Structural Characterization and Assessment of the Cytotoxicity of 2,3-Dihydro-1H-indene Derivatives and Coumarin Glucosides from the Bark of Streblus indicus

Abstract

A pair of enantiomers and a pair of 2,3-dihydro-1H-indene epimers, rac-indidene A (rac-1), indidenes B and C (2, 3); four new coumarin glucosides (4-7); and four known coumarin glucosides (8-11) were isolated from the bark of Streblus indicus (Bur.) Corner. The structures of 1-11 were defined by physical data analyses, including MS, NMR, and single-crystal X-ray diffraction. The absolute configurations of the 2,3-dihydro-1H-indene derivatives were defined via experimental and calculated ECD data. rac-Indidene A and indidenes B and C showed inhibitory activity against A549 and MCF-7 tumor cells with IC values in the range of 2.2 ± 0.1 to 7.2 ± 0.9 μM.

Six New Coumarin Glycosides from the Aerial Parts of Gendarussa vulgaris

“…The EtOAc and n -BuOH layers were fractionated and purified by repeated column chromatography, allowing the isolation of sixteen coumarins ( 1 – 16 ), including six new coumarin glycosides, genglycoside A–F ( 1 – 6 ), along with ten known analogues. The known metabolites were identified as indidene F ( 7 ) [12], isofraxetin 6- O - β - d -glucopyranoside ( 8 ) [13], fraxin ( 9 ) [14], scopoletin 7- O - β - d -glucopyranoside ( 10 ) [15], cleomiscosin A ( 11 ) [16], fraxetin ( 12 ) [17], scopoletin ( 13 ) [18], fraxidin ( 14 ) [19], isofraxidin ( 15 ) [17], scoparone ( 16 ) [20], by comparison of their spectroscopic data with values reported in the literature.…”

Aromatic Constituents from the Leaves of Actinidia arguta with Antioxidant and α-Glucosidase Inhibitory Activity

“…The HMBC correlations from H-1 of a glucose to C-7 of a 6,7-dihydroxycoumarin group suggested the linkage between 6,7-dihydroxycoumarin and a glucose, and the HMBC correlations from H-6 of a glucose to C-9" of trans-caffeoyl group suggested the linkage between a glucose and a trans-caffeoyl group. Based on these data, the structure of compound 5 was defined as esculetin 7-O-(6 -O-trans-caffeoyl)-βglucopyranoside and named argutoside E. The known compounds were identified as esculetin 7-O-(6 -O-trans-coumaroyl)-βglucopyranoside (6) [23], umbelliferone 7-O-(6 -O-trans-coumaroyl)-β-glucopyranoside (7) [23], esculetin (8) [22], 7,8-Dihydroxycoumarin (9) [24], umbelliferone (10) [25], 4hydroxybenzoic acid (11) [26], protocatechuic acid (12) [26], vanillic acid (13) [27], isovanillic acid (14) [28], hydroxytyrosol (15) [28], (-)-rhodolatouchol (16) [29], p-E-coumaric acid (17) [30], p-E-coumaric acid-9-O-glucopyranoside (18) [23], E-caffeic acid (19) [28], E-ferulic acid (20) [31], 3,5-dimethoxy-4-hydroxycinnamic alcohol (21) [32], kaempferol (22) [33], kaempferol 3-O-β-glucopyranoside (23) [34], kaempferol 3-O-β-galactopyranoside (24) [35], quercetin (25) [36], tamarixin (26) [37], isorhamnetin 3-O-β-glucopyranoside (27) [30], rhamne...…”

“…As described above, the leaf of A. arguta is rich in phenolic compounds, and a total of 48 compounds were purified in this study. All 48 of the compounds that were isolated in this study are aromatic compounds and can be subdivided according to the compound skeleton as follows: phenylpropanoid derivatives (1-4, 16-21), coumarins (5-10), simple phenolics (11)(12)(13)(14)(15), flavonoids (22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39) and lignans (40)(41)(42)(43)(44)(45)(46)(47)(48). The biological activity of the isolated compounds differs depending on their structure, and flavonoid showed excellent efficacy while lignan showed comparatively weak efficacy in our assay system.…”

The complete chloroplast genome of Streblus indicus

“…He et al. ( 2016 ) reported that the bark extract of S. indicus showed inhibitory activity against A549 and MCF-7 tumor cells. It is the ingredients of Chinese patent medicine Yunnan red medicine capsule (Liu et al.…”

“…Streblus indicus is a traditional medicine in Chinese, which is often used for hemostasis and the treatments of inflammation and various rheumatoid diseases (Zhao et al 1999;He et al 2017). He et al (2016) reported that the bark extract of S. indicus showed inhibitory activity against A549 and MCF-7 tumor cells. It is the ingredients of Chinese patent medicine Yunnan red medicine capsule (Liu et al 2018).…”