Cytotoxic and renoprotective diterpenoids from Clerodendranthus spicatus

Luo, Yong Ming; Li, Xiaozhen; Xiang, Bin; Luo, Qi; Liu, Jia-Wang; Yan, Yong‐Ming; Sun, Qing; Cheng, Yong‐Xian

doi:10.1016/j.fitote.2018.01.003

Cited by 19 publications

(24 citation statements)

References 17 publications

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“…Their anti‐inflammation effect was further evaluated on same model, and the results indicated that two subfractions were responsible anti‐inflammation effect mainly. After then, 25 compounds, orthosiphol M ( 1 ), (Awale et al., 2001) orthosiphonone A ( 2 ), (Shibuya et al, 1999a) orthosiphol N ( 3 ), (Awale et al., 2001), orthosiphol A ( 4 ), (Masuda et al, 1992a) orthosiphol B ( 5 ), (Masuda et al, 1992b) neoorthosiphol A ( 6 ), (Shibuya et al, 1999a) orthosiphol D ( 7 ), (Takeda et al., 1993) orthosiphonone D ( 8 ), (Nguyen et al., 2004) spicatusene B ( 9 ), (Luo et al., 2018) spicatusene C ( 10 ), (Luo et al., 2018) orthosiphol K ( 11 ), (Awale et al., 2001) orthosiphol L ( 12 ), (Awale et al., 2001) norstaminol B ( 13 ), (Stampoulis et al., 1999) 2‐ o ‐deacetylorthosiphol J ( 14 ), (Awale,et al., 2003) orthosiphol E ( 15 ), (Takeda et al., 1993) neoorthosiphol B ( 16 ), (Shibuya et al, 1999b) fragransin B1 ( 17 ), (Miyachi et al., 1987) syringaresinol ( 18 ), (Sharp et al., 2001) asperglaucidev ( 19 ), (Ishiguro et al., 1991) salvigenin ( 20 ), (Miana et al., 1985) sinensetin ( 21 ), (Akowuah et al., 2004) 5,6,7,4′‐tetramethoxyflavone ( 22 ), (Lee et al., 2008) eupatorin ( 23 ), (Ramaraj et al., 2018) 5,6,7,3′,4′‐pentamethoxyflavanone ( 24 ), (Iwase et al., 2001) and caffeic acid methyl ester ( 25 ) (Starkov et al., 1975) were isolated from the two bioactive subfractions. Further pharmacological investigation on pure compounds indicated that most of the isolates remarkably inhibited productions of inflammatory mediators (IL‐8, IL‐1 β , and TNF‐ α ) in LPS‐induced HK ‐2 cells, and compounds 1 , 2 , 5 – 7 , 17 , 21, and 22 showed significantly anti‐inflammatory on xylene‐induced acute inflammatory mice model.…”

Section: Introductionmentioning

confidence: 99%

Bioassay‐guided isolation of anti‐inflammatory diterpenoids with highly oxygenated substituents from kidney tea ( Clerodendranthus spicatus )

et al. 2020

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The whole plant of Clerodendranthus spicatus (Thunb.) is one of popular functional food in south of China, named as "kidney tea" and used to ameliorate renal inflammation. In order to verify this potential function and explore the accurate compounds responsible for inflammation, the ethanol extract, fractions, and subfractions of this plant were prepared to evaluate anti-inflammation effect on xylene-induced acute inflammatory mice model, and the results indicated that two subfractions from EtOAc fraction show potential activities. Subsequent bioassay-guided isolation of the bioactive subfractions led to isolation of 25 compounds. Among them, compounds 2, 4, 5, 9-11, 13, 16, 17, and 20-22 inhibited the productions of pro-inflammation factors TNF-α, IL-1β, and IL-8 in lipopolysaccharide (LPS)-induced renal epithelia (HK-2) cells, respectively. Further anti-inflammation evaluation in vivo indicated that the major bioactive compounds 1, 2, 5-7, 17, 21, and 22 from C. spicatus were even better than aspirin. Practical applications C. spicatus as a healthy tea has been available in the Chinese market and as a medicine for various disorders such as nephritis, rheumatism, inflammation, gout, and diabetes. Previous pharmacological investigation of the plant revealed the potential antiinflammatory activities, but the material basis of anti-inflammatory activity remains to be elucidated. In our study, the anti-inflammatory fractions and compounds were obtained by the bioassay-guide isolation and the results showed that the highly oxygenated diterpenoids were major anti-inflammatory compounds, in which 1, 2, 5-7, 17, 21, and 22 were even better than aspirin. This information supported kidney tea as a functional food for treatment of renal inflammation reasonably and may add a new dimension to biological activity of this plant in the field of agriculture as a functional food were cultivated.

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Section: Introductionmentioning

confidence: 99%

Bioassay‐guided isolation of anti‐inflammatory diterpenoids with highly oxygenated substituents from kidney tea ( Clerodendranthus spicatus )

et al. 2020

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“…Clerodendranthus spicatus (Thunb.) 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 .…”

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

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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.

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“…Pharmacological studies have shown that CSH has antimicrobial, antioxidant, hepatoprotective, antigenotoxic, antiplasmodial, cytotoxic, cardioactive, antidiabetic and anti‐inflammatory activities . Polymeric phenolic acids, flavonoids, diterpenes, triterpenes, essential oils and polysaccharides have been isolated from CSH by phytochemical approaches . Published literature concerning CSH has mainly focused on the quantification of several phenolic acids or flavonoids by high‐performance liquid chromatography–photodiode array detector method or high‐performance liquid chromatography/tandem mass spectrometry .…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4][5][6] Polymeric phenolic acids, flavonoids, diterpenes, triterpenes, essential oils and polysaccharides have been isolated from CSH by phytochemical approaches. [7][8][9][10][11] Published literature concerning CSH has mainly focused on the quantification of several phenolic acids or flavonoids by high-performance liquid chromatography-photodiode array detector method or high-performance liquid chromatography/ tandem mass spectrometry. 12 activities.…”

Section: Introductionmentioning

confidence: 99%

Characterization of polymeric phenolic acids and flavonoids in Clerodendranthi Spicati Herba using ultrahigh‐performance liquid chromatography coupled to quadrupole time‐of‐flight tandem mass spectrometry with target and nontarget data mining strategy

Luo

Wen

Lai

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Clerodendranthi Spicati Herba (CSH) is often used to treat urinary stones, urinary tract infections and nephritis in China. Much literature has reported that polymeric phenolic acids and flavonoids are the major bioactive components in CSH. Therefore, it is very meaningful to identify the polymeric phenolic acids and flavonoids in CSH. Methods Ultrahigh‐performance liquid chromatography coupled to quadrupole time‐of‐flight tandem mass spectrometry (UHPLC/QTOF‐MS/MS) analysis with target and nontarget data mining strategy was proposed to rapidly profile the polymeric phenolic acids and flavonoids in CSH. Diagnostic product ions and neutral loss filter were beneficial for identifying the polymeric phenolic acids and flavonoids from complex compounds in CSH. Results A total of 118 compounds, including 85 polymeric phenolic acids and 33 flavonoids, were reasonably identified in CSH by comparing their main fragmentation pathways with literature data, and 85 of them were discovered in CSH firstly by nontarget analysis. Nine potential compounds were characterized tentatively as new pentameric and hexameric phenolic acids in CSH. Six types of polymeric phenolic acids (monomer, dimer, trimer, tetramer, pentamer and hexamer) and four types of flavonoids (apigenin, kaempferol, luteolin and quercetin) were identified in CSH. Conclusions The results indicated that the UHPLC/QTOF‐MS/MS method coupled with target and nontarget data mining strategy was feasible and rational for identifying the polymeric phenolic acids and flavonoids in complex chemical constituents of CSH. The findings will be conducive to the discovery of the active ingredients of CSH and the establishment of quality standards.

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Cytotoxic and renoprotective diterpenoids from Clerodendranthus spicatus

Cited by 19 publications

References 17 publications

Bioassay‐guided isolation of anti‐inflammatory diterpenoids with highly oxygenated substituents from kidney tea ( Clerodendranthus spicatus )

Bioassay‐guided isolation of anti‐inflammatory diterpenoids with highly oxygenated substituents from kidney tea ( Clerodendranthus spicatus )

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

Characterization of polymeric phenolic acids and flavonoids in Clerodendranthi Spicati Herba using ultrahigh‐performance liquid chromatography coupled to quadrupole time‐of‐flight tandem mass spectrometry with target and nontarget data mining strategy

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