Isoengeletin

Decoding active components in a formulation of multiple herbs for treatment of psoriasis based on three cell lines fishing and liquid chromatography-mass spectrometry analysis.[Pubmed:32380350]

J Pharm Biomed Anal. 2020 Jul 15;186:113331.

Chinese medicine formula (CMF) usually contains multiple herbs and its components are very complicated, which therapeutic effects are derived from the integrative activity of multiple components. Therefore, the screening of bioactive compounds in the formula is necessary, though it is very difficult, not only for elucidating the therapeutic components but also for developing the quality control method. In this work, three cell lines fishing combined with LC-MS analysis was developed for screening the potential bioactive compounds in Fuzhengzhiyanghefuzhiyang decoction (FZHFZY), a CMF for the treatment of psoriasis in clinic. Nineteen potential active compounds were discovered and thirteen of them were identified as rehmannioside D, melittoside or rehmannioside A, tufulingoside, neoastilbin, astilbin, neoisoastilbin, isoastilbin, engeletin, Isoengeletin, spinosin, cnidimoside A, rutaevin and limonin, respectively. The effects of identified components were also analyzed in vitro. The results showed that IL-1beta expression of RAW 264.7 cells treated with spinosin and melittoside as well as the TNF-alpha level of RAW 264.7 cells treated with rehmannioside D and melittoside were not significantly different compared with lipopolysaccharide (LPS)-treated cells. Though all identified potential active components had no apoptosis effect to HaCaT cells, rehmannioside D, rehmannioside A, astilbin and neoisoastilbin could significantly suppress HUVEC cells migration compared with control. These results indicated that the target cell fishing combined with LC-MS analysis is a useful tool for screening bioactive compounds from complicated CMF, and the identified active components may mainly contribute to the therapeutic effects of FZHFZY.

Integrating Network Pharmacology and Component Analysis Study on Anti-Atherosclerotic Mechanisms of Total Flavonoids of Engelhardia roxburghiana Leaves in Mice.[Pubmed:31943763]

Chem Biodivers. 2020 Mar;17(3):e1900629.

Engelhardia roxburghiana Wall. leaves are widely used to develop herbal teas in southeast of China due to medicinal use for diabetes mellitus and hyperlipidemia. Studies have demonstrated that the total flavonoids of E. roxburghiana leaves (TFER) exhibited regulatory effects on blood glucose and lipids. To clarify the active ingredients of TFER and their targets in treating atherosclerosis, the present study integrated chemical analysis, network pharmacology analysis and animal experimental studies. Firstly, high performance liquid chromatography-mass spectrometry/mass spectrometry (HPLC/MS/MS) was utilized to identify components of TFER. Then, active ingredients were screened by oral bioavailability (OB) and drug-likeness (DL) index. Thirdly, network was constructed to predict major targets of active ingredients against atherosclerosis. Finally, to verify parts of predicted signaling, Apoe(-/-) mice were used to develop atherosclerosis. Atherosclerotic plaques in aorta were evaluated by echocardiography. Then, serum lipids, target genes expressions in thoracic aorta were determined by qRT-PCR and ELISA methods. Chemical analysis revealed 10 components in TFER sample, 7 of which acted as active ingredients, including naringenin, kaempferol, quercetin, Isoengeletin, engeletin, astilbin and quercitrin. KEGG pathway analysis highly enriched in some inflammatory signalings, including NF-kappaB signaling, Toll-like receptor signaling and TNF signaling. The animal studies indicated that TFER reduced atherosclerotic plaques size in aorta and significantly decreased the serum lipids, down-regulated NF-kappaB signaling by decreasing mRNA level of NF-kappaB p65 subunit, TNF-alpha and VCAM-1, as well as IL-1beta expressions in thoracic aorta, eventually alleviating atherosclerosis progression, which was in consistent with our prediction.

Protective effects of Rhizoma smilacis glabrae extracts on potassium oxonate- and monosodium urate-induced hyperuricemia and gout in mice.[Pubmed:31005813]

Phytomedicine. 2019 Jun;59:152772.

BACKGROUND: Rhizoma smilacis glabrae (RSG, tufuling) has been widely used in traditional Chinese medicine for deoxidation, dampness relief, and easing joint movement. The chemical composition of RSG has been systematically confirmed, and some of its compounds have been revealed to possess antioxidant, anti-inflammatory, immunomodulatory, hypouricemic, and hepatoprotective effects. PURPOSE: We aimed to clarify whether a RSG extract attenuates hyperuricemia, paw edema, and renal injury in mice with potassium oxonate (PO)- and monosodium urate (MSU)-induced chronic hyperuricemia and gout. METHODS: RSG water extract was obtained and analyzed by HPLC-DAD-MS/MS. To establish a murine model with chronic hyperuricemia and gout, PO was orally administered daily from day 0 to day 24, whereas MSU was injected into the tibiotarsal joint on day 21. The mice in the drug intervention groups were treated once daily with doses of allopurinol or RSG extract from day 21 to day 24. The diameter of the ankle joints was measured with calipers. Serum TNF-alpha and IL-1beta concentrations, hepatic XOD activity, and uric acid, creatinine, and blood urea nitrogen (BUN) levels were also determined. The right kidney and articular cavities were fixed, cut into sections, and stained with hematoxylin and eosin. RESULTS: Nine compounds in the RSG water extract were unambiguously identified as 5-O-caffeoylshikimic acid, neoastilbin, astilbin, taxifolin, neoisoastilbin, isoastilbin, engeletin, Isoengeletin, and trans-resveratrol. The RSGE treatment dose-dependently reduced PO- and MSU-induced paw edema, serum TNF-alpha, IL-1beta, IL-6, IL-12, uric acid, and BUN, while significantly elevated serum IL-10, urinary uric acid and creatinine levels as compared with the respective values in the hyperuricemic and gouty mice group (vehicle group). Moreover, the hepatic XOD activity was dose-dependently reduced by the RSGE treatment. In addition, RSGE treatment not only ameliorated the infiltration of inflammatory cells, tubular dilation and vacuole formation in renal tubular, but also improved the synovial hyperplasia, reduced inflammatory cells infiltration into the synovium, and diminished the erosive damage in the cartilage. CONCLUSION: The murine model with chronic hyperuricemia and gout be built in present study is consistent with the clinical symptoms of patients with long-standing hyperuricemia and acute gouty arthritis. RSG water extract has potent efficacy in ameliorating murine hyperuricemia and gout induced by PO and MSU.

Antioxidant and Anti-Inflammatory Activities of Phenolic-Enriched Extracts of Smilax glabra.[Pubmed:25477999]

Evid Based Complement Alternat Med. 2014;2014:910438.

Smilax glabra Roxb. has been used for a long time as both food and folk medicine. In the present study, phenolic-enriched extract of S. glabra (PEESG) was extracted with 70% ethanol and purified by HP-20 column chromatography. Its antioxidant and anti-inflammatory activities were evaluated by radical scavenging assay, reducing power determination, and lipopolysaccharide (LPS)-induced RAW264.7 cells assays, respectively. PEESG exhibited obviously scavenging capacity for DPPH and ABTS radicals, as well as significant reducing power for ferric ion. Particularly, PEESG (12.5-50 mug/mL) showed a significantly higher efficiency for scavenging ABTS than that of ascorbic acid and no significant difference with ascorbic acid for DPPH scavenging. PEESG also possessed a significant suppression effect on proinflammatory mediators production, such as nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), and interleukin-6 (IL-6), in LPS-induced RAW264.7 cells. In addition, the main ingredients of PEESG were identified using ultrahigh pressure liquid chromatography coupled to electrospray mass spectrometry (U-HPLC-ESI-MS). Seventeen components, including 5-O-caffeoylshikimic acid, neoastilbin, astilbin, neoisoastilbin, isoastilbin, engetin and Isoengeletin were identified. These findings strongly suggest the potential of PEESG as a natural antioxidant and anti-inflammatory agent.

Chemical constituents comparison between Rhizoma Smilacis Glabrae and Rhizoma Smilacis Chinae by HPLC-DAD-MS/MS.[Pubmed:22400809]

Nat Prod Res. 2013;27(3):277-81.

Rhizoma Smilacis Glabrae (RSG) and Rhizoma Smilacis Chinae (RSC) are two herbal materials that belong to the same genera and are both listed in the Chinese Pharmacopoeia. Chemical constituents in the two species were compared by HPLC-DAD-MS/MS. Many common constituents were found in both species, including shikimic acid, 5-O-caffeoylshikimic acid, trans-resveratrol, taxifolin, astilbin and its three stereoisomers, engeletin and Isoengeletin. However, syringic acid was found only in RSG, while chlorogenic acid was found only in RSC.

Development of HPLC fingerprint for species differentiation and quality assessment of Rhizoma Smilacis Glabrae.[Pubmed:22382863]

J Nat Med. 2013 Jan;67(1):207-11.

Rhizoma Smilacis Glabrae (RSG) is a commonly used herbal material in functional food and Traditional Chinese Medicine. A HPLC chromatographic fingerprint was developed for its quality control and species differentiation. Nine peaks were found in the chromatogram of RSG and all these peaks were identified by diode array detection and electrospray ionization-MS/MS: 5-O-caffeoylshikimic acid, taxifolin, engeletin, Isoengeletin, trans-resveratrol, astilbin and its three stereoisomers. Six of these constituents were consistently found in 18 batches of samples. The standard fingerprint of RSG was generated by mean simulation of all tested samples. Using the standard fingerprint, RSG could be easily differentiated from Rhizoma Smilacis Chinae and Rhizoma Heterosmilacis, the two species that can be confused with RSG.

[Studies on chemical constituents of rhizomes of Smilax china].[Pubmed:19149257]

Zhongguo Zhong Yao Za Zhi. 2008 Nov;33(21):2497-9.

OBJECTIVE: To study the chemical constituents of the rhizomes of Smilax china. METHOD: The constituents of the rhizomes of S. china were isolated and purified by repeated silica gel and Sephadex LH-20 chromatography, and their structures were elucidated on the basis of spectral analysis. RESULT: Thirteen compounds were obtained and identified as kaemperol-7-O-beta-D-glucopyranoside (1), engeletin (2), Isoengeletin (3), kaempferol (4), dihydrokaempferol (5), dihydrokaempferol-5-O-P-D-glucopyranoside (6), rutin (7), kaempferol- 5-O-beta-D-glucopyranoside (8), 3, 5, 4'-trihydroxystibene (9), vanillic acid (10), 3, 5-dimethoxy4-O-beta-D-glu-copyranosylcinnamic acid (11), beta-sitosterol (12), and beta-daucosterol (13) , respectively. CONCLUSION: Compounds 1, 3, 7, 8, and 11 were isolated from this plant for the first time, and compounds 8 and 11 were isolated from the genus Smilax for the first time.

[Dihydroflavonol glycosides and flavan-3-ols from Bauhinia aurea].[Pubmed:17639982]

Zhongguo Zhong Yao Za Zhi. 2007 May;32(9):815-8.

OBJECTIVE: To study the chemical constituents of Bauhinia aurea. METHOD: The compounds were isolated by column chromatography over silica gel, reversed-phase RP-18, and Sephadex LH -20. MS and NMR spectroscopic methods were used to determine structures of purified compounds. RESULT: Eight compounds were isolated from the ethyl acetate soluble fraction of the ethanolic extract and their structures were elucidated as Isoengeletin (1), astilbin (2), neoastilbin (3), isoastilbin (4), neoisoastilbin (5), (+)-catechin (6), (-)-epicatechin (7) and (-)-epicatechin 3-O-gallate (8). CONCLUSION: Five compounds were isolated from this genus for the first time except for 2, 6 and 8.

Antiinflammatory constituents from the roots of Smilax bockii warb.[Pubmed:15918511]

Arch Pharm Res. 2005 Apr;28(4):395-9.

From 70% ethanol extract of the roots of Smilax bockii warb., seven flavonoids, kaempferol (1), kaempferol-7-O-beta-D-glucopyranoside (2), quercetin (3), isorhamnetin (4), (+)-dihydro-kaempferol (5), engeletin (6), Isoengeletin (7), and n-butyl-beta-D-fructopyranoside (8), caffeic acid n-butyl ester (9) were isolated and identified by means of chemical and spectroscopic. Compounds 2, 4, and 6-9 were isolated for the first time from the roots of S. bockii and compounds 2, 8, and 9 were firstly isolated from the genus Smilax. In addition, using the SEAP (Secreted alkaline phosphatase) assay system, we investigated the in vitro anti-inflammatory activity of the 70% ethanol extract of the roots of S. bockii, which showed moderate activity in inhibiting TNF-alpha-induced NF-kappaB activation with an IC50 value of 166.6 microg/mL.