Terpenoids from Tripterygium wilfordii

An abietane diterpenoid, triptobenzene Y and six sesquiterpene polyol esters, wilforsinines C-H, together with 14 known compounds, have been isolated from the roots of Tripterygium wilfordii. The structures of the compounds were elucidated on the basis of spectroscopic analyses. The quinone reductase (QR) induction assay indicated that two compounds showed moderate QR-inducing activities at concentrations of 25 μM and 50 μM, respectively.     

Sesquiterpene polyol esters from Tripterygium wilfordii

The extract (T(II)) of Tripterygium wilfordii Hook f. afforded four sesquiterpene esters: 1beta,2beta,5alpha,8beta,11-pentaacetoxy-4alpha-hydroxy-3alpha(2'-methylbutanoyl)-15-nicotinoyl-7-oxo-dihydroagarofuran; 1beta,5alpha,11-triacetoxy-7beta-benzoyl-4alpha-hydroxy-8beta-nicotinoyl-dihydroagarofuran; 1beta,2beta,5alpha,11-tetraacetoxy-8alpha-benzoyl-4alpha-hydroxy-7beta-nicotinoyl-dihydroagarofuran; 5alpha-benzoyl-4alpha-hydroxy-1beta,8alpha-dinicotinoyl-dihydro- agarofuran as well as one other known sesquiterpene ester. Their structures were established on the basis of spectroscopic studies.     

Polyhydroxyagarofuran derivatives from Tripterygium wilfordii H.

Three new and two known dihydroagarofuran derivatives were isolated from the leaves of T. wilfordii and their structures established by chemical and spectroscopic means.     

Anti-inflammatory and immunosuppressive compounds from Tripterygium wilfordii

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.     

Euphane and friedelane triterpenoids from Tripterygium wilfordii

Four hitherto unknown triterpenoids, including one euphane, namely wilfordeuphone (1), and three friedelanes, namely wilforic acids G − I (2–4), were isolated from the ethanol extract of the roots of Tripterygium wilfordii. The absolute configuration of 1 was established by single crystal X-ray diffraction. In addition, this study is the first to report euphane-type triterpenoid in the genus Tripterygium. Compound 1 exhibited the moderate cytotoxic activity when evaluated against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480), with IC50 values ranging from 14.0–26.7 μM.     

Terpenoids from Tripterygium wilfordii var. regelii

The methanol extract of dried stem barks of Tripterygium wilfordii Hook fil. var regelii afforded two new triterpenes: 22-hydroxy-3, 19,24-trinor-D:A-friedoolenane-1(10), 5, 7-triene-2-oic acid methyl ester, named regelone, and 3-methyl-23-ol-oxotingenol; a new diterpene—8β, 19-dihydroxy-3-oxopimar- 15-ene; and three known triterpenes-3-methyl-22-β, 23-diol-6-oxotingenol, tingenin B and cangoronin. Their structures were established on the basis of chemical and spectroscopic studies. ©1997 Elsevier Science Ltd. All rights reserved     

Structural Study of Dichlorotriptetraolide Isolated from Tripterygium wilfordii

A new chlorinated diterpene epoxide, dichlorotriptetraolide (L5) was isolated from the leaves of Tripterygium wilfordii Hook. f. Dichlorotriptetraolide was crystallized from CH3OH as colorless needle-like crystal, with amp of 252.0～253.5 ℃. Its molecular formula is C2oH26O7Cl2. The structure was identified on the basis of spectral analyses (UV, 1H-NMR, 13C-NMR. 13C-NOE. 2D-cosy. LD/FTMS. EIMS, selective long-range DEPT spectrum and X-ray fluorescence spectrum) and computerization of molecular mechanics and molecular graph.     

Structural Study of Triptriolide Isolated from Tripterygium wilfordii

A novel diterpene bisepoxide, ,riptriolide was isolated from the root and leaves of Tripterygium wilfordii Hook- f. Triptriolide was obtained as white cluster crystal, mp. 260-262℃. Its molecular formula is C20H26O7. The structure and stereochemistry of triptriolide were determined by UV, IR, MS, 1H-NMR, 13C-NMR, 2d-NMR, 13C-NOE, NOE difference spectroscopy and direct X-ray crystallographic analysis. Preliminary pharmacologic assay revealed that triptriolide has a potent anti-inflammatory action.     

雷公藤化学成分的研究

研究雷公藤(Tripterygium wilfordii Hook．f．)根心部分的化学成分。采用硅胶柱色谱法进行分离,从其氯仿提取物中分得五个化合物,经波谱分析化合物分别鉴定为：5α-stigmastane-3β,6α-diol(1)、epigallocatechin(2)、2,5-二甲氧基苯醌(3)、琥珀酸(4)和卫矛碱(5)。化合物1—4均为首次从该植物中分离得到。     

Structural Study of 12-epitriptriolide Isolated from Tripterygium wilfordii

A new diterpene bisepoxide, 12-epitriptriolide (L1) was isolated from the leaves and roots of Tripterygium wilfordii Hook f. and from the marketed drug "Total Glycoside of Tripterygium wilfordii". This compound was crystallized from CHC13 as colorless needles,mp 267.5-269.5 C. Its molecular formula is C20H26O7. The structure was identified on the basis of spectral data (IR, MS, UV,1H-NMR,13C NMR, 2D-NMR,13C-NOE, NOE difference spectroscopy and selective long-range DEPT NMR) analyses. 12-epitriptriolide was shown to have a potent anti-inflammatory action. Its effective dose was 40 mg/kg with the murine model of ear swelling induced by croton oil while that of triptriolide was 70 mg/kg . The results showed that the action of the structure in connection with 12-αOH was about 2 times stronger than that of 12-βOH. 12-epitriptriolide showed no immunosuppressive and antifertility (male) actions in mice and had low toxicity (LD50>250 mg/kg ) in experimental animals. The preliminary assay for the structure-activity relationship revealed that the epoxide group on C12.13 of diterpene from T. wilfordii was one of the key positions associated with immunosuppressive and antifertility actions and toxicioty.     

Insecticidal compounds from Tripterygium wilfordii active against Mythimna separata

In the course of screening for novel naturally occurring insecticides from plants, the ethanol extract of the root bark of Tripterygium wilfordii Hook f. was found to show insecticidal activity against larvae of Mythimna separata Walker. Three active compounds were isolated by bioassay-guided fractionation of the extract and characterized as triptolide (1), triptonide (2) and euonine (3) by IR, 1H and 13C NMR and mass spectral analysis. Compounds 1 and 2 showed strong contact activity against 3rd or 5th larvae of M. separata (LD50 1.6 microg/insect for 1, 2.9 microg/insect for 2, no contact activity for 3; LD50 is the lethal dose for 50% mortality). The antifeedant activity against the 3rd larvae of M. separata after a 24-h treatment was demonstrated; 1, 2 and 3 gave EC50 (effective concentration causing 50% antifeedance) values of 0.25, 0.35 and 0.02 mM, respectively. 1 and 2 were inferior to the positive control represented by toosendanin (12a-acetoxyamoorastatin), 3 was superior to toosendanin. For the ingested toxicity against M. separata, 1 had the more potent activity with an KD50 value of 13.5 microg/g (insect body weight) than toosendanin. This is the first report on insecticidal activity of these three compounds.     

Study of Sesquiterpene Alkaloids from Tripterygium wilfordii (IV)

Two sesquiterpene alkaloids,wilforine and wilfordsuine were isolated from Tripterygium wilfordii Hook. f. Wilfordsuine was a new alkaloid. The structures of wilforine and wilfordsuine were elucidated on the basis of spectral data,especially 2D-NMR techniques　(H'-'H COSY,H'-13C COSY, NOESY, COLOC methods).     

Study on the Triterpenoids of Tripterygium regeli

Ten triterpenoids were isolated from the ethanol extract of the roots of Tripteryglum regeli collected from Jilin Province, north-eastern China. They were identified as wilforlide A(1), wilforlide B(2), regelide (3) 3β-hydroxy-olean-ll,13(18)-diene (4), orthosphenic acid (5), salaspermic acid (6), 3-epikatonic acid(7), maytenfolic acid (8), 3β-acetyl-oleanolic acid (9), and celastrol (19), by spectroscopic analyses and chemical correlations. Compound 3—10 were isolated from T. regeli for the first time, among them regelide 3 was a new comound and its structure was elucidated to be 3-keto-22α-hydroxy-olean-ll,13(18)-dien-29-oic acid(29, 22α)-lactone. 3-epikatonic acid(7)showed obvious spermicidal effect, while cealstrol (10)revealed significant immunosuppressive activity.     

Studies on Neotriptetraolide Isolated from Tripterygium wilfordii Hook. f.

A new diterpenoid bisepoxide, neotriptetraolide, was isolated from the leaves and root of Tripterygium wilfordii Hook. f. Neotriptetraolide was crystallized from CH3OH as colorless needle-like crystal, with amp of 237～238 ℃. Its molecular formula was C20H2608. Its structure was elucidated by means of spectral analysis (UV, IR, MS, 1H-NMR, 13C- NMR, 2D-COSY, 2D-NOESY, 13C-NOE, and selective long-range DEPT spectroscopy) and the computation of molecular mechanics and molecular graph.     

Molecular Cloning and Characterisation of Farnesyl Pyrophosphate Synthase from Tripterygium wilfordii

Farnesylpyrophosphate synthase (FPS) catalyzes the biosynthesis of farnesyl pyrophosphate (FPP), which is an important precursor of sesquiterpenoids such as artemisinin and wilfordine. In the present study, we report the molecular cloning and characterization of two full-length cDNAs encoding FPSs from Tripterygium wilfordii (TwFPSs). TwFPSs maintained their capability to synthesise FPP in vitro when purified as recombinant proteins from E. coli. Consistent with the endogenous role of FPS in FPP biosynthesis, TwFPSs were highly expressed in T. wilfordii roots, and were up-regulated upon methyl jasmonate (MeJA) treatment. The global gene expression profiles suggested that the TwFPSs might play an important regulatory role interpenoid biosynthesis in T. wilfordii, laying the groundwork for the future study of the synthetic biology of natural terpene products.     

The Isolation and Structure of Three New Diterpenes from Tripterygium wilfordii Hook

This paper deals with the isolation of three new diterpenes: triptono-terpene, triptonoterpene methyl ether and triptolidenol from Tripterygium wilfordiiHook. F. Their structures are assigned as Ⅰ, Ⅱ, and Ⅲ, respectively by means of spectors-copic analyses (UV, IR, 1HNMR and MS), preparation of the derivative and chemicaltransformations.     

雷公藤组织培养技术体系建立

以生长健壮、无病虫害的雷公藤Tripterygium wilfordii为材料,采用正交试验设计,探讨其茎段的再生技术。结果表明,雷公藤芽诱导最适培养基为MS + 6-BA 1.5 mg·L-1 + IBA 0.1 mg·L-1;继代增殖最适培养基为MS + 6-BA 1.0 mg·L-1 + NAA 0.1 mg·L-1;壮苗培养最适培养基为MS + 6-BA 0.5 mg·L-1 + VB1 0.5 mg·L-1 + 蛋白胨0.5 g·L-1;生根培养最佳培养基为1/2MS + NAA 2.0 mg·L-1 + KT 0.1 mg·L-1;炼苗移栽时,基质配比为蛭石与泥炭土 1:1。移栽30 d后,成活率达84.5%。     

Anti-inflammatory oleanane triterpenes from Tripterygium wilfordii cell suspension cultures by fungal elicitation

Summary Treatment of cell suspension cultures of Tripterygium wilfordii with an autoclaved Botrytis sp. homogenate rapidly increased the synthesis of a family of oleanane and friedelane triterpenes, including the antiinflammatory oleanane triterpene 3,22-dihydroxyolean-12-en-29-oic acid. This compound exceeded 30 mg · l^–1 in 13 day elicitations with 12 l bioreactors, in contrast to control levels of less than 5 mg · l^–1. Cell cultures treated with the fungal elicitor provided higher triterpene yields in less time than cultures in a diterpene production medium or whole plants. Elicited production has been developed for commercial application in light of the successful treatment of rheumatoid arthritis with Tripterygium extracts.     

雷公藤粗提物毒力测定及甲素含量分析

以无水乙醇为溶剂从雷公藤根皮中提取有效成分,用高效液相色谱法分析雷公藤粗提物中甲索含量,并将雷公藤粗提物配成5％的乳油,用浸叶法和药膜法测定小菜蛾二龄幼虫、烟粉虱成虫以及无翅成蚜的室内毒力,并以几种杀虫剂作为对比。结果表明：该批雷公藤粗提物中甲素含量为0．0012％;5％雷公藤粗提物乳油对小菜蛾二龄幼虫、烟粉虱成虫以及无翅成蚜具有一定的生物活性,但与其他几种常用杀虫剂相比活性较低,还需对其进一步精制和提纯。