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１ H NMR spectrum of group B obtained from hexane extract by bulb-to-bulb distillation (200 MHz, CDCl 3 ).
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... performed bulb-to-bulb distillation of the hexane extract. Two fractions were obtained, and the residue was composed of -santalol and -santalol. The first fraction was a mixture of santalol hydrocarbon derivatives and the second fraction was santalyl aldehydes and formates, as determined by NMR spectroscopy (Fig. 6). The obtained fractions were analyzed, and santalol derivatives with a formyl group (Group B) were found to play an important role in the odor of sandalwood chips. The diagram (Fig. 4) indicates the scent profile of sandalwood obtained by this method. - Santaol has been reported to be the principal constituent of sandalwood odor. In ...
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... Torr), Group C (oven temperature >103°C/0.30 Torr), and residue as described elsewhere (Hasegawa, 2014). ...
... This tendency was also observed in a previous report (Hammer et al., 1999). To investigate the compounds responsible for the antibacterial activity, we used fractional distillation to divide the commercial Vetiver EO into groups A to C with different characteristic odors (Hasegawa, 2014). Then, each group was used for the disc diffusion assay, and only the Group C extract showed significant antibacterial activity against B. subtilis (Fig. 1). ...
... It was reported that tricyclic sesquiterpenes, khusimol (Fig. 5A), are the main constituents of the Vetiver EO (Champagnat et al., 2006;Mallavarapu et al., 2012), and khusimol and khusenic acid (Fig. 5) show antibiotic activity against mycobacteria (Dwivedi et al., 2013). In fact, it was shown that khusimol is fractionated into Group C by fractional distillation (Hasegawa, 2014). From our composition analysis, the steam distillation sample contained khusimol and khusenic acid (Fig. S3A), whereas the hexane extraction sample was rich in khusenic acid (Fig. S3B). ...
Recently, the antibacterial effects of essential oils have been investigated in addition to their therapeutic purposes. Owing to their hydrophobic nature, they are thought to perturb the integrity of the bacterial cell membrane, leading to cell death. Against such antibiotic challenges, bacteria develop mechanisms for cell envelope stress responses (CESR). In Bacillus subtilis, a gram-positive sporulating soil bacterium, the extracytoplasmic function (ECF) sigma factor-mediated response system plays a pivotal role in CESR. Among them, σM is strongly involved in response to cell envelope stress, including a shortage of available bactoprenol. Vetiver essential oil, a product of Chrysopogon zizanioides (L.) Roberty root, is also known to possess bactericidal activity. σM was exclusively and strongly induced when the cells were exposed to Vetiver extract, and depletion of multi-ECF sigma factors (ΔsigM, ΔsigW, ΔsigX, and ΔsigV) enhanced sensitivity to it. From this quadruple mutant strain, the suppressor strains, which restored resistance to the bactericidal activity of Vetiver extract, emerged, although attempts to obtain resistant strains from the wild type did not succeed. Whole-genome resequencing of the suppressor strains and genetic analysis revealed inactivation of xseB or pnpA, which code for exodeoxyribonuclease or polynucleotide phosphorylase, respectively. This allowed the quadruple mutant strain to escape from cell death caused by Vetiver extract. Composition analysis suggested that the sesquiterpene, khusimol, might contribute to the bactericidal activity of the Vetiver extract.
... Odour evaluation of fractions from patchouli extracts or essential oils may be biased by the presence of contaminants such as anethole. 349 Many authors have used a set of three basic odour descriptors repeatedly: earthy, woody and camphoraceous. 155,350 Whereas the earthy, "cellar like" note is clearly reminiscent of mould, the woody descriptor is more vague, since there are many natural products, including fragrant wood extracts and synthetic odorants, which belong to this category, all providing various nuances and effects (e.g., "dry cedarwood", "warm agarwood", iso-E Super, etc.). ...
The leaves of Pogostemon cablin (Blanco) Benth. (Lamiaceae) are the source of patchouli essential oil, which is – with an annual production of about 1300 tonnes – an important and unique commodity in the fragrance industry. All the literature pertaining to patchouli was critically reviewed with an emphasis on the qualitative and quantitative chemical analysis of the oil but also harvesting, fermentation, drying, distillation, used analytical techniques, sensory aspects including molecules responsible for the odour, adulteration and toxicological aspects, i.e., skin sensitisation, are discussed. In total 72 constituents have been convincingly identified in the oil and another 58 tentatively. The main constituent is the sesquiterpene patchoulol. For this review over 600 papers were consulted and in the supplementary information all patchouli-related references not relevant enough to be cited in the paper itself are listed.
... We have studied the aroma profile of incense using methods developed in our laboratory [4,5] and we reported that the odors of incense materials comprise several constituents with similar molecular shapes. ...
Cinnamic acid derivatives are important odorants due to their characteristic scent. Some fragrance materials, such as cinnamon bark, matsutake mushrooms, and Kaempferia galanga L. rhizome (galangal), contain several cinnamic acid derivatives as important odor constituents. The main odor constituent of galangal is (E)-ethyl 4-methoxycinnamate, but the odor of this compound is different from that of galangal. We investigated the aroma profile of galangal using our previously described method that considers the intermolecular interactions of the odorant compounds with their receptors. Odorant compounds in galangal were extracted by hexane extraction, steam distillation, and headspace sampling. The odor of the hexane extract was different from that of the steam distillate and similar to that of galangal; therefore, we searched for the key compounds contributing to the aroma profile of galangal by separating the constituents of the hexane extract. A fraction with a galangal-like odor was obtained by bulb-to-bulb distillation of the hexane extract. The main component of this fraction was not (E)-ethyl 4-methoxycinnamate, but rather ethyl cinnamate. These results indicate that ethyl cinnamate is more important in the aroma profile of galangal than (E)-ethyl 4-methoxycinnamate. GC-MS analysis revealed that this fraction contained aromatic compounds, cyclic terpenes, and linear chain compounds in addition to ethyl cinnamate. We synthesized cinnamic acid derivatives and examined the importance of the odor expression of these cinnamic acid derivatives. Cinnamic acid derivatives lacking a p-methoxy group had a strong fruity odor. Replacement of the hydrogen atom at the para position with a methoxy group altered and weakened the odor. We found that a p-methoxy group in cinnamic acid derivatives plays an important role in the aroma profile of galangal.
... These results indicate that the interactions between the constituents are important in creating the characteristic odor of frankincense. Our approach for evaluating the complex odor of the materials considers these interactions [1][2][3][4][5][6]. ...
... Distilling the hexane extract of turmeric produced a lower boiling point fraction (H-LF) and a higher boiling point fraction (H-HF) ( Figure 2). The odor of H-HF was more similar to that of the original material than that of the odor of H-LF. 1 H NMR analysis showed that both these fractions were composed of ar-turmerone (1) and β-turmerone (2) in almost equal ratios. ar-Turmerone (1) and β-turmerone (2) were the main constituents of H-HF, which is similar to the hexane extract. ...
... The constituents of the hexane extract of turmeric were divided into two groups. One was group A, which had the characteristic odor of turmeric and was made up mostly of ar-turmerone (1) and β-turmerone (2). The other was group B, which had a different characteristic odor from turmeric and mostly contained lower boiling point constituents, such as α-curcumene (3) and β-sesquiphellandrene (4). ...
Turmeric is a popular material that plays an important role in the flavor and fragrance industries. Although many compounds have been reported as components of turmeric, its aroma profile has not been clarified. Recently we have developed a new approach for evaluating the complex odors of materials based on recent research on the mechanism of odor recognition. Here we report the characteristic aroma properties of turmeric obtained through the investigation of its aroma profile. The hexane extract of turmeric had a turmeric-like odor, whereas the steam distillate of turmeric had a pungent, non-turmeric-like odor. We carried out bulb-to-bulb distillations of the extract and the steam distillate. For the hexane extract, two fractions with completely different odors were obtained. One was a high boiling point fraction (group A) with a turmeric-like odor, which consisted of ar-turmerone and β-turmerone as the main components, and the other was a low boiling point fraction (group B), which consisted of α-curcumene and β-sesquiphellandrene. In contrast, the bulb-to-bulb distillation of the steam distillate gave a fraction (group C) with a very different odor from groups A and B. Group C was composed of several kinds of alcohols that were not present in groups A and B. These results indicate that the group C fraction causes the different, pungent odor of the turmeric oil obtained by steam distillation. The variation in the aroma of turmeric depended on the combination of these three groups of odor constituents.
... We have previously evaluated the aroma profile of sandalwood and identified the key compounds [5]. We investigated the odor profile of star anise by using similar methods. ...
Star anise is an important fragrance material that has a characteristic anise-like odor. Although the main component of star anise is (E)-anethole, which accounts for over 90% of the constituents, the odor of (E)-anethole is different from that of the material itself. Here, we examined the aroma profile of star anise. GC-MS analysis of star anise extracts showed that it contains many compounds with structures similar to (E)-anethole. Our results indicate that (E)-anethole is the key compound in the odor of star anise, but structurally similar compounds play an important role in creating its odor. We examined the structure-odor relationship of (E)-anethole, focusing on the methoxy and 1-propenyl substituents. Altering the 1-propenyl group changed the odors of all the anethole derivatives. Replacing the methoxy group with a hydrogen atom created compounds with similar fatty odors. This shows that the methoxy group is important for the characteristic odor of anethole. We synthesized anethole derivatives where the methoxy group was replaced with a methyl group. In both methoxy- and methyl-substituted anethole derivatives, altering the 1-propenyl group changed the odors of the derivatives. Therefore, the methoxy and methyl benzene moieties are important structural features for the odor of star anise. The structural characteristics of anethole are closely related to its odor expression.
Spikenard is a valuable material in perfumery because of its animalic odor, but its aroma profile has not yet been clarified. We have developed a method to clarify the aroma profiles of odor materials (sandalwood, frankincense, vetiver, etc.) that are composed of many odor components. Here we investigated the aroma profile of spikenard using our method. The aroma components were extracted by three different methods (hexane extraction, headspace extraction, and hydrodistillation). The odor of the hexane extract was similar to that of the material itself. The hexane extract was separated into two fractions by fractional distillation. The lower boiling fraction had an animalic odor, and the higher boiling fraction had a plant-like odor with the characteristic animalic odor of spikenard. We found that the key component was isovaleric acid from analysis of these fractions by gas chromatography-olfactometry and gas chromatography-mass spectrometry. Tsovaleric acid is a chain carboxylic acid and has a strong characteristic animalic odor.
Tea cultivated in Saitama, where it is said to be the far north of main production of tea ─ the economical northern limit, is called SAYAMA-CHA (tea). Tea cultivar with cold resistance has been cultivated because Saitama is too cold for tea plants. Recently, a cultivar ‘Okuharuka’ having cherry-leaves-like aroma was bred. Not only tea experts but also consumers can notice its aroma. In addition, there are many other cultivars, such as ‘Yumewakaba’ having osmanthus-like sweet aroma, and ‘Fukumidori’ having graceful aroma, and ’Musashikaori’ having brisk aroma.
Incense is central to traditional fragrance in Japanese culture. Many materials with unique characteristic odors, such as sandalwood, are used in incense. Although the constituent odor compounds have been extensively studied, the aroma profiles of the materials are not fully understood. We have analyzed three aspects of the aroma profiles of Japanese incense materials : (1) the dependence of aroma profiles on the extraction method ; (2) the classification of the constituent odor compounds of the materials ; and (3) the time-dependence of the odors of the materials.
Patchouli is used as an incense material and essential oil. The characteristic odor of patchouli leaves results from the drying process used in their production; however, there have to date been no reports on the changes in the odor of patchouli leaves during the drying process. We investigated the aroma profile of dried patchouli leaves using the hexane extracts of fresh and dried patchouli leaves. We focused on the presence or absence of the constituents of the fresh and dried extracts, and the differences in the content of the common constituents. Fourteen constituents were identified as characteristic of dried patchouli extract odor by gas chromatography-olfactometry analysis. The structures of seven of the 14 constituents were determined by gas chromatography-mass spectrometry (α-patchoulene, seychellene, humulene, α-bulnesene, isoaromadendrene epoxide, caryophyllene oxide, and patchouli alcohol). The aroma profile of the essential oil obtained from the dried patchouli leaves was clearly different from that of dried patchouli. The aroma profile of the essential oil was investigated by a similar method. We identified 12 compounds as important odor constituents. The structures of nine of the 12 constituents were determined by gas chromatographymass spectrometry (cis-thujopsene, caryophyllene, α-guaiene, α-patchoulene, seychellene, α-bulnesene, isoaromadendrene epoxide, patchouli alcohol, and corymbolone). Comparing the odors and constituents demonstrated that the aroma profile of patchouli depends on the manufacturing process.
Green tea is a popular world-wide beverage with health benefits that include preventive effects on cancer as well as cardiovascular, liver and Alzheimer's diseases (AD). This study will examine the preventive effects on AD of a unique aroma of Japanese green tea. First, a transgenic Caenorhabditis elegans (C. elegans) CL4176 expressing human β-amyloid peptide (Aβ) was used as a model of AD. A hexane extract of processed green tea was further fractionated into volatile and non-volatile fractions, named roasty aroma and green tea aroma fractions depending on their aroma, by microscale distillation. Both hexane extract and green tea aroma fraction were found to inhibit Aβ-induced paralysis, while only green tea aroma fraction extended lifespan in CL4176. We also found that green tea aroma fraction has antioxidant activity. This paper indicates that the green tea aroma fraction is an additional component for prevention of AD.
