammatory, antiproliferative, Plant hybrids of the Epiphyllum Haw. genus are hepatoprotective, antidiabetic, antihyperlipidaemic, cultivated mostly as ornamental plants. Besides, antibacterial, anti-ulcerogenic, neuroprotective, hepato- fruits of Epiphyllum hybrids are edible. The genus protective and diuretic activity and wound healing Hylocereus (Berger) Britt. is famous for its interestingly activities [2, 9, 10, 13-18, 20, 22, 24, 26, 28, 30, 33]. looking edible fruits (pitaya/pitahaya, or dragon fruit). The main objective of this study was to analyse the Opuntia ssp. Mill. fruits (tuna, cactus pears or prickly volatile compounds content and their composition in pears) and cladodes are widely consumed. The fruits Epiphyllum ssp., Opuntia ssp. and Hylocereus ssp. can be used as natural colourants safe sources. Main fruits (Cactaceae) originating from plants cultivated classes of compounds present in this genus include in the Central Europe. The plant materials were betalains (red betacyanins and yellow betaxanthins), collected from three gardens. This work is part of phenolic compounds, triterpenes, sterols, fatty acids, comprehensive pharmacognostic analyses. The efficient mucilage, vitamins, minerals and fibre [9, 11, 14, 15, 18, 864 FARMACIA, 2020, Vol. 68, 5 potent novel analytical method employed in this study placed in vials and directly used for HS-SPME GC- used a combination of headspace solid phase micro- MS analysis. extraction (HS-SPME) and gas chromatography–mass Equipment spectrometry (GC-MS). The composition of volatile compounds was measured by SPME GC-MS [AGILENT 6890/5973N GC/FID Materials and Methods (Santa Clara, USA), CTC Combi PAL sampler (CTC Analytics AG, CH)]. Details of the analytical procedures Plant material have been published in a recent paper from our Fruits of seven taxa of the Cactaceae family were laboratory [8]. analysed for the presence and quantity of volatiles. Epiphyllum ssp. Haw. (Hylocereeae tribe) hybrids Results and Discussion (EE × EK – violet, EE × EE – pink and EK × EE – green fruits) from a private garden in Modra, SK [11]; We determined the volatile compounds’ content in Hylocereus (Berger) Britt. (Hylocereeae tribe; H. fruits of plants of the Epiphyllum, Hylocereus and costaricensis – red-fleshed pitaya and H. undatus Opuntia genera cultivated in Central Europe using white-fleshed pitaya) from the Botanical Garden in the HS-SPME GC-MS technique. This method is a Szeged, HU; Opuntia ssp. Mill. (Opuntieae tribe; O. relatively new, very sensitive analytical method, humifusa – violet and O. ficus-indica – orange fruits) particularly when used in pharmacognostic analyses/ from the Comenius University Botanical Garden in control. The benefits of the HS-SPME method in Bratislava, SK. Ripe fruits were collected in September pharmagnostic analysis are: small sample weight, direct 2018. The Epiphyllum ssp. and Opuntia ssp. fruits handling of fresh, frozen or dry herbal drugs – without originated from 5-years to 10-years old fruticose the need of hydrodistillation, the possibility to analyse plants, and the pitaya/pitahaya (Hylocereus) from volatile compounds of any plant – not restricted to arboreous plants. Herbarium samples have been deposited typical essential oil bearing plants. The sensitivity of at the Department of Pharmacognosy and Botany the GS-MS method is very good. Results of the HS- (FPHARM CU, SK). At the time of analysis, frozen SPME GC-MS analyses are summarized in Table I. (-18C) fruits were cut into small pieces. They were Table I Percentage compositions of volatile oil components of Epiphyllum ssp., Hylocereus ssp. and Opuntia ssp. RT Essential oil compounds KI EV EP EG HW HR OV OO [min] [%] [%] [%] [%] [%] [%] [%] 3.23 2,3-butanediol 773 27.1 0.2 – – – – – – 3.34 unknown 820 – – – – – 3.1 0.2 – 7.31 ethyl hexanoate 998 – – – – – 2.0 0.1 6.3 0.5 7.43 1-octanol 1068 – – – – – 7.4 0.6 – 9.55 nonanal 1100 – – – – – 43.5 2.1 11.8 1.0 9.62 cis-rose oxide 1108 2.1 0.1 1.1 0.1 9.0 0.7 – – – – 11.35 ethyl octanoate 1196 – – – – – – 5.1 0.4 11.46 α-terpineol 1186 1.9 0.1 – 6.7 0.5 – – – – 12.06 neral 1238 – 1.6 0.1 – – – – – 12.41 geraniol 1249 – 11.7 0.1 – – – – – 12.71 orcinol dimethyl ether 1259 – 2.3 0.2 – – – – – 14.61 (3E)-1,3-octadecadiene 1267 – – – – – – 21.9 2.0 13.09 (E)-anethol 1282 0.6 0.0 28.1 2.2 20.5 2.0 – – – – 14.86 ethyl decanoate 1395 – – – – – 12.1 1.1 35.1 3.2 15.88 unknown 1495 – – – – 1.4 0.1 – – 16.61 methyl eugenol 1403 0.5 0.0 – 14.7 1.1 – – – – 16.65 (Z)-methyl isoeugenol 1459 – – – – – 1.1 0.1 – 17.95 dimethyl ionone 1565 – – – – 1.1 0.1 – – 18.03 ethyl dodecanoate 1595 – – – – – 4.0 0.3 10.6 1.0 18.35 unknown 1609 – – – – – 3.3 0.2 – 19.08 unknown 1620 – – – 1.7 0.1 0.7 0.0 – – 19.16 1-heptadecene 1689 1.1 0.1 2.0 0.2 – – – – – 19.46 heptadecane 1700 – 2.3 0.2 – 3.0 0.3 3.6 0.3 – – 19.56 unknown 1638 – – – – – 3.1 0.2 – 19.81 unknown 1356 – – – 0.8 0.0 1.0 0.0 – – 20.74 unknown 1699 – – – – – 3.0 0.1 – 21.43 3,4,5-trimethoxy benzoic acid 1771 – 6.5 0.4 – – – – – 865 FARMACIA, 2020, Vol. 68, 5 RT Essential oil compounds KI EV EP EG HW HR OV OO [min] [%] [%] [%] [%] [%] [%] [%] 21.62 hexahydrofarnesyl acetone 1845 – 3.9 0.3 – – – – – 21.93 1-hexadecanol 1874 – – – 64.2 5.0 63.7 5.3 – – 22.07 1-nonadecene 1891 5.4 0.5 14.0 1.2 – 7.2 0.6 6.8 0.5 – – 22.35 nonadecane 1900 – 3.8 0.3 – 7.8 0.6 8.0 0.6 – – 22.81 methyl hexadecanoate 1921 – – – 6.00 0.5 6.3 0.5 – – 23.43 hexadecanoic acid 1959 15.2 1.2 10.2 1.0 7.0 0.6 2.00 0.2 1.6 0.1 9.4 0.8 3.9 0.3 23.92 ethyl hexadecanoate 1993 10.4 0.9 – 13.2 1.2 – – 25.23 1-octadecanol 2077 – – – – – – – 25.35 heneicosane 2100 2.9 0.2 3.4 0.3 3.8 0.3 – 3.5 0.3 – – 25.41 1-eicosanol 2276 – – – 4.2 0.3 – – – 26.12 linoleic acid methyl ester 2092 – – – – – 4.2 0.3 4.4 0.3 26.22 linoleic acid ethyl ester 2155 8.4 0.7 – 7.5 0.6 – – – – 26.34 ethyl oleate 2185 17.8 1.5 – 12.7 1.1 – – – – Total identified 93.4 9.9 95.1 96.9 97.4 96.2 98.3 RT – retention time; KI – Kovats’ retention index (obtained by GC-MS in this study using a DB-5MS column); EV – violet Epiphylli fructus; EP – pink Epiphylli fructus; EG – green Epiphylli fructus; HW – white-fleshed Hylocerei fructus, HR – red-fleshed Hylocerei fructus; OV – violet Opuntiae fructus; OO – orange Opuntiae fructus Three Epiphyllum ssp.
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