Eleven new sesquiterpenoids from peeled stems of Syringa pinnatifolia / 中国中药杂志

The peeled stems of Syringa pinnatifolia(SP) is a representative Mongolian folk medicine with the effects of anti-depression, heat clearance, pain relief, and respiration improvement. It has been clinically used for the treatment of coronary heart disease, insomnia, asthma, and other cardiopulmonary diseases. As part of the systematic study on pharmacological substances of SP, 11 new sesquiterpenoids were isolated from the terpene-containing fractions of the ethanol extract of SP by liquid chromatography-mass spectrometry(LC-MS) and proton nuclear magnetic resonance(~1H-NMR) guided isolation methods. The planar structures of the sesquiterpenoids were identified by MS, 1D NMR, and 2D NMR data analysis, and were named pinnatanoids C and D(1 and 2), and alashanoids T-ZI(3-11), respectively. The structure types of the sesquiterpenoids included pinnatane, humulane, seco-humulane, guaiane, carryophyllane, seco-erimolphane, isodaucane, and other types. However, limited to the low content of compounds, the existence of multiple chiral centers, the flexibility of the structure, or lack of ultraviolet absorption, the stereoscopic configuration remained unresolved. The discovery of various sesquiterpenoids enriches the understanding of the chemical composition of the genus and species and provides references for further analysis of pharmacological substances of SP.

Microscopic histochemical comparison during mountain-agarwood formation / 中国中药杂志

Mountain-agarwood plays an important role in ethnic medicine in China for its pharmaceutical value. Modern pharmacological researches demonstrated that mountain-agarwood was effective for its anti-myocardial ischemia, antibacterial, anti-inflammatory, antitumor and analgesic effects. Mountain-agarwood derives from the peeled roots, stems or twigs of Syringa pinnatifolia which belongs to Syringa genus. It often depends on the purple substance and fragrance to estimate the formation of mountain-agarwood. However, the mechanism of mountain-agarwood formation has not been reported. To observe the microcosmic change in the process during the formation of mountain-agarwood, this study described the microscopic and histochemical characteristics of mountain-agarwood formation through histochemical staining. Our results showed that a significant difference of the distribution of tyloses existed during mountain-agarwood formation. It was observed that inchoate mountain-agarwood had more starch granules and viable cells than mountain-agarwood formed with high level or low level. The amount of polysaccharide and degree of lignification were increased during the mountain-agarwood formation. The results indicated that the mountain-agarwood, which meets the quality requirements for pharmaceutical use, contained the following characteristics: a large amount of purple tyloses in heartwood; yellow-brown tyloses distributing in heartwood and sapwood which were less in the latter; lignification with high level; a few viable cells; lots of polysaccharide and few starch granules in xylem rays cell. This study is aimed to reveal the change of histochemical characteristics during mountain-agarwood formation, and lay the foundation for exploring the mechanism of mountain-agarwood formation.

Analgesic and sedative effects of Mongolian medicine Syringa pinnatifolia / 中国中药杂志

The peeled root,stem or twig of Syringa pinnatifolia is a representative Mongolian folk medicine with the effects of antidepression and pain relief. It has been used for the treatments of heart tingling,heart palpitations,upset,insomnia and other symptoms. Inspired by Mongolian medical theory and clinical practices,this study evaluated the analgesic effect of S. pinnatifolia ethanol extract( T) through three analgesic models including acetic acid writhing test,formalin test,and hot plate test,and the sedative effect of T was evaluated by locomotor activity and synergistic sleeping experiments,and furthermore the effects of T on the GABAergic nervous system were investigated by ELISA,immunohistochemistry,Western blot,and PCR methods. The results showed that T can significantly reduce the number of writhing,the time of paw licking and extend the thermal threshold of mice,suggesting the analgesic effect of T.T also can indicate its sedative effect by reducing the number of activities,decreasing latency of sleeping and extending sleeping time of mice. ELISA results showed that T can increase the content of GABA/Glu in rat cortex,hippocampus,and hypothalamus,and the most significant increase in hypothalamus. The immunohistochemistry and Western blot results showed that T can up-regulate the expression of GAD67 protein in hypothalamus,and the PCR results showed that T can up-regulate the expression of GABAA Rα1,α2,α3,α5,β1-3,γ1-3 genes,suggesting a sedative effect through the GABAergic nervous system. In conclusion,this study shed insight into the theoretical basis and clinical application of S. pinnatifolia,and also provides inspiration for subsequent development and application.

Pharmacological evaluation of Mongolian medicine Syringa pinnatifolia fraction I against acute myocardial ischemia in mice / 中国中药杂志

Syringa pinnatifolia Hemsl.( SP) is a representative Mongolian folk medicine with the effects of inhibiting Heyi related diseases,clearing heat and relieving pain. It has been used for the treatment of Heyi-induced heart tingling,heart palpitations,upset,insomnia and other symptoms. Total ethanol extract( T) and major fraction( M) of SP have been evaluated its anti-ischemic effects,and the mechanism was related to the regulation of cyclooxygenase( COX)-mediated inflammatory pathway and p53-mediated apoptosis pathway in our previous studies. This study reports the chemical fractionation on M by which to obtain subfractions( I and M_3),and the pharmacological evaluation of M,I,and M_3 against myocardial ischemia in mice. The result showed that I and M reduced the values of LVEDd and LVEDs,significantly increased EF and FS values,increased serum CK-MB and LDH levels in mice,and reduced in inflammatory cells infiltration and collagen deposition in the infarcted myocardial tissue,suggesting that M and I possess the same degree anti-myocardial is chemia equally whereas M_3 has no this effect. Related mechanism studies suggested that I can reduce the expression of COX-1,COX-2 and p53 protein in myocardial tissue in a dose-dependent manner. This study lays the foundation for further chemical segmentation and clarification of pharmacological substance groups,paving the way for the full use and benefits to be use of systematic biological methods to analyze the pharmacological basis of SP against myocardial ischemia.

Chemical constituents from Mongolian medicinal materials Ramulus syringae / 中草药

Objective: To study the chemical components from Mongolian medicinal materials Ramulus syringae (the peeled roots and branches of Syringa pinnatifolia). Methods: The compounds were purified by column chromatography on silica gel, ODS, and Sephadex LH-20. Their structures were elucidated on the basis of spectroscopic methods. Results: Twenty-one compounds were isolated from R. syringae and their structures were identified as O-ethylcubebin (1), pinnatifone B (2), 3β-O-acetyl-11α,12α- epoxy-oleanan-28,13β-olide (3), coniferyl aldehydel (4), (8R,8’R,9S)-cubebin (5), isovanillic acid (6), (+)-dihydrocubebin (7), 6,10- eposoy-4α-hydroxy guaiane (8), (+)-1β,4β,6α-trihydroxyl-eudesmane (mucrolidin, 9), acutissimalignan B (10), 2-piperonylidene-3- piperonyl-1,4-butanediol (11), 4,4’-dihydroxy-3,3’,9’-triMethoxy-9,9’-epoxylignan (12), 2β-hydroxy-α-cadinol (13), cadinane-4β,5α, 10α-triol (14), larixnaphthanoe (15), lariciresinol (16), 4,4’9-trihydroxy-3,3’-dimethoxy-9,9’-epoxylignan (17), (-)-secoisolariciresino- 9,9’-acetonide (18), berchemol (19), daucosterol (20), and ecoisolariciresinol (21). Conclusion: Compounds 1, 7, 8, 9, 10, 13, 14, and 18 are isolated from the genus Syringa for the first time. Compounds 3 and 20 are isolated from S. pinnatifolia for the first time.

A new lignan from stem bark of Syringa pinnatifolia / 中国中药杂志

One new lignan, named Z-pinnatifolin A, along with ten known analogues, were isolated from the stem bark of Syringa pinnatifolia by various chromatographic methods. Their structures were extensively determined on basis of MS and NMR spectroscopic data analyses, and comparison with those in literature. Among them, compounds 3,4, and 8-11 were isolated from this genus for the first time, and 5-7 were isolated from the specie for the first time. Compound 1 showed a moderate inhibition on NO production in BV-2 cells. The present study provides a preliminary data for clarification of bioactive ingredients of S.pinnatifolia with anti-myocardial ischemic effect.

Iridoids from stem bark of Syringa pinnatifolia / 中国中药杂志

One new iridoid, named alashanidoid A, and five known analogues, were isolated from the stem bark of Syringa pinnatifolia by various chromatographic methods. Their structures were determined on the basis of MS and NMR spectroscopic data analyses, and comparison with those in literature. Among them, compounds 3-5 were isolated from this genus for the first time, and 2 and 6 were isolated from the species for the first time.These isolates were tested for their in vitro anti-inflammatory activities against NO production in lipopolysaccharide(LPS)-induced RAW264.7 macrophages in mice and cytotoxicity of HepG2 cell line, however, no obvious activity was observed at the concentration of 40 μmol•L⁻¹.

Chemical constituents from Mongolian herb Syringa pinnatifolia var. alashanensis / 中国天然药物

Two new sesquiterpenes, innatifolone A (1) and pinnatifolone B (2), along with 6 known compounds, furostan (3), isocalamendiol (4), pluviatolide (5), (8S,8'R,9S)-cubebin (6), 2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dimethoxybenzyl) tetrahydrofuran (7), and methyl 3-acetoxy-12-oleanen-28-oate (8), were isolated from Mongolian herb Syringa pinnatifolia.

Sesquiterpenes from stems of syringa pinnatifolia var. alashanensis / 中草药·英文版

Objective: To study the chemical constituents of the volatile oil from the stems of Syringa pinnatifolia var. alashanensis. Methods: The volatile oil from the stems of S. pinnatifolia var. alashanensis was obtained by steam distillation. They were isolated by chromatography on silica gel, Sephadex LH-20 columns and TLC, etc. The structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Results: Five sesquiterpenes were isolated from the volatile oil. Conclusion: Compound 1 is a new sesquiterpene. © 2013 Tianjin Press of Chinese Herbal Medicines.

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.

Extraction and structure elucidation of three lignans from peeled dried roots and stems of Syringa pinnatifolia / 中草药

Objective: To study the chemical constituents from the peeled dried roots and stems of Syringa pinnatifolia. Methods: The chemical constituents from the peeled dried roots and stems of S. pinnatifolia were isolated and purified by silica gel and Sephadex LH-20 column chromatography, and preparative HPLC. The structures were identified by spectral methods. Results: Three compounds were obtained and identified as lignan, namely 3, 3', 4-trimethoxy-4', 8, 9, 9'-tetrahydroxy simple lignan (1), 3, 3', 4, 9-tetramethoxy-4', 8-dihydroxy-9'-ethoxy simple lignan (2), and 3, 3', 4, 9-tetramethoxy-4', 8, 9'-trihydroxy simple lignan (3). Conclusion: Compounds 1-3 are new, named syripinnalignan C, syripinnalignan D, and syripinnalignan E.