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Flavonoids from Symplocos racemosa.

ABSTRACT: A novel isoflavone glycoside, peseudobatigenin 7-O-[?-d-apiofuranosyl-(1''''?5''')-O-?-d-apiofuranosyl-(1'''?6'')]-?-d-glucopyranoside, namely sympracemoside (1), was isolated from the aerial parts of Symplocos racemosa along with 15 known flavonoids (2-16). Their structures were characterized by Q-TOF mass, optical rotation, UV, 1D and 2D-NMR spectroscopic data. Compounds 3, 9, 16 showed moderate inhibitory activities against NO production with IC50 value of 88.2, 42.1 and 74.3 ?M, respectively.

SUBMITTER: Jung M

PROVIDER: S-EPMC6272286 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Flavonoids from Symplocos racemosa.

Jung Mila M Choi Janggyoo J Chae Hee-Sung HS Cho Jae Youl JY Kim Young-Dong YD Htwe Khin Myo KM Lee Woo-Shin WS Chin Young-Won YW Kim Jinwoong J Yoon Kee Dong KD

Molecules (Basel, Switzerland) 20141226 1

A novel isoflavone glycoside, peseudobatigenin 7-O-[β-d-apiofuranosyl-(1''''→5''')-O-β-d-apiofuranosyl-(1'''→6'')]-β-d-glucopyranoside, namely sympracemoside (1), was isolated from the aerial parts of Symplocos racemosa along with 15 known flavonoids (2-16). Their structures were characterized by Q-TOF mass, optical rotation, UV, 1D and 2D-NMR spectroscopic data. Compounds 3, 9, 16 showed moderate inhibitory activities against NO production with IC50 value of 88.2, 42.1 and 74.3 μM, respectively ...[more]

PMID: 25549060

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Project description:BackgroundPlants provide a ray of hope to combat the ever increasing antibiotic resistance and Symplocos racemosa is a valuable medicinal plant. The study focused on highlighting the importance of this plant's phytoconstituents as potential source of novel antimicrobials against planktonic as well as biofilm forming microorganisms, along with their antiproliferative activity. The biosafety of the phytoconstituents was also established, followed by detection of probable antimicrobial components.MethodsThe best organic extractant and major groups of phytoconstituents were tested for their antimicrobial activity against reference microbial strains and drug-resistant clinical isolates. The anti-proliferative potential of the most active group of phytoconstituents was evaluated against cancerous cell lines. The in vitro biosafety of phytoconstituents was evaluated by Ames and MTT assay, while in vivo biosafety of the most active phytoconstituents, i.e., flavonoids was determined by acute oral toxicity. Further, the probable antimicrobial components in the flavonoids were detected by TLC and GC-MS.ResultsEthyl acetate extract was the most effective among various organic extracts, whereas phytoconstituents such as flavonoids, cardiac glycosides, saponins, tannins, triterpenes and phytosterols were the major groups present, with flavonoids being the most potent antimicrobials. The phytoconstituents displayed a significant antibiofilm potential, as exhibited by inhibition of initial cell attachment, disruption of the pre-formed biofilms and reduced metabolic activity of biofilms. The phytoconstituents were significantly active against the drug-resistant strains of E.coli, MRSA and Salmonella spp. Further, flavonoids showed significant cytotoxic effect against the cancerous cell lines but were non-cytotoxic against Vero (normal) cell line. All the test preparations were biosafe, as depicted by the Ames test and MTT assay. Also, flavonoids did not induce any abnormality in body weight, clinical signs, biochemical parameters and organs' histopathology of the Swiss albino mice during in vivo acute oral toxicity studies. The flavonoids were resolved into 4 bands (S1-S4), where S3 was the most active and its GC-MS analysis revealed the presence of a number of compounds, where Bicyclo [2.2.1]heptan-2-one,1,7,7-trimethyl-, (1S)- was the most abundant.ConclusionsThese findings suggest that the phytoconstituents from Symplocos racemosa bark could act as potential source of antimicrobial as well as antiproliferative metabolites.

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Flavonoids from Symplocos racemosa.

Publications

Flavonoids from Symplocos racemosa.

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