Patcharee Pripdeevech

Identification of Odor-active Components of Agarwood Essential Oils from Thailand by Solid Phase Microextraction-GC/MS and GC-O

Abstract Volatile components from the essential oils of Aquilaria malaccensis, A. subintegra and A. crassna were investigated by gas chromatography (GC), gas chromatography-mass spectrometry (GC/MS), and gas chromatography-olfactometry (GC-O). A total of 31 volatile constituents were identified from the three agarwood oils. A subset of 18 out of the 31 components was identified from the essential oil of A. malaccensis with the major components being isoamyl dodecanoate, guaia-1(10),11-dien-15-ol, karanone, cyclocolorenone and jinkoheremol. Aquilaria subintegra oil yielded 28 identified compounds with the most abundant components being isoamyl dodecanoate, kusunol, jinkoh-eremol, epoxybulnesene and β-agarofuran, while 30 volatile compounds from A. crassna were identified, with isoamyl dodecanoate, β-agarofuran, kusunol, dehydrojinkoh-eremol and 9,11-eremophiladien-8-one as the main constituents. The aroma-active compounds of the three samples were analyzed by HS-SPME-GC-O. A total of 74 odor-active components were characterized by using the GC-O technique. The major components responsible for the aroma included β-agarofuran, 4-phenyl-2-butanone, furfural and benzaldehyde, while the minor aroma notes were attributed to (E)-α-bergamotene, α-humulene, α-bulnesene, α-agarofuran, nor-ketoagarofuran, epoxybulnesene, agarospirol, jinkoh-eremol, kusunol, acorenone B, selina-3,11-dien-14-al and 9,11-eremophiladien-8-one, considered to be the most important aroma impact compounds for the characteristic aroma of agarwood essential oils

Chemical compositions, antifungal and antioxidant activities of essential oil and various extracts of Melodorum fruticosum L. flowers.

This research presents the chemical composition antifungal and antioxidant activities of essential oils and various extracts from Melodorum fruticosum flowers. The essential oil composition of M. fruticosum flowers were investigated by GC-MS with 88 identified volatile constituents. Phenyl butanone, linalool, benzyl alcohol, alpha-cadinol, globulol and viridiflorol were found to be the major components, respectively. The dichloromethane extract played a major role as a remarkable fungicide according to their inhibition action against all tested pathogens followed by hexane extract, essential oil and methanol extract, respectively, along with their respective MIC values ranging from 125 to 1000 microg/ml. The dichloromethane extracts were also evaluated to be superior to all extracts tested with an IC(50) value of 87.6 microg/ml whereas other extracts showed their IC(50) values ranging from 100.13 to 194.50 microg/ml.

Odor and Flavor Volatiles of Different Types of Tea

The fingerprints and individual volatile flavor components of teas grown in different areas of the world are discussed, along with classical to modern analytical methods applied to teas. The structures of most volatiles were investigated by gas chromatography-mass spectrometry. The odor and flavor volatiles of various teas are controlled by specific combinations of key chemical components. These volatiles are terpenes, together with their derivatives, and other organic compounds. The terpenoids and their derivatives found in teas impart sweet and floral aromas, while other odors of teas are from non-terpenoids and products of the lipid degradation which occurs during manufacturing. The variation of quality and volatile flavor components in teas is also due to different environmental and ecological conditions, along with tea-processing methods.

Composition of essential oils from the rhizomes of three Alpinia species grown in Thailand

The genus Alpinia is an herbaceous plant belonging to the family Zingiberaceae and comprising more than 230 species. It has medicinal properties especially useful in conditions such as flatulence, dyspepsia, vomiting, and stomach sickness [1, 2]. Products of Alpinia rhizome have also been used as biological agents, for example, antibacterial [3], antifungal [4], anticlastogenic [5], antimutagenic [6], and as antioxidant agents [7]. The essential oil of Alpinia is useful in the treatment of respiratory illnesses and has been used as a flavoring agent for beverages in some European countries. Chemical studies of some main species of Alpinia have been widely reported [8–12], while a few studies have been conducted on the chemical compositions of some less common species [13–14]. In this study, the composition of essential oil obtained from rhizome of the rare A. malaccensis, which grows wild in areas of Northern Thailand, was investigated in comparison with those of the common species, A. galanga and A. officinarum, which are cultivated extensively. The essential oils extracted by SDE from rhizome parts of A. galanga, A. officinarum, and A. malaccensis appeared as pale yellow viscous liquids with percentage yields of 0.5, 0.1, and 0.2 (w/w), respectively. GC×GC profiles of rhizome oils from common species, A. galanga and A. officinarum, were almost the same, while those for a wild Alpnia, A. malaccensis, were different. The volatile constituents in the monoterpene region of all essential oil profiles are similar, thus are the characteristic of Alpinia rhizome oil. The overall GC×GC profile of volatile constituents of A. galanga oil was similar to that obtained from oil of A. officinarum, which revealed the similar genotype of both plants. These profiles of the common Alpinia were rather different from that of A. malaccensis. GC-MS analysis of the three Alpinia essential oils confirmed the regions of monoterpenes and sesquiterpenes as well as their derivatives. Overall, 71 volatile components were identified among the three Alpinia essential oils. The structural assignments of these volatiles, their relative percentages, and retention indices are summarized in Table 1. Individually, A. galanga essential oil yielded 60 identified components. The dominant components were 1,8-cineole (21.6%), chavicol (17.7%), and α-bisabolene (15.6%). Fifty-three components were identified in the essential oil of A. officinarum; the major component was α-bisabolene (10.6%) followed by α-trans-bergamotene (7.9%), and β-sesquiphellandrene (6.9%). Forty-one constituents were investigated in A. malaccensis, with 1,8-cineole (11.9%) as the major component followed by linalool (9%), and fenchyl acetate (8.6%). According to the GC×GC profiles, at least 122, 117, and 145 volatile components were detected in A. galanga, A. officinarum, and A. malaccensis essential oils, of which the extents of the identified components were 49, 45, and 28%, respectively. Comparison of the oil compositions of these Alpinia species by GC-MS showed that the high proportion of oxygenated monoterpenes was typical both in the A. galanga oil (72%) and A. malaccensis oil (45%), whereas sesquiterpene hydrocarbons dominated in A. officinarum essential oil (47%). Although most of the identified components were similar in all the essential oils, the quantity of some of these components in each essential oil was significantly different.

Adaptogenic-active components from Kaempferia parviflora rhizomes

Kaempferia parviflora rhizome extracts obtained by maceration with hexane, chloroform, methanol, and ethanol were screened for their adaptogenic activities using swimming tests of mice. The effective adaptogenic extract dose was 500mg/kg of body weight and was given orally once a day. Crude hexane extract showed significantly shorter mouse immobilisation time than those of the other and control extracts. This crude hexane extract was separated into three fractions by column chromatography. Among these fractions, the fraction rich in terpenoids possessed the highest adaptogenic activity and was comparable to that of the crude ginseng root powder used as a reference control. Therefore, terpenes contained in this fraction could be attributed to the decrease in exhaustion during the swimming of mice. There was no effect on body weight, heart, liver, kidneys, and adrenal glands of the mice. Chemical characterisation of this adaptogenic-active fraction by NMR and GC-MS showed germacene D, β-elemene, α-copaene, and E-caryophyllene as major constituents. Accordingly, these terpenes are considered the adaptogenic agents of K. parviflora rhizomes.

Analysis of odor constituents of Melodorum fruticosum flowers by solid-phase microextraction-gas chromatography-mass spectrometry

0009-3130/11/4702-0292 2011 Springer Science+Business Media, Inc. Program of Applied Chemistry, School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand, fax: +66 53 916776, e-mail: patcharee_pri@mfu.ac.th. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 264–266, March–April, 2011. Original article submitted October 28, 2009. Chemistry of Natural Compounds, Vol. 47, No. 2, May, 2011 [Russian original No. 2, March–April, 2011]

Antibacterial secondary metabolites from an endophytic fungus, Arthrinium sp. MFLUCC16-1053 isolated from Zingiber cassumunar

ABSTRACT Forty-four endophytes were isolated from Zingiber cassumunar and identified morphologically. The ethyl acetate extracts of all endophytes were obtained. The ethyl acetate extracts were subjected to study antibacterial and antioxidant activities. The ethyl acetate extract of the Arthrinium sp. MFLUCC16-1053 showed activity against both gram-positive and gram-negative bacteria. Specifically, the minimum inhibition concentration against Staphylococcus aureus and Escherichia coli was 31.25 and 7.81 µg/mL, respectively. In addition, the crude extract showed highest antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl scavenging at IC50 value of 28.47 µg/mL. Gas chromatography-mass spectrometry analysis revealed that the extract of the Arthrinium sp. MFLUCC16-1053 contains various antibacterial and antioxidant compounds which are β-cyclocitral, 3E-cembrene A, laurenan-2-one, sclareol, 2Z,6E-farnesol, cembrene, β-isocomene and γ-curcumene. The fungus Arthrinium sp. MFLUCC16-1053 was also identified by molecular and phylogenetic methods.

Incubation of Aquilaria subintegra with Microbial Culture Supernatants Enhances Production of Volatile Compounds and Improves Quality of Agarwood Oil

Incubation with microbial culture supernatants improved essential oil yield from Aquilaria subintegra woodchips. The harvested woodchips were incubated with de man, rogosa and sharpe (MRS) agar, yeast mold (YM) agar medium and six different microbial culture supernatants obtained from Lactobacillus bulgaricus, L. acidophilus, Streptococcus thermophilus, Lactococcus lactis, Saccharomyces carlsbergensis and S. cerevisiae prior to hydrodistillation. Incubation with lactic acid bacteria supernatants provided higher yield of agarwood oil (0.45% w/w) than that obtained from yeast (0.25% w/w), agar media (0.23% w/w) and water (0.22% w/w). The composition of agarwood oil from all media and microbial supernatant incubations was investigated by using gas chromatography-mass spectrometry. Overall, three major volatile profiles were obtained, which corresponded to water soaking (control), as well as, both YM and MRS media, lactic acid bacteria, and yeast supernatant incubations. Sesquiterpenes and their oxygenated derivatives were key components of agarwood oil. Fifty-two volatile components were tentatively identified in all samples. Beta-agarofuran, α-eudesmol, karanone, α-agarofuran and agarospirol were major components present in most of the incubated samples, while S. cerevisiae-incubated A. subintegra provided higher amount of phenyl acetaldehyde. Microbial culture supernatant incubation numerically provided the highest yield of agarwood oil compared to water soaking traditional method, possibly resulting from activity of extracellular enzymes produced by the microbes. Incubation of agarwood with lactic acid bacteria supernatant significantly enhanced oil yields without changing volatile profile/composition of agarwood essential oil, thus this is a promising method for future use.

Antibacterial potential of secondary metabolites produced by Aspergillus sp., an endophyte of Mitrephora wangii

Mitrephora wangii, an ethnomedicinal plant, has been used as a natural antibiotic and immunity booster in Thailand. A total of 22 fungi were isolated from M. wangii flowers. The fungal isolates were categorized into six genera including Agrocybe, Aspergillus, Colletotrichum, Nigrospora, Puccinia and Ustilago. Most extracts exhibited antibacterial activity against at least one of the test bacteria. Aspergillus sp. MFLUCC16-0845 was identified as the most bioactive fungus. Chemical composition of Aspergillus sp. MFLUCC16-0845 investigated using gas chromatography–mass spectrometry indicated that the major antibacterial compound was β-thujaplicin. Moreover, the newly isolated Aspergillus sp. MFLUCC16-0845 could be exploited as a potential source of bioactive compounds and plant defense activators. In addition, it is the first time that strain of Aspergillus sp. isolated and cultured from M. wangii flowers could produce β-thujaplicin at high yield with strong antimicrobial spectrum, which may lead to wide utilization in producing cosmetics and clinical products.

Chemical Composition and Antibacterial Activities of Goniothalamus marcanii Flower Essential Oil

Article history: Received on: 25/09/2016 Revised on: 18/11/2016 Accepted on: 03/12/2016 Available online: 31/01/2017 The essential oil of Goniothalamus marcanii flowers extracted by hydrodistillation was investigated in terms of its chemical composition by gas chromatography-mass spectrometry with their retention indices. The analyses revealed the presence of 116 compounds, representing 93.83% of the essential oil. The major compounds of the oil were caryophyllene oxide, E-caryophyllene, -humulene, -cadinene and linalool. Essential oil of Goniothalamus marcanii flowers were tested in vitro antibacterial activities against six human pathogens including Staphylococcus epidermidis, Staphylococcus aureus, Staphylococcus agalactiae, Proteus mirabilis, Escherichia coli and Salmonella typhimurium by using agar paper disc diffusion assay. Flower oil of Goniothalamus marcanii exhibited broad spectrum antibacterial activities along with their respective minimum inhibitiory concentration values ranging from 15.62 to 1000 μg/mL according to various terpenes and its derivatives.