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Yoshihisa Takaishi - One of the best experts on this subject based on the ideXlab platform.
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immunosuppressive terpenoids from Tripterygium wilfordii
Chinese Chemical Letters, 2008Co-Authors: Qian Shen, Yoshihisa Takaishi, Yan-wen Zhang, Hong Quan DuanAbstract:Abstract Two new terpenes, triptobenzene P (1) and wilforone (2) were isolated from Tripterygium wilfordii, as well as 10 known terpenes. Their structures were elucidated by spectroscopic methods. Compounds 2–4, 8, 10, and 11 showed significant immunosuppressive activities.
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tripfordines a c sesquiterpene pyridine alkaloids from Tripterygium wilfordii and structure anti hiv activity relationships of Tripterygium alkaloids
Journal of Natural Products, 2006Co-Authors: Masafumi Horiuch, Yoshihisa Takaishi, Kenneth F Bastow, De Cheng Zhang, Chihiro Murakami, Narihiko Fukamiya, Donglei Yu, Tzu Hsuan Chen, Yasuo ImakuraAbstract:Three new sesquiterpene pyridine alkaloids, tripfordines A−C (1−3), were isolated from an ethanolic extract of the roots of Tripterygium wilfordii, along with eight known pyridine alkaloids, and tested for in vitro cytotoxic and anti-HIV activity. The structures of the new compounds were established on the basis of spectroscopic data interpretation. Anti-HIV structure−activity relationships (SAR) for this compound type are proposed on the basis of the screening results from the newly isolated compounds and prior data of known sesquiterpene pyridine alkaloids. The position of a carboxyalkyl chain on the pyridine moiety was not critical since both 2‘- and 4‘-substituted compounds exhibited high anti-HIV activity (EC50 0.1 μg/mL). In contrast, a hydroxy group at C-8‘ (carboxypropyl side chain) or C-9‘ (carboxybutyl side chain) was found to affect anti-HIV activity.
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kaurane and abietane diterpenoids from Tripterygium doianum celastraceae
Phytochemistry, 2004Co-Authors: Naonobu Tanaka, Hong Quan Duan, Yoshihisa Takaishi, Nobuyuki Ooba, Yuka Nakanishi, Kenneth F Bastow, Kuo Hsiung LeeAbstract:Extraction of Tripterygium doianum (Celastraceae) afforded five new diterpenoids and 11 known diterpenoids belonging to the ent-kaurane and abietane families. Their structures were established based on spectroscopic studies. The isolated compounds showed moderate cytotoxicity against human tumor cell assays.
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immunosuppressive terpenoids from extracts of Tripterygium wilfordii
Tetrahedron, 2001Co-Authors: Hong Quan Duan, Hiroshi Momota, Takao Taki, Yasukazu Ohmoto, Yoshihisa Takaishi, Motoo Tori, Shigeru Takaoka, Duan LiAbstract:Abstract The clinically used extract (TΠ) of Tripterygium wilfordii Hook f. give 19 new compounds, including five kaurane diterpenes (1–5), one manoyl oxide diterpene (6), and one abietane diterpene (7), three ursene triterpenes (8, 9 and 15), six oleanane triterpenes (10–13, 16 and 19), and three friedelane triterpenes (14, 17 and 18), as well as 15 known compounds (20–34). Their structures were elucidated by spectroscopy and X-ray analysis. Based on the screening of isolated compounds and other compounds reported in previous papers [J. Nat. Prod. 62 (1999) 1522; J. Nat. Prod. (2001) in press; Phytochemistry 53 (2000) 805], we identified the main components that are responsible for the therapeutic effect of TΠ.
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immunosuppressive sesquiterpene alkaloids from Tripterygium wilfordii
Journal of Natural Products, 2001Co-Authors: Hong Quan Duan, Hiroshi Momota, Takao Taki, Yasukazu Ohmoto, Yoshihisa Takaishi, Duan LiAbstract:: Nine new sesquiterpene pyridine alkaloids [wilfornines A (1), B (2), C (3), D (4), E (5), F (8), and G (9); wilfordinines I (6) and J (7)] and six known compounds (10-15) were isolated from a clinically used extract (T(II)) of Tripterygium wilfordii. The structures of 1-9 were elucidated by spectroscopic and chemical methods. The inhibitory effects on cytokine production of 1-3 and several related compounds were evaluated. Compounds 10 and 14 showed significant inhibitory effects on cytokine production.
Hong Quan Duan - One of the best experts on this subject based on the ideXlab platform.
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immunosuppressive terpenoids from Tripterygium wilfordii
Chinese Chemical Letters, 2008Co-Authors: Qian Shen, Yoshihisa Takaishi, Yan-wen Zhang, Hong Quan DuanAbstract:Abstract Two new terpenes, triptobenzene P (1) and wilforone (2) were isolated from Tripterygium wilfordii, as well as 10 known terpenes. Their structures were elucidated by spectroscopic methods. Compounds 2–4, 8, 10, and 11 showed significant immunosuppressive activities.
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kaurane and abietane diterpenoids from Tripterygium doianum celastraceae
Phytochemistry, 2004Co-Authors: Naonobu Tanaka, Hong Quan Duan, Yoshihisa Takaishi, Nobuyuki Ooba, Yuka Nakanishi, Kenneth F Bastow, Kuo Hsiung LeeAbstract:Extraction of Tripterygium doianum (Celastraceae) afforded five new diterpenoids and 11 known diterpenoids belonging to the ent-kaurane and abietane families. Their structures were established based on spectroscopic studies. The isolated compounds showed moderate cytotoxicity against human tumor cell assays.
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immunosuppressive terpenoids from extracts of Tripterygium wilfordii
Tetrahedron, 2001Co-Authors: Hong Quan Duan, Hiroshi Momota, Takao Taki, Yasukazu Ohmoto, Yoshihisa Takaishi, Motoo Tori, Shigeru Takaoka, Duan LiAbstract:Abstract The clinically used extract (TΠ) of Tripterygium wilfordii Hook f. give 19 new compounds, including five kaurane diterpenes (1–5), one manoyl oxide diterpene (6), and one abietane diterpene (7), three ursene triterpenes (8, 9 and 15), six oleanane triterpenes (10–13, 16 and 19), and three friedelane triterpenes (14, 17 and 18), as well as 15 known compounds (20–34). Their structures were elucidated by spectroscopy and X-ray analysis. Based on the screening of isolated compounds and other compounds reported in previous papers [J. Nat. Prod. 62 (1999) 1522; J. Nat. Prod. (2001) in press; Phytochemistry 53 (2000) 805], we identified the main components that are responsible for the therapeutic effect of TΠ.
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immunosuppressive sesquiterpene alkaloids from Tripterygium wilfordii
Journal of Natural Products, 2001Co-Authors: Hong Quan Duan, Hiroshi Momota, Takao Taki, Yasukazu Ohmoto, Yoshihisa Takaishi, Duan LiAbstract:: Nine new sesquiterpene pyridine alkaloids [wilfornines A (1), B (2), C (3), D (4), E (5), F (8), and G (9); wilfordinines I (6) and J (7)] and six known compounds (10-15) were isolated from a clinically used extract (T(II)) of Tripterygium wilfordii. The structures of 1-9 were elucidated by spectroscopic and chemical methods. The inhibitory effects on cytokine production of 1-3 and several related compounds were evaluated. Compounds 10 and 14 showed significant inhibitory effects on cytokine production.
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triterpenoids from Tripterygium wilfordii
Phytochemistry, 2000Co-Authors: Hong Quan Duan, Hiroshi Momota, Takao Taki, Yasukazu Ohmoto, Yoshihisa Takaishi, Duan LiAbstract:Abstract The extract (T II ) of Tripterygium wilfordii Hook f. afforded four triterpenoids: wilforic acid D (3β,24-epoxy-2α-hydroxy-24R ∗ -ethoxy-29-friedelanoic acid); (E) 3β,24-epoxy-2-oxo-3α-hydroxy-29-friedelanoic acid; (F) 2β-hydroxy-3-oxo-friedelan-29-oic acid; 29-hydroxy-3-oxo-olean-12-en-28-oic acid and 17 known triterpenoids. Their structures were established on the basis of spectroscopic studies. In a bioactivity analysis, only the known dulcioic acid compound showed a significant inhibitory effect on cytokine production.
Dongming Zhang - One of the best experts on this subject based on the ideXlab platform.
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triptergosidols a d nerolidol type sesquiterpene glucosides from the leaves of Tripterygium wilfordii
Fitoterapia, 2018Co-Authors: Chuangjun Li, Lin Ni, Li Li, Fangyou Chen, Dongming ZhangAbstract:Abstract Four new nerolidol-type sesquiterpene glucosides, triptergosidols A-D (1-4) were isolated from the leaves of Tripterygium wilfordii. Three aglycones, named triptergerols A (1a), B (2a), and C (3a), were acquired by enzymatic hydrolysis of 1-3. The structures of nerolidol-type sesquiterpenes were elucidated on base of kinds of spectroscopic analysis, and their absolute configurations were determined by CD method. In addition, compounds 1-4 were tested for cytotoxicity against two cell lines and inhibitory effects against NO production in RAW264.7 macrophage.
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neuroprotective dihydroagarofuran sesquiterpene derivatives from the leaves of Tripterygium wilfordii
Journal of Natural Products, 2018Co-Authors: Fangyou Chen, Chuangjun Li, Li Li, Jian Zhou, Zhao Zhang, Naihong Chen, Dongming ZhangAbstract:Thirteen dihydroagarofuran derivatives, including 12 new sesquiterpenoid esters and one known sesquiterpenoid alkaloid, were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques and the ECD method were used for the structure elucidation of the compounds. The structures of compounds 1 and 8 were confirmed by single-crystal X-ray crystallographic analyses. Compounds 8, 9, 11, 12, and 13 increased cell viability of the okadaic acid treated PC12 cells from 60.4 ± 23.0% to 72.4 ± 14.1, 71.5 ± 11.5, 75.7 ± 15.6, 81.2 ± 13.1, and 86.2 ± 25.5% at 10 μM, respectively.
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New 18(4→3)-Abeo-Abietanoids from Tripterygium wilfordii
MDPI AG, 2018Co-Authors: Ying-da Zang, Jingzhi Yang, Dongming ZhangAbstract:Three 18(4→3)-abeo-abietanoids, a new natural product and two new compounds, named tripordolides A–C (1–3), were isolated from the leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of compounds was confirmed by CD and X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1 and 3 showed moderate inhibitory activities against NO production in lipopolysaccharide-induced (LPS) RAW 264.7 macrophages in vitro
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Neuroprotective Dihydroagarofuran Sesquiterpene Derivatives from the Leaves of Tripterygium wilfordii
2018Co-Authors: Fangyou Chen, Jian Zhou, Zhao Zhang, Naihong Chen, Dongming ZhangAbstract:Thirteen dihydroagarofuran derivatives, including 12 new sesquiterpenoid esters and one known sesquiterpenoid alkaloid, were obtained from the leaves of Tripterygium wilfordii. Spectroscopic techniques and the ECD method were used for the structure elucidation of the compounds. The structures of compounds 1 and 8 were confirmed by single-crystal X-ray crystallographic analyses. Compounds 8, 9, 11, 12, and 13 increased cell viability of the okadaic acid treated PC12 cells from 60.4 ± 23.0% to 72.4 ± 14.1, 71.5 ± 11.5, 75.7 ± 15.6, 81.2 ± 13.1, and 86.2 ± 25.5% at 10 μM, respectively
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Anti-inflammatory Sesquiterpene Derivatives from the Leaves of Tripterygium wilfordii
2016Co-Authors: Chao Wang, Xiaoguang Chen, Jingzhi Yang, Qi Hou, Dongming ZhangAbstract:Twelve new dihydroagarofuran sesquiterpene polyol esters, triptersinines A–L (1–12), and eight known sesquiterpene pyridine alkaloids were isolated from the leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of spectroscopic analyses, including UV, IR, and NMR experiments (1H–1H COSY, NOESY, HSQC, and HMBC). Furthermore, in an in vitro bioassay, compounds 1, 9, 11, 13, 14, and 18 showed moderate inhibitory effects on nitric oxide production in LPS-induced macrophages at 5 μM; all compounds were inactive when tested against five human cancer cell lines (IC50 values >1 μM)
Ilya Raskin - One of the best experts on this subject based on the ideXlab platform.
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corrigendum to medicinal chemistry and pharmacology of genus Tripterygium celastraceae phytochemistry 68 2007 732 766
Phytochemistry, 2007Co-Authors: Anita M Brinker, Peter E Lipsky, Ilya RaskinAbstract:Corrigendum Corrigendum to ‘‘Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)’’ [Phytochemistry 68 (2007) 732–766] Anita M. Brinker , Jun Ma , Peter E. Lipsky , Ilya Raskin a,* a Biotechnology Center for Agriculture and the Environment, Furan Hall, Cook College, The State University of New Jersey, 59 Dudley Road, New Brunswick, NJ 08901-8520, USA b Autoimmunity Branch, National Institute of Arthritis and Musculoskeletal and Skin Diseases, National Institutes of Health, Rockville Pike, Bethesda, MD 20892, USA Available online 26 April 2007
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anti inflammatory and immunosuppressive compounds from Tripterygium wilfordii
Phytochemistry, 2007Co-Authors: Hui Yang, Peter E Lipsky, Alexander Poulev, Reneta Pouleva, Ruth Dorn, Edward J Kennelly, Ilya RaskinAbstract:The extract of Tripterygium wilfordii Hook F. (TwHF), which showed anti-inflammatory and immunosuppressive activities in human clinical trials for rheumatoid arthritis, was subjected to the activity-guided fractionation and spectroscopic characterization of bioactives. A tetrahydrofuran lignan, tripterygiol (1), and eight known compounds, all capable of suppressing pro-inflammatory gene expression were identified. Most of the pharmacological activity of the extract can be attributed to triptolide, its most abundant and active component, with some contribution from tripdiolide.
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medicinal chemistry and pharmacology of genus Tripterygium celastraceae
Phytochemistry, 2007Co-Authors: Anita M Brinker, Peter E Lipsky, Ilya RaskinAbstract:Plants in the genus Tripterygium, such as Tripterygium wilfordii Hook.f., have a long history of use in traditional Chinese medicine. In recent years there has been considerable interest in the use of Tripterygium extracts and of the main bioactive constituent, the diterpene triepoxide triptolide (1), to treat a variety of autoimmune and inflammation-related conditions. The main mode of action of the Tripterygium extracts and triptolide (1) is the inhibition of expression of proinflammatory genes such as those for interleukin-2 (IL-2), inducible nitric oxide synthase (iNOS), tumor necrosis factor-alpha (TNF-alpha), cyclooxygenase-2 (COX-2) and interferon-gamma (IFN-gamma). The efficacy and safety of certain types of Tripterygium extracts were confirmed in human clinical trials in the US and abroad. Over 300 compounds have been identified in the genus Tripterygium, and many of these have been evaluated for biological activity. The overall activity of the extract is based on the interaction between its components. Therefore, the safety and efficacy of the extract cannot be fully mimicked by any individual constituent. This review discusses the biochemical composition and biological and pharmacological activities of Tripterygium extracts, and their main bioactive components.
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determination of triptolide in root extracts of Tripterygium wilfordii by solid phase extraction and reverse phase high performance liquid chromatography
Journal of Chromatography A, 2005Co-Authors: Anita M Brinker, Ilya RaskinAbstract:Abstract Extracts of Tripterygium wilfordii roots have a long history of use in traditional Chinese medicine and have shown great promise in recent clinical trials as a treatment for rheumatoid arthritis. The major active component of Tripterygium root extracts is the diterpenoid triptolide. This paper describes a method for the determination of triptolide in root extracts that is suitable for the analysis of many small samples simultaneously. Extracts are applied to aminopropyl solid-phase extraction (SPE) tubes that are then eluted with dichloromethane–methanol (49:1, v/v). The eluate is chromatographed on a pentafluorophenyl HPLC column using an acetonitrile:water gradient. Triptolide is quantified by ultraviolet detection at 219 nm. Using this method, it was shown that smaller diameter roots with secondary growth contained higher triptolide concentrations than larger roots. This suggests that roots to be used for production of the drug extract could be harvested while still small, which would reduce the growing time necessary and thus be economically beneficial for the growers.
Kuo Hsiung Lee - One of the best experts on this subject based on the ideXlab platform.
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diterpenoids from the stems of Tripterygium hypoglaucum celastraceae and cytotoxic evaluation
Phytochemistry Letters, 2015Co-Authors: Ling Huan Gao, Kuo Hsiung Lee, Li Ting WangAbstract:Abstract Four new diterpenoids, 2α,16α-hydroxy- ent -kauran-19,20-olide ( 1 ), isopimara-8(14),15-diene-11β,19-diol ( 2 ), isopimara-8(14),15-diene-12α,19-diol ( 3 ), and 3-oxo-14,15-dihydroxyabieta-8,11,13-trien-19-ol ( 4 ), along with seven known compounds ( 5 – 11 ) were isolated from Tripterygium hypoglaucum . Their structures were established on the basis of extensive spectroscopic analysis. Triptolide ( 5 ) and 2-epitripdiolide ( 6 ) showed significant cytotoxicity against A549, DU145, KB, KBvin and MDA-MB-231 cell lines with IC 50 values of 0.0012–0.1306 μM in vitro .
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kaurane and abietane diterpenoids from Tripterygium doianum celastraceae
Phytochemistry, 2004Co-Authors: Naonobu Tanaka, Hong Quan Duan, Yoshihisa Takaishi, Nobuyuki Ooba, Yuka Nakanishi, Kenneth F Bastow, Kuo Hsiung LeeAbstract:Extraction of Tripterygium doianum (Celastraceae) afforded five new diterpenoids and 11 known diterpenoids belonging to the ent-kaurane and abietane families. Their structures were established based on spectroscopic studies. The isolated compounds showed moderate cytotoxicity against human tumor cell assays.
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novel sesquiterpene esters with alkaloid and monoterpene and related compounds from Tripterygium hypoglaucum a new class of potent anti hiv agents
Tetrahedron Letters, 1999Co-Authors: Hong Quan Duan, Yoshihisa Takaishi, Masaru Kido, Masahiko Bando, Yasuo Imakura, Kuo Hsiung LeeAbstract:Abstract Two new sesquiterpene polyol esters (triptonine A and B) with alkaloid and monoterpene were isolated from Tripterygium hypoglaucum (Levl.) Hutch. Their structures were elucidated by spectroscopic means and X-ray analysis. Triptonine A ( 1 ) and hypoglaunine B 3) ( 4 ) demonstrated potent anti-HIV activity with EC 50 values of 2.54 and 0.13μg/ml and therapeutic index values of 39.4 and >1000, respectively.
