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Anise (Pimpinella anisum L.) is a spice, an essential oil crop, and a medicinal plant with a long history of use. Anise seed oil is extracted from anise seed through steam distillation. There is no experimentally established optimal time for distillation of anise seed. We hypothesized that the distillation time (DT) can be customized for optimum yield and composition of anise essential oil. In this study, we determined the effect of nine steam DTs (5, 15, 30, 60, 120, 180, 240, 360, and 480 minutes) on essential oil yield and essential oil composition of anise seed. We developed regression models to predict essential oil yield, the concentration of individual constituents, and the yield of these constituents as a function of DT. Highest essential oil yield (2.0 g/100 g seed, 2%) was obtained at 360-minute DT. The concentration of transanethole, the major anise oil constituent, varied from 93.5% to 96.2% (as a percent of the total oil) and generally was high at 15to 60-minute DT and low at 240to 480-minute DT. However, the yield of transanethole (calculated from the essential oil yield and the concentration of transanethole in the oil) increased with increasing DT to reach maximum at 360-minute DT. The concentration of the other oil constituents varied significantly depending on the DT, and some of them were higher at the shorter DT than at the longer DT. However, the yields of these constituents were highest at longer DT (either 360 or 480 minutes). DT can be used to obtain anise essential oil with different composition that would benefit the essential oil industry. This study demonstrated the need for providing DT in reports where anise seed essential oil yield and composition are discussed. This article can also be used as a reference point for comparing studies in which different DTs were used to extract essential oil from anise seed. Anise (Pimpinella anisum L.) is one of the most widely used plants in the world; anise seed is used as a spice (Leela and Vipin, 2008), and anise seed essential oil has a number of applications as an aromatic agent in the food and liquor industry (Leela and Vipin, 2008; Stojanov, 1973; Tonutti and Liddle, 2010). Commercial production of anise seed and anise essential oil is concentrated in countries in south Asia, Europe, North Africa, and also in Russia. Anise has been used as a medicinal plant since ancient times (Leela and Vipin, 2008). Many folk medicinal systems from Asia to the Mediterranean are still using anise seed as a medicinal plant (Leela and Vipin, 2008; Stojanov, 1973). For example, Bulgarian traditional medicine has been using anise seed or anise seed extract as an anesthetic, antispasmodic, carminative, for treating coughs, bronchitis, asthma, other inflammatory diseases, kidney stones, and for increasing lactation in nursing mothers (Stojanov, 1973). Anise fruits are widely used in the preparation of traditional bread and baking goods, in liquor, and for aromatization of traditional Bulgarian liquor annasonliika, whereas anise essential oil is used as an aromatic agent in the pharmaceutical, perfumery, cosmetics, and candy production industries (Stojanov, 1973; Tonutti and Liddle, 2010). Anise seed essential oil is also an ingredient in various beverages such as aquebuse, Italian sambuca, Bulgarian mastika, Greek ouzo, in French spirits absinthe, anisette, pastis, German Jägermeister, Spanish anis, and many other alcoholic and nonalcoholic beverages (Tonutti and Liddle, 2010). Anise essential oil has also antimicrobial and other medicinal properties (Gende et al., 2009; Leela and Vipin, 2008) and has been explored as a food preservative and for decreasing aflatoxin B1 in maize grain (Bluma and Etcheverry, 2008). Anise seed essential oil content and composition vary depending on the environment and the genotype (Leela and Vipin, 2008). Steam distillation has been traditionally used for extracting essential oil from anise seed. Steam DT has been demonstrated to alter essential oil yield and composition of other crops such as peppermint (Mentha ·piperita L.), lemongrass (Cymbopogon flexuosus Steud.), and palmarosa (Cymbopogon martini Roxb.) (Cannon et al., 2013), pine (Pinus ponderosa Dougl. ex Laws) (Zheljazkov et al., 2012a), Japanese cornmint (Mentha canadensis L.) (Zheljazkov and Astatkie, 2012), oregano (Origanum vulgare L.) (Zheljazkov et al., 2012b), female and male Rocky Mountain juniper (Juniperus scopulorum Sarg.) (Zheljazkov et al., 2012c, 2013). However, there are no reports on the effect of DT on anise seed essential oil yield and composition. We hypothesized that DT can alter anise seed essential oil yield and composition, and hence, DT can be customized to obtain essential oil with a desired profile. Materials and Methods Steam distillation and distillation times. All steam DTs were conducted in 2-L steam distillation units (Hearthmagic, Rancho Santa Fe, CA) as described previously for extraction of basil essential oil (Zheljazkov et al., 2008) and for the distillation of Juniperus virginiana L. (Gawde et al., 2009). Certified organic bulk anise seed was purchased from Starwest Botanicals (Rancho Cordova, CA). The country of origin for the organic anise seed used in this study was Egypt. The DT experiments were conducted at the University of Wyoming Sheridan Research and Extension Center in 2012. The sample size was 500 g of anise seed; all samples were generated randomly from the bulk seed lot. All DTs were performed in three replicates. Nine steam DTs were studied: 5 min, 15 min, 30 min, 60 min, 120 min, 180 min, 240 min, 360 min, and 480 min. We have chosen the DTs based on our preliminary studies, indicating that sufficient amount (for handling and analyses) of essential oil can be obtained at 5-min DT, on literature data, and on the commonly used DT by the essential oil industry extracting anise oil (Dr. Nedko Nedkov, personal communication). The individual DTs were measured from the beginning of the distillation, considered the moment the first drop of essential oil was deposited. At the end of each individual DT, the power was turned off and the Florentine vessel (the separator) removed from the apparatus. The extracted essential oils were separated, measured on an analytical Received for publication 7 June 2013. Accepted for publication 25 Sept. 2013. This research was supported by start-up funds from the University of Wyoming awarded to Dr. V.D. Zheljazkov. To whom reprint requests should be addressed; e-mail vjeliazk@uwyo.edu, valtcho.pubs@gmail.com. HORTSCIENCE VOL. 48(11) NOVEMBER 2013 1393 scale, and placed in a freezer at –5 C until they were analyzed. The essential oil yield (content) was calculated as grams of oil per 100 g weight of anise seed. The water content of the seed was 8.9%. Gas chromatography analysis of essential oil. The anise seed essential oil samples (all samples in three replicates) were analyzed on a gas chromatograph (GC; Hewlett Packard Model 6890; Hewlett-Packard, Palo Alto, CA). The carrier gas was helium at flow rate of 40 cm·sec, 11.7 psi (60 C), and 2.5 mL·min constant flow rate. The injection was split 60:1, 0.5 mL, and the injector temperature was 220 C. The GC oven temperature program was as follows: 60 C for 1 min and 10 C/min to 250 C. The column was HP-INNOWAX (crosslinked polyethylene glycol; 30 m · 0.32 mm · 0.5 mm), and the flame ionization detector temperature was 275 C. Individual constituents of the anise essential oil are expressed as percentage of the total oil. The identification of individual constituent peaks was done with the use of internal standards by retention time and by mass spectroscopy. Statistical analyses. The effect of DT on essential oil content and on the concentration and yield of linalool, methyl chavicol, para-anis-aldehyde, transanethole, gammahimachalene, transpseudoisoeugenyl-2-methyl, and epoxy-pseudoisoeugenyl-2-methyl was determined using a one-way analysis of variance. For each response, the validity of model assumptions was verified by examining the residuals as described in Montgomery (2013). Because the effect of DT was significant (P value < 0.05) on all responses, multiple means comparison was completed using Duncan’s multiple range test at the 5% level of significance, and letter groupings were generated. The analysis was completed using the GLM Procedure of SAS (SAS Institute Inc., 2010). Regression analysis to model the relationship between DT and essential oil content as well as the concentration of each of the constituents suggested that six of them (essential oil content and the concentration of linalool, methyl chavicol, transanethole, epoxy-pseudoisoeugenyl-2-methyl, and transpseudoisoeugenyl-2-methyl) can be adequately modeled (Bates and Watts, 2007) using the Asymptotic (Eq. 1), Power (Eq. 2), or the third-order polynomial (Eq. 3) model. There was no clear relationship between DT and the concentration of para-anis-aldehyde and gamma-himachalene. The relationship between DT and the yields of all seven constituents was adequately modeled by either the Asymptotic (Eq. 1) or the third-order polynomial (Eq. 3) model. Although the Asymptotic and the Power models are nonlinear, the third-order polynomial model is linear. The parameters of the nonlinear models were estimated iteratively using the NLIN Procedure of SAS (SAS Institute Inc., 2010). Y 1⁄4 q1 q2e q3x þ e (1)

Essential Oil Composition and Yield of Anise from Different Distillation Times