Characteristic odor components of kumquat (Fortunella japonica Swingle) peel oil

This study was conducted to determine the composition of kumquat (Fortunella japonica Swingle) cold-pressed peel oil and to determine which volatile components are primarily responsible for the aroma of this oil. Eighty-two compounds were identified in the oil by GC and GC-MS. The major compounds were limonene (93.73%), myrcene (1.84%), and ethyl acetate (1.13%). Flavor dilution (FD) factors and relative flavor activities (RFA) of volatile constituents were evaluated by aroma extract dilution analysis with gas chromatography-olfactometry (GC-O). Camphene, terpinen-4-ol, citronellyl formate, and citronellyl acetate showed high FD factors (>/=5) and RFA (>20). Citronellyl formate and citronellyl acetate were regarded as the characteristic odor components of the kumquat peel oil from the results of FD factor, RFA, and GC-sniffing. Citronellyl acetate is considered to be the odor component most similar to kumquat by organoleptic evaluation with GC-O.     

Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage

The chemical changes and artifact formation in daidai (Citrus aurantium L. var. Cyathifera Y. Tanaka) cold-pressed peel oil upon storage at 20, 5, and -21 degrees C for 3, 6, and 12 months were investigated using capillary gas chromatography (GC) and GC-MS. Major changes occurred in the oil stored at 20 and 5 degrees C. No changes were found at -21 degrees C. Monoterpene hydrocarbons decreased from 98.0 to 66.4% upon 12 months at 20 degrees C, while sesquiterpene hydrocarbons and alcohols increased from 0.1 to 2.4% and from 0.3 to 7.9%, respectively. Notable decreases of germacrene D, myrcene, linalyl acetate, and limonene occurred. Prominent increases of cis-carveol, trans-beta-farnesene, trans-p-2,8-menthadien-1-ol, linalool, and beta-caryophyllene were found. Thirty-four artifact compounds constituting 17.0% of the total volatile compounds were formed upon 12 months at 20 degrees C. The artifacts consisted of 13 alcohols (6.0%), five carbonyl compounds (5.3%), seven esters (4.9%), three epoxides (0.4%), four hydrocarbons (0.3%), and two unidentified. The prominent artifact compounds were (+)-carvone, trans,trans-farnesyl acetate, sabinene hydrate, 1-octen-3-ol, cis,cis-farnesyl acetate, and dihydrocarveol acetate. The results could be applied for monitoring and control of the flavor quality of daidai essential oil and related products.     

Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu)

The composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu), isolated by the cold-pressing method, was investigated by capillary GC and GC-MS. The effects of harvesting time, degree of freshness, and size of fruits on the composition of Hyuganatsu peel oils were also determined. A total of 126 volatile constituents were confirmed in the Hyuganatsu oils. The Hyuganatsu oils contained hydrocarbons (95.95-96.95%), aldehydes (0.33-0.62%), alcohols (1.91%-2.64%), ketones (0.40-0.62%), esters (0.28-0.39%), oxides (0.04-0.06%), acids (0.01%), and trace amounts of fugenol methyl ether. Monoterpene hydrocarbons were predominant. Limonene (80.35-82.39%), gamma-terpinene (7.71-9.03%), myrcene (2.11-2.28%), linalol (1.37-2.01%), and alpha-pinene (1.17-1.43%) were the most abundant components in Hyuganatsu oils. The principal sesquiterpene hydrocarbon was trans-beta-farnesene (0.60-1.04%), and its content in Hyuganatsu oils was higher than in oils of other citrus fruits. The number of ketones and the content of l-carvone in Hyuganatsu oils were higher than in other citrus oils.     

Volatile constituents of wild citrus Mangshanyegan (Citrus nobilis Lauriro) peel oil

Volatiles of a wild mandarin, Mangshanyegan (Citrus nobilis Lauriro), were characterized by GC-MS, and their aroma active compounds were identified by aroma extract dilution analysis (AEDA) and gas chromatography-olfactometry (GC-O). The volatile profile of Mangshanyegan was compared with those of other four citrus species, Kaopan pummelo (Citrus grandis), Eureka lemon (Citrus limon), Huangyanbendizao tangerine (Citrus reticulata), and Seike navel orange (Citrus sinensis). Monoterpene hydrocarbons predominated in Mangshanyegan, in particular d-limonene and β-myrcene, which accounted for 85.75 and 10.89% of total volatiles, respectively. Among the 12 compounds with flavor dilution factors (FD) = 27, 8 oxygenated compounds, including (Z)- and (E)-linalool oxides, were present only in Mangshanyegan. The combined results of GC-O, quantitative analysis, odor activity values (OAVs), and omission tests revealed that β-myrcene and (Z)- and (E)-linalool oxides were the characteristic aroma compounds of Mangshanyegan, contributing to the balsamic and floral notes of its aroma.     

Character impact odorants of Citrus Hallabong [(C. unshiu Marcov x C. sinensis Osbeck) x C. reticulata Blanco] cold-pressed peel oil

The volatile components of Hallabong ([C. unshiu Marcov x C. sinensis Osbeck] x C. reticulata Blanco) cold-pressed peel oil were quantitatively and qualitatively determined by use of two internal standards with GC, GC-MS, and GC-olfactometry. According to instrumental analysis by GC and GC-MS, limonene (90.68%) was the most abundant compound, followed by sabinene (2.15%), myrcene (1.86%), and gamma-terpinene (0.88%). Flavor dilution (FD) factors of the volatile flavor components from Hallabong peel oil were determined by aroma extract dilution analysis. Furthermore, relative flavor activity was investigated by means of FD factor and weight percent. The highest FD factors were found for citronellal and citronellyl acetate, and delta-murollene showed a higher relative flavor activity. Results of sniff testing of the original oil and its oxygenated fraction revealed that citronellal, cis-beta-farnesene, and citronellyl acetate were regarded as the character impact odorants of Hallabong peel oil, and citronellal gave the most odor-active character of Hallabong aroma.     

Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract

Three active components were identified by bioassay-guided fractionation of bitter orange ( Citrus aurantium L.) fruit peel petroleum ether extract. Silica gel fractionation of the extract yielded a fraction that inflicted up to 96% mortality to adults of the olive fruit fly Bactrocera oleae (Gmelin) three days post-treatment. Subsequent HPLC purification of the active fraction resulted in the isolation of three components, eluted in fractions F 222, F 224, and F 226, that induced adult mortality. Considering the data obtained from UV, FTIR, MS, and (1)H NMR spectra, they were identified as 7-methoxy-8-(3'-methyl-2'-butenyl)-2 H-1-benzopyran-2-one (osthol), 4-methoxy-7 H-furo[3,2- g]benzopyran-7-one (bergapten), and 4-(( E)-3'-methyl-5'-(3',3'-dimethyloxiran-2'-yl)pent-2'-enyloxy)-7 H-furo[3,2- g][1]benzopyran-7-one (6',7'-epoxybergamottin). Our results are in concordance with those reported in the literature and were further verified by direct comparison to authentic components. 6',7'-Epoxybergamottin was toxic when tested individually, while bergapten and osthol were found to act synergistically to 6',7'-epoxybergamottin.     

Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya

The volatile constituents of cold-pressed peel essential oils of redblush grapefruit (Citrus paradisi Macfadyen forma Redblush) and pummelo (Citrus grandis Osbeck) from the same locality in Kenya were determined by GC and GC-MS. A total of 67 and 52 compounds, amounting to 97.9 and 98.8% of the two oils, respectively, were identified. Monoterpene hydrocarbons constituted 93.3 and 97.5% in the oils, respectively, with limonene (91.1 and 94.8%), alpha-terpinene (1.3 and 1.8%), and alpha-pinene (0.5%) as the main compounds. Sesquiterpene hydrocarbons constituted 0.4% in each oil. The notable compounds were beta-caryophyllene, alpha-cubebene, and (E,E)-alpha-farnesene. Oxygenated compounds constituted 4.2 and 2.0% of the redblush grapefruit and pummelo oils, respectively, out of which carbonyl compounds (2.0 and 1.3%), alcohols (1.4 and 0.3%), and esters (0.7 and 0.4%) were the major groups. Heptyl acetate, octanal, decanal, citronellal, and (Z)-carvone were the main constituents (0.1-0.5%). Perillene, (E)-carveol, and perillyl acetate occurred in the redblush grapefruit but were absent from the pummelo oil. Nootkatone, alpha- and beta-sinensal, methyl-N-methylanthranilate, and (Z,E)-farnesol were prominent in both oils.     

黔东南椪柑种植的生态气候适应性研究

在分析椪柑生产生态气候适应性的基础上,用统计学方法定量计算气候因子对椪柑产量的影响,确定椪柑生态气候主导指标,依此对黔东南山区椪柑果树种植进行气候区划,提出较好利用当地气候资源的有效途径。     

Characterization of flavonoids and pectins from bergamot (Citrus bergamia Risso) peel, a major byproduct of essential oil extraction

Bergamot peel is an underutilized byproduct of the essential oil and juice-processing industry. As with other Citrus peels, it still contains exploitable components, such as pectins and flavonoids. Commercial glycoside hydrolases, specifically a combination of pectolytic and cellulolytic enzymes, solubilized a high percentage of the material (81.94%). The flavonoid profile of the peel consisted of characteristic Citrus species flavanone rutinosides and neohesperosides derived from naringenin, eriodictyol, and hesperetin. In addition, a number of minor flavanone and flavone glycosides, not found in orange and lemon peels, were identified. The majority of flavonoids were extracted in the two 70% v/v EtOH extractions. Processing this material clearly has economic potential leading to low environmental impact.     

Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka)

The volatile components of Hyuganatsu (Citrus tamurana Hort. ex Tanaka) peel oil, isolated by cold-pressing, were investigated by chemical and sensory analyses. According to chemical analysis by GC and GC-MS, limonene (84.0%) was the most abundant compound, followed by gamma-terpinene (6.9%), myrcene (2.2%), alpha-pinene (1.2%), and linalool (1.0%). Monoterpene hydrocarbons were predominant in Hyuganatsu peel oil. The odor-active volatiles in Hyuganatsu flavor were studied by GC-olfactometry and omission tests. The characteristic flavor was present in the oxygenated fraction. Flavor dilution (FD) factors of the volatile flavor components of the Hyuganatsu cold-pressed oil were determined by aroma extraction dilution analysis (AEDA). Furthermore, relative flavor activity was investigated by means of FD factor and weight percent. Ten kinds of odor compounds having Hyuganatsu-like aroma were detected by AEDA: limonene, linalool, octanol, neral, neryl acetate, tridecanal, trans-carveol, cis-nerolidol, trans,trans-farnesyl acetate, and trans,trans-farnesol. Linalool and octanol were regarded as the most odor-active or key compounds of Hyuganatsu aroma. Diluted solutions of linalool and octanol of approximately 2 ppm gave a fresh and fruity aroma note similar to Hyuganatsu flavor.     

Hydroxylated polymethoxyflavones and methylated flavonoids in sweet orange (Citrus sinensis) peel

Polymethoxyflavones (PMFs) from citrus genus have been of particular interest because of their broad spectrum of biological activities, including antiinflammatory, anticarcinogenic, and antiatherogenic properties. There have been increasing interests in the exploration of health beneficial properties of PMFs in citrus fruits. Therefore, the isolation and characterization of PMFs from sweet orange (Citrus sinensis) peel will lead to new applications of the byproducts from orange juice processes and other orange consumption in nutraceutical and pharmaceutical products. In our study, eight hydroxylated PMFs, six PMFs, one polymethoxyflavanone, one hydroxylated polymethoxyflavanone, and two hydroxylated polymethoxychalcones were isolated from sweet orange peel and their structures were elucidated by various MS, UV, and different NMR techniques. Some of the hydroxylated PMFs and chalcones are newly isolated from sweet orange peel.     

Enzymatic hydrolysis of flavonoids and pectic oligosaccharides from bergamot (Citrus bergamia Risso) peel

Pectinolytic and cellulolytic enzymes (Pectinase 62L, Pectinase 690L, and Cellulase CO13P) were used to evaluate the solubilization of carbohydrates and low molecular weight flavonoids from bergamot peel, a major byproduct of the essential oil industry. The enzymes were characterized for main-chain and side-chain polysaccharide hydrolyzing activities and also against pure samples of various flavonoids previously identified in bergamot peel to determine various glycosidase activities. The addition of Pectinase 62L or 690L alone, or the combination of Pectinase 62L and Cellulase CO13P, was capable of solubilizing between 70 and 80% of the bergamot peel, and up to 90% of the flavonoid glycosides present were cleaved to their aglycones. Cellulase CO13P alone solubilized 62% of the peel but had no deglycosylating effect on the flavonoid glycosides. Over a 24-h time course, a rapid release of cell wall carbohydrates was observed after treatment with Pectinase 62L, with a concurrent gradual hydrolysis of the flavonoid glycosides. Size-exclusion chromatography of the solubilized extract showed that after 24-h incubation, the majority of the solubilized carbohydrates were present as monosaccharides with a smaller proportion of oligosaccharides.     

Isolation and identification of terpene chlorohydrins found in cold-pressed orange oil

Three terpene chlorohydrins found in cold-pressed orange oil were concentrated by silica adsorption chromatography and purified by preparative HPLC. Formation of these chlorohydrins was determined to be the result of a reaction of d-limonene, the major component of cold-pressed oil, with hypochlorous acid, found in chlorinated treatment water used in the oil recovery process. NMR analyses indicated that the major chlorohydrin present was the diequatorially substituted (1R,2R,4R)-2-chloro-8-p-menthen-1-ol (1). The other two compounds were the diaxial trans stereoisomer, (1S,2S,4R)-2-chloro-8-p-menthen-1-ol (2), and the dichlorohydrin, (1R,2R,4R)-2,9-dichloro-8-p-menthen-1-ol (3).     

Variation in major antioxidants and total antioxidant activity of Yuzu (Citrus junos Sieb ex Tanaka) during maturation and between cultivars

Epidemiological studies suggest that a high consumption of fruits can reduce the risk of some cancers and cardiovascular disease, and this may be attributable to the antioxidant activity of vitamins and phenolic compounds. The present study investigated the variations in vitamin C, total phenolic, hesperidin, and naringin contents, and total antioxidant activity of yuzu (Citrus junos Sieb ex Tanaka)-which is a popular citrus fruit in Korea and Japan-between cultivars and during maturity. The amounts of phenolics and vitamin C and the antioxidant activity in all tested yuzu cultivars were higher in peel than in flesh. Ripening increased the total antioxidant activity and vitamin C content in both peel and flesh of yuzu. However, the amounts of all total phenolics, hesperidin, and naringin in peel increased with ripening, whereas they decreased slightly in flesh. There was a highly linear relationship between the vitamin C content and the total antioxidant activity in both peel (r(2) = 1.000) and flesh (r(2) =0.998), suggesting that vitamin C plays a key role in the antioxidant activity of yuzu. In addition, the contribution of each antioxidant to the total antioxidant activity of yuzu was determined using a 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging assay and is expressed here in terms of the vitamin C equivalent antioxidant capacity (VCEAC). The means of vitamin C, naringin, and hesperidin in yuzu were 90.4, 63.8, and 65.7 mg/100 g fresh yuzu, respectively. The relative VCEAC values of these compounds were in the following order: vitamin C (1.00) > naringin (0.195) > hesperidin (0.162). Therefore, the estimated contribution of each antioxidant to the total antioxidant capacity of 100 g of fresh yuzus is as follows (in mg of VCEAC): vitamin C (90.36 mg) > naringin (12.44 mg) > hesperidin (10.64 mg). Our results indicate that mature yuzu contains higher amounts of vitamin C and phenolics than other citrus fruits and could therefore be used as a significant dietary source of antioxidants.     

双螺杆冷榨茶籽油的中试生产

为了提高油茶籽的综合利用价值,克服传统高温热榨和精炼导致茶籽油的一些营养成分和固有香味的损失,一种双螺杆冷榨茶籽油的生产工艺被开发。中试生产试验结果表明,当入榨油料含水率6.0%,仁中含壳率8.0%时,最大榨膛温度不超过60℃,饼中残油率为3.6%,所生产的冷榨茶籽油达到国标压榨成品油茶籽油一级标准。与传统的精炼茶籽油相比,冷榨茶籽油中维生素E质量分数大大高于精炼油(P0.05),是精炼油的2.6倍,不饱和脂肪酸和不皂化物的质量分数也明显高于精炼油(P0.05)。冷榨茶籽饼的粗蛋白、可溶性糖和淀粉的质量分数均高出浸出饼粕1倍左右,而粗纤维质量分数下降55.16%,茶皂素的质量分数也显著增加了1倍左右(P0.05)。经济可行性分析表明,一个日处理30 t油茶籽冷榨茶籽油生产车间的效益/费用比为1.28,投资回收期为0.78 a,社会经济效益显著,适合于中国油茶籽产区较大规模的生产应用。研究为油茶籽的高效加工与利用提供参考。     

Lipolytic effects of citrus peel oils and their components

This study was conducted to determine the lipolytic effects of eight kinds of citrus peel oils and their components. All of the citrus peel oils revealed lipolytic effects on olive oil model solution ranging from 10.9 to 73.8%. Hakyul (Citrus natsudaidai Hayata) showed the highest lipolytic effect (73.8%), followed by yuza (Citrus junos Sieb. ex Tanaka, 68.1%) and lemon (Citrus limonium, 63.4%), and their effects were comparable with or stronger than that of 5 mM raspberry ketone (p < 0.05). Among 17 authentic compounds relating to citrus peel oils, octanal (78.6%) showed the highest lipolytic effect, followed by gamma-terpinene (76.3%), limonene (75%), terpinen-4-ol (70.7%), nerol (69.9%), p-cymene (67.7%), and geranyl acetate (67.2%), and their effects were stronger than that of 5 mM raspberry ketone (p < 0.05). Ethyl acetate, alpha-pinene, myrcene, citronellal, linallyl acetate, and citronellol exhibited poor lipolytic effect in the model solution. Lipolytic effect was found to be high when the oils included a higher content of gamma-terpinene and p-cymene. Limonene showed potential lipolytic effect, and its effect is likely to be enhanced by the presence of gamma-terpinene and p-cymene. It is considered that monoterpene hydrocarbons consisting of one or two double bonds would have stronger lipolytic effect than those having three double bonds.     

Comparison of the volatile constituents in cold-pressed bergamot oil and a volatile oil isolated by vacuum distillation

The vacuum distillation of bergamot peels furnishes a high-quality essential oil that is totally bergapten-free. This oil was compared with that produced by distillation of cold-pressed oils and those commercially available. The oil obtained by vacuum distillation of the bergamot vegetable matrix shows a composition quite similar to that of the cold-pressed oil. It also displays qualitative characteristics that are superior with respect to those normally observed for essential oils isolated by distillation of cold-pressed oils. Oils isolated by the method presented here can constitute ideal candidates in producing foods, for example, Earl Grey tea, and cosmetic preparations.     

Effects of rootstock on the composition of bergamot (Citrus bergamia Risso et Poiteau) essential oil

This paper reports the composition of bergamot oils obtained from plants grafted on the following rootstocks: sour orange, Carrizo citrange, trifoliate orange, Alemow, Volkamerian lemon, and Troyer citrange. The aim of this study is to evaluate the possibility of using rootstocks other than sour orange, checking their effect on the composition of the essential oil. Results are reported for analysis of 203 bergamot oils during the years 1997-1998, 1998-1999, and 1999-2000. The oils were analyzed by HRGC and HRGC/MS; 78 components were identified, and the results were in agreement with those reported in the literature for the Calabrian bergamot oils obtained from industry. Because of the quality of their essential oils, Alemow and Volkamerian lemon can be considered as substitutes for sour orange rootstocks.     

Identification of components responsible for the odor of cigar smoker's breath

Following smoking 1/2 of a cigar, the most odorous cigar tobacco smoke components extracted from the surface of the tongue by nylon-meshed swabs and then extracted from the swab headspace by solid phase microextraction were ethyl pyrrole, 2,3-dimethyl pyrazine, and 2-ethyl pyridine. Similar classes of compounds were identified from the headspace of an aqueous simulated saliva solution treated with cigar smoke. The most odorous compounds were 2,3,5-trimethyl pyridine, 2,5-dimethyl pyrazine, and 2-ethyl-3,5-dimethyl pyridine. Pyridines and pyrazines, the most prominent classes of odorous compounds identified in this experiment, may be generated during cigar pyrrolysis by cleavage of nicotine or by Maillard reaction.     

Juice components of a new pigmented citrus hybrid Citrus sinensis (L.) Osbeck x Citrus clementina Hort. ex Tan

Fruit juice of a new pigmented citrus hybrid named Omo-31 and those of its parents clementine cv. Oroval (Citrus clementina Hort. ex Tan.) and Moro orange [Citrus sinensis (L.) Osbeck] were analyzed during fruit maturation to determine juice yield, total soluble solids (TSS), total acidity (TA), TSS/TA ratio (classical parameters of quality), and potential health beneficial components, such as vitamin C, flavanones, anthocyanins, and phenolic acids. Results showed that juice yield, TA, TSS, and TSS/TA ratio values of Omo-31 were similar to those of the Moro orange. Vitamin C content of the new hybrid was slightly higher than that of clementine and lower than that of the Moro orange, but at maturity stage no differences were observed among the three genotypes. The phenolic compounds content of the new hybrid and those of the parents and their evolution during maturation were studied. At maturity stage the amount of anthocyanins, flavanones, and hydroxycinnamic acids in Omo-31 was found to be notably higher than those of the parents. The high level of antioxidant substances makes this new fruit important for its nutritional benefits.