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Keywords = cis-anethole

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18 pages, 2855 KB  
Article
Baihe Dihuang Tang Exerts Antidepressant Effects via Modulation of MAOA-Mediated Serotonin Metabolism and Synaptic Plasticity
by Defu Tie, Yuting Wang, Jieru Zhou, Yiting Zhang, Hua Ji, Yue Yu, Haijun Han, Zheng Xiang and Wenlong Li
Pharmaceuticals 2025, 18(12), 1786; https://doi.org/10.3390/ph18121786 - 24 Nov 2025
Viewed by 646
Abstract
Background/Objectives: Baihe Dihuang Tang (BDT), a classical herbal formula from Zhang Zhongjing’s Han Dynasty work Jin Gui Yao Lue, is widely used to treat depressive disorder by nourishing Yin, clearing heat, and tonifying the heart and lungs. However, its pharmacological mechanisms remain [...] Read more.
Background/Objectives: Baihe Dihuang Tang (BDT), a classical herbal formula from Zhang Zhongjing’s Han Dynasty work Jin Gui Yao Lue, is widely used to treat depressive disorder by nourishing Yin, clearing heat, and tonifying the heart and lungs. However, its pharmacological mechanisms remain unclear. This study aims to explore BDT’s antidepressant effects via MAOA-regulated serotonin (5-HT) metabolism and synaptic plasticity, supported by experimental validation, while using network pharmacology to predict MAOA-targeting active components. Methods: Active components and targets of BDT were screened using TCMSP, TCMID, and other databases, and then a component-target-pathway network was constructed. A chronic restraint stress (CRS)-induced depressive mouse model was established. Behavioral tests, including open field test (OFT), elevated plus maze (EPM), forced swimming test (FST) and tail suspension test (TST), were conducted to evaluate antidepressant effects. ELISA, qRT-PCR, and Western blot were employed to assess hippocampal 5-HT metabolism (MAOA, 5-HT/5-HIAA ratio) neurotrophic signaling (BDNF, TrkB) and synaptic plasticity-related proteins (PSD-95, SYN1). Results: BDT significantly reduced FST/TST immobility time and improved anxiety-like behaviors in OFT/EPM. BDT treatment downregulated MAOA expression, elevated hippocampal 5-HT/5-HIAA ratio, activated BDNF/TrkB pathway, and upregulated PSD-95/SYN1. Network pharmacology confirmed MAOA’s central role, identifying MAOA/serotonergic synapse modulation as BDT’s main mechanism and pinpointing Ferulic acid, Caffeate, Stigmasterol, (−)-nopinene, Eugenol, and cis-Anethol as MAOA-targeting bioactive components. Conclusions: BDT ameliorates depressive-like behaviors. This effect is mechanistically linked to suppression of MAOA-mediated 5-HT catabolism—a key validated target. This suppression elevates hippocampal 5-HT bioavailability, thereby activating BDNF/TrkB signaling and promoting synaptic plasticity. Network pharmacology confirmed MAOA as a primary target and identified specific modulatory bioactive components. Full article
(This article belongs to the Section Pharmacology)
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20 pages, 6083 KB  
Article
Characteristic Changes and Potential Markers of Flavour in Raw Pu-Erh Tea with Different Ageing Cycles Analysed by HPLC, HS-SPME-GC-MS, and OAV
by Jiayi Xu, Xiujuan Deng, Yamin Wu, Miao Zhou, Cen Du, Qiaomei Wang, Yuxin Xia, Junjie He, Wenxia Yuan, Wendou Wu, Hongxu Li, Yankun Wang, Tong Li and Baijuan Wang
Foods 2025, 14(5), 829; https://doi.org/10.3390/foods14050829 - 27 Feb 2025
Cited by 8 | Viewed by 2491
Abstract
To investigate the flavour evolution mechanism of raw Pu-erh tea (RPT) during storage, the volatile and non-volatile compounds of RPT with different storage years (1–10 years) from the same raw material origin, manufacturer, and storage location in Wenshan Prefecture, Yunnan Province, were systematically [...] Read more.
To investigate the flavour evolution mechanism of raw Pu-erh tea (RPT) during storage, the volatile and non-volatile compounds of RPT with different storage years (1–10 years) from the same raw material origin, manufacturer, and storage location in Wenshan Prefecture, Yunnan Province, were systematically analysed by HPLC, HS-SPME-GC-MS, and OAV. The results showed that both cluster analyses based on non-volatile and volatile compounds could classify RPT of different storage years into three ageing cycles, with key turning points in the third and eighth years of storage, which is also accompanied by the colour changing from green to orange or brown, the aroma changing from a faint scent to woody and ageing, the astringency diminishing, and the sweet and mellow increasing. Theophylline was identified as the potential marker of RPT stored 1–3 years, while (−)-catechin gallate, (−)-gallocatechin gallate, quercetin, and rutin as those for a storage of 9–10 years. The volatile compounds indicate a general trend of an initial increase followed by a decrease. Forty-four key aroma compounds (OAV ≥ 1) were identified. Eucalyptol, β-Caryophyllene, 2-Amylfuran, Copaene, Estragole, and α-Terpinene originated as potential markers for RPT stored 1–3 years, while (Z)-Linalool oxide (furanoid), α-Terpineol, Terpinen-4-ol, and cis-Anethol were for RPT stored 8–10 years. This study revealed the flavour characteristics and quality changes of RPT over the course of storage, and constructed a sensory flavour wheel, providing theoretical underpinnings for the quality control and assessment of RPT. Full article
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18 pages, 23298 KB  
Article
Habitat Suitability Assessment for Illicium verum Hook. f. (Star Anise) Under Climate Change Conditions, Using the MaxEnt Model and Comprehensive 2D Chromatography
by Peng Gu, Qiuling Li, Liangbo Li, Ding Huang, Kexin Cao, Rumei Lu, Rongshao Huang and Jianhua Chen
Agronomy 2024, 14(12), 2858; https://doi.org/10.3390/agronomy14122858 - 29 Nov 2024
Cited by 2 | Viewed by 1763
Abstract
Illicium verum Hook. f. (star anise) is a highly important plant in terms of both its edible and medicinal properties and its economic value. The suitable habitat for star anise may undergo alterations in response to climate changes and human activities, which in [...] Read more.
Illicium verum Hook. f. (star anise) is a highly important plant in terms of both its edible and medicinal properties and its economic value. The suitable habitat for star anise may undergo alterations in response to climate changes and human activities, which in turn might impact its quality. To ensure the future introduction and protection of star anise, it is crucial to analyze the impacts of climate change on the potential distribution of the species. The approach presented in this study integrates the MaxEnt model and chemical composition analysis to assess the potential distribution patterns of star anise in response to climate change and evaluate the impact of environmental variables on its quality. The results revealed that the soil pH, mean temperature of the coldest quarter, mean diurnal range, precipitation of the warmest quarter and annual precipitation were the main factors affecting the current distribution of I. verum. The current area of suitable habitat is approximately 17.6 × 104 km2, accounting for 74% of the total area of Guangxi Province. Under the future climate scenarios, the overall pattern of the potential distribution range shifted northwards, and the SSP3126 scenario showed the most significant increase in the area. By utilizing comprehensive 2D chromatography technologies, 111 volatile compounds present in the 61 batches of star anise were identified. Further analysis via chemometric methods revealed that the components β-bisabolene, caryophyllene, 4-methoxyphenylacetone, cis-β-farnesene, anethole and linalool could serve as potential markers for distinguishing the quality of star anise from different geographical origins. Finally, a stepwise regression model between chemical compositions and environmental variables was established, and based on this, a quality zoning map was subsequently plotted. This study provides valuable scientific insights for resource conservation, planting site selection and quality control for star anise. Full article
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18 pages, 12397 KB  
Article
Metabolite Profiling and Identification of Sweet/Bitter Taste Compounds in the Growth of Cyclocarya Paliurus Leaves Using Multiplatform Metabolomics
by Liang Chen, Dai Lu, Yuxi Wan, Yaqian Zou, Ruiyi Zhang, Tao Zhou, Bin Long, Kangming Zhu, Wei Wang and Xing Tian
Foods 2024, 13(19), 3089; https://doi.org/10.3390/foods13193089 - 27 Sep 2024
Cited by 7 | Viewed by 2265
Abstract
Cyclocarya paliurus tea, also known as “sweet tea”, an herbal tea with Cyclocarya paliurus leaves as raw material, is famous for its unique nutritional benefits and flavor. However, due to the unique “bittersweet” of Cyclocarya paliurus tea, it is still unable to fully [...] Read more.
Cyclocarya paliurus tea, also known as “sweet tea”, an herbal tea with Cyclocarya paliurus leaves as raw material, is famous for its unique nutritional benefits and flavor. However, due to the unique “bittersweet” of Cyclocarya paliurus tea, it is still unable to fully satisfy consumers’ high-quality taste experience and satisfaction. Therefore, this study aimed to explore metabolites in Cyclocarya paliurus leaves during their growth period, particularly composition and variation of sweet and bitter taste compounds, by combining multi-platform metabolomics analysis with an electronic tongue system and molecular docking simulation technology. The results indicated that there were significant differences in the contents of total phenols, flavonoids, polysaccharides, and saponins in C. paliurus leaves in different growing months. A total of 575 secondary metabolites were identified as potential active metabolites related to sweet/bitter taste using nontargeted metabolomics based on UHPLC-MS/MS analysis. Moreover, molecular docking technology was utilized to study interactions between the candidate metabolites and the sweet receptors T1R2/T1R3 and the bitter receptors T2R4/T2R14. Six key compounds with high sweetness and low bitterness were successfully identified by using computational simulation analysis, including cis-anethole, gluconic acid, beta-D-Sedoheptulose, asparagine, proline, and citrulline, which may serve as candidates for taste modification in Cyclocarya paliurus leaves. These findings provide a new perspective for understanding the sweet and bitter taste characteristics that contribute to the distinctive sensory quality of Cyclocarya paliurus leaves. Full article
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20 pages, 2939 KB  
Article
Chemical Constituents, Antioxidant Potential, and Antimicrobial Efficacy of Pimpinella anisum Extracts against Multidrug-Resistant Bacteria
by Aisha Nawaf AlBalawi, Alaa Elmetwalli, Dina M. Baraka, Hadeer A. Alnagar, Eman Saad Alamri and Mervat G. Hassan
Microorganisms 2023, 11(4), 1024; https://doi.org/10.3390/microorganisms11041024 - 14 Apr 2023
Cited by 29 | Viewed by 5988
Abstract
Aniseeds (Pimpinella anisum) have gained increasing attention for their nutritional and health benefits. Aniseed extracts are known to contain a range of compounds, including flavonoids, terpenes, and essential oils. These compounds have antimicrobial properties, meaning they can help inhibit the growth [...] Read more.
Aniseeds (Pimpinella anisum) have gained increasing attention for their nutritional and health benefits. Aniseed extracts are known to contain a range of compounds, including flavonoids, terpenes, and essential oils. These compounds have antimicrobial properties, meaning they can help inhibit the growth of nasty bacteria and other microbes. The purpose of this study was to determine if aniseed extracts have potential antioxidant, phytochemical, and antimicrobial properties against multidrug-resistant (MDR) bacteria. A disc diffusion test was conducted in vitro to test the aniseed methanolic extract’s antibacterial activity. The MIC, MBC, and inhibition zone diameters measure the minimum inhibitory concentration, minimum bactericidal concentration, and size of the zone developed when the extract is placed on a bacterial culture, respectively. HPLC and GC/MS are analytical techniques used for identifying the phenolics and chemical constituents in the extract. DPPH, ABTS, and iron-reducing power assays were performed to evaluate the total antioxidant capacity of the extract. Using HPLC, oxygenated monoterpenes represented the majority of the aniseed content, mainly estragole, cis-anethole, and trans-anethole at 4422.39, 3150.11, and 2312.11 (g/g), respectively. All of the examined bacteria are very sensitive to aniseed’s antibacterial effects. It is thought that aniseed’s antibacterial activity could be attributed to the presence of phenolic compounds which include catechins, methyl gallates, caffeic acid, and syringic acids. According to the GC analysis, several flavonoids were detected, including catechin, isochiapin, and trans-ferulic acid, as well as quercitin rhamnose, kaempferol-O-rutinoside, gibberellic acid, and hexadecadienoic acid. Upon quantification of the most abundant estragole, we found that estragole recovery was sufficient for proving its antimicrobial activity against MDR bacteria. Utilizing three methods, the extract demonstrated strong antioxidant activity. Aniseed extract clearly inhibited MDR bacterial isolates, indicating its potential use as an anti-virulence strategy. It is assumed that polyphenolic acids and flavonoids are responsible for this activity. Trans-anethole and estragole were aniseed chemotypes. Aniseed extracts showed higher antioxidant activity than vitamin C. Future investigations into the compatibility and synergism of aniseed phenolic compounds with commercial antibacterial treatments may also show them to be promising options. Full article
(This article belongs to the Section Plant Microbe Interactions)
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12 pages, 1698 KB  
Article
Essential Oil Yield, Composition, and Antioxidant Activity in Two Umbel Maturity Stages of Wild Carrot (Daucus carota L. ssp. carota) from Montenegro
by Jelena Stanojević, Zoran S. Ilić, Ljiljana Stanojević, Lidija Milenković, Renata Kovač, Dragana Lalević, Ljubomir Šunić, Aleksandra Milenković and Dragan Cvetković
Horticulturae 2023, 9(3), 328; https://doi.org/10.3390/horticulturae9030328 - 2 Mar 2023
Cited by 6 | Viewed by 3992
Abstract
The purpose of this study was to determine essential oil yield, composition, and antioxidant activity during two different maturation stages of umbels with seeds(I stage: premature–waxy; and II stage: mature–fully ripening) of wild carrot (Daucus carrota var. carota) from the Montenegrin [...] Read more.
The purpose of this study was to determine essential oil yield, composition, and antioxidant activity during two different maturation stages of umbels with seeds(I stage: premature–waxy; and II stage: mature–fully ripening) of wild carrot (Daucus carrota var. carota) from the Montenegrin coast. A higher yield of carrot essential oil (CEO) was determined in mature, fully ripening umbels (1.96 mL/100 g p.m) than in premature umbels at the waxy stage (mL/100 g p.m). Thirty-three components were identified in premature umbels, with β-bisabolene (32.3%), 11-α-(H)-himachal-4-en-1-β-ol (27.9%), elemicin (10.1%), and α-longipipene (7.7%) being the main components. They were followed by α-pinene (3.7%), (E)-asarone (3.4%), (E)-anethole (3.2%), and β-himachalene (2.0%). Thirty-two components were identified in CEO from mature umbels, with β-bisabolene (41.0%), 11-α-(H)-himachal-4-en-1-β-ol(21.1%), elemicin (14.8%), andα-longipipene (5.7%) being the most abundant. These components were followed by (E)-asarone (3.9%), cis-α-bisabolene (2.4%), and β-himachalene (2.0%). The CEO isolated from mature umbelsshowed better antioxidant activity (EC50 value of 31.80 mg/mL) in comparison to the CEO isolated from premature umbels (EC50 value of 49.18 mg/mL) during the incubation time of 60 min. The degree of DPPH radical neutralization increased as the incubation time increased from 20 to 60 min. Therefore, our findings recommend that wild carrot could be harvested in the fully ripening stage when the umbel improves CEO yield and antioxidant activity, without the risk of seed shedding from the umbel and seed losses. Full article
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13 pages, 2026 KB  
Article
Effect of Date of Sowing and Spacing of Plants on Yield and Quality of Chamomile (Matricaria chamomilla L.) Grown in an Arid Environment
by Moti Lal Mehriya, Devendra Singh, Aman Verma, Shailendra Nath Saxena, Abed Alataway, Ahmed A. Al-Othman, Ahmed Z. Dewidar and Mohamed A. Mattar
Agronomy 2022, 12(12), 2912; https://doi.org/10.3390/agronomy12122912 - 22 Nov 2022
Cited by 4 | Viewed by 4859
Abstract
Little is known about how Indian farming practices affect German chamomile (Matricaria chamomilla L.). This study examines the effects of the sowing date and spacing of plants on flower productivity, essential oil concentration, and the composition of German chamomile grown in the [...] Read more.
Little is known about how Indian farming practices affect German chamomile (Matricaria chamomilla L.). This study examines the effects of the sowing date and spacing of plants on flower productivity, essential oil concentration, and the composition of German chamomile grown in the arid zone of Rajasthan, India. In a factorial randomized block design (FRBD), the treatments consisted of four sowing dates (15 and 25 October, 5 and 15 November) and three spacings of plants (20 × 10 cm, 30 × 10 cm, and 40 × 10 cm). The dried flower yield (Kg ha−1), fresh flower yield (Kg ha−1), and number of flowers per plant of chamomile crop were significantly affected by the varying spacing of plants and the date of sowing. The highest values for dry weight, fresh weight, and number of flowers were obtained from the second date of sowing (25 October) with 40 × 10 cm geometry. Likewise, the highest values for total oil (12.44%) and essential oil (0.94%) contents were also obtained from the D2P3 combination (D2—sowing date 25 October, P3—40 × 10 cm spacing of plants). GC/MS analyses of the samples showed that p-menth-1-en-4-ol, acetate, cis-alpha-farnesene, anethole+estragol, 1,4-cyclohexadiene,1-methyl-4-(1-methylethyl)- and 3,6-dihydro-4-(4-methyl-3-pentenyl)-1,2-dithiin were the main identified compounds in the essential oil of chamomile fresh flowers. The treatments altered the quality profile of the essential oils in general. The principal components of chamomile essential oil were significantly affected by the D2P3 treatment. The findings of this study add to our understanding of how to grow high-quality chamomile flowers in arid regions. Full article
(This article belongs to the Special Issue Research Progress and Application Prospect of Medicinal Plants)
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16 pages, 2269 KB  
Article
Agricultural Parameters and Essential Oil Content Composition Prediction of Aniseed, Based on Growing Year, Locality and Fertilization Type—An Artificial Neural Network Approach
by Lato Pezo, Biljana Lončar, Olja Šovljanski, Ana Tomić, Vanja Travičić, Milada Pezo and Milica Aćimović
Life 2022, 12(11), 1722; https://doi.org/10.3390/life12111722 - 27 Oct 2022
Cited by 12 | Viewed by 3272
Abstract
Predicting yield is essential for producers, stakeholders and international interchange demand. The majority of the divergence in yield and essential oil content is associated with environmental aspects, including weather conditions, soil variety and cultivation techniques. Therefore, aniseed production was examined in this study. [...] Read more.
Predicting yield is essential for producers, stakeholders and international interchange demand. The majority of the divergence in yield and essential oil content is associated with environmental aspects, including weather conditions, soil variety and cultivation techniques. Therefore, aniseed production was examined in this study. The categorical input variables for artificial neural network modelling were growing year (two successive growing years), growing locality (three different locations in Vojvodina Province, Serbia) and fertilization type (six different treatments). The output variables were morphological and quality parameters, with agricultural importance such as plant height, umbel diameter, number of umbels, number of seeds per umbel, 1000-seed weight, seed yield per plant, plant weight, harvest index, yield per ha, essential oil (EO) yield, germination energy, total germination, EO content, as well as the share of EOs compounds, including limonene, cis-dihydro carvone, methyl chavicol, carvone, cis-anethole, trans-anethole, β-elemene, α-himachalene, trans-β-farnesene, γ-himachalene, trans-muurola-4(14),5-diene, α-zingiberene, β-himachalene, β-bisabolene, trans-pseudoisoeugenyl 2-methylbutyrate and epoxy-pseudoisoeugenyl 2-methylbutyrate. The ANN model predicted agricultural parameters accurately, showing r2 values between 0.555 and 0.918, while r2 values for the forecasting of essential oil content were between 0.379 and 0.908. According to global sensitivity analysis, the fertilization type was a more influential variable to agricultural parameters, while the location site was more influential to essential oils content. Full article
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11 pages, 1030 KB  
Article
Anethole Stability in Aniseed Spirits: Storage Condition Repercussions on Commercial Products
by Veronica Vendramin, Antonio Pesce and Simone Vincenzi
Beverages 2021, 7(4), 73; https://doi.org/10.3390/beverages7040073 - 30 Oct 2021
Cited by 7 | Viewed by 6806
Abstract
Background: trans-anethole is the main component of anise, and its flavor is characteristic of all the aniseed spirits. It is known that trans-anethole oil/ethanol/water solution could result in the undesirable emulsion effect called the “ouzo effect”. Moreover, trans-anethole can undergo [...] Read more.
Background: trans-anethole is the main component of anise, and its flavor is characteristic of all the aniseed spirits. It is known that trans-anethole oil/ethanol/water solution could result in the undesirable emulsion effect called the “ouzo effect”. Moreover, trans-anethole can undergo chemical decay, producing unhealthy compounds, mainly cis-anethole and para-anisaldehyde. In this work, the trans-anethole stability was challenged simulating commercial products’ long-term storage. Methods: Anethole standard solutions and two Italian aniseed spirits, namely Sambuca and Mistrà, were used to evaluate the trans-anethole response to light (both ultraviolet and visible) and its stability under thermal stress. Anethole decay was monitored by trans-anethole quantification using an HPLC method. Results: Light and high-temperature exposure affect the trans-anethole content of aniseed spirits during the storage, but sucrose revealed a role in the trans-anethole protection. Conclusions: as transport and storage are involved in the anethole decay, the Regulations on the minimum of the anethole that must be a guarantee in the aniseed spirits should be revised. Full article
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12 pages, 171 KB  
Article
Antifungal Activity of the Essential Oil of Illicium verum Fruit and Its Main Component trans-Anethole
by Yongfu Huang, Jianglin Zhao, Ligang Zhou, Jihua Wang, Youwen Gong, Xujun Chen, Zejian Guo, Qi Wang and Weibo Jiang
Molecules 2010, 15(11), 7558-7569; https://doi.org/10.3390/molecules15117558 - 27 Oct 2010
Cited by 157 | Viewed by 17206
Abstract
In order to identify natural products for plant disease control, the essential oil of star anise (Illicium verum Hook. f.) fruit was investigated for its antifungal activity on plant pathogenic fungi. The fruit essential oil obtained by hydro-distillation was analyzed for its [...] Read more.
In order to identify natural products for plant disease control, the essential oil of star anise (Illicium verum Hook. f.) fruit was investigated for its antifungal activity on plant pathogenic fungi. The fruit essential oil obtained by hydro-distillation was analyzed for its chemical composition by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). trans-Anethole (89.5%), 2-(1-cyclopentenyl)-furan (0.9%) and cis-anethole (0.7%) were found to be the main components among 22 identified compounds, which accounted for 94.6% of the total oil. The antifungal activity of the oil and its main component trans-anethole against plant pathogenic fungi were determined. Both the essential oil and trans-anethole exhibited strong inhibitory effect against all test fungi indicating that most of the observed antifungal properties was due to the presence of trans-anethole in the oil, which could be developed as natural fungicides for plant disease control in fruit and vegetable preservation. Full article
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19 pages, 429 KB  
Article
Anethole Isomerization and Dimerization Induced by Acid Sites or UV Irradiation
by Hans T. Castro, Jairo René Martínez and Elena Stashenko
Molecules 2010, 15(7), 5012-5030; https://doi.org/10.3390/molecules15075012 - 22 Jul 2010
Cited by 20 | Viewed by 10563
Abstract
The formation of cis-anethole and various dimers as a result of the exposure of trans-anethole to microporous solid acids (dealuminated HY zeolites), or UV-Vis irradiation was established by means of high resolution gas chromatography coupled to mass spectrometry. 3,4-bis-(4-Methoxyphenyl)-(E)-hex-2-ene [...] Read more.
The formation of cis-anethole and various dimers as a result of the exposure of trans-anethole to microporous solid acids (dealuminated HY zeolites), or UV-Vis irradiation was established by means of high resolution gas chromatography coupled to mass spectrometry. 3,4-bis-(4-Methoxyphenyl)-(E)-hex-2-ene was the most abundant compound among eight different methoxyphenyl-disubstituted hexenes produced by electrophilic addition and elimination reactions induced by HY zeolites. (1a,2a,3b,4b)-1,2-bis(4-Methoxyphenyl)-3,4-dimethylcyclobutane was the principal component in the mixture of 5 methoxyphenyl-disubstituted cyclobutanes found, together with cis-anethole, after UV-Vis irradiation of a trans-anethole solution in toluene. Full article
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