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ABSTRACT: A new resveratrol trimer derivative, named as gnetubrunol A (1), together with five known stilbene derivatives, shegansu B (2), resveratrol (3), isorhapontigenin (4), gnetifolin E (5), and isorhapontigenin-11-O-β-d-glucopyranoside (6) were isolated from the lianas of Gnetum brunonianum Griff. Their structures were elucidated on the basis of spectral analysis (UV, IR, MS, (1)H NMR, (13)C NMR, and 2D NMR). The anti-inflammatory activities of 1, 5, and 6 have also been assayed.
Journal of Asian natural products research 08/2012; 14(9):918-22. · 0.61 Impact Factor
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ABSTRACT: The aim of the present study is to investigate the effects of Vam3 which is one of the dihydroxystilbene compounds on expressions of ICAM-1 in the lungs of OVA-induced asthmatic mice and the mechanisms of anti-airway inflammation. Balb/c mice were challenged with OVA inhalation. Lung tissues were stained with Mayer's hematoxylin and eosin for histopathologic examination. The expression of ICAM-1 in the lungs of mice was analyzed by Western blotting and immunohistochemistry method. The NF-kappaB activities were detected by NF-kappaB-luc reporter genetic transient transfection method. The activities of MMP-9 induced by LPS, TNF-alpha and PMA in THP-1 cells were determined by gelatin zymography method. The results showed that Vam3 could inhibit the expression of ICAM-1 in the OVA-induced mouse model. In addition, Vam3 could significantly suppress the activities of NF-kappaB in A549 cells and MMP-9 in THP-1 cells induced by LPS, TNF-alpha and PMA. These results suggested that Vam3 could alleviate the asthmatic inflammation by decreasing ICAM-1 expression in asthmatic mice, down regulating NF-kappaB and MMP-9 activities. Compound Vam3 showed inhibitory effects on inflammatory signal pathways involved in asthma.
Yao xue xue bao = Acta pharmaceutica Sinica 12/2010; 45(12):1503-8.
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ABSTRACT: Resveratrol, isorhapontigenin and pinosylvin, isolated from Gnetum parvifolium, and their analogues have been synthesized and tested for their inhibitory activity of HIV-1. Natural product 12a and analogues (12d, 12e, 12g) display significant inhibitory activity of HIV-1 replication. Among them, compound 12d (trans-3, 4, 5, 4'-tetrahydroxystilbene) exhibits the most potent anti-HIV-1 activity with an IC50 value of 1.84 micromol x L(-1).
Yao xue xue bao = Acta pharmaceutica Sinica 12/2010; 45(12):1509-15.
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ABSTRACT: The anti-influenza viral activities of six stilbenoids from the lianas of Gnetum pendulum C. Y. Cheng were evaluated with two different assays, neuraminidase (NA) activity assay and cytopathic effect (CPE) reduction assay. The NA assay results showed that all six stilbenoids exerted an NA inhibitory effect, while the CPE assay indicated that among them, isorhapontigenin (2), gnetupendin B (3), shegansu B (4), and gnetin D 6) exhibit significant in vitro anti-influenza viral activity in MDCK cells, with IC(50) values from 0.67 to 11.99 µg/mL in comparison to the positive controls oseltamivir acid and ribavirin whose IC(50) values were 0.040 and 5.54 µg/mL, respectively.
Planta Medica 11/2010; 76(16):1874-6. · 2.15 Impact Factor
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ABSTRACT: Two new stilbenoids, cis-ϵ-viniferin (3) and 2b, 14b-dehydro-bisresveratrol (4) were synthesized by photooxidation reaction of trans-ϵ-viniferin (2) prepared from tram-resveratrol (1). Pentamethoxyl trans-ϵ-viniferin (5) and pentamethoxyl cis-ϵ-viniferin (6) were also obtained by methylation of trans-ϵ-viniferin (2) with (MeO)2SO2. Their structures were elucidated on the basis of spectral evidence. Compounds 3 and 4 showed potent inhibition of TNF-α at concentrations of 10−-5 mol.L−1 with inhibitory ratios of 51.43% and 36.64%. respectively.
Chinese Journal of Chemistry 08/2010; 22(11):1350 - 1355. · 0.75 Impact Factor
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ABSTRACT: One new stilbenolignan, gnetucleistol F (1), and four known stilbenolignans, gnetofuran A (2), lehmbachol D (3), gnetifolin F (4) and gnetumontanin C (5) were isolated from the lianas of Gnetum cleistostachyum C. Y. CHENG (Gnetaceae). Their structures and relative configurations were determined by means of spectroscopic evidence. Compounds 1, 2, 3 and 4 were synthesized for the first time on the basis of their biogenetic pathway, and their possible biomimetical synthetic mechanisms were discussed. The pharmacological activities of all stilbenolignans have been tested. Among them, 1, 2, 3, 4 and 5 showed moderate inhibitory activities on TNF-alpha and 1 also showed potent inhibitory activity on malondialdehyde.
CHEMICAL & PHARMACEUTICAL BULLETIN 08/2006; 54(7):1053-7. · 1.59 Impact Factor
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ABSTRACT: To explore the anti-inflammatory effects of amurensin H on asthma-like reaction induced by allergen in sensitized mice.
BALB/c mice were sensitized by ovalbumin (OVA, ip) on d 0 and d 14 and challenged with 1% OVA on d 18 to 22. Mice developed airway eosinophilia, mucus hypersecretion, and elevation in cytokine levels. Mice were administered amurensin H orally at the doses of 49, 70, or 100 mg/kg once every day from d 15 to the last day. Bronchoalveolar lavage fluid (BALF) were collected at 24 h and 48 h after the last OVA challenge. Levels of tumor necrosis factor-alpha (TNF-alpha), interleukin 4 (IL-4), interleukin 5 (IL-5), and interleukin 13 (IL-13) in BALF were measured using ELISA method. Differential cell counts of macrophages, lymphocytes, neutrophils and eosinophils were performed in 200 cells per slide (one slide per animal). Lung tissue sections of 6-mum thickness were stained with Mayer's hematoxylin and eosin for assessment of cell infiltration, mucus production, and tissue damage.
Oral administration of amurensin H significantly inhibited OVA-induced increases in total cell counts, eosinophil counts, and TNF- alpha, IL-4, IL-5 and IL-13 levels in BALF. In addition, amuresin H dramatically decreased OVA-induced lung tissue damage and mucus production.
Amurensin H may have therapeutic potential for the treatment of allergic airway inflammation.
Acta Pharmacologica Sinica 07/2006; 27(6):735-40. · 1.95 Impact Factor
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ABSTRACT: Two new stilbene dimers, named bisisorhapontigenin A (1) and cis shegansu B (2), together with gnetuhainin P (3) and gnetulin (4), were isolated from the lianas of Gnetum cleistostachyum C. Y. Cheng. Their structures were elucidated by means of spectroscopic evidences, including UV, IR, MS, 1H NMR, 13C NMR, NOE and 2D NMR, respectively. The pharmacological activities of compounds 1, 2 and 3 also have been tested.
Natural Product Research 08/2005; 19(5):443-8. · 1.01 Impact Factor
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ABSTRACT: Three new stilbene derivatives, named gnetucleistol A (1), B (2) and C (3), together with four known compounds, gnetifolin A (4), p-hydroxycinnamic acid (5), piceatannol (6) and resveratrol (7), were isolated from Gnetum cleistostachyum C.Y. Cheng (Gnetaceae). Their structures were elucidated on the basis of spectroscopic evidence (EI-MS, UV, IR, NOE, 1H, 13C and 2D NMR).
Journal of Asian Natural Products Research 05/2005; 7(2):131-7. · 0.94 Impact Factor
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ABSTRACT: Four new compounds 1-4 were obtained from an oxidative coupling reaction of (E)-isorhapontigenin using FeCl(3) as oxidant. Their structures and stereochemistry were determined on the basis of spectroscopic evidence [UV, IR, MS, (1)H-, (13)C-NMR, NOE and 2D NMR], and their possible formation mechanisms were also discussed, respectively.
CHEMICAL & PHARMACEUTICAL BULLETIN 03/2004; 52(2):238-43. · 1.59 Impact Factor
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ABSTRACT: From the lianas of Gnetum montanum Markgr. f. megalocarpum Markgr., four new stilbenoids, gnetumontanins A - D ( 1 - 4) were obtained together with 16 known compounds. Gnetumontanin A ( 1) is the first oligostilbene dimerized from two oxyresveratrol units, gnetumontanin B ( 2) is a new stilbene trimer oligomerized from two oxyresveratrol and one resveratrol units, gnetumontanin C ( 3) is a new stilbenoid with a novel skeleton having a delta-lactone moiety and gnetumontanin D ( 4) is a glucoside of 3. Their structures were determined by means of spectroscopic evidence, especially 2D NMR techniques. Gnetumontanin B showed potent inhibition of TNF-alpha with an inhibitory ratio of 58.1 % (P < 0.05) at a concentration of 10 ( - 5) mol L (-1) and the IC (50) was 1.49 x 10 ( - 6) mol L (-1).
Planta Medica 02/2004; 70(2):160-5. · 2.15 Impact Factor
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ABSTRACT: The first new isorhapontigenin dimer glucoside gnetupendin D (1) and a stilbene dimer coupled by a resveratrol and an oxyresveratrol with a cis-dihydrobenzofuran were obtained from the lianas of Gnetum pendulum C. Y. Cheng (Gnetaceae), along with nine known compounds. Their structures and stereochemistry were elucidated by chemical and spectral evidence, especially 2D NMR spectroscopic techniques. Pharmacological activities on anti-inflammation have been tested.
Journal of Asian Natural Products Research 07/2003; 5(2):113-9. · 0.94 Impact Factor
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ABSTRACT: The formic acid-catalyzed dimerization of stilbenes, isorhapontigenin and resveratrol, offers a route to tetralin derivatives. Seven products have been obtained, four of which were trisubstituted tetralins and three of which were formed from tetralins by losing substituted benzene groups and methoxy groups during the Diels–Alder reaction. The structures and configurational assignments of the compounds were elucidated mainly by spectroscopic analysis and a possible mechanism is proposed for the reaction. The anti-inflammatory activities of some derivatives obtained were also evaluated.
Tetrahedron. 01/2003; 59(24):4405-4413.
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ABSTRACT: The first isorhapontigenin tetramer, gnetuhainin R (1) and a novel dimeric stilbene, gnetuhainin S (2) were isolated from the lianas of Gnetum hainanense. Their structures were elucidated on the basis of spectroscopic and chemical evidence, especially 2D NMR analysis. The structure of 2 was further supported by X-ray crystallographic analysis. The anti-inflammatory activity of 1 has been tested, and it showed potent activity of histamine receptor antagonism.
Planta Medica 11/2002; 68(10):916-20. · 2.15 Impact Factor
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Yao xue xue bao = Acta pharmaceutica Sinica 02/2002; 37(1):69-74.
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ABSTRACT: Two novel resveratrol trimers, amurensins C (1), D (2), and two novel resveratrol pentamers, amurensins E (3), F (4) were isolated from the roots of Vitis amurensis Rupr. Their structures and relative or absolute configurations were determined by means of spectroscopic evidence, especially HMBC and NOE experiments. 2, 3 and 4 are new types of resveratrol oligomers and are reported here for the first time. The pharmacological activities on anti-inflammation of all amurensins have been tested. Among them, compound 4 showed potent inhibition on biosynthesis of leukotriene B4 (LTB4).
Tetrahedron. 56(10):1321-1329.
