Monoterpenoids from Paeoniae Radix Rubra based on UPLC-Q-TOF-MS / 中国中药杂志

The ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry(UPLC-Q-TOF-MS) was used to conduct the qualitative analysis of the monoterpene chemical components from Paeoniae Radix Rubra. Gradient elution was performed on C_(18) HD(2.1 mm×100 mm, 2.5 μm) column with a mobile phase of 0.1% formic acid(A) and acetonitrile(B). The flow rate was 0.4 mL·min~(-1) and the column temperature was 30 ℃. MS analysis was conducted in both positive and negative ionization modes using electrospray ionization(ESI) source. Qualitative Analysis 10.0 was used for data processing. The identification of chemical components was realized by the combination of standard compounds, fragmentation patterns, and mass spectra data reported in the literature. Forty-one monoterpenoids in Paeoniae Radix Rubra extract were identified. Among them, 8 compounds were reported in Paeoniae Radix Rubra for the first time and 1 was presumed to be the new compound 5″-O-methyl-galloylpaeoniflorin or its positional isomer. The method in this study realizes the rapid identification of monoterpenoids from Paeoniae Radix Rubra and provides a material and scientific basis for quality control and further study on the pharmaceutical effect of Paeoniae Radix Rubra.

Microbial synthesis of monoterpenoids: a review / 生物工程学报

Monoterpenoids that belong to the terpenoids family are usually volatile and have strong aroma. Some monoterpenoids also have antioxidant, antibacterial and anti-inflammatory activities, which make them important raw materials for medicine, food and cosmetics industry. In recent years, the heterologous synthesis of monoterpenoids by microorganisms has attracted extensive attention. However, its large-scale application is greatly hampered by the low yield and high production cost. Nowadays, the rapid development of synthetic biology provides new approaches for enhancing the production of monoterpenoids by microorganisms. Different kinds of recombinant strains can be obtained via engineering of microbial cells to produce a variety of monoterpenoids with different properties. This paper summarized the latest strategies and progress in the application of synthetic biology to produce monoterpenoids by microorganisms, including the design and modification of biosynthetic pathway, as well as the design and optimization of high-yield monoterpenoids producing chassis cells.

Isolation and Identification of Chemical Constituents from Paeonia veitchii / 中国实验方剂学杂志

Objective::To investigate the chemical constituents from Paeonia veitchii. Method::P. veitchii samples (30 kg) were extracted with 95% ethanol for four times and then filtrated, and the combined filtrates were concentrated under vacuum to get the extracts. After suspension with water, exaction was conducted with petroleum ether, dichloromethane, ethyl acetate, n-butanol and water successively to obtain five corresponding fractions. The compounds were isolated and purified by silica gel, Sephadex LH-20, ODS column chromatography and prep-HPLC, and the structures of these compounds were determined by such spectrum technologies as infrared spectroscopy (IR), mass spectroscopy (MS), and nuclear magnetic resonance (NMR). Result::Sixteen compounds were isolated and their structures were identified as follows (1S, 5R, 6R)-1, 8-dihydroxypin-2-en-4-one (1), (2-hydroxyl)-phenyl-methyl-β-D-xylopyranoside (2), flufuran (3), 6′-O-vanillylpaeoniflorin (4), methyl 2, 5-dihydroxycinnamate (5), (1S, 2S, 5R, 6R)-1, 8-dihydroxypin-4-one (6), palbinone (7), 4-O-methylpaeoniflorin (8), 4-O-ethylpaeoniflorin (9), benzoyloxypaeoniflorin (10), benzoic acid (11), gallic acid (12), methyl gallate (13), ethyl gallate (14), β-sitosterol (15), and 1, 2, 3, 4, 6-penta-O-galloyl-β-D-glucopyranose (16). Conclusion::Compounds 1, 2 were new natural compounds; compound 3 was isolated from genus Paeonia for the first time, and compounds 4-7 were isolated from this plant for the first time.

Chemical constituents from aerial parts of Chloranthus angustifolius / 中草药

Objective: To study the chemical constituents from the aerial parts of Chloranthus angustifolius. Methods: The chemical constituents were isolated by various chromatography techniques and their structures were elucidated on the basis of physiochemical properties and spectrascopic analysis. Results: Eight compounds were isolated and identified as 1-acetoxy-2,3,4,5- tetrahydroxy-5-p-metoxyphenylpentane (1), (E)-5-(4-methoxyphenyl) pent-4-ene-1,2,3-trihydroxyamyl (2), isofraxidin (3), (-)-dihydrodehydrodiconiferyl alcohol (4), (±)-erythro-guaiacyl-glycerol-β-O-4'-dihydroconiferyl ether (5), (-)-rosiridol (6), (4S)-p-menth-1-ene-4,7-diol (7), and loliolide (8), respectively. Conclusion: Compounds 1 and 2, named chloranthus pentitol and chloranthus enol, are two new p-methoxyphenyl pentitol derivatives, while compounds 3-8 are obtained from C. angustifolius for the first time.

Seasonal variability of the essential oil of Hesperozygis ringens (Benth.) Epling. / Variabilidade sazonal do óleo essencial de Hesperozygis ringens (Benth.) Epling.

Abstract This study was developed to evaluate the effect of seasonality on the yield and chemical composition of the essential oil (EO) of Hesperozygis ringens (Benth.) Epling, a native species from the Brazilian Pampa. Leaves were collected from four specimens of a single population in each of the four seasons for a year and were extracted in triplicate by hydro-distillation for 2 hours. The yield of EO (% w/w) was calculated on fresh weight basis (FWB), and the 16 oil samples were analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) were used as statistical tools to evaluate differences in chemical composition. The highest yields were obtained in autumn, spring and summer (2.32-4.38%), while the lowest yields were detected in winter, ranging from 1.15 to 1.91%. Oxygenated monoterpenoids were the predominant class of chemical constituents in the EO obtained in all seasons, showing the highest contents in autumn and summer, and pulegone was identified as a major compound, whose contents varied between 54.13 and 81.17%. The EO samples were divided into three chemical groups by HCA and PCA and were assigned to the same group, except for the three samples gathered in winter. The results showed a seasonal influence on the yield and chemical composition of the EO.

Resumo Este estudo foi desenvolvido a fim de avaliar o efeito da sazonalidade no rendimento e composição química do óleo essencial (OE) de Hesperozygis ringens (Benth.) Epling., uma espécie nativa do Pampa brasileiro. Folhas foram coletadas de quatro indivíduos de uma mesma população, em cada uma das quatro estações de um ano, e foram extraídas em triplicada por hidrodestilação durante 2 horas. O rendimento do OE (% m/m) foi calculado considerando a base fresca (BF) e as 16 amostras de óleo foram analisadas por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e cromatografia gasosa com detector de ionização de chamas (CG-DIC). Análise Hierárquica de Cluster (AHC) e Análise de Componentes Principais (ACP) foram utilizadas como ferramentas estatísticas para avaliar as diferenças na composição química. Os maiores rendimentos foram obtidos no outono, primavera e verão (2,32-4,38%), enquanto que os menores foram detectados no inverno, variando de 1,15 até 1,91%. Os monoterpenoides oxigenados foram a classe predominante dos constituintes do OE obtido em todas as estações, apresentando os maiores teores no outono e no verão, e a pulegona foi identificada como o constituinte majoritário, cujos teores variaram entre 54,13 e 81,17%. As amostras de OE foram divididas em três grupos químicos por AHC e ACP e foram classificadas no mesmo grupo, com exceção de três amostras coletadas no inverno. Os resultados demonstraram influência sazonal no rendimento e na composição química dos OE.

Monoterpenoids from whole plants of Carpesium macrocephalum / 中草药

Objective: To investigate the chemical constituents from the whole plants of Carpesium macrocephalum. Methods: Its constituents were isolated and purified by means of silica gel, ODS, and Sephadex LH-20 column chromatography. Their structures were elucidated on the basis of chemical evidences, spectroscopic methods, and X-ray data. Results: Five thymol monoterpenoids were isolated from the acetone extract in the whole plants of C. macrocephalum and identified as (Z)-10-isobutyryloxy-9-chloro-8,9-dihydrothymol (1), 9-isobutyryloxy-7,8-epoxythymol isobutyrate (2), 8-hydroxy-9-isobutyryloxy-10(2)-methylbutyrylthymol (3),8,10-dihydroxy-9-isobutyryloxythymol (4), and 10-isobutyryloxy-8,9-dihydrothymol (5), respectively. Conclusion: Compound 1 is a new chlorinated thymol monoterpenoid named carpemacrom. Compounds 2-5 are isolated from the plants of Carpesium L. for the first time.

Composição química e repelência de óleos essenciais de Drimys angustifolia Miers e Drimys brasiliensis Miers em cupins de madeira Cryptotermes brevis (Isoptera: Kalotermitidae) / Chemical composition of essential oils of Drimys angustifolia Miers and Drimys brasiliensis Miers and their repellency to drywood termite Cryptotermes brevis (Isoptera: Kalotermitidae)

The essential oils extracted from leaves of the Southern Brazilian native species Drimys angustifolia Miers (DA) and Drimys brasiliensis Miers (DB) by Clevenger distillation were analyzed by gas chromatography/mass spectrometry (GC/MS). The oils of DA and DB consisted predominantly of monoterpenoids and sesquiterpenoids. The largest components of DA oil were bicyclogermacrene (19.6%), sabinene (9.7%)and myrcene (5.2%), while DB oil was characterized by cyclocolorenone (18.2%), followed by terpinen-4-ol (8.7%) and alpha-gurjunene (6.9%). Laboratory tests were carried out to determine the repellency of the essential oils to the drywood termite Cryptotermes brevis (Isoptera: Kalotermitidae). It was observed that the oil showed repellency at the concentrations 25, 12.5, and 6.25 μg/mL. The oils of both species exhibited a negative repellency index, which represents repellent activity, except for DA oil at the highest concentration, which was attractive. Five deaths (11% of the termitesample) were observed at 25 μg/mL DA, in the fourhour repellency test, while four deaths occurred at 12.5 μg/mL (approximately 9%). The essential oil of DB did not cause any termite deaths...

Os óleos essenciais obtidos das folhas das árvores nativas do sul do Brasil Drimys angustifolia Miers (DA)e Drimys brasiliensis Miers (DB) foram analisados por cromatografia gasosa acoplada a espectrometria de massas (CG/EM). O óleo de DA foi caracterizado pela presença de monoterpenóides e sesquiterpenóides, biciclogermacreno (19,6%), seguido por sabineno (9,7%) e mirceno (5,2%). O óleo de DB foi caracterizado por sesquiterpenóides e monoterpenóides, ciclocolorenona (18,2%), seguido por terpinen-4-ol (8,7%) e alfagurjuneno(6,9%). Os testes foram realizados a fim de se determinar o potencial repelente dos óleos essenciais contra o cupim de madeira seca Cryptotermes brevis (Isoptera: Kalotermitidae) nas doses de 25, 12,5, e 6,25 μg/mL. Ambas as espécies mostraram índice de repelência negativo, o que representa a ocorrência da atividade repelente, exceto na maior concentração de DA, na qual o óleo mostrou-se atraente. Cinco mortes foram observadas na concentração de 25 μg/mL de DA, correspondendo a 11% do total em quatro horas de análise, sendo que 9% ocorreram na concentração de 12,5 μg/mL. No caso do óleo essencial de DB não foram observadas mortes de cupins...

Chemical constituents in essential oils from elsholtzia ciliata and their antimicrobial activities / 中草药·英文版

Objective: To compare the chemical constituents in the essential oils from the leaves, flowers, and seeds of Elsholtzia ciliata and their antimicrobial activities. Methods: The chemical constituents in essential oils were extracted by the hydro-distillation method and analyzed by GC-MS. The chemical constituents in essential oils were identified on the basis of comparison on their retention indices and MS spectrum with published data. Moreover, the antimicrobial activities of the chemical constituents in the oils against the growth of six bacteria strains and one pathogenic yeast strain were evaluated by using minimum inhibitory concentration and minimum bactericidal concentration methods. Results: A total of 58 compounds were identified, while compounds 31, 35, and 36 were identified in the essential oils from the leaves, flowers, and seeds, respectively. Fifteen compounds were identified as shared constituents in the leaves, flowers, and seeds. The chemical constituents in the essential oils showed the inhibitory activities against the six bacteria strains and the yeast strain. Conclusion: The major constituents are different in the essential oils of the leaves, flowers, and seeds. The major chemical constituents in the essential oils are monoterpenoids and sesquiterpenoids. And the chemical constituents in the essential oils obtained from the leaves show higher inhibitory activities especially against Bacillus subtillis CMCC63501 and Escherichia coli ATCC25922. © 2013 Tianjin Press of Chinese Herbal Medicines.

Monoterpenoids from Schizonepeta tenuifolia / 中草药

Object To study the chemical constituents of Schizonepeta tenuifolia (Benth.) Briq.. Methods The monoterpenoid constituents of S. tenuifolia were separated on silica gel column and their structures were elucidated by spectral. Results Two new compounds and three known compounds were obtained. Conclusion The new compounds were identified as 3-hydroxy-4(8)-ene-p-menthane-3(9)-lactone and 1, 2-dihydroxy-8(9)-ene-p-menthane.