Tag: 232.275

Vasorelaxing effect in rat thoracic aorta caused by fraxinellone and dictamine isolated from the Chinese herb Dictamnus dasycarpus Turcz: comparison with cromakalim and Ca²⁺ channel blockers was written by Yu, Sheu Meei;Ko, Feng Nien;Su, Ming Jai;Wu, Tian Shung;Wang, Meei Ling;Huang, Tur Fu;Teng, Che Ming. And the article was included in Naunyn-Schmiedeberg’s Archives of Pharmacology in 1992.Related Products of 28808-62-0 This article mentions the following:

The components of D. dasycarpus Turcz were tested for their vasorelaxing effect on the rat aorta, and fraxinellone (I) and dictamine (II) were shown to be effective vasorelaxants. In high K⁺ (60 mmol/L) medium, Ca²⁺ (0.03 to 3 mmol/L)-induced vasoconstriction was inhibited concentration-dependently by both agents. The IC₅₀ for I and II were calculated to be about 25 μmol/L and 15 μmol/L (for Ca²⁺ concentration of 1 mmol/L), resp. Cromakalim (0.2-10 μmol/L) relaxed aortic rings precontracted with 15 but not 60 mmol/L of K⁺. I and verapamil were more potent and effective in producing relaxation in 60 mmol/L than in 15 mmol/L K⁺-induced contraction. However, II was more potent in producing relaxation in 15 mmol/L K⁺-induced contraction. Nifedipine (1 μmol/L), II (100 μmol/L) and I (100 μmol/L) relaxed the aortic contraction caused by KCl or Bay K 8644. The tonic contraction elicited by noradrenaline (NA, 3 μmol/L) was also relaxed by II (500 μmol/L), but not by I (500 μmol/L) in the nifedipine (1 μmol/L)-treated aorta. This relaxing effect of II persisted in endothelium-denuded aorta. Glibenclamide (10 μmol/L) shifted the concentration-relaxation curve of cromakalim, but not that of II, to the right in rat aortic rings precontracted with NA. II (500 μmol/L) did not affect tonic contraction of NA which are reduced by H-7 (1 μmol/L) in Ca²⁺-depleted medium. In conclusion, I is a selective blocker of voltage-dependent Ca²⁺ channel, while II relaxes the rat aorta by suppressing the Ca²⁺ influx through both voltage-dependent and receptor-operated Ca²⁺ channels. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Related Products of 28808-62-0).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Related Products of 28808-62-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation was written by Zheng, Bingfeng;Yuan, Manman;Wang, Shenglan;Tan, Yang;Xu, Yizhu;Ye, Jing;Gao, Yanjie;Sun, Xueqing;Wang, Tianyi;Kong, Lingdong;Wu, Xingxin;Xu, Qiang. And the article was included in Toxicology and Applied Pharmacology in 2021.Formula: C14H16O3 This article mentions the following:

Chronic Kidney Disease (CKD) is a serious threat to human health. In addition, kidney fibrosis is a key pathogenic intermediate for the progression of CDK. Moreover, excessive activation of fibroblasts is key to the development of kidney fibrosis and this process is difficult to control. Notably, fraxinellone is a natural compound isolated from Dictamnus dasycarpus and has a variety of pharmacol. activities, including hepatoprotective, anti-inflammatory and anti-cancer effects. However, the effect of fraxinellone on kidney fibrosis is largely unknown. The present study showed that fraxinellone could alleviate folic acid-induced kidney fibrosis in mice in a dose dependent manner. Addnl., the results revealed that fraxinellone could effectively down-regulate the expression of CUGBP1, which was highly up-regulated in human and murine fibrotic renal tissues. Furthermore, expression of CUGBP1 was selectively induced by the Transforming Growth Factor-beta (TGF-β) through p38 and JNK signaling in kidney fibroblasts. On the other hand, downregulating the expression of CUGBP1 significantly inhibited the activation of kidney fibroblasts. In conclusion, these findings demonstrated that fraxinellone might be a new drug candidate and CUGBP1 could be a promising target for the treatment of kidney fibrosis. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Formula: C14H16O3).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Formula: C14H16O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Antimicrobial and pesticidal activity of fraxinellone from Dictamnus dasycarpus was written by Yuan, Chunlan;Wang, Xiaoling;Yang, Desuo. And the article was included in Chemical Journal on Internet in 2006.Application of 28808-62-0 This article mentions the following:

By means of solvent partition, preparative TLC, and spectral anal., a main active substance with the biol. activity was fraxinellone contained in D. dasycarpus. Its antifeeding rate and mortality of 72 h at 0.21% (mass percent) against 3rd armyworm (Mythimna separata) were 90.4% and 95.2%, resp. Then antimicrobial activity of fraxinellone had been tested against 7 kinds of bacteria and 10 kinds of plant diseases. The inhibition rate of fraxinellone at 50 ppm reached 100, 99.8, and 99.8% against Escherichia coli, Staphlococcus aureus, and Bacillus megatherium, resp. Its inhibition rate at 100 ppm against Rhizoctonia cerealis van der Hoeven apud. Boerema & Verhoeven was 100% and at 50 ppm against Colletrichurm lagenarium & verhoeven was 72%. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Application of 28808-62-0).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Application of 28808-62-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Effects of fraxinellone on the peritrophic membrane of Mythimna separata(Lepidoptera:Noctuidae) was written by Lu, Min;Chen, Su-ying;Han, Li-bo;Hu, Jun-yun;Xu, Hui;Wu, Wen-jun. And the article was included in Kunchong Xuebao in 2014.Formula: C14H16O3 This article mentions the following:

Isolated from the root-bark of Diatamnus dasycarpus Turcz., fraxinellone exhibits stomach toxicity against pests. This study aims to clarify the insecticidal mechanism of fraxinellone by investigating the effects of fraxinellone on the peritrophic membrane of the 6th instar larvae of Mythimna separata. Through biochem. methods and SEM observation, the content of carbohydrates, the contents and components of proteins and the surface structure of the peritrophic membrane of the 6th instar larvae of M. separata after in vivo and in vitro treatments with fraxinellone were studied. In vivo treatment of fraxinellone (20 mg/mL) resulted in a drop of the protein content in the 6th instar larvae of M. separata. However, after M. separata larvae were subjected to in vivo (20 mg/mL fraxinellone) and in vitro (8 mg/mL fraxinellone) treatments with fraxinellone, the contents of carbohydrates of both treatments increased, which were 1.75 and 2.17 folds as high as those of the control, resp. SDS-PAGE result showed that partial proteins were hydrolyzed in the 6th instar larvae of M. separata subjected to in vivo and in vitro treatment with fraxinellone. SEM observation showed that the surface structure of peritrophic membrane changed after the 6th instar larvae of M. separata were treated with fraxinellone in vivo and in vitro. These results showed that fraxinellone affected the contents of carbohydrates and the contents and components of proteins, and altered the surface structure of the peritrophic membrane of M. separata larvae. This study provides a basis for further research on the insecticidal mechanisms of fraxinellone against pests. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Formula: C14H16O3).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Formula: C14H16O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Semisynthesis and Insecticidal Activity of Some Fraxinellone Derivatives Modified in the B Ring was written by Guo, Yong;Qu, Huan;Zhi, Xiaoyan;Yu, Xiang;Yang, Chun;Xu, Hui. And the article was included in Journal of Agricultural and Food Chemistry in 2013.Category: benzofurans This article mentions the following:

A series of novel fraxinellone derivatives modified at the C-1 or C-8 position in the B ring were prepared as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata Walker at 1 mg/mL. Five key steric configurations of five compounds were further determined by single-crystal X-ray diffraction. It was found that the kinds and the amount of the reduction products of fraxinellone were related to the molar ratio between the reduction agent Red-Al and the substrate fraxinellone. Among all of the derivatives, compounds (I) and (II), (III) and (IV) displayed more promising insecticidal activity than their precursors fraxinellone and toosendanin. The preliminary structure-activity relationships revealed that the lactone (B-ring) of fraxinellone contributed to the observed insecticidal activity; the double bond at the C-2 position of fraxinellone was not necessary for the insecticidal activity; conversion of the oxygen atom of carbonyl group on the lactone of fraxinellone to a sulfur one does not improve the insecticidal activity; introduction of electron-withdrawing groups on the Ph ring of (V), to the benzoyloxy series, could result in more potent compounds In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Category: benzofurans).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The protein adduction derived from reactive metabolites of multiple furanoids in cortex Dictamni-treated mice was written by Wu, Kaili;Pan, Hong;Li, Yi;Huang, Linyan;Fang, Chao;Shi, Fuguo. And the article was included in Toxicology Letters in 2022.Reference of 28808-62-0 This article mentions the following:

The association of herb medicine Cortex Dictamni (CD) with severe even fatal hepatotoxicity has been widely reported. Recently, we demonstrated that the metabolic activation of at least ten furanoids in CD was responsible for the liver injury caused by the ethanol extract of CD (ECD) in mice. Protein adduction by reactive metabolites is considered to initiate the process of liver injury. Unlike single chems., the mode of and the details of protein modification by multiple components in an herb is unclear. This study aimed to characterize protein adductions derived from the reactive metabolite of furanoids in ECD-treated mice and define the association of protein adduction with liver injury. The hepatic cysteine- and lysine-based protein adducts derived from epoxide or cis-enedione of at least six furanoids were identified in mice. The furanoids with an earlier serum content Tmax were mainly to bind with hepatic glutathione and no protein adducts were formed except for dictamnine. The hepatic proteins were modified by the later absorbed furanoids. The levels of hepatic protein adduct were correlated with the degree of liver injury. In addition, the reactive metabolites of different furanoids can simultaneously bind to the model peptide by the identical reactive moiety, indicating the additive effects of the individual furanoids in the modification of hepatic proteins. In conclusion, hepatic protein adduction by multiple furanoids may play a role in ECD-induced liver injury. The earlier absorbed furanoids were mainly to bind with glutathione whereas the hepatic proteins were modified by the later furanoids. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Reference of 28808-62-0).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Reference of 28808-62-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Study on chemical constituents of the root of Dictamnus dasycarpus was written by Li, Xiang;Tang, Huazhao;Gou, Xiaojun;Tu, Jie. And the article was included in Zhongyaocai in 2008.Computed Properties of C14H16O3 This article mentions the following:

The chem. constituents of Dictamnus dasyarpus were studied. The root of Dictamnus dasycarpus was extracted by 95% ethanol. Fifteen compounds were isolated and identified from its stems. Fifteen compounds were dictamnol (1), fraxinellone (2), β-sitosterol (3), preskimminanine (4), dictamine (5), skimmianine (6), pregnendone (7), γ-fagarine (8), 11,12,13-trinorguai-6-ene-4β,10β-diol (9), obacunone (10), limonin diosphend (11), rutaevin (12), limonin (13), daucosterol (14) and KihadaninB (15). Among them, Corapounds 9, 11 and 15 are found from Dictamnus dasycarpus for the first time, and KihadaninBA and KihadaninBB are a pair of new enantiomorph. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Computed Properties of C14H16O3).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Computed Properties of C14H16O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Degraded limonoids and quinoline alkaloids from Dictamnus angustifolius G. Don ex Sweet. and their anti-platelet aggregation activity was written by Sun, Jian-Bo;Qu, Wei;Wang, Pei;Wu, Fei-Hua;Wang, Li-Ying;Liang, Jing-Yu. And the article was included in Fitoterapia in 2013.Electric Literature of C14H16O3 This article mentions the following:

A new degraded limonoid, named isodictamdiol A (1), two known degraded limonoids (2, 3) and a new nature product of quinoline alkaloid (4) along with five known quinoline alkaloids (5-9) were isolated from the root bark of Dictamnus angustifolius G. Don ex Sweet.. Certain useful NMR data were generalized to determine the structures of compounds 1 and 4. The structural elucidation of Compound 4 was first reported herein. Compounds 1-9 showed significant inhibitory effects on platelet aggregation induced by ADP at 250 μM, while Compound 4 showed potent anti-platelet aggregation activity. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Electric Literature of C14H16O3).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Electric Literature of C14H16O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Chemotaxonomic significance of limonoids and triterpenoids from Dictamnus angustifolius G. Don ex Sweet was written by Lv, Meng-ying;Tang, Ben-qin;Teng, Jing;Liang, Jing-yu;Xu, Feng-guo;Zhang, Zun-jian;Sun, Jian-bo. And the article was included in Biochemical Systematics and Ecology in 2015.SDS of cas: 28808-62-0 This article mentions the following:

Phytochem. investigation of the root bark of Dictamnus angustifolius G. Don ex Sweet (Rutaceae) resulted in the isolation and characterization of three degraded limonoids (1-3), five limonoids (4-8) and four triterpenoids (9-12). All structures were elucidated on the basis of spectral anal. Among them, compounds 4, 6, 8, 9 and 12 were isolated from the genus Dictamnus for the first time. Compounds 10 and 11 were obtained from D. angustifolius for the first time. Moreover, the chemotaxonomic significance of these compounds was summarized. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0SDS of cas: 28808-62-0).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.SDS of cas: 28808-62-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Semisynthesis of new ethers from furyl-ring-based acylation derivatives of fraxinellone as insecticidal agents against Mythimna separata Walker in vivo was written by Yang, Ruige;Guo, Yong;Zhang, Yuanyuan;Xu, Hui. And the article was included in Chinese Chemical Letters in 2018.Product Details of 28808-62-0 This article mentions the following:

Fraxinellone, a naturally occurring degraded limonoid, is mainly isolated from Dictamnus dasycarpus and Melia azedarach. In continuation of our program aimed at the discovery of plant natural products-based insecticidal agents, twenty-two new ethers from furyl-ring-based acylation derivatives were prepared by structural modifications of fraxinellone. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Among them, compounds I (R = 4-chlorophenyl) and I (R = 2-bromo-6-fluorophenyl) exhibited more potent insecticidal activity than toosendanin with the final mortality rates greater than 60%. Their structure-activity relationships were also discussed. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Product Details of 28808-62-0).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Benzofurans are stable towards alkali and readily polymerize on treatment with sulfuric acid, due to which they are useful for the preparation of low cost chemically relatively inert resins.Product Details of 28808-62-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem