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α-Asarone and β-asarone are reported as bioactive constituents of Acorus calamus . Phase I metabolism of asarone isomers results in a multiple spectrum of genotoxic metabolites. Thus, the question arises whether structural analogues of the known phase I metabolites also naturally occur in A. calamus -based food products. A liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed and validated for three product classes, herbal infusions, alcoholic beverages, and food supplements. High asarone contents were detected in herbal infusions (total mean 9.13 mg/kg, n = 8) and food supplements (total mean 14.52 mg/kg, n = 6); hence, these food products can highly contribute to human exposure to genotoxic asarone derivatives. Also, the occurrence of asarone oxidation products found in food and food supplements has to be taken under consideration because data on toxicity is limited so far.

Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole and spiroketalization., (© 2011 American Chemical Society)

Three novel sesquinlignans, tatanans A (1), B (2), and C (3), have been isolated from the rhizomes of Acorus tatarinowii Schott. Their structures were established by spectroscopic techniques and single-crystal X-ray analysis. Tatanans A-C potently increase GK enzymatic activity with EC(1.5) values in the range of 0.16-1.85 μM. The potent GK activity and unique structural features of tatanans make them promising leads for therapeutic development of antihyperglycemic drugs.

Acortatarins A (1) and B (2), two novel spiroalkaloids with a naturally unusual morpholine motif, were isolated from the rhizome of Acorus tatarinowii. Their structures with absolute configuration were determined by spectroscopic methods, X-ray diffraction analysis, and Mosher's method. Importantly, compound 1 could significantly inhibit reactive oxygen species production in high-glucose-stimulated mesangial cells in a dose- and time-dependent manner.

Volatile concentrates from the oleo-gum resin of Commiphora myrrha (Nees) Engl. and from the rhizomes of Acorus calamus were isolated by supercritical extraction with carbon dioxide. The volatile oil of myrrh was obtained at 9.0 MPa and 50 degrees C and at a CO2 flow of 1.5 kg/h. Acorus calamus was extracted at 9.0 MPa and 45 degrees C and at a CO2 flow of 1.6 kg/h. In both cases, an oil devoid of cuticular waxes was obtained with a single depressurization stage. The SFE myrrh oil had a yield, Y, of 3.2%. Its main components, identified and quantified by GC/MS, were furanoeudesma-1,3-diene, 34.9%; lindestrene, 12.9%; curzerene, 8.5%; and germacrone, 5.8%. The essential oils from the same starting material by hydrodistillation, HD, (Y = 2.8%) and by steam distillation, SD, (Y = 0.4%) were quite similar to the SFE extract. The main components of the SFE oil of A. calamus (Y = 3.5%) were acorenone, 13.4%; iso-acorone, 11.6%; (Z)-sesquilavandulol, 11.0%; dehydroxy isocalamendiol, 7.7%; and beta-asarone, 5.5%. The comparison with hydrodistilled (Y = 1.8%) and steam distilled (Y = 1.0%) oils revealed large differences in the content of iso-acorone and crypto-acorone.

Volatile extracts were isolated from dried medicinal plants [Angelica tenuissimae roots (AT, Angelica tenuissima Nakai), peppermint leaves (PL, Mentha arvensis L.), pine needles (PN, Pinus sylvestris L.), and sweet flag leaves (SF, Acorus gramineus Rhizoma)] using steam distillation under reduced pressure, followed by continuous liquid-liquid extraction (DRP-LLE). The extracts were then analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The major volatile constituents of AT, PL, PN, and SF were 3-butylidene-4,5-dihydrophthalide (32 mg/g), menthol (18 mg/g), thunbergol (2.1 mg/g), and cis-asarone (37 mg/g), respectively. The inhibitory activity (%) of the extracts against hexanal oxidation ranged from 33 to 98% at a level of 50 microg/mL. Among the volatile extracts, PL and PN increased cell viabilities by 10 and 24%, respectively, at a dose of 1 microg/mL, compared to that of H2O2-treated brain neuroblastoma cells, SK-N-SH. However, a 20% reduction in the malonaldehyde level, an index for lipid peroxidation, was observed at only 1 microg/mL concentration of PN.

This study was conducted to determine the volatile flavor composition of fresh changpo (Acorus calamus var. angustatus Bess) leaves quantitatively and qualitatively by use of two internal standards and to determine which volatile compounds are primarily responsible for the aroma of this aquatic herb. The headspace composition of fresh changpo leaves was also analyzed by a solid-phase microextraction method. Aroma extract dilution analysis (AEDA) and sniffing test by gas chromatography-olfactometry were used for the detection of aroma-active compounds of this herb. According to the instrumental analyses of the changpo oil, octanoic acid (49.13%), alpha-cedrene (16.71%), alpha-phellandrene (4.46%), and gamma-elemene (3.75%) were the most abundant compounds. n-Butylidene dihydrophthalide (8.61%), trans,trans-farnesyl acetate (7.29%), and trans-2-dodecenal (7%) were the main components of changpo headspace. cis-beta-Farnesene was evaluated as the key aroma compound of this herb from results of AEDA and sniffing test.

An antifungal substance was isolated from the extract of Acorus gramineus using various chromatographic procedures. The antibiotic was identified as beta-asarone, cis-2,4,5-trimethoxy-1-propenylbenzene, on the basis of the high-resolution EI-mass, NMR, and UV spectral data. Beta-asarone completely inhibited mycelial growth of some plant pathogenic fungi, Cladosporium cucumerinum,Colletotrichum orbiculare, Magnaporthe grisea, and Pythium ultimum, in a range of 0.5-30 microg/mL. The growth of Bacillus subtilis, Erwinia carotovora subsp. carotovora, Ralstonia solanacearum, and Xanthomonas campestris pv. vesicatoria was slightly suppressed by beta-asarone. As the concentration of beta-asarone increased, M. grisea infection was drastically inhibited on rice leaves. Treatment with 500 microg/mL of beta-asarone also greatly suppressed lesion formation of Co. orbiculare on cucumber leaves. This is the first study to demonstrate in vitro and in vivo antifungal activity of beta-asarone against plant fungal pathogens M. grisea and C. orbiculare.