[Show abstract][Hide abstract] ABSTRACT: Winolides A–C (1–3), three bioactive sesquiterpene lactones with irregular 5,6-secoeudesmane frameworks, which probably arise from different dienol-benzene rearrangements, were isolated from Inula wissmanniana. Their structures and absolute configurations were established by extensive analysis of spectroscopic data, computational methods, and asymmetric synthesis.
[Show abstract][Hide abstract] ABSTRACT: γ-Hydroxynitrile glucosides (prinsepicyanosides A-E) were isolated alongside 11 known compounds from seeds of Prinsepia utilis Royle. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. The relative configuration of prinsepicyanoside C was established by Cu-Kα X-ray crystallography. Prinsepicyanoside A, osmaronin, and 4-(hydroxylmethyl)-5H-furan-2-one exhibited borderline antibacterial activity against Salmonella gallinarum, Vibrio parahaemolyticus, and Vibrio cholera with MIC values of 30.1, 20.7, and 22.8μg/mL, respectively.
[Show abstract][Hide abstract] ABSTRACT: Five previously unreported γ-hydroxynitrile glucosides (prinsepicyanoside A–E) together with 11 known compounds were isolated from the seeds of Prinsepia utilis. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. Co-occurrence of the hydroxynitrile glucosides and their corresponding furanones supported the possibility of the proposed biosynthetic mechanism for furanones generated from γ-hydroxynitrile glucosides.
[Show abstract][Hide abstract] ABSTRACT: Phytochemical investigation of Inula wissmanniana Hand.-Mazz. afforded 21 eudesmane and germacrane derivatives, including rare 4,5-secoeudesman-12,5-olide, eudesman-12,5-olide, 3,4-secoeudesman-12-oic acid, and germacra-4-en-12,6-olides. Their structures were elucidated by combinative analyses of MS, NMR, electronic circular dichroism, and X-ray crystallography data. Moreover, most of the isolates exhibited inhibition against lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages and cytotoxicity in HepG2, PC-3, and MGC-803 tumor cells.
[Show abstract][Hide abstract] ABSTRACT: Four new sesquiterpenoid dimers (lineariifolianoids E-H, 1-4), five new sesquiterpenoids (5-9), and seven known sesquiterpenoids (10-16) were isolated from the aerial parts of Inula lineariifolia Turcz. Their structures were determined by spectroscopic data analysis and X-ray diffraction studies. The compounds were then evaluated for their in vitro cytotoxicity against two human breast cancer cell lines (MCF-7 and MDA-MB-231) and one normal breast cell line (MCF-10A). Lineariifolianoid E (1) showed IC50 values of 1.56 μM and 2.75 μM against MCF-7 and MDA-MB-231, respectively. However, lineariifolianoid E demonstrated low toxicity to MCF-10A cells, which indicated a selective cytotoxicity for tumor cells. Further studies also presented that lineariifolianoid E had significant, dose-dependent effects on cell cycle progression and apoptosis in breast cancer cells.
European Journal of Medicinal Chemistry 08/2013; 68C:473-481. · 3.43 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC(50) value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC(50) values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC(50)=14.7 μM).
[Show abstract][Hide abstract] ABSTRACT: Abiestetranes A (1) and B (2), two unique tetraterpenes formed by Diels–Alder cycloaddition between a lanostane triterpenoid and a monoterpenoid, were isolated from Abies fabri. Their structures were elucidated by extensive analysis of NMR data. The electronic circular dichroism was utilized to assign the absolute configuration of 1. Compounds 1 and 2 showed significant cytotoxic activities against ZR-75-30 tumor cell with IC50 values of 6.26 and 1.63 μg/mL, respectively.
[Show abstract][Hide abstract] ABSTRACT: Phytochemical investigation of the aerial parts of Inula hupehensis Ling. led to the isolation and identification of 27 sesquiterpene lactones (1-27), including three new eudesmanolides (3-5), three new germacranolides (9-11), one new xanthanolide (16), two new carabrone derivatives (25-26), and 18 known sesquiterpene lactones. The structures were elucidated by extensive spectroscopic methods and comparison to previously reported spectroscopic data. All compounds were evaluated for their inhibitory effects against LPS-induced nitric oxide production in RAW264.7 macrophages, and compound 5 showed the strongest activity with the IC₅₀ value of 3.2 ± 0.4 µM.
[Show abstract][Hide abstract] ABSTRACT: A new acylated flavonoid, 3-O-rhamnocitrin-6-O-benzoyl-β-D-glucopyranoside (1), together with five known flavonoids, rhamnocitrin (2), pratensein (3), (3R)-7,3'-dihydroxy-2',4'-dimethoxyisoflavan (4), (3R)-7,2'-dihydroxy-3',4'-dimethoxyisoflavan (5) and isoliquiritigenin (6), was isolated from Oxytropis ochrocephala Bunge. The structural elucidation of the isolated compounds was primarily based on HRESIMS, IR and 1-D- and 2-D-NMR analyses.
Natural product research 04/2012; · 1.23 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Incarvilleatone (1), an unprecedented dimeric cyclohexylethanoid analog with a racemic nature, was isolated from the whole plant of Incarvillea younghusbandii. HPLC chiral separation of 1 gave two enantiomers (-)-incarvilleatone and (+)-incarvilleatone. The structure of 1 was established by spectroscopic methods and single crystal X-ray diffraction. The absolute configurations of enantiomers were determined by quantum mechanical calculation. (-)-Incarvilleatone exhibited a potent inhibitory effect against NO production in LPS-induced RAW264.7 macrophages.
[Show abstract][Hide abstract] ABSTRACT: Lineariifolianoids A–D (1–4), a rare class of unsymmetrical sesquiterpenoid dimers with xanthane and guaiane frameworks have been isolated for the first time from Inula lineariifolia. Notably, lineariifolianoid D (4) features the first exo-adduct of such dimers through a plausible Diels–Alderase catalyzed biogenetic pathway. Moreover, the absolute configuration of japonicone A (5) has been revised by the Flack method. The inhibitory effects of the new isolates on TNF-α-mediated L929 cytotoxicity have also been evaluated and only the exo-adduct lineariifolianoid D (4) displays the inhibitory property.
[Show abstract][Hide abstract] ABSTRACT: Four new sesquiterpene lactones, (1 S,5 R,6 S,7 S,8 R,9 R,10 S,11 S)-6-acetoxy-9-hydroxy-4-oxo-pseudoguai-2(3)-en-12,8-olide, (1 S,2 R,5 R,6 S,7 R,8 S,10 R)-6-acetoxy-2-ethoxy-4-oxo-pseudoguai-11(13)-en-12,8-olide, (1 S,2 R,5 R,6 S,7 R,8 S,10 R)-6-acetoxy-2-hydroxy-4-oxo-pseudoguai-11(13)-en-12,8-olide, and 14-acetoxy-1 β,5 α,7 αH-4 β-hydroxy-guai-9(10),11(13)-dien-12,8 α-olide, along with 26 known sesquiterpene lactones, were isolated from the whole plants of Inula hookeri C. B. Clarke. Their structures were established based on spectroscopic methods including HRESIMS, 1D and 2D NMR, and CD techniques. All compounds were evaluated for their cytotoxic activities against HepG2, HeLa, PC-3, and MGC-803 cell lines by CCK-8 assay. Some of the isolates, especiallly pseudoguaianolides and guaianolides, exhibited significant cytotoxicities against these four examined cell lines.
[Show abstract][Hide abstract] ABSTRACT: A novel trinorsesquiterpene (1), three new (2-4), and 10 known sesquiterpenes were isolated from the roots of Inula racemosa Hook. f. The structures and absolute configurations of the new sesquiterpenes were elucidated by extensive spectroscopic and computational methods. All compounds were evaluated for their inhibition of LPS-induced nitric oxide production in RAW264.7 macrophages, and the results indicated that compounds 9, 12, and 13 moderately inhibited nitric oxide production with IC₅₀ values of 7.39 ± 0.36, 6.35 ± 0.26, and 5.39 ± 0.18 µM, respectively.
[Show abstract][Hide abstract] ABSTRACT: Eight new pseudoguaianolides (1-8), two new guaianolides (9 and 10), and 14 known sesquiterpenes were isolated from the aerial parts of Inula hupehensis. The structures were elucidated using spectroscopic methods and circular dichroism analysis. All compounds were tested for inhibitory activities against LPS-induced nitric oxide production in RAW264.7 macrophages. Compounds 13 and 22 were found to inhibit nitric oxide production potently, with IC50 values of 0.9 and 0.6 μM, respectively. Preliminary structure-activity relationships for these compounds are proposed.
Journal of Natural Products 09/2011; 74(9):1881-7. · 3.95 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: Four new compounds: an abietane (1), two isopimarane (2 and 3) diterpenes, and a dihydrobenzofuran neolignan (5), together with a sesquiterpene glycoside (6) firstly isolated from a natural source, and a known phenol glycoside (4) were isolated from leaves of Platycladus orientalis. The structures and relative configurations of these compounds were assigned on the basis of MS, IR, 1D and 2D NMR data. The absolute configuration of compound 1 was determined via density functional theory calculations of its electronic circular dichroism. In addition, the results of bioassays indicated that compounds 4 and 6 showed a potent inhibitory effect on NO production with IC₅₀ values of 24.4 and 11.9 µM, respectively. Meanwhile, compounds 1, 2, and 3 moderately inhibited TNF- α release.
[Show abstract][Hide abstract] ABSTRACT: With the development of stem cells and regenerative medicine (treatment of various diseases using stem cells) research, the induction of differentiation of human stem cell technology has also made significant progress. The development of chemical biology offers a variety of small biological molecules for stem cell biology. This review focuses on how small molecule compounds (natural and synthetic) induce differentiation of stem cells.
Yao xue xue bao = Acta pharmaceutica Sinica 02/2011; 46(2):121-6.
[Show abstract][Hide abstract] ABSTRACT: Twenty-two new sesquiterpenes were isolated from the aerial parts of Inula japonica Thunb., together with fifteen known ones. Their structures were determined by detailed spectroscopic analysis, X-ray diffraction studies, and modified Mosher method. All 37 compounds were evaluated for the inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, and most of isolates significantly inhibited the NO production with IC50 values in the range of 3.5–20 μM. Besides, results obtained in our studies provided a structure–activity relationship that would be used to design anti-inflammatory agents in the future.Graphical abstractTwenty-two new sesquiterpenes were isolated from the aerial parts of Inula japonica Thunb., together with fifteen known ones.