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Concept: Illicium

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Shikimic acid (SA) produced from the seeds of Chinese star anise (Illicium verum) is a key intermediate for the synthesis of neuraminidase inhibitors such as oseltamivir (Tamiflu®), an anti-influenza drug. However, plants cannot deliver a stable supply of SA. To avoid the resulting shortages and price fluctuations, a stable source of affordable SA is required. Although recent achievements in metabolic engineering of Escherichia coli strains have significantly increased SA productivity, commonly-used plasmid-based expression systems are prone to genetic instability and require constant selective pressure to ensure plasmid maintenance. Cofactors also play an important role in the biosynthesis of different fermentation products. In this study, we first constructed an E. coli SA production strain that carries no plasmid or antibiotic marker. We then investigated the effect of endogenous NADPH availability on SA production.

Concepts: Genetics, Bacteria, Escherichia coli, Anise, Japanese star anise, Star anise, Illicium, Shikimic acid

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Anethole [1-methoxy-4-(1-propenyl)benzene] occurs naturally as a major component of the essential oil of star anise (Illicium verum Hook.f., family Illiciaceae), comprising more than 90 % of its volatile components. Studies showed that this substance has antioxidant, antibacterial, antifungal, and anesthetic properties. In this study, the anti-inflammatory properties of anethole in animal models of nonimmune acute inflammation such as croton oil-induced ear edema and carrageenan-induced pleurisy were investigated. The investigated parameters were edema formation, leukocyte migration, and inflammatory mediators involved. Oral administration of anethole at a dose of 250 and 500 mg/kg reduced both the volume of pleural exudates and the number of migrated leukocytes. Levels of nitric oxide (NO) and prostaglandins (PGE(2)) in the inflammatory exudate were reduced by treatment with anethole, but levels of tumor necrosis factor-α and interleukin-1β were not significantly altered. In ear edema, the oral treatment with anethole inhibited the formation of exudate and the activity of myeloperoxidase, but not after topical administration. These results suggest that the anethole may be effective in controlling some nonimmune acute inflammation-related disease, probably by an inhibitory action on production and/or release of PGE(2) and NO.

Concepts: Immune system, Inflammation, Anti-inflammatory, Anise, Star anise, Anethole, Illicium, Austrobaileyales

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A new, practical, rapid, and high-yielding process for the pressurized hot water extraction (PHWE) of multigram quantities of shikimic acid from star anise (Illicium verum) using an unmodified household espresso machine has been developed. This operationally simple and inexpensive method enables the efficient and straightforward isolation of shikimic acid and the facile preparation of a range of its synthetic derivatives.

Concepts: Absinthe, Anise, Japanese star anise, Star anise, Anethole, Illicium, Austrobaileyales, Shikimic acid

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Interferon-gamma (IFN-γ) signaling in keratinocytes plays an important role in mediating inflammatory conditions such as psoriasis and contact dermatitis. Illicium verum Hook. f. has been used in traditional medicine for treating skin inflammation, rheumatism, asthma, and bronchitis in Asia.

Concepts: Immune system, Inflammation, Asthma, Eczema, Dermatitis, Star anise, Illicium

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A new compound, illiciumflavane acid (1), along with 13 known compounds (2-14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC50 values of 4.63 μM and 9.17 μM, respectively.

Concepts: Spectroscopy, Optics, Stereochemistry, Nuclear magnetic resonance, Chemical structure, Circular dichroism, Star anise, Illicium

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Three new compounds, a sesquilignan (1) and two glucosylated phenylpropanoids (2, 3), and seven known compounds (4-10), were isolated from the fruits of Illicium verum Hook. Fil. (Illiciaceae). The structures of 1-3 were determined based on one and two dimensional (1D- and 2D-) NMR data and ECD spectra analyses. Compounds 3, 5, 6, and 8-10 exhibited potent inhibitory activities against topoisomerase II with IC50 values of 54.6, 25.5, 17.9, 12.1, 0.3 and 1.0 μM, respectively, compared to etoposide, the positive control, with an IC50 of 43.8 μM.

Concepts: DNA, Chemotherapy, Space, Real number, DNA supercoil, Topoisomerase, Illicium, Austrobaileyales

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Illicium verum Hook. fil. Illiciaceae (Illicium v.) has been traditionally used in herbal medicine for treating many inflammatory diseases, including skin inflammation and rheumatism. We investigated its use as a preventive agent against inflammatory and vascular diseases in a murine model of atherosclerosis using apolipoprotein E-knockout (ApoE (-/-)) mice fed on a high-fat diet (HFD).

Concepts: Inflammation, Atherosclerosis, Blood vessel, Apolipoprotein E, Endothelium, Star anise, Illicium, Austrobaileyales

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The fruit of Illicium verum Hook. f. (star anise) is used by many as a spice. The fragrance of I. verum fruit is characteristically anise-like. In this study, hexane-extracted I. verum fruit oil (IVO), trans-anethole as the main component, and related compounds (propiophenone, 4'-methoxy-propiophenone, trans-β-methylstyrene) were analyzed in order to clarify the emotional effect of inhaling the fragrance of I. verum fruit. As a result, although 4 μL/L air IVO did not exhibit an anxiolytic-like effect, 1 μL/L air trans-anethole exhibited a significant effect (p < 0.05). Moreover, the anxiolytic-like effect of 1 μL/L air trans-anethole was significantly greater than 1 μL/L air propiophenone and 1 μL/L air 4'-methoxy-propiophenone (p < 0.05). Thus, the anxiolytic-like effect of trans-anethole was confirmed, and it is proposed that the methoxyl group and 1-propenyl group in the para position of the benzene ring are necessary for the effect. Copyright © 2014 John Wiley & Sons, Ltd.

Concepts: Absinthe, Spice, Anise, Japanese star anise, Star anise, Anethole, Illicium, Austrobaileyales

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Three new germacrane sesquiterpenes and a new m-menthane monoterpene were isolated together with four known compounds from the pericarp of Illicium lanceolatum, an adulterant to star anise (Illicium verum). All compounds were isolated from Illicium plants for the first time. The absolute stereochemistry of all germacranes and m-menthane was established by a combination of NMR and the modified Mosher’s ester method. The biological activity was evaluated on SH-SY5Y neuroblastoma cell line. (1S,5R,7R)-1,5-Dihydroxygermacra-4(15),10(14),11(12)-triene (at 62.5 µM) and (1R,5R,7R)-1,5-dihydroxygermacra-4(15),10(14),11(12)-triene (at 15.6 µM) promoted the proliferation of SH-SY5Y by 36.2% and 45.8%, respectively, after 48 h incubation, indicating potential neurotrophic activity.

Concepts: Absinthe, Anise, Japanese star anise, Star anise, Anethole, Illicium, Austrobaileyales

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Ingestion of products containing Chinese star anise (Illicium verum) fruits contaminated or adulterated with Japanese star anise (Illicium anisatum) fruits can cause poisoning due to the neurotoxin anisatin that is present in Japanese star anise. Thus a rapid, simple and unambiguous distinction between the morphologically similar Chinese star anise and toxic Japanese star anise fruits is important for guaranteeing food safety. After adding ∼200μL of methanol to one star anise carpel placed at 7-10mm from the inlet of a mass spectrometer and applying a potential of ∼5kV to the carpel, an electrospray is created. The formation of the electrospray is immediate, robust and stable and lasts for at least a minute. The presence or absence of anisatin could be monitored by orbitrap high resolution mass spectrometry (HRMS) in negative mode by observing the [M-H](-) ion at m/z 327.1074 (C15H19O8) or in positive mode the [M+K](+) ion at m/z 367.079 (C15H20KO8). Several parameters like wetting solvent, voltage, distance and set-up were optimised. The anisatin signal was ∼250 times higher in Japanese than in Chinese star anise. An existing Direct Analysis in Real Time (DART) HRMS for anisatin was used for benchmarking. Alternatively a linear ion trap mass spectrometer could be used in negative selective reaction monitoring (SRM) mode albeit with lower selectivity than the HRMS method. The transition of the [M-H](-) ion at m/z 327 to the fragment at m/z 265 was monitored. Direct plant spray and DART ionisation are both robust and provided the same yes/no answer in seconds without any prior sample preparation. Compared with the DART-HRMS procedure, the direct plant spray method is simpler in terms of equipment, yields a more stable signal, does not require heating of the sample but is slightly less selective and requires working with high voltages.

Concepts: Mass spectrometry, Fourier transform ion cyclotron resonance, Anise, Japanese star anise, Star anise, Incense, Illicium, Austrobaileyales