New ursane-type triterpenoids from Clerodendranthus spicatus

Luo, Yong Ming; Cheng, Likun; Luo, Qi; Yan, Yong‐Ming; Wang, Shumei; Sun, Qing; Cheng, Yong‐Xian

doi:10.1016/j.fitote.2017.04.001

Cited by 22 publications

(13 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 95% EEF was separately subjected to preparative HPLC-DAD with 45% ACN water solution [Cosmosil C 18 column (10 mm × 250 mm, 5.0 μm; Kyoto, Japan), flow rate 2 mL/min, UV detection at 254 nm], which led to the isolation of compound 20′ (22.0 mg; t R = 40 min), compound 21′ (10 mg; t R = 41 min), compound 22′ (19 mg; t R = 42 min), and compound 25′ (6.4 mg; t R = 50 min). 13 C-NMR spectra were recorded on an AVANCE600 instrument (Bruker, Karlsruhe, Germany).…”

Section: Isolation Of Four Methoxylated Flavonoidsmentioning

confidence: 99%

“…Herein, comprehensive chemical profiling of CSH was necessary for uncovering the anti-hyperglycemic active compounds. Many chemists have isolated phenolic acids [9,10], methoxylated flavonoids (MFs) [11], diterpenoids [12], and triterpenoids [13] from CSH by phytochemical approaches, which is very slow, time consuming, and uneconomical to identify complex chemical compositions of CSH. To solve this problem, UHPLC-QTOF-MS/MS is applied to quickly identify chemical constituents in CSH.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Comprehensive chemical and metabolic profiling of anti‐hyperglycemic active fraction from Clerodendranthi Spicati Herba

Luo

Liu

Wen

et al. 2021

J of Separation Science

View full text Add to dashboard Cite

Extensive pharmacological research has demonstrated that Clerodendranthi Spicati Herba has an obvious anti-hyperglycemic effect via α-glucosidase inhibitory activity. However, the anti-hyperglycemic active fraction and its metabolic behavior in vivo have not been elaborated clearly. In this study, ultra-high-performance liquid chromatography coupled to quadrupole time of flight tandem mass spectrometry with data filtering strategy, including mass defect screening, diagnostic product ions and neutral loss identification, was established for chemical and metabolic profiling of anti-hyperglycemic active fraction from Clerodendranthi Spicati Herba. A total of 28 methoxylated flavonoids and 61 diterpenoids were rapidly identified. Four main known methoxylated flavonoids were purified and unambiguously identified by nuclear magnetic resonance analysis. Thirty-one absorbed diterpenoids, 12 absorbed methoxylated flavonoids, and 56 methoxylated flavonoids metabolites were identified in rat plasma, urine, bile, and feces after oral administration of anti-hyperglycemic active fraction. The methoxylated flavonoids were predominantly metabolized by demethylation, sulfation, and glucuronidation. Glucuronidation metabolites found in bile and urine after demethylation were dominant metabolites. Diterpenoids were absorbed into the blood mainly in the form of prototypes and excreted through bile and urine. These results indicated that methoxylated flavonoids and diterpenoids were responsible for α-glucosidase inhibitory activity, which might provide novel drug candidates for the management of diabetes mellitus.

show abstract

Section: Isolation Of Four Methoxylated Flavonoidsmentioning

confidence: 99%

mentioning

confidence: 99%

Comprehensive chemical and metabolic profiling of anti‐hyperglycemic active fraction from Clerodendranthi Spicati Herba

Luo

Liu

Wen

et al. 2021

J of Separation Science

View full text Add to dashboard Cite

show abstract

“…C. Y. Wu (C. spicatus), popularly known as "Orthosiphon" or "kidney tea", is a perennial herb of the Labiatae family, which is an endemic specie distributing in southern of China, such as Yunnan, Fujian and Guangxi provinces 11,12 . C. spicatus is a kind of medi-edible plant medicine, which has been used as an herbal remedy for gout, acute and chronic nephritis in Dai medicine with a history of more than 2,000 years in local ethnic groups in Yunnan Province, China 13,14 . In addition, earlier report had indicated that this plant contains high amount of avonoids, phenolic acids, anthraquinones and other ingredients 15 .…”

Section: Introductionmentioning

confidence: 99%

Bioactivity-Guided Separation of Potential α-glycosidase Inhibitor from Clerodendranthus Spicatus based on HSCCC with Molecular Docking

Zhu

Niu

Nie

et al. 2020

Preprint

View full text Add to dashboard Cite

Clerodendranthus Spicatus is a traditional Dais medi-edible plant and it has been proven to have good blood glucose-lowering efficacy. However, the material basis of Clerodendranthus Spicatus has not been clarified yet. Therefore, in this paper, the compounds were purified by high-speed counter-current chromatography (HSCCC) and the potential activity of compounds were determined by molecular docking. In the separation process, the solvent system was determined by a 9 × 9 map-based solvent selection strategy and the solvent system hexane/ethyl acetate/methanol/water (3:5:3:5, v/v) was used for HSCCC. Finally, five compounds were purified and identified as 2-Caffeoyl-L-tartaric acid (1), N-(E)-caffeoyldopamine (2), rosmarinc acid (3), Methyl rosmarinate (4), 6,7,8,3',4'-Pentamethoxyflavone (5). Then, the identified compounds were individually docked with α-glycosidase. The affinity energies of the identified compounds ranged from -7.6 to -8.6 kcal/mol, which are all better than acarbose (-6.6 kcal/mol). In particularly, rosmarinc acid with the lowest affinity energy of -8.6 kcal/mol was wrapped by the active site of α-glycosidase. The docking results indicated that the target compounds have potential α-glycosidase inhibitory activity and may be responsible for the blood glucose-lowering activity of Clerodendranthus Spicatus. The results indicated that the bioactivity-guided method is practical for the effective separation of active compounds from natural resources.

show abstract

“…So far, previous documented reports on the chemical composition of Clerodendranthus spicatus showed the existence of plenty of diterpenes, flavonoids, triterpenes and phenolic acids [19]. Water extract of Clerodendranthus spicatus was often investigated because water soluble phenolic acids were considered to be responsible for those activities [20,21]. However, more systematical research on Clerodendranthus spicatus was still necessary since many valuable active compounds in Clerodendranthus spicatus were not clear.…”

Section: Introductionmentioning

confidence: 99%

Analysis of Xanthine Oxidase Inhibitors from Clerodendranthus spicatus with Xanthine Oxidase Immobilized Silica Coated Fe3O4 Nanoparticles

et al. 2018

View full text Add to dashboard Cite

Abstract:In this study, xanthine oxidase immobilized silica coated Fe 3 O 4 nanoparticles (Fe 3 O 4 @SiO 2 -XO) were successfully prepared and characterized by transmission electron microscope, X-ray powder diffraction, Fourier transform infrared spectroscopy and vibrating sample magnetometer. The average diameter of the Fe 3 O 4 nanoparticles was about 300 nm to 350 nm with a shell thickness of 60 nm. The maximum saturation magnetization of the Fe 3 O 4 @SiO 2 -XO nanoparticles was 44.9 emu/g, which ensured the separation from the medium within one minute by using an ordinary magnet. A xanthine oxidase (XO) inhibitor screening method using Fe 3 O 4 @SiO 2 -XO nanoparticles was established and utilized in the extract of Clerodendranthus spicatus. Under the optimized conditions, two compounds were screened out and identified as gardenin B and eupatorin. The half maximal inhibitory concentration (IC 50 ) values of these two compounds were 1.488 µg/mL and 11.197 µg/mL, respectively. The interactions between these two compounds and XO were investigated by the fluorescence spectroscopic method. The results suggested that the quenching effects of gardenin B and eupatorin were due to a static quenching mechanism. Furthermore, gardenin B showed stronger binding capacity than that of eupatorin. In conclusion, this screening method exhibited efficiency and reusability in screening, identification and analysis of enzyme inhibitors from complex mixtures.

show abstract

New ursane-type triterpenoids from Clerodendranthus spicatus

Cited by 22 publications

References 9 publications

Comprehensive chemical and metabolic profiling of anti‐hyperglycemic active fraction from Clerodendranthi Spicati Herba

Comprehensive chemical and metabolic profiling of anti‐hyperglycemic active fraction from Clerodendranthi Spicati Herba

Bioactivity-Guided Separation of Potential α-glycosidase Inhibitor from Clerodendranthus Spicatus based on HSCCC with Molecular Docking

Analysis of Xanthine Oxidase Inhibitors from Clerodendranthus spicatus with Xanthine Oxidase Immobilized Silica Coated Fe3O4 Nanoparticles

Contact Info

Product

Resources

About