A Concise Total Synthesis of Triptolide

Yang, Dan; Ye, Xiang‐Yang; Xu, Ming; Pang, Kwan‐Wah; Zou, Ning; Letcher, R. M.

doi:10.1021/jo981362g

Cited by 38 publications

(17 citation statements)

References 27 publications

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“…Along with anti-inflammatory activity, it shows anticancer, immunosuppressive, and antifertility effects (Qiu and Kao, 2003). It was isolated in 1972, and several synthetic routes have been described since then (Yang et al, 1998 and references therein). Like artemisinin, however, triptolide is currently derived from its plant of origin with low yield: 6-16 ng/g in one study (Brinker and Raskin, 2005).…”

Section: Triptolide and Celastrol: Harnessing The Power Of The Thundementioning

confidence: 99%

Molecular Understanding and Modern Application of Traditional Medicines: Triumphs and Trials

Corson

Crews

2007

Cell

547

378

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Section: Triptolide and Celastrol: Harnessing The Power Of The Thundementioning

confidence: 99%

Molecular Understanding and Modern Application of Traditional Medicines: Triumphs and Trials

Corson

Crews

2007

Cell

547

378

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“…A single crystal of 29 suitable for X‐ray analysis was obtained, which allowed unambiguous determination of its relative configuration (Figure 2). The mechanism of the reaction was proposed based on Snider’s and Nishino’s mechanistic studies (Scheme ) 13c. 15a We considered that the reaction of the acyl tetramic acid moiety in 1 with Mn(OAc) 3 formed the manganese enolate 30 , which then underwent a 5‐ exo cyclization to give the radical 31 .…”

Section: Resultsmentioning

confidence: 99%

Fabrication and optical characterization of poly(2,5‐di‐n‐butoxyphenylene) nanofibril arrays

Gao

2003

J of Applied Polymer Sci

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Anodic aluminum oxide (AAO) membrane can be used as template for the synthesized nanostructures. In this article, we have prepared the AAO membrane by using electrooxidation of aluminum substrate in phosphoric acid, and fabricated poly(2,5-di-n-butoxyphenylene) (BuO-PPP) nanofibril arrays by oxidative coupling polymerization of 1,4-di-n-butoxybenzene (DBB) within the pores of the AAO template membrane. The detailed molecular structure of the polymer nanofibrils was characterized by using infrared and 1 H nuclear magnetic resonance spectra, and estimated to consist of almost equal fractions of 1,4-and 1,3-linkages. We have used transmission electron microscopy, scanning electron microscopy, and atom force microscopy to confirm the morphologies and images of the AAO template membrane and the fabricated nanometer scale of BuO-PPP nanofibril arrays. The experimental results demonstrated that the pores of the AAO membrane were regular and uniform, and parallel each other, and the BuO-PPP chains in the narrowest template-synthesized nanofibrils were oriented parallel to the porous axes of the AAO membrane and perpendicular to the surface of the aluminum substrate. The polymer chain orientation was partially responsible for the enhanced conductivity. The ultraviolet absorption spectrum of the BuO-PPP nanofibril arrays shown that the polymer contains a better extended -conjugation system along poly-(p-phenylene) backbone, which resulted in longer wavelength shift of the absorption band, the absorption maxima were located at 258 nm (E 1 absorption band) and 332 nm (E 2 absorption band), respectively. Photoluminescence spectrum of the BuO-PPP nanofibril arrays exhibited a blue emission.

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“…1. All derivatives were synthesised in the Department of Chemistry at the University of Hong Kong, according to previously reported techniques 20 . All stock solutions of the naturally occurring compounds and synthetic derivatives were prepared by dissolving them in dimethylsulphoxide (Sigma, St Louis, MO, USA) 21 .…”

Section: Methodsmentioning

confidence: 99%

IMMUNOCHEMICAL CHARACTERIZATION OF THE FUNCTIONAL CONSTITUENTS OF TRIPTERYGIUM WILFORDII CONTRIBUTING TO ITS ANTI‐INFLAMMATORY PROPERTY

Wong

Chan

et al. 2007

Clin Exp Pharma Physio

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1. Tripterygium wilfordii (TW) contains bioactive compounds that possess immunosuppressive properties. These compounds are considered to be potential drugs in the treatment of acute graft rejections. However, their structure-activity relationships remain unknown. 2. The aim of the present study was to delineate the molecular moieties of triptolide that could account for its ability to inhibit inflammatory responses. In this context, purified TW active compounds (triptolide and triptonide) and synthetic triptolide derivatives were prepared to investigate the structure-activity relationships of triptolide. To this end, rat splenocytes were treated with increasing concentrations of the compounds and then allogenically stimulated using a mixed lymphocyte reaction to determine their antiproliferative activities. From the results, the IC50 value of each compound was calculated. 3. Modification of the beta-hydroxyl group at the C-14 position of the triptolide molecule significantly affected the immunosuppressive activity of T59, as demonstrated by a sevenfold increase of the IC50. Conversely, reduction of the gamma-butyrolactone group in T60 and T61 completely abrogated the antiproliferative effect. Alterations in the C-14 beta-hydroxyl and gamma-butyrolactone groups also resulted in reduced cytotoxicity. 4. The present findings demonstrate that the C-14 beta-hydroxyl and gamma-butyrolactone moieties of the triptolide molecule are crucial for its anti-inflammatory properties and cytotoxicity and are responsible for the compound's antiproliferative activity.

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A Concise Total Synthesis of Triptolide

Cited by 38 publications

References 27 publications

Molecular Understanding and Modern Application of Traditional Medicines: Triumphs and Trials

Molecular Understanding and Modern Application of Traditional Medicines: Triumphs and Trials

Fabrication and optical characterization of poly(2,5‐di‐n‐butoxyphenylene) nanofibril arrays

IMMUNOCHEMICAL CHARACTERIZATION OF THE FUNCTIONAL CONSTITUENTS OF TRIPTERYGIUM WILFORDII CONTRIBUTING TO ITS ANTI‐INFLAMMATORY PROPERTY

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