Essential oils analysis. II. Mass spectra identification of terpene and phenylpropane derivatives

Oprean, Radu; Oprean, Luminița; Martos, Tamás; Săndulescu, Robert; Roman, L.

doi:10.1016/s0731-7085(00)00578-1

Cited by 39 publications

(18 citation statements)

References 1 publication

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“…6,7 Among these components, the major components are known to be phenylpropanoids, including β-asarone, α-asarone, euasarone, and methyleugenol. Sesquiterpenes including caryophyllene were also observed as characteristic components of Acorus species.…”

Section: Introductionmentioning

confidence: 99%

Development of Fingerprints for Quality Control of Acorus species by Gas Chromatography/Mass Spectrometry

Yu¹,

Kim²,

Lee³

et al. 2011

Bulletin of the Korean Chemical Society

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An effective analytical method of gas chromatography/mass spectrometry (GC/MS) was developed for the rapid determination of essential oils in the crude extract of Acorus species (Acorus gramineus, Acorus tatarinowii, and Acorus calamus). Major phenypropanoids (β,α-asarone isomers, euasarone, and methyleugenol) and β-caryophyllene in Acorus species were used as marker compounds and determined for the quality control of herbal medicines. To extract marker compounds, various extraction techniques such as solvent immersion, mechanical shaking, and sonication were compared, and the greatest efficiency was observed with sonication extraction using petroleum ether. The dynamic range of the GC/MS method depended on the specific analyte; acceptable quantification was obtained between 10 and 2000 μg/mL for β-asarone, 10 and 500 μg/mL for α-asarone, 10 and 200 μg/mL for methyleugenol, and between 5 and 100 μg/mL for β-caryophyllene. The method was deemed satisfactory by inter-and intra-day validation and exhibited both high accuracy and precision, with a relative standard deviation < 10%. Overall limits of detection were approximately 0.34-0.83 μg/mL, with a standard deviation (σ)-to-calibration slope (s) ratio (σ/s) of 3. The limit of quantitation in our experiments was approximately 1.13-3.20 μg/mL at a σ/s of 10. On the basement of method validation, 20 samples of Acorus species collected from markets in Korea were monitored for the quality control. In addition, principal component analysis (PCA) and hierarchical cluster analysis (HCA) were performed on the analytical data of 20 different Acorus species samples in order to classify samples that were collected from different regions.

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Section: Introductionmentioning

confidence: 99%

Development of Fingerprints for Quality Control of Acorus species by Gas Chromatography/Mass Spectrometry

Yu¹,

Kim²,

Lee³

et al. 2011

Bulletin of the Korean Chemical Society

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“…The GC-MS total ion chromatograms for the three alternative cyclisation products are shown in Figure 1 For a tentative structural identification, we compared MS fragmentation patterns for each new compound against a NIST spectral database containing a special natural product extension and relevant literature data. [42,43] For the CotB2 F107A(G) mutant, the MS fragmentation patterns of the GGDP cyclisation product 8 could be matched, which are in contrast to those of products 6 and 7 a and b. Therefore, we set out to conduct a series of NMR experiments to elucidate the structures of these new products.…”

Section: Cotb2 Saturation Mutagenesis and Screening For Alternative Gmentioning

confidence: 99%

“…The cembrene family is widely distributed in nature, bears various functional decoration, and demonstrates different bioactivities. [40][41][42][43][44][45][46][47][48][49][50][51] In tobacco, only three stereoselective hydroxylations confer significant antimicrobial activity to the cembrene macrocycle. [40] Therefore, minimal chemical modifications of the cembrene scaffold may yield new bioactive compounds.…”

Section: Chemical Aspects Of New Ggdp Cyclisation Productsmentioning

confidence: 99%

Targeted Engineering of Cyclooctat‐9‐en‐7‐ol Synthase: A Stereospecific Access to Two New Non‐natural Fusicoccane‐Type Diterpenes

et al. 2013

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The structural diversity of bioactive diterpenes is due to variations in their macrocyclic carbon skeletons. The chemical synthesis of these macrocycles is challenging. However, the bacterial diterpene synthase cyclooctat‐9‐en‐7‐ol synthase (CotB2) generates a complex macrocycle in a single step with geranylgeranyl diphosphate as an aliphatic substrate. This study investigates the catalytic mechanisms of the native and mutant CotB2, with a focus on identifying new carbon macrocycles. The combination of in silico modelling, targeted diterpene cyclase engineering and structural elucidation by using GC–MS, HRMS and NMR analysis resulted in the identification of new terpene olefins. CotB2 mutants produced two new non‐natural fusicoccane‐type macrocycles with potential bioactivities and the monocyclic compound cembrene. The observed product pattern allowed insights into the mechanistic features of CotB2. Applied strategies enable new consolidated synthesis of natural and non‐natural terpenoid bioactives.

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“…The oil of AC rhizomes has been analyzed by various workers for their chemical constituents (Oprean et al, 2001;Raina et al, 2003). The oil was found to contain varying concentrations of a-asarone (1), b-asarone (2), c-asarone (3), calamene, calamenenol, calameone (4), a-pinene (5), b-pinene (6), camphene, p-cymene, eugenyl acetate, eugenol (7), isoeugenol (8), methyl isoeugenol (9), calamol, azulene (10), eugenol methyl ether, dipentene (11), methyleugenol, asaronaldehyde (12), terpinolene (13), 1,8-cineole (14), camphor (15), a-caryophyllene (16), and hydrocarbons ( Fig.1) (Nigam et al, 1990;Srivastava et al, 1997;Mukherjee, 2002).…”

Section: Chemical Constituentsmentioning

confidence: 99%

Acorus calamus.: Scientific Validation of Ayurvedic Tradition from Natural Resources

Mukherjee

Venkatesan

Mal

et al. 2007

Pharmaceutical Biology

113

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Acorus calamus Linn. (Araceae), commonly known as ''sweet flag'' or ''calamus'', is a semiaquatic, perennial, aromatic herb with creeping rhizomes. The plant is found in the northern temperate and subtropical regions of Asia, North America, and Europe. The plant exhibits polyploidy. Many ethnomedicinal and ethnobotanical uses have been ascribed to the rhizomes of the plant. A. calamus Linn. (AC) has been used as traditional Chinese and Indian prescriptions for its beneficial effects on memory disorder, learning performance, lipid peroxide content, and anti-aging and anticholinergic activity. Moreover, pharmacological studies have revealed that Acorus rhizome and its constituents, particularly a-and b-asarone, possess a wide range of pharmacological activities such as sedative, CNS depressant, behavior modifying, anticonvulsant, acetylcholinesterase inhibitory, memory enhancing, anti-inflammatory, antioxidant, antispasmodic, cardiovascular, hypolipidemic, immunosuppressive, cytoprotective, antidiarrheal, antimicrobial, anthelmintic, insecticidal, adulticidal, diuretic, antioxidant, genotoxic, and mutagenic activities. This review is an effort to explore the different phytoconstituents and pharmacological activities of Acorus calamus.

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Essential oils analysis. II. Mass spectra identification of terpene and phenylpropane derivatives

Cited by 39 publications

References 1 publication

Development of Fingerprints for Quality Control of Acorus species by Gas Chromatography/Mass Spectrometry

Development of Fingerprints for Quality Control of Acorus species by Gas Chromatography/Mass Spectrometry

Targeted Engineering of Cyclooctat‐9‐en‐7‐ol Synthase: A Stereospecific Access to Two New Non‐natural Fusicoccane‐Type Diterpenes

Acorus calamus.: Scientific Validation of Ayurvedic Tradition from Natural Resources

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