Chemical constituents from ethyl acetate extract of Eupatorium adenophorum / 中草药

Objective: To study the chemical constituents of the Eupatorium adenophorum. Methods: The chemical constituents were isolated and purified by silica gel chromatography repeatedly from the ethyl acetate extract of E. adenophorum, and their structures were identified by spectral analysis and chemical methods. Results: Fourteen compounds were isolated from E. adenophorum and identified as p-hydroxybenzoic acid ethyl ester (1), (1R,4R)-8aα-hydroxy-1-isopropyl-4,7-dimethyl- 1,2,3,4,6,8a-hexahydro-naphthalene-2,6-dione (2), daedalin A (3), 10-oxo-7-hydroxy-nordehydrotremetone (4), caffeoyl acetate (5), syringic acid (6), 3-hydroxy-4-(1-oxo-ethane)-benzoic acid (7), ferulic acid (8), p-hydroxyphenylethyl alcohol (9), protocatechuic acid ethyl ester (10), 4-hydroxy-3-isopropyl benzoic acid (11), balanophonin (12), indole-3-carboxylic acid (13), and 6-methoxy kaempferol (14). Conclusion: Compound 11 is obtained from natural products for the first time, compounds 1, 3, 6, 7, 9, 10, 12-14 are obtained from this genus for the first time, and compound 5 is obtained from this plant for the first time.

A New Neolignan Derivative, Balanophonin Isolated from Firmiana simplex Delays the Progress of Neuronal Cell Death by Inhibiting Microglial Activation

Excessive activation of microglia causes the continuous production of neurotoxic mediators, which further causes neuron degeneration. Therefore, inhibition of microglial activation is a possible target for the treatment of neurodegenerative disorders. Balanophonin, a natural neolignoid from Firmiana simplex, has been reported to have anti-inflammatory and anti-cancer effects. In this study, we aimed to evaluate the anti-neuroinflammatory effects and mechanism of balanophonin in lipopolysaccharide (LPS)-stimulated BV2 microglia cells. BV2 microglia cells were stimulated with LPS in the presence or absence of balanophonin. The results indicated that balanophonin reduced not only the LPS-mediated TLR4 activation but also the production of inflammatory mediators, such as nitric oxide (NO), prostaglandin E2 (PGE2), Interleukin-1β (IL-1β), and tumor necrosis factor-α (TNF-α), in BV2 cells. Balanophonin also inhibited LPS-induced inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX2) protein expression and mitogen activated protein kinases (MAPKs), including extracellular signal-regulated kinase (ERK1/2), c-Jun N-terminal kinase (JNK), and p38 MAPK. Interestingly, it also inhibited neuronal cell death resulting from LPS-activated microglia by regulating cleaved caspase-3 and poly ADP ribose polymerase (PARP) cleavage in N2a cells. In conclusion, our data indicated that balanophonin may delay the progression of neuronal cell death by inhibiting microglial activation.

Chemical constituents from aerial part of Polygonatum cyrtonema / 中草药

Objective: To study the chemical constituents from the aerial part of Polygonatum cyrtonema. Methods: The compounds were isolated and purified by means of chromatographic techniques and their structures were identified on the basis of spectral features. Results: Fifteen known compounds were isolated in methanol extract from the aerial part of P. cyrtonema and their structures were identified as (3R)-5,7-dihydroxy-3-(2'-hydroxy-4'-methoxybenzyl)-chroman-4-one (1), 5,7-dihydroxy-6-methyl-3-(2',4'-dihydroxybenzyl)- chroman-4-one (2), 5,7-dihydroxy-6-methyl-3-(4'-hydroxybenzyl)-chroman-4-one (3), (3S)-3,7-dihydroxy-8-methoxy-3-(3',4'- methylenedioxybenzyl)-chroman-4-one (4), apigenin (5), kaempferol (6), vanillic acid (7), trans-p-hydroxycinnamic acid (8), trans-p-hydroxycinnamic acid methyl ester (9), saliylic acid (10), (+)-syringaresinol (11), balanophonin B (12), caffeic acid (13), phenylalanine (14), and coniferaldehyde (15). Conclusion: Compounds 1, 2, 7, 11, 14, and 15 are firstly obtained from P. cyrtonema. Compounds 3, 4, and 12 are isolated from the plants of Polygonatum Mill. for the first time.

Chemical constituents from Syringa pinnatifolia / 中草药

Objective: To investigate the chemical constituents from the stems of Syringa pinnatifolia. Methods: The chemical constituents were isolated and identified by chromatography on silica gel, ODS, and Sephadex LH-20 columns, as well as RP-HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral analyses. Results: Eleven compounds were isolated from S. pinnatifolia and their structures were identified as secoisolariciresinol (1), (8R, 8'R, 9R)-4, 4'-dihydroxy-3, 3', 9-trimethoxy-9, 9'-epoxylignan (2), (8R, 8'R, 9S)-4, 4'-dihydroxy-3, 3', 9-trimethoxy-9, 9'-epoxylignan (3), (-)-pinoresinol (4), (8R, 8'R, 9'S)-4, 4'-dihydroxy-3, 3', 9'-trimethoxy-9, 9'-epoxylignan (5), (8R, 8'R, 9'R)-4, 4'-dihydroxy-3, 3', 9'-trimethoxy-9, 9'-epoxylignan (6), (9S)-9-O-methylcubebin (7), dibutylphthalate (8), piperphilippinin VI (9), balanophonin (10), and larixnaphthaone (11). Conclusion: Compounds 2-11 are isolated from the plant for the first time.