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Two new phenolic glucosides from Lagerstroemia speciosa.

ABSTRACT: Two new phenolic glucosides, 1-O-benzyl-6-O-E-caffeoyl-?-d-glucopyranoside and 1-O-(7S,8R)-guaiacylglycerol-(6-O-E-caffeoyl)-?-d-glucopyranoside, were isolated from the aerial parts of Lagerstroemia speciosa, along with ten known compounds. The structures of the isolated compounds were determined based on 1D- and 2D-NMR, Q-TOF MS and optical rotation spectroscopic data. All of the compounds showed moderate inhibitory activities against nitric oxide production in lipopolysaccharide-treated RAW264.7 cells, with IC50 values of 69.5-83.3 ?M.

SUBMITTER: Choi J

PROVIDER: S-EPMC6272251 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Two new phenolic glucosides from Lagerstroemia speciosa.

Choi Janggyoo J Cho Jae Youl JY Choi Soo Jung SJ Jeon Heejin H Kim Young Dong YD Htwe Khin Myo KM Chin Young Won YW Lee Woo Shin WS Kim Jinwoong J Yoon Kee Dong KD

Molecules (Basel, Switzerland) 20150310 3

Two new phenolic glucosides, 1-O-benzyl-6-O-E-caffeoyl-β-d-glucopyranoside and 1-O-(7S,8R)-guaiacylglycerol-(6-O-E-caffeoyl)-β-d-glucopyranoside, were isolated from the aerial parts of Lagerstroemia speciosa, along with ten known compounds. The structures of the isolated compounds were determined based on 1D- and 2D-NMR, Q-TOF MS and optical rotation spectroscopic data. All of the compounds showed moderate inhibitory activities against nitric oxide production in lipopolysaccharide-treated RAW264 ...[more]

PMID: 25764490

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Project description:BACKGROUND:Human rhinoviruses (HRVs) are responsible for more than half of all cases of the common cold and cause billions of USD annually in medical visits and school and work absenteeism. An assessment was made of the cytotoxic and antiviral activities and possible mode of action of the tannin ellagic acid from the leaves of Lagerstroemia speciosa toward HeLa cells and three rhinoviruses, HRV-2, -3, and -4. METHODS:The antiviral property and mechanism of action of ellagic acid were evaluated using a sulforhodamine B assay and real-time reverse transcription-PCR (RT-PCR) with SYBR Green dye. Results were compared with those of the currently used broad-spectrum antiviral agent, ribavirin. RESULTS:As judged by 50% inhibitory concentration values, natural ellagic acid was 1.8, 2.3, and 2.2 times more toxic toward HRV-2 (38 ?g/mL), HRV-3 (31 ?g/mL), and HRV-4 (29 ?g/mL) than ribavirin, respectively. The inhibition rate of preincubation with 50 ?g/mL ellagic acid was 17%, whereas continuous presence of ellagic acid during infection led to a significant increase in the inhibition (70%). Treatment with 50 ?g/mL ellagic acid considerably suppressed HRV-4 infection only when added just after the virus inoculation (0 h) (87% inhibition), but not before -1 h or after 1 h or later (<20% inhibition). These findings suggest that ellagic acid does not interact with the HRV-4 particles and may directly interact with the human cells in the early stage of HRV infections to protect the cells from the virus destruction. Furthermore, RT-PCR analysis revealed that 50 ?g/mL ellagic acid strongly inhibited the RNA replication of HRV-4 in HeLa cells, suggesting that ellagic acid inhibits virus replication by targeting on cellular molecules, rather than virus molecules. CONCLUSIONS:Global efforts to reduce the level of antibiotics justify further studies on L. speciosa leaf-derived materials containing ellagic acid as potential anti-HRV products or a lead molecule for the prevention or treatment of HRV infection.

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Two new phenolic glucosides from Lagerstroemia speciosa.

Publications

Two new phenolic glucosides from Lagerstroemia speciosa.

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