Evofolin B

Investigating the pharmaceutical substances and action mechanisms of Changmaxifeng granules against tic disorders.[Pubmed:41357924]

World J Psychiatry. 2025 Dec 19;15(12):112055.

BACKGROUND: Tic disorders (TDs) are a type of neurological and psychiatric disorder characterized by vocal or motor tics in the head, body, or limbs. Clinical studies have shown that Changmaxifeng granules (CG) can treat TDs. However, the pharmaceutical substances and mechanism of action of CG remain unclear. AIM: To investigate the pharmaceutical substances and action mechanisms of CG against TDs, this study employs serum medicinal chemistry, network pharmacology, and molecular docking analysis. METHODS: Ultrahigh-performance liquid chromatography with quadrupole time-of-flight mass spectrometry was used to identify the blood-absorbed constituents of CG; Network pharmacology was then used to integrate these compounds with disease targets, followed by protein-protein interaction (PPI) networks analysis to pinpoint key proteins. Finally, Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analyses combined with molecular docking elucidated the underlying mechanism of action. RESULTS: Overall, 187 chemical components, including terpenoids, sugars, phenolic acids, and flavonoids, were identified in vitro. In addition, 75 components, namely 49 prototype components and 26 metabolites, were identified in vivo. The PPI results revealed 225 overlapping targets, with TNF, IL-6, FOS, VEGFA, and ESR1 being the major targets. GO and KEGG analyses were performed to identify key signaling pathways and biological processes. Paeonol, Evofolin B, aspalathin, and paeoniflorin were identified as potential pharmacodynamic substances based on the results of the "compound-target" network. The maximum binding energy between the core target and the active ingredient was less than -4.7 kcal/mol, indicating that the pharmacophore exhibited a strong affinity toward the core ingredient. CONCLUSION: This study elucidated the in vitro and in vivo chemical components of CG and outlined their potential targets and action mechanisms. This study provides a basis for further research into the action mechanism and clinical application of CG.

[Chemical constituents from seeds of Hydnocarpus anthelminthica].[Pubmed:35718521]

Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2989-2993.

The present study investigated the chemical constituents from the dry seeds of Hydnocarpus anthelminthica. The compounds were isolated and purified from the dry seeds of H. anthelminthica by various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic analysis. The in vitro cytotoxic activities were determined by MTT assay. Ten compounds were isolated and identified as 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol(1), threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(2), erythro-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(3), 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol(4), 3-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one(5), chrysoeriol(6), Evofolin B(7), apigenin-3'-methoxy-7-O-rutinoside(8), luteolin(9), and vitexin(10). Compound 1 is a new compound. Compounds 4 and 5 were isolated from this genus for the first time. All compounds showed no significant cytotoxic activity.

[Lignans from Agrimonia pilosa].[Pubmed:35718520]

Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2982-2988.

Thirteen lignans were isolated from 60% ethanol extract of Agrimonia pilosa by column chromatography over silica gel, ODS, and MCI and preparative high performance liquid chromatography(HPLC). Their chemical structures were identified by physiochemical properties and spectral data as(7S,8S)-threo-4,7,9,9'-tetrahydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan(1),(+)-4,9,9'-trihydroxy-3-methoxy-3',7-epoxy-8,4'-oxyneolignan(2), dihydrodehydro-diconiferyl alcohol(3), 4,9,9'-trihydroxy-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan(4),(-)-secoisolariciresinol(5), 4,7,9,9'-tetrahydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan(6),(+)-isolariciresinol(7), 4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan(8), burselignan(9),(-)-Evofolin B(10), icariol A2(11), ciwujiatone(12), and(+)-4'',4-dihydroxy-3,3',3'',3,5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8'';4',8-bisoxy-8,8'-dineolignan-7'',7,9'',9-tetraol(13). Compound 1 was a new compound, and compounds 1-13 were isolated from Agrimonia plant for the first time. This study can enrich the chemical components in A. pilosa and provide material conditions for the follow-up study of its biological activity and the elucidation of its pharmacodynamic substances.

[Active constituents of Urtica fissa in inhibition of benign prostatic hyperplasia].[Pubmed:35178984]

Zhongguo Zhong Yao Za Zhi. 2022 Jan;47(2):419-427.

The present study investigated the material basis of Urtica fissa for the inhibition of benign prostatic hyperplasia(BPH). The active fractions were screened, and the extracts of dichloromethane and ethyl acetate exhibited significantly inhibitory activities against 5alpha-reductase in vitro and BPH in model rats. The chemical constituents in the active fractions were systematically investigated, and 28 compounds were obtained, which were identified as lobechine methyl ester(1), dibutyl-O-phthalate(2), 1-monolinolein(3), epipinoresinol(4), 5-hydroxy-3,4-dimethyl-5-pentanyl-2(5H)-furanone(5), E-7,9-diene-11-methenyl palmitic acid(6), Evofolin B(7), ficusal(8), threo-2,3-bis-(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol(9), alpha-viniferin(10),(9R,7E)-9-hydroxy-5,7-mengatigmadien-4-one-9-O-beta-D-glucopyranoside(11), indole-3-carboxaldehyde(12), p-hydroxy ethyl cinnamate(13), benzyl alcohol-O-beta-D-glucoside(14), L-methionine(15), 4-methoxyaniline(16), 6-aminopurine(17), 8'-acetyl oilvil(18), 4-methoxyl-8'-acetyl oilvil(19), vanillic acid(20), beta-hydroxypropiovanillone(21), 7-hydroxy-6-methoxycoumarin(22), p-hydroxybenzaldehyde(23), pinoresinol(24), erythro-1,2-bis-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol(25), urticol(26), urticol-7-O-beta-D-glucopyranoside(27), and lobechine(28). Compounds 1-17 were isolated from U. fissa for the first time. Meanwhile, compound 1 was a new natural product. Compounds 10, 11, 19, 21, and 27 exhibited significant inhibitory effects on 5alpha-reductase.

[Study on non-flavonoids chemical constituents from Spatholobi Caulis].[Pubmed:32237455]

Zhongguo Zhong Yao Za Zhi. 2020 Mar;45(5):1120-1127.

To study the non-flavonoids chemical constituents in water extract of Spatholobi Caulis. Some purification and analysis techniques like silica gel, D101-macroporous adsorptive resins, and Sephadex LH-20 column chromatographies as well as reversed phase high-performance liquid chromatography were used to isolate and analyze the phenolic acid esters and other type compounds from Spatholobi Caulis integrally. The structures of these compounds were identified by spectroscopic techniques such as nuclear magnetic resonance and high resolution mass spectrometries. Twenty-seven compounds, including phenolic acid, coumarin, lignan, terpene, alkaloid, and steroid compounds, were isolated from ethyl acetate and n-butanol fractions in water extract of Spatholobi Caulis, and they were identified as beta-sitosterol(1), feruli acid methyl ester(2), syringaresinol(3),(+)-medioresinol(4),(+)-epipinoresinol(5), p-acetylphenol(6), bolusanthin Ⅳ(7), Evofolin B(8), salicylic acid(9), trans-p-hydroxy-cinnamic acid(10), abscisic acid(11), m-hydroxyphenol(12), C-veratroylglycol(13), p-hydroquinone(14), 8,9-dihydroxymegastigma-4,6-dien-3-one(15), p-hydroxybenzoic acid(16), 6,9-dihydroxymegastigma-4,7-dien-3-one(17), protocatechuic acid(18), protocatechuic acid methyl ester(19), 5,7-dihydroxycoumarin(20), isolariciresinol(21), nicotinic acid(22), daucosterol(23),(+)-pinoresinol(24), stigmasterol(25), allantoin(26) and koaburaside(27), respectively. Furthermore, compounds 2-15, 19-22, 24 and 26 were isolated from genus Spatholobus for the first time.

[Lignans from seed of Hydnocarpus anthelminthica].[Pubmed:31090297]

Zhongguo Zhong Yao Za Zhi. 2019 Apr;44(7):1397-1402.

This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were elucidated as(+)-syringaresinol(1), lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8'R)-4'-guaiacylglyceryl-Evofolin B(4), leptolepisol C(5),(-)-(7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5,5',5''-hexamethoxy-7,9':7',9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol(6),(-)-(7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5,5'-pentamethoxy-7,9':7',9-diepoxy-4,8''-oxy-8,8'ses-quineolignan-7'',9''-diol(7), ceplignan(8), hydnocarpusol(9), isohydnocarpin(10),(-)-hydnocarpin(11), hydnocarpin(12), and hydnocarpin-D(13) by spectroscopic data analysis. Compounds 1-8 were obtained from the genus Hydnocarpus for the first time.

[Studies on liposoluble constituents from Momordicae Semen].[Pubmed:29676125]

Zhongguo Zhong Yao Za Zhi. 2018 Mar;43(6):1175-1181.

The liposoluble constituents in Momordicae Semen were investigated in the present study. By silica gel, Sephadex LH-20 column chromatography, and semi-preparative HPLC, 22 compounds were isolated and purified from dichloromethane and ethyl acetate fraction. Based on NMR and MS spectra analyses, these compounds were identified as lupeol (1), 5-(1'-hydroxypentyl)-5H-furan-2-one (2), palmitic acid (3), viscumamide (4), clavatustide C (5), laxanol (6), threo-1-(4-hydroxyphenyl)-2-4-[2-formyl-(E)-vinyl]-2-methoxyphenoxyl-propane-1, 3-diol (7), alpha-spinasterol-3-O-beta-D-glucoside (8), chushizisin F (9), ehletianol C (10), tanegool (11), (7R, 8R, 8'R)-4'-guaiacylglyceryl-Evofolin B (12), ligballinone (13), (7R, 8S, 8'R)- 4, 4', 9-trihydroxy- 7, 9'-epoxy- 8, 8'-lignan (14), chushizisin I (15), chushizisin A (16), chushizisin G (17), p-coumaraldehyde (18), alpha-spinasterol (19), p-hydroxybenzoic acid (20), chushizisin E (21), and 3-[2-(4-hydroxyphenyl)-3-hydroxyphenyl-2, 3-dihydro-1-benzofuran-5-yl] propane-1-ol (22), respectively. Compounds 1-17 were isolated from Momordica cochinchinensis for the first time. Compound 2 was a new natural product while compounds 4 and 5 were first found in the terrestrial organism.

[Chemical consitituents from root of Isatis indigotica].[Pubmed:23944031]

Zhongguo Zhong Yao Za Zhi. 2013 Apr;38(8):1172-82.

Thirty-three compounds were isolated from the root decoction of Isatis indigotica by using a combination of various chromatographic techniques including silica gel, macroporous adsorbent resin, Sephadex LH-20, and reversed-phase HPLC. Their structures were elucidated by spectroscopic data as (+)-dehydrovomifoliol (1), (S)-(+)-abscisic acid (2), vomifoliol (3), cyclo (L-Phe-L-Leu) (4), cyclo(L-Phe-L-Tyr) (5), cyclo(L-Tyr-L-Leu) (6), cyclo(L-Pro-L-Tyr) (7), Evofolin B (8), (+)-syringaresinol (9), (-)-(7R,7'R,8S,8'S)-4,4'-dihydroxy-3-methoxy-7,9';7',9-diepoxy-lignan (10), (-)-medioresinol (11), (+) -(7R,7'R,8S,8'S) -neo-olivil (12), (-) -5-methoxyisolariciresinol (13), 1,3-dihydro-2H-indol-2-one (14), isalexin (15), dihydroneoascorbigen (16), indican (17), (-) -(S) -cyanomethyl-3-hydroxyoxindole (18), isoformononetein (19), calycosin (20), stigamast-5-ene-3beta-ol-7-one (21), acetovanillone (22), 3, 5-dimethoxy-4-hydroxyacetophenone (23), dihydroconiferyl alcohol (24), dihyroferulic acid (25), 3-hydroxy-1-(4-hydroxyphenyl) propan-1-one (26), beta-hydroxypropiovanillone (27), 4-aminobenzoic acid (28), 3-(4-hydroxyphenyl) propan-1-ol (29), 4-(2-hydroxyethyl) phenol (30), 2-methoxy-4-vinylphenol (31), pyrocatechol (32), and 4-pentenamide (33). These compounds were isolated from the root of I. indigotica for the first time. In preliminary in vitro assays, compound 19 showed activity against the influenza virus A/Hanfang/359/95 (H3N2), the herpes simplex virus 1 (HSV-1), and Coxsackie virus B3 (Cox-B3), with IC50 values of 2.06, 6.84, and 8.70 micromol x L(-1), respectively, but other compounds were in-active at a concentration of 1.0 x 10 x (-5) mol x L(-1).

Evofolin B (CAS 138171-64-9) is a natural product offered by BioCrick for research applications. Customers can buy or order Evofolin B from BioCrick, a supplier and manufacturer of research chemicals, with product specifications, purity, packaging, and pricing information available upon request.