Impaginato 471 Adv. Hort. Sci., 2018 32(4): 471-477 DOi: 10.13128/ahs-21989 Essential oil production of Murraya paniculata (L.) Jack at different harvest times C.I.M. Semarayani, S.A. Aziz (*), M. Melati Department of Agronomy and Horticulture, Faculty of Agriculture, Bogor Agricultural University, 16680 Bogor, Indonesia. Key words: β-methylesculetin, caryophyllene, murralongin, solvent extraction. Abstract: Murraya paniculata (L.) Jack has a fragrant flower, from which the fragrance is due to the essential oil. The study aimed to investigate the produc- tion of essential oil and its chemical compounds at different harvest times. The research was conducted at an organic experimental farm, Bogor Agricultural University, Bogor, Indonesia (6°30’-6°45’ S, 106°30’-106°45’ E) from October 2016 to February 2017 using randomized complete block design. The experi- ment consisted of one factor, namely the harvest times, comprised of harvest at 05.00-07.00 and 07.00-09.00 a.m. M. paniculata flowers were collected at three different flower ages, comprised of two days before anthesis, one day before anthesis and the day of anthesis (blooming). The different flower ages indicated by the flower size. Ethanol extraction method was used to extract the essential oil of the flowers from different harvesting times and then chemical compounds were analyzed by Gas Chromatography-Mass Spectrometry. The result showed that flower number and weight were not affected by harvesting times. The flower collected on the day of anthesis had the highest flower num- ber and weight. Harvesting flowers at anthesis can be done at 05.00-09.00 a.m. The highest quantity and quality of essential oils were obtained by harvesting the flowers at anthesis. β-methylesculetin and murralongin were the primary compounds in M. paniculata flowers that harvested at 05.00-09.00 a.m. 1. Introduction Murraya paniculata (l.) Jack well known as orange jessamine is an ornamental plant and belongs to family rutaceae (Shah et al., 2014), it has white flowers with sweet fragrance (Gilman, 1999). the plants are native to Southeastern Asia, i.e. cambodia, laos, myanmar, thailand, Vietnam, indonesia, malaysia, and Philippine (Dosoky et al., 2016). M. paniculata has been used in traditional medicine because the plant has anti-amnesic, anti-inflammatory, anti-diabetic, anti-fungal, anti-bacterial, anti-helminthic, anti-cancer, and anti-oxidative properties (Sharma and Arora, 2015). Beside as a source for perfumery, M. paniculata is also used as a source of flavors (el-Sakhawy et al., 1998) because the flowers are highly aromatic and contain sufficient amount of essential oil (naseem et al., 2015). Plants essential oils are aromatic components that composed (*) Corresponding author: sandra.a.aziz@gmail.com Citation: SemArAyAni c.i.m., Aziz S.A., melAti m., 2018 - Essential oil production of Murraya paniculata (L.) Jack at different harvest times. - Adv. Hort. Sci., 32(4): 471-477 Copyright: © 2018 Semarayani c.i.m., Aziz S.A., melati m. this is an open access, peer reviewed article published by Firenze University Press (http://www.fupress.net/index.php/ahs/) and distributed under the terms of the creative commons Attribution license, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Data Availability Statement: All relevant data are within the paper and its Supporting information files. Competing Interests: the authors declare no competing interests. received for publication 3 november 2017 Accepted for publication 18 may 2018 AHS Advances in Horticultural Science Adv. Hort. Sci., 2018 32(4): 471-477 472 of different chemical compounds (younis et al., 2011). Different compositions of chemical compound of M. paniculata essential oils have been studied. rout et al. (2007) found that pentane extraction was the best method to obtain the highest amount of essen- tial oil of M. paniculata flowers in india. this study also found that manool and (E)-nerolidol were the major component of essential oil (rout et al., 2007). the chemical compounds of M. paniculata flowers can also be extracted with liquid cO 2 (rout et al., 2010). Different compounds from M. exotica flowers w e r e f o u n d , n a m e l y ( E , E , E ) - α - s p r i n g e n e , ( E ) - nerolidol, (E,E)-α-farnesene, methyl palmitate and germacrene B (raina et al., 2006). the variation of chemical composition in the essential oil from Murraya flowers is affected by the place where the plants are planted (el-Sakhawy et al., 1998) and harvesting time. concerning the latter, harvesting time may influence the quantity and quali- ty of essential oils of M. paniculata flowers; this has been reported in four Rosa cultivars (younis et al., 2009) and Jasminum sambac flowers (younis et al., 2011). younis et al. (2011) reported that the best time to collect J. sambac flowers was in the morning before sunrise because highly volatile of jasmine oil. therefore, the purpose of this research was to investigate the effect of harvest time on the produc- tion and chemical compounds of M. paniculata essential oil. 2. Materials and Methods Plant material t h e f i e l d e x p e r i m e n t w a s c o n d u c t e d f r o m October 2016 to February 2017. the experiment used 30 (62 month-old) plants that were planted in 1 m x 1 m on latosol soil, at the organic experimental farm, Bogor Agricultural University, Bogor, indonesia (6°30’-6°45’ S, 106°30’-106°45’ e) at 250 m above sea l e v e l . A v o u c h e r s p e c i m e n w a s d e p o s i t a t t h e Herbarium Bogoriense, Bogor, indonesia. type-A cli- mate based on Schmidt-Ferguson with the average monthly rainfall, temperature and humidity of 305 mm, 26°c and 85%, respectively (mcGA, 2017). Before treatment, each plant was fertilized with 3.0 kg rice-hull ash, followed eliazar and Aziz (2015). Experimental design the experiment was arranged in randomized com- plete block design, with single factor (Petersen, 1994) with harvest times as treatments, comprised of har- vest at 05.00-07.00 and at 07.00-09.00 a.m. the flow- ers were collected at three different ages, comprised of two days before anthesis, one day before anthesis, and at the day of anthesis. the two ages of flower before anthesis were indicated by the size of flower buds which have been observed in the preliminary study. the anthesis of the flower bud with 1.00±0.06 cm length and 0.48±0.06 cm width will occur two days later; while flower bud with 1.16±0.06 cm length and 0.56±0.04 cm width will occur in the next day. the observations include developmental stages, number, fresh weight, the content of essential oils and chemical compounds of M. paniculata flowers. Data were analyzed using t-student with α= 5% (Petersen, 1994). Essential oil extraction the analysis of essential oils was conducted at t r o p i c a l B i o p h a r m a c a r e s e a r c h c e n t e r , B o g o r Agricultural University, Bogor, indonesia. All harvest- ed flowers (from different harvesting times) were extracted with solvent extraction method of ethanol. the flowers were immersed in ethanol until all sam- ples were submerged, for two days. this mixture was filtered, then, the extract was separated from the solvent by rotary evaporator with a temperature of 40°c. the oil yield percentage was calculated from the weight of extract (g) divided by weight of fresh flower (g). Gas chromatography-mass spectrometry analysis chemical compounds of essential oils were ana- lyzed at Health laboratory of DKi Jakarta Province. t h e e s s e n t i a l o i l s w e r e i n j e c t e d i n t o G a s chromatography-mass Spectrometry (GcmS). An Agilent technologies 7890 Gas chromatography instrument with an Auto Sampler and 5975 mass Selective Detector and chemstation Data System, equipped with a 30 m x 0.25 mm HP Ultra 2 capillary column with 0.25 µm film thickness. Helium was used as the carrier gas. the initial temperature was pro- grammed at 80°c and then increased at the rate of 3°cmin-1 to 150°c held for 1 min and finally raised to 280°c at the rate of 20°c min-1 held for 26 min. the injector and interface temperatures were 250°c and 280°c, respectively. the ionization voltage was 70eV and a sample injection volume 5 µl. the individual peaks were identified by retention times, compared with those of compounds in Health laboratory of DKi Jakarta Province database. the percentage of each compound detected from samples was calculated according to the area of the chromatographic peaks. Semarayani et al. - Essential oil production of Murraya paniculata L. 473 3. Results the results showed that the average of flower number (regardless the flower ages) harvested at 05.00-07.00 Am was not significantly different to those harvesting at 07.00-09.00 a.m. (table 1). At both har- vest times, it was found the following order of flower number based on flower stages: flowers at anthesis, flowers that would bloom two days later, and the least was flowers that would bloom in the next day. the differences in flower number between flower stages were not always significant. the difference of flower number between harvesting time was 8.96%. the average flower weight (regardless the flower stages) of M. paniculata was not significantly different between the times of harvesting (table 2). A similar trend as of flower number was also found in flower weight based on flower stages. the highest flower weight was blooming flowers (flowers at anthesis), and the lowest was flowers at the stage of one day before anthesis. the difference in flower weight between harvesting time was 16.59%. the extraction of M. paniculata flowers at differ- ent harvesting times with ethanol resulted in a yel- lowish-brown solution called concrete. these results were in line with that of Paibon et al. (2011), that reported how the extraction of J. Sambac flowers with ethanol produced a solution of yellowish brown to reddish. On the other hand, M. paniculata flowers that extracted with pentane produced a deep yellow waxy residue (rout et al., 2007). there was an indication that the essential oil per- centage between harvest times was different. the percentage of essential oils from flowers harvested at 07.00-09.00 was higher than that at 05.00-07.00 a.m., regardless the flower stages, the difference was 0.38% (table 3). comparing among flower stages, it was found that anthesis flowers harvested at 05.00- 07.00 Am had the highest percentage of essential oils. On the other hand, the highest percentage of essen- tial oils at 07.00-09.00 Am was obtained from flowers at the stage of one day before anthesis. From this calculation, the production of essential oils from flowers harvested at 07.00-09.00 was higher than that from 05.00-07.00 Am. Based on flower stages, blooming flowers (at anthesis stage) produced the highest amount of essential oils at both harvesting times, this related to the highest fresh flower weight. the analysis of chemical compounds showed 41 types that were contained in M. paniculata flowers at different harvesting times. the highest number of chemical compound types was found in flowers at anthesis when they were harvested at 07.00-09.00 Am. this result was in line with younis et al. (2011), where J. Sambac flowers harvested at anthesis had table 1 - number of orange jessamine flowers at different har- vesting times if P-value>α; α= 0.05, then means between the treatments were statistically equal; (k) = average of flower number at three flower age criteria; x= comparison between the flower 2 days before anthesis with 1 day before anthesis; y= comparison between the flower 2 days before anthesis with anthesis; z= comparison between the flower 1 day before anthesis with anthesis. Harvesting time Average of flower number/plant P-value Percentage of flower number (%) At 05.00-07.00 Am, flower ages 29.40 (k) 2 days before anthesis 24.67 x: 0.3349 nS 27.97 1 day before anthesis 14.07 y: 0.1742 nS 15.95 At anthesis 49.47 z: 0.0397 * 56.08 At 07.00-09.00 Am, flower ages 31.11 (k) 2 days before anthesis 35.53 x: 0.0150 * 38.82 1 day before anthesis 12.87 y: 0.5056 nS 14.06 At anthesis 44.93 z: 0.0282 * 47.12 table 2 - Weight of orange jessamine flowers at different har- vesting times if P-value>α; α= 0.05, then means between the treatments were statistically equal; k: average of flower number at three flower age criteria; x: comparison between the flower 2 days before anthesis with 1 day before anthesis; y: comparison between the flower 2 days before anthesis with anthesis; z: comparison between the flower 1 day before anthesis with anthesis. Harvesting time Average of flower weight (g/plant) P-Value Percentage of flower weight (%) At 05.00-07.00 Am, flower ages 3.43 (k) 2 days before anthesis 2.05 x: 0.4572 nS 19.92 1 day before anthesis 1.34 y: 0.0884 nS 13.21 At anthesis 6.88 z: 0.0355 * 66.86 At 07.00-09.00 Am, flower ages 4.72 (k) 2 days before anthesis 5.70 x: 0.0819 nS 40.35 1 day before anthesis 1.33 y: 0.4398 nS 9.38 At anthesis 7.13 z: 0.0029 ** 50.27 table 3 - the percentage and production of essential oil of orange jessamine flowers at different harvesting times Data were not analyzed statistically; (k ) = average of essential oils at three flower age criteria; * = Production of essential oils based on the weight of the harve- sted flowers. treatment essential oil (%) Production of essential oil (g/g fresh flower) * At 05.00-07.00 Am, flower ages 3.13 (k) 4.83 2 days before anthesis 2.06 0.63 1 day before anthesis 3.40 0.69 At anthesis 3.94 4.07 At 07.00-09.00 Am, flower ages 3.51 (k) 7.47 2 days before anthesis 3.49 3.00 1 day before anthesis 3.80 0.76 At anthesis 3.25 3.47 Adv. Hort. Sci., 2018 32(4): 471-477 474 more chemical compounds than those in flower bud. the analysis on M. paniculata flowers revealed the presence of coumarins, esters, fatty acids, phenolics, triterpenes, sesquiterpenes and other compounds (table 4). coumarin was the most common com- pound found in all treatments. Harvesting time at 0 5 . 0 0 - 0 7 . 0 0 a . m . g a v e t h e h i g h e s t n u m b e r o f coumarins, esters, fatty acids, and sesquiterpenes. coumarin was the highest amount of bioactive compound found in M. paniculata essential oils, ( t a b l e 4 ) a n d t h e d o m i n a n t c o m p o u n d s i n t h e coumarin group were β-methylesculetin and murra- longin (table 5). the amount of β-methylesculetin from flowers harvested at 07.00-09.00 Am was higher than those from 05.00-07.00 a.m. Different flower s t a g e s h a d a d i f f e r e n t d o m i n a n t c o m p o u n d . Harvesting flowers at the stage of one day before anthesis gave the highest percentage of β-methyles- culetin at both harvesting times, but harvesting at anthesis delivered the highest percentage of murra- longin. the analysis of chemical compounds showed that terpenoid groups found in the essential oil of M. pan- iculata flowers were triterpenes and sesquiterpenes (table 4). the percentage of triterpenes was higher than sesquiterpenes, this finding was different from the previous study which showed that sesquiter- penes were the main compound in essential oils. the current study showed that sesquiterpenes deriva- tives found in the essential oils of M. paniculata flow- ers and found at both harvesting times were α- zingiberene, α-bergamotene, and caryophyllene (table 6). Flowers harvested at 05.00-07.00 Am had a higher percentage of α-zingiberene, α-bergamotene, and caryophyllene compare to those harvested at 07.00-09.00 a.m. there was an indication that differ- ent flower ages have different compositions of chemi- cal compounds, except caryophyllene that was found at the same flower age at both harvesting times. 4. Discussion and Conclusions the above results showed that there were no sig- nificant differences between the number and weight of flowers harvested at 05.00-07.00 and 07.00-09.00 Am. the different harvesting times reflected the posi- table 4 - chemical compounds of orange jessamine essential oils at different harvesting times Data were not analyzed statistically; k= average of chemical compounds at three flower age criteria. treatment % Peak area coumarin ester Fatty acid Phenolic triterpene Sesquiterpene Other compound At 05.00-07.00 am, flower ages 71.29 k 1.80 k 9.12 k 4.34 k 3.27 k 0.77 k 9.42 k 2 days before anthesis 69.68 3.16 12.39 5.52 1.55 0.47 7.24 1 day before anthesis 74.33 1.41 10.09 4.43 1.33 0.55 7.87 At anthesis 69.85 0.83 4.89 3.06 6.93 1.30 13.14 At 07.00-09.00 am, flower ages 68.07 k 1.60 k 10.40 k 5.09 k 1.93 k 0.72 k 12.20 k 2 days before anthesis 66.98 2.15 11.91 6.20 1.03 0.41 11.33 1 day before anthesis 70.52 1.21 5.87 5.13 1.21 0.71 15.34 At anthesis 66.72 1.44 13.41 3.94 3.55 1.04 9.92 table 5 - coumarins compounds of orange jessamine essential oils at different harvesting times Data were not analiyzed statistically; k: average of chemical com- pounds at three flower age criteria. treatment % Peak area β-methylesculetin murralongin At 05.00-07.00 am, flower ages 60.65 (k) 7.36 (k) 2 days before anthesis 59.46 5.36 1 day before anthesis 61.59 7.76 At anthesis 60.89 8.96 At 07.00-09.00 am, flower ages 62.07 (k) 5.71 (k) 2 days before anthesis 61.00 5.12 1 day before anthesis 65.51 5.01 At anthesis 59.71 7.01 table 6 - Sesquiterpenes compounds of orange jessamine essential oils at different harvesting times Data were not analyzed statistically; k: average of chemical com- pounds at three flower age criteria. zBn, zingiberene; BGn, berg- amotene; cP, caryophyllene. treatment % Peak area α-zBn α-BGn cP At 05.00-07.00 Am, flower ages 0.75 (k) 0.55 (k) 0.27 (k) 2 days before anthesis 0.47 0.00 0.00 1 day before anthesis 0.00 0.55 0.00 At anthesis 1.03 0.00 0.27 At 07.00-09.00 Am, flower ages 0.71 (k) 0.41 (k) 0.17 (k) 2 days before anthesis 0.00 0.41 0.00 1 day before anthesis 0.57 0.00 0.15 At anthesis 0.85 0.00 0.19 Semarayani et al. - Essential oil production of Murraya paniculata L. 475 tion of sunrise where higher light intensity was found at 07.00-09.00 Am. the current study showed that the anthesis of M. paniculata flowers occurred before 05.00 Am, therefore there was no increase in the number and weight of flower after that time. De Souza et al. (2004) reported that the anthesis of Metrodorea nigra St. Hill. flowers, belonging to rutaceae family, occurs in the morning. time of har- vesting is important because it is related to the amounts of essential oils produced. Filho et al. (2006) reported that harvest at 08.00 Am resulted in the highest yield of the essential oil from fresh leaves of basil (Ocimum basilicum l.). the importance of har- v e s t i n g t i m e i s a l s o s h o w n b y D o b r e v a a n d Kovacheva (2010) where the essential oils content of Rosa damascena mill. and R. alba l. drops dramati- cally when the flowers collected after noon. Besides investigating the effect of harvesting time, this study also observed the essential oil pro- duction at different flower developmental stages of M. paniculata. the results showed that harvesting flowers at anthesis stage (blooming flower) yielded the highest percentage of essential oils. Flowering plants released diverse blends of volatile to attract pollinator and seed disseminators. the floral scent is a signal, which pollinators can use to discriminate a particular flower. it may contain from one to 100 volatile substances, but most species emit between 20 and 60 different compounds, so there won’t be any identical floral scents (Dudareva et al., 2006). therefore, the presence of essential oil at anthesis will ensure the reproductive success. Azam et al. (2013) also reported that the highest amounts of volatile compounds were present in fully opened flowers of Citrus reticulata Blanco, C. unshiu marc., C. sinensis (l.) Osbeck, C. limon (l.) Burm., C. medica (l.), and C. changshanensis chen et. Fu. in general, essential oils are a mixture of com- pounds belonging to different chemical entities such as terpenes, phenols, aliphatic compounds, ben- zenoid, and heterocyclic compounds (Shakeel-u- rehman et al., 2018). chemical compounds found in M. paniculata flowers in india were monoterpenes, sesquiterpenes, benzenoids, diterpenes, and fatty acids (rout et al., 2007). Different from those study, the current experiment showed that coumarins were the dominant compounds in M. paniculata flowers. coumarins are also present in leaves of M. paniculata in indonesia (Kinoshita and Firman, 1996) and taiwan (Kinoshita et al., 1996). Furthermore, from the cur- r e n t s t u d y , i t w a s f o u n d t h e p r e s e n c e o f t w o c o u m a r i n s d e r i v a t i v e s i n e s s e n t i a l o i l s o f M . paniculata, β-methylesculetin and murralongin. β- methylesculetin compounds can function as antioxi- dants (Kontogiorgis and Hadjipavlou-litina, 2005) and anti-inflammatory (Kontogiorgis and Hadjipavlou- litina, 2005; zuoqi et al., 2008). murralongin is thought to be a chemical compound identifier of M. paniculata essential oils. Harvesting at anthesis pro- duced the highest percentage of murralongin. the previous study reported that murralongin was found in essential oils from leaves and flowers of M. panicu- lata (Gill et al., 2014), and leaves of M. omphalocarpa in taiwan (chen et al., 2003). terpenoids compounds that were identified in this study were triterpenes and sesquiterpenes. in gener- al, terpenoids are the dominant compounds in essen- tial oils (Sangwan et al., 2001). the current study showed that the percentage of triterpenes com- pounds is higher than sesquiterpenes (table 4). this was not in line with Butu et al. (2014) who reported that the basic compound in the essential oil was sesquiterpenes. terpenoids have many volatile com- pounds that have high enough vapor pressures at nor- mal atmospheric conditions to allow significant release into the air (Dudareva et al., 2004). therefore, despite the same plant, may have different types of compounds. Sesquiterpenes compounds that could be identified in this current study were α-zingiberene, α-bergamotene, and caryophyllene. there were simi- larity and difference between this finding and the pre- vious study. the similarity was reported by raina et al. (2006) where those three compounds were also found in M. exotica essential oils from flowers. raina et al. (2006) found that caryophyllene had the highest percentage, on the contrary, the current study showed that caryophyllene had the lowest percent- age. the different finding indicates that the chemical composition and yield of essential oils are affected by many factors, such as provenance, weather, soil con- ditions, time of harvest, and the extraction method (Boira and Blanquer, 1998). caryophyllene is one of the compounds in perfume ingredient (Salvador- carreno and chisvert, 2005), but it also used as a mix- ture of spices, citrus scents, soaps, detergents, lotions as well as in various food products (Sabulal et al., 2006). 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