AbstractTwo new isoxazoline compounds, 1-oxa-2-azaspiro[4.5]dec-2-ene-8β-ol (1) and 1-oxa-2-azaspiro[4.5]dec-2-ene-8α-ol (2), were isolated from the husks of fruits of Xanthoceras sorbifolia Bunge and their structures were determined by spectroscopic analyses, including X-ray crystallography, HRESI-MS, UV, IR, and 1D and 2D NMR (HSQC, HMBC, NOESY) methods. Neither compound showed significant inhibitory effects on butyrylcholinesterase (BuchE) and acetylcholinesterase (AChE), nor the selected tumor cells growth. Based on an online activity prediction program (PASS ONLINE), the structures with isoxazoline skeletons were found to show potential anti-asthmatic (AM) and anti-anaphylaxis (AP) activities; moreover, compounds 1 and 2 were predicted to possess high affinities for many enzymes involved in AM and AP according to the RCSB Protein Data Bank. High-affinity binding to phosphodiesterase IV (PDE-4), an important inflammatory modulator in asthma, was demonstrated experimentally, beside that, the predicted ...
Last. Xian Li(SPU: Shenyang Pharmaceutical University)H-Index: 21
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In order to find out new natural barrigenol type triterpenenoids as antitumor agent and reveal the difference on material basis of different parts of Xanthoceras sorbifolia Bunge, the bioassay-directed separation of the saponin fraction from leaves of X. sorbifolia Bunge was carried out to afford 5 new barrigenol type triterpenoids (1–5), together with 2 known ones. The antitumor activities were evaluated and compounds 2 and 7 showed significant cytotoxic activity. Furthermore, the SAR was discu...
Last. Feng Qiu(SPU: Shenyang Pharmaceutical University)H-Index: 29
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Abstract Xanthoceras sorbifolia Bunge is widely used as healthy food material and folk medicine in China. Phytochemical investigation on its seeds oil leavings has led to the isolation and identification of seven new oleanane-type triterpenoid saponins named sorbifoliasides A–F ( 1–6 ) and bunkankasaponin F ( 7 ), along with five known ones ( 8 – 12 ). The structures of the new compounds were elucidated through spectroscopic analysis and chemical derivatization. Among the isolated compounds, 16-...
#1Hao Cui(LNUTCM: Liaoning University of Traditional Chinese Medicine)H-Index: 2
#2Hang Xiao(LNUTCM: Liaoning University of Traditional Chinese Medicine)H-Index: 71
Last. Ting-Guo Kang(LNUTCM: Liaoning University of Traditional Chinese Medicine)H-Index: 12
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Two new triterpenoid saponins (1, 2) and a known saponin (3) were isolated from the husks of Xanthoceras sorbifolia Bunge., and their structures were elucidated as 3-O-β-d-glucopyranosyl(1 → 6)-[angeloyl(1 → 2)]-β-d-glucopyranosyl-28-O-α-l-rhamnopyranosyl(1 → 2)-[β-d-glucopyranosyl(1 → 6)]-β-d-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (1), 3-O-β-d-glucopyranosyl-28-O-[β-d-glucopyranosyl(1 → 2)]-β-d-glucopyranosyl-21β,22α-dihydroxyl-olean-12-ene (2), and 3-O-β-d-glucopyranosyl-28-O-[α-l-rham...
In this communication, we describe the synthesis and biological evaluation of tacripyrimedones 1 – 5 , a series of new tacrine-1,4-dihydropyridine hybrids bearing the general structure of 11-amino-12-aryl-3,3-dimethyl-3,4,5,7,8,9,10,12-octahydrodibenzo[ b , g ][1,8]naphthyridine-1(2 H )-one. These multifunctional compounds are moderately potent and selective AChEIs, with no activity toward BuChE. Kinetic analysis and molecular modeling studies point out that the new compounds preferentially bind...
Last. Ning Li(SPU: Shenyang Pharmaceutical University)H-Index: 19
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Two new triterpenoid saponins (1, 2) and a known sapogenin (3) were isolated from the dried carpophore of Xanthoceras sorbifolia Bunge. (Sapindaceae), and their structures were established as 3-O-β-d-glucopyranosyl, 28-O-[α-l-rhamnosyl (1 → 2)]-β-d-glucopyranosyl 16-deoxybarrin-gtogenol C (1), 3-O-[β-d-glucopyranosyl(1 → 6)] 3′-angeloyl)-β-d-glucopyranosyl, 28-O-[α-l-rhamnosyl(1 → 2)]-β-d-glucopyranosyl 16-deoxybarringtogenol C (2), 16-deoxybarringtogenol C (3), by spectral and chemical methods....
Last. Henry J. Lee(FAMU: Florida A&M University)H-Index: 13
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Abstract A series of new anti-inflammatory steroidal antedrugs with C-16,17-isoxazoline ring system were synthesized and their pharmacological activities were evaluated. We reported earlier that these compounds are promising antedrugs based on the results of 5-day rat croton oil ear edema assay. In the present study, most of these compounds showed high binding affinities to the glucocorticoid receptor of liver cytosol. 21-Acetyloxy-9α-fluoro-11β-hydroxy-3,20-dioxo-1,4-pregnadieno [16α,17α-d] iso...
From a methanolic extract of the wood of Xanthoceras sorbifolia, two new compounds, 29-hydroxy-3-oxotirucalla-7,24-dien-21-oic acid (3, xanthocerasic acid) and epigallocatechin-(4β→8,2β→O-7)-epicatechin (6), were isolated, together with 11 known compounds. Of the isolated compounds, 3-oxotirucalla-7,24-dien-21-oic acid (2), oleanolic acid (4), and 6 were found to be inhibitory substances against human immunodeficiency virus (HIV-1) protease, with their 50% inhibitory concentrations (IC50) being ...
Last. Yukio Ogihara(Nagoya City University)H-Index: 36
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The prosapogenins from the partial hydrolysate of fruit saponin of Xanthoceras sorbifolia BUNGE (Sapindaceae) were examined. On the basis of chemical and spectral analyses, compound G was identified as protoaescigenin (1). Two new prosapogenins were characterized as 16-O-acetyl-21-O-(3', 4'-di-O-angeloyl)-β-D-fucopyranosylprotoaescigenin (5) and 22-O-acetyl-21-O-(3', 4'-di-O-angeloyl)-β-D-fucopyranosylprotoaescigenin 3-O-β-D-glucuronopyranoside (7).
Last. Yukio Ogihara(Nagoya City University)H-Index: 36
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Four new saponins were isolated from the fruits of Xanthoceras sorbifolia BUNGE. The structures of these saponins were deduced on the basis of chemical and spectral evidence as 22-O-acetyl-21-O-(4-O-acetyl-3-O-angeloyl)-β-D-fucopyranosyl-3-O-[β-D-glucopyranosyl- (1→2)-β-D-glucuronopyranosyl] protoaescigenin (7), 22-O-acetyl-21-O- (3, 4-di-O-angeloyl) -β-D-fucopyranosyl-3-O- [β-D-glucopyranosyl- (1→2)-β-D-glucuronopyranosyl] protoaescigenin (8), 28-O-acetyl21-O- (4-O-acetyl-3-O-angeloyl) -β-D-fuc...
Last. Shenlin Huang(NFU: Nanjing Forestry University)H-Index: 15
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A catalytic, transition-metal-free synthesis of spiroisoxazolines is outlined. This protocol provides, for the first time, a direct access to spiroisoxazolines from aryl (thio)ethers or (thio)pheno...
Last. Dan-Yi Li(SPU: Shenyang Pharmaceutical University)
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Abstract Four tyrosine-derived spiro-isoxazoline analogues, including two new ones (3–4), were isolated from the flowers of Xanthoceras sorbifolia Bunge. The planar structures and the conformations were established by the analyses of the 1D and 2D NMR spectroscopic data, and the absolute configuration of compound 4 was determined via ECD calculation by time-dependent density functional theory (TDDFT). The biosynthetic pathway involving oxidative cyclization of the aldoxime precursor and the subs...
Abstract The high edible oil content of Xanthoceras sorbifolia Bunge seeds contributes to its economic value. In this study, we analysed the barrigenol-like triterpenoids derived from X. sorbifolia husks. We also identified anti-tumour agents that could enhance the health benefits and medicinal value of X. sorbifolia. We isolated 10 barrigenol triterpenoids, including six new compounds (1–6) and four known compounds (7–10). New compounds 3 and 5 showed significant inhibitory activity against the...