To explore potential anti-inflammatory lead compounds, ten new physalin steroids, including three neophysalins (1, 4, and 9) and seven physalins (2, 3, 5-8, and 10), along with eleven known analogs, were isolated from an ethanol extract of the calyx of Physalis alkekengi. The new structures were rigorously determined through comprehensive HRESIMS, 1D/2D-NMR, and X-ray diffraction analysis. Among these compounds, 1 was identified as a new 1,10-seco-neophysalin, and 2 was identified as a new 11,15-cyclo-9,10-seco-physalin characterized by an aromatic A-ring.
View Article and Find Full Text PDFInvestigation of the fruits of G. Don led to the isolation of three new grayanane-type diterpenoids, rhodomolleins LIV-LVI (). The structures and absolute configurations of new compounds were fully elucidated by spectroscopic analysis and single-crystal X-ray diffraction, including HRESIMS, 1 D and 2 D NMR data.
View Article and Find Full Text PDFThree new cadinane sesquiterpenes (-) and three known sesquiterpenes were isolated from the stems and branches of A. C. Smith.
View Article and Find Full Text PDFA 1,2:3,4:9,10:9,19-tetraseco-cycloartane triterpene spiroketal lactone, pseudoamaolide P (), two new labdane-type diterpenoids, pseudoamains A and B (), and four known cembrane-type diterpenoids () were isolated from the seeds of . The structures of these compounds were elucidated by spectroscopic analyses, including HRESIMS, 1D-, and 2D-NMR. The anti-inflammatory activities of the compounds were evaluated by suppressing the transcription of the NF-κB-dependent reporter gene in LPS-induced 293 T/NF-κB-luc cells.
View Article and Find Full Text PDFFifteen unreported prenylated C-C derivatives (1-15) were isolated from the stems and branches of Illicium ternstroemioides A. C. Smith, including one bis-prenylated C-C derivative (1), three prenylated C-C derivative-shikimic acid ester hybrids (2-4) and 11 prenylated C-C monomers (5-15).
View Article and Find Full Text PDFPTP1B plays an important role as a key negative regulator of tyrosine phosphorylation associated with insulin receptor signaling in the therapy for diabetes and obesity. In this study, the anti-diabetic activity of dianthrone derivatives from Polygonum multiflorum Thunb., as well as the structure-activity relationships, mechanism, and molecular docking were explored.
View Article and Find Full Text PDFEight undescribed β-bergamotene-type sesquiterpene oliganins A-H (1-8) and one known α-bergamotene-type sesquiterpene (9) were isolated from the leaves and twigs of Illicium oligandrum Merr. & Chun. The structures of compounds 1-8 were elucidated by extensive spectroscopic data, and the absolute configurations were determined by using a modified Mosher's method and electronic circular dichroism calculations.
View Article and Find Full Text PDFZhongguo Zhong Yao Za Zhi
January 2023
By various chromatographic techniques and extensive spectroscopic methods, 17 abietane diterpenoids were isolated from the dichloromethane fraction of the 95% ethanol cold-soak extracts of the seeds of Pseudolarix amabilis, namely pseudoamaol A(1), 12α-hydroxyabietic acid(2), 12-methoxy-7,13-abietadien-18-oic acid(3), 13-hydroxy-8,11,13-podocarpatrien-18-oic acid(4), 15-hydroxy-7,13-abietadien-12-on-18-oic acid(5), 8(14)-podocarpen-13-on-18-oic acid(6), holophyllin K(7), metaglyptin B(8), 7α-hydroxydehydroabietinsaure-methylester(9), 7-oxodehydroabietic acid(10), 15-hydroxy-7-oxodehydroabietinsaure-methy-lester(11), 15-methoxydidehydroabietic acid(12), 7-oxo-15-hydroxy-dehydroabietic acid(13), 15-hydroxydehydroabietic acid(14), 8,11,13-abietatriene-15,18-diol(15), 8,11,13-abietatriene-15-hydroxy-18-succinic acid(16), and 7β-hydroxydehydroabie-tic acid(17). Compound 1 was a new compound. The isolated compounds were evaluated for their antitumor activities(HepG2, SH-SY5Y, K562), and compounds 8 and 17 showed potential cytotoxic activity against K562 cells, with IC_(50) values of 26.
View Article and Find Full Text PDFChemical investigation of an alcohol extract from the twigs and leaves of Illicium henryi Diels resulted in the isolation of two new acorane-related seco-sesquiterpenes (1 and 3), two new acorane-related seco-norsesquiterpenes (2 and 4), one new 2-epi-cedrane sesquiterpene (5), eight new acorane-type sesquiterpenes (6-13), and a known major constituent of acorenone B (14). Their structures were established by interpreting extensive spectroscopic data, including HRESIMS, NMR (H and C NMR, H-H COSY, HSQC, and HMBC), and NOE difference spectra analysis. The absolute configurations of 1, 2, 4-7, 9, 10, and 14 were determined by X-ray crystallography, while chemical transformation methods were performed with compound 14 as the starting material to elegantly solve the absolute configuration issue of compounds 8 and 11-13.
View Article and Find Full Text PDFFive undescribed dihydroflavonoid glycoside derivatives, namely albvisosides A‒E, together with two known compounds were isolated from the roots and stem leaves of Viscum album L. var. album.
View Article and Find Full Text PDFOne undescribed diterpenoid illisimonone A, four undescribed sesquiterpenes named (±)-simonones A, simonterpenoids A and B, and two undescribed lignans, illisimonins A and B, along with five known compounds were isolated from the fruits of Illicium simonsii. Their structures were elucidated by extensive spectroscopic data. The absolute configuration of illisimonone A was determined by single-crystal X-ray diffraction analysis.
View Article and Find Full Text PDFA phytochemical investigation guided by H NMR and LC-MS data on the ethanol extract of Syringa pinnatifolia stems led to the isolation of 11 new dimeric eremophilane sesquiterpenoids, namely, syringenes A-K (1-11) and one known analog (12, syringene L). These structures were elucidated by extensive analysis of spectroscopic data, single-crystal X-ray diffraction, and computational methods. Biological assays revealed that 1-12 exhibited different degrees of anti-inflammatory effects, and 5 and 6 showed significant cytotoxicity against human hepatoma HepG2 cells with IC values of 12.
View Article and Find Full Text PDFA pair of enantiomers with a rearranged dimeric phenylethanol skeleton, namely (±)-disyringol A (1a and 1b), were isolated from the stem barks of Syringa pinnatifolia. The structures were established using IR, UV, MS, and NMR data, and their absolute configurations were resolved by experimental and calculated ECD data analysis. Their biosynthetic pathway was speculated on the basis of a phenylethanoid precursor and was proved by a total synthesis.
View Article and Find Full Text PDFTwo new diterpenoids, dauricumins A () and B (), together with two known aromatic meroterpenoids ( and ), were isolated from the petroleum ether soluble fraction of the stems from through an HPLC-MS-SPE-NMR combination strategy. The absolute configurations of and were elucidated by ECD calculations and [Rh (OCOCF)]-induced CD spectrum analysis. In a membrane potential FLIPR assay, confluentin () showed an agonistic effect on GABA receptor (EC = 20 µM).
View Article and Find Full Text PDFThirteen compounds were isolated from the lipid-soluble extracts of Illicium ternstroemioides A. C. Smith, including eleven previously undescribed prenylated C-C compounds, a previously undescribed prenylated C-C derivative-abscisic acid ester hybrid, and a known compound (4S)-illicinone I.
View Article and Find Full Text PDFThree pairs of enantiomeric sesquiterpenoids, (∓)-syringanoid A ( and ) and (±)-pinnatanoids A ( and ) and B ( and ), that represent an unprecedented 5/4/6 tricyclic backbone and a rare 6/7 bicyclic backbone, respectively, were isolated from the peeled stems of . The structures were elucidated by extensive spectroscopic analysis, single-crystal X-ray diffraction, a modified Mosher's method, and quantum chemical calculations. A plausible biotransformation pathway for - was proposed, and their cardiomyocyte-protective and anti-inflammatory activities were evaluated.
View Article and Find Full Text PDFSeventeen new prenylated C-C derivatives, namely, illifargeins A-M (1-13), including three pairs of enantiomers (1, 5, and 12) and one norillifargeal A (14), together with eight known analogues (15-22), were isolated from the stems and leaves of Illicium fargesii. The structures of the new compounds were elucidated using spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). Their absolute configurations were determined by using experimental and calculated ECD data analysis, as well as a modified Mosher's method.
View Article and Find Full Text PDFIllihenin A (), a novel sesquiterpenoid, was isolated from the roots of . The structure was determined by spectroscopic analyses, ECD calculation, and single-crystal X-ray diffraction. Compound represents a class of novel 5/7/6 tricyclic sesquiterpenoids featuring a rare cage-like tricyclo[6.
View Article and Find Full Text PDFBurchellin and its analogues are a class of neolignan natural products containing a rare core with three contiguous stereogenic centers. In previous reports, racemic burchellin was synthesized without accessing each of the enantiomers. In this paper, a concise and efficient total synthetic route to divergently access the enantiomers of burchellin and those of its 1'-epi-diastereoisomer over six steps for each is disclosed, where each of the enantiomers was obtained by preparative chiral phase HPLC purification.
View Article and Find Full Text PDFFourteen new sesquiterpenoids, alashanoids A-H (1, 2, and 4-9), (+)-2,9-humuladien-6-ol-8-one (3b), and five pairs of enantiomers (1 and 4-7), along with eight known analogues (3a and 10-16) were isolated from the stems of Syringa pinnatifolia. The structures were established using IR, UV, MS, and NMR data. The absolute configurations of the new compounds were resolved by X-ray diffraction, a modification of Mosher's method, and experimental and calculated ECD data analysis.
View Article and Find Full Text PDFTransforming growth factor (TGF)-β1 has been implicated in the pathogenesis of restenosis. However, the role of TGF-β1 polymorphisms in development of in-stent restenosis (ISR) after coronary bare metal stent (BMS) implantation in Chinese Han population has not been reported to date. The aim of this study was to explore the association between TGF-β1 gene polymorphisms (-509C/T and 869T/C) and its plasma level in Chinese Han patients with BMS-ISR.
View Article and Find Full Text PDFOne 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.
View Article and Find Full Text PDFJ Asian Nat Prod Res
April 2017
One new norlignan, noralashinol B (1), and one new natural product, proposed noralashinol C (2), were isolated in a continuous phytochemical investigation on the stem barks of Syringa pinnatifolia. Their structures were elucidated based on the analysis of spectroscopic data, including mass spectrometry and 1D and 2D NMR spectroscopies, and the absolute configuration was determined by experimental and calculated electronic circular dichroism. Compound 1 showed a weak cytotoxicity against HepG2 hepatic cancer cells with its IC value of 31.
View Article and Find Full Text PDFFour new lignans, alashinols A-D (1-4), a new hydrolysis product, alashinols E (5), and seven known analogues were isolated from the stem bark of Syringa pinnatifolia Hemsl. These new lignans were characterized using 1D and 2D NMR and MS data, and their absolute configurations were determined by experimental and calculated electronic circular dichroism and X-ray diffraction analyses. Alashinol B (2) exhibited two conformers that adopted an unusual unit cell packing.
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