- Metabolism of carcinogenic alpha-asarone by human cytochrome P450 enzymes
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Major metabolites of alpha-asarone in liver microsomes are epoxide-derived side-chain diols. The intermediately formed epoxides are mutagenic and form DNA adducts and thus are likely responsible for the (hepato) carcinogenic effect of alpha-asarone observ
- Cartus, Alexander T.,Schrenk, Dieter
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- The asarone-derived phenylpropanoids from the rhizome of Acorus calamus var. angustatus Besser
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Phenylpropanoids comprise a broad spectrum of biologically active natural products. As part of our ongoing research on antiepileptic active compounds from traditional Chinese herb, Acorus calamus var. angustatus Besser, three undescribed phenylpropanoids and twenty-two known ones were isolated. All the undescribed structures were determined by a combination of 1D and 2D NMR, HRMS. In addition, γ-asaronol was identified as racemates and its absolute configuration were determined by the modified Mosher's method and ECD spectral data. Furthermore, some selected isolated compounds were evaluated for their cell viability and neuroprotective activities in H2O2-induced SH-SY5Y cells. α-Asaronol, β-asaronol, 3-(2,4,5-trimethoxyphenyl)propan-1-ol and 1,2,4-trimethoxy-5-(3-methoxypropyl)benzene exerted potential protective activity from neuronal oxidative stress in all test concentrations ranging from 0.01 to 100 μM, in which the neuroprotective activity of β-asaronol was the best.
- Bai, Yajun,Sun, Ying,Xie, Jing,Li, Bin,Bai, Yujun,Zhang, Dongxu,Liang, Jing,Xiao, Chaoni,Zhong, Aiguo,Cao, Yanjun,Zheng, Xiaohui
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- Synthesis methods of alpha-asarinol acetate and alpha-asarinol
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The invention discloses synthesis methods of alpha-asarinol acetate and alpha-asarinol. The synthesis method of alpha-asarinol acetate comprises the following step that: in the presence of a palladium catalyst and a ligand, 1, 2, 4-trimethoxybenzene reacts with allyl acetate to generate the alpha-asarinol acetate, wherein the ligand is one or a combination of more than two of acetylglycine, acetylproline and nicotinoyl glycine. The synthesis method of the alpha-asarinol comprises the step of hydrolyzing alpha-asarinol acetate under an alkaline condition to obtain the alpha-asarinol. The methods have the advantages of simple and easily available raw materials, high atom economy and step economy, high yield and suitability for large-scale industrial production.
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Paragraph 0026; 0062-0067
(2021/08/14)
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- Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study
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Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic α-asaronol esters and analogues were designed by Combination of Traditional Chinese Medicine Molecular Chemistry (CTCMMC) strategy, synthesized and tested systematically not only for anticonvulsant activity in three mouse models but also for LDH inhibitory activity. Thereinto, 68–70 and 75 displayed excellent and broad spectra of anticonvulsant activities with modest ability in preventing neuropathic pain, as well as low neurotoxicity. The protective indices of these four compounds compared favorably with stiripentol, lacosamide, carbamazepine and valproic acid. 68–70 exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Notably, 70, as a representative agent, was also shown as a moderately positive allosteric modulator at human α1β2γ2 GABAA receptors (EC50 46.3 ± 7.3 μM). Thus, 68–70 were promising candidates for developing into anti-epileptic drugs, especially for treatment of refractory epilepsies such as Dravet syndrome.
- Bai, Yajun,He, Xirui,Bai, Yujun,Sun, Ying,Zhao, Zefeng,Chen, Xufei,Li, Bin,Xie, Jing,Li, Yang,Jia, Pu,Meng, Xue,Zhao, Ye,Ding, Yanrui,Xiao, Chaoni,Wang, Shixiang,Yu, Jie,Liao, Sha,Zhang, Yajun,Zhu, Zhiling,Zhang, Qiang,Zhao, Yuhui,Qin, Fanggang,Zhang, Yi,Wei, Xiaoyang,Zeng, Min,Liang, Jing,Cuan, Ye,Shan, Guangzhi,Fan, Tai-Ping,Wu, Biao,Zheng, Xiaohui
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- a-ASARY-LALDEHYDE ESTER, PREPARATION METHOD THEREFOR, AND APPLICATION THEREOF
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The present invention relates to α-asary-laldehyde ester, a preparation method therefor, and an application thereof. The chemical structure of the related α-asary-laldehyde ester is represented by formula I. A related application is an application of the compound in preparation of drugs for calming, mind tranquillizing, senile dementia resisting, convulsion resisting, epilepsy resisting and depression resisting.
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- Α - Herba Asari (asarum herb) alcohol and its preparation method and application
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The invention relates to (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol, and a preparation method and application thereof. Related (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol has the structural formula I shown in the specification. The related preparation method comprises: performing decarboxylation reaction on 2,4,5-trimethoxybenzaldehyde, isopropylidene malonate (meldrum's acid) and a fatty alcohol under catalytic effect of pyridine and piperidine, so as to obtain (E)-2,4,5-trimethoxycinnamate, and processing by using a reducing agent, so as to obtain (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol. The preparation method is simple and relatively high in yield. The related application comprises that (E)-3-(2,4,5-trimethoxy-phenyl)-prop-2-en-1-ol is applied to prepare medicines for calming, tranquilizing, resisting senile dementia, resisting convulsion, resisting epilepsy or protecting heart and cerebral vessels.
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Paragraph 0012; 0044-0046
(2017/03/08)
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- Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells
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The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.
- Barcelos, Rosimeire Coura,Pastre, Julio Cezar,Caixeta, Vanessa,Vendramini-Costa, Débora Barbosa,De Carvalho, Jo?o Ernesto,Pilli, Ronaldo Aloise
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experimental part
p. 3635 - 3651
(2012/07/27)
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