Two Prenylated and C-methylated Flavonoids from Tripterygium wilfordii Hook. F. (Celastraceae)

Zeng, Fanhao; Wang, W; Wu, Yuefeng; Ye, M; Avery, MA; Khan, IA; Guo, Di

doi:10.1055/s-0030-1251804

Cited by 5 publications

(11 citation statements)

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“…Triptolide (1) was purchased from Sichuan Victory Biotechnology Co. Triptonide (2) was purchased from Shanghai Yuanye Biology Co. Reserpine (i. s.) was obtained from Chengdu Munster Biotechnology Ltd., Co., and celastrol (17) was purchased from Shanghai Forever Biotech Co., Ltd. Their purities were above 98 % as shown by HPLC-UV analysis. Triptonoterpenol (3), triptonoditerpenic acid (4), isoneotriptophenolide (5), triptophenolide (6), triptonoterpene methyl ether (7), triptonoterpene (8), wilfortrine (9), wilfordine E (10), peritassine A (11), wilfordinine D (12), wilforine (13), demethylastral (14), cangoronine (15), wilforic acid F (16), and wilforlide B (18), were all isolated from an ethyl acetate extract of T. wilfordii, and their structures were elucidated through NMR and MS techniques. All isolated compounds were purified (above 98%) by preparative HPLC and their purities determined by 1 H-NMR and HPLC analysis.…”

Section: Solvents and Chemicalsmentioning

confidence: 99%

“…Thus, the quantitative determination of these and other terpenoids is essential for the quality control of T. wilfordii and its preparations. More than 300 terpenoids including sesquiterpenoid alkaloids, diterpenoids, and triterpenes have been isolated from plants of the genus Tripterygium [7], and several rare flavonoids have been isolated from T. wilfordii [15]. Due to the lack of chromophores, diterpenoids usually display very weak absorption in the UV range, which is a major hurdle for the establishment of a sensitive HPLC-UV method for their quantification, especially when their concentration is low in the raw plant materials.…”

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confidence: 99%

“…l " Fig. 1 shows the structures of the eighteen analyzed compounds, triptolide (1), triptonide (2), triptonoterpenol (3), triptonoditerpenic acid (4), isoneotriptophenolide (5), triptophenolide (6), triptonoterpene methyl ether (7), triptonoterpene (8), wilfortrine (9), wilfordine E (10), peritassine A (11), wilfordinine D (12), wilforine (13), demethylastral (14), cangoronine (15), wilforic acid F (16), celastrol (17), wilforlide B (18), and the internal standard reserpine.…”

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confidence: 99%

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Simultaneous Quantification of 18 Bioactive Constituents in Tripterygium wilfordii Using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry

et al. 2013

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A liquid chromatography-electrospray ionization-mass spectrometry method with multiple reaction monitoring was established for simultaneous quantification of 18 bioactive constituents from the stem and root of Tripterygium wilfordii Hook. f. collected from different places in China and various commercial preparations. The chromatographic separations were achieved on an Agilent Poroshell SB-C₁₈ column (150 × 4.6 mm, 3.5 µm) with gradient elution using acetonitrile and 0.03 % formic acid aqueous solution in 45 min. Detection was performed in the positive ionization mode by monitoring the precursor-product combination. The validation of the method included tests of linearity, sensitivity, precision, repeatability, stability, and accuracy. All calibration curves showed good linearity (r > 0.9990) within the test range. The established method showed good precision and accuracy with intraday and interday variations of 2-5 % and 1-4 %, respectively, and recoveries of 95.5-104.5 %.

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Section: Solvents and Chemicalsmentioning

confidence: 99%

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Simultaneous Quantification of 18 Bioactive Constituents in Tripterygium wilfordii Using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry

et al. 2013

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“…2). The optical rotation was found zero, which implied it should be a racemate [8,15]. and δH 7.85 (1H, d, J = 2.1 Hz, H-2''') were located at δC 107.6 (C-1''') and 145.7 (C-2'''),…”

Section: Resultsmentioning

confidence: 96%

“…Previous phytochemical investigations revealed sesquiterpenoid alkaloids, diterpenoids and triterpenes as main chemical constituents of T. wilfordii [6][7]. However, limited study focused on the isolation of flavonoids from T. wilfordii, except for one of our previous phytochemical investigations on the plant, which reported two prenylated and C-methylated flavanones with moderate antiproliferative activity [8].…”

Section: Introductionmentioning

confidence: 98%

Prenylated flavonoids from the stems and roots of Tripterygium wilfordii

et al. 2017

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Phytochemical investigation on the stems and roots of Tripterygium wilfordii led to the isolation and characterization of three new prenylated flavanones, tripteryols A-C (1-3), along with (±)-5,4'-dihydroxy-2'-methoxy-6',6″-dimethypyraro-(2″,3″:7,8)-6-methyflavanone (4), and ((2S)-5,7,4'-trihydroxy-2'-methoxy-8,5'-di(3-methyl-2-butenyl)-6-methylflavanone (5). Structures of the compounds 1-5 were elucidated using spectroscopic techniques, such as UV, IR, NMR (1D and 2D), and HRESI-MS. Tripteryols B (2) was found active in the antimicrobial assay against Cryptococcus neoformans, Pseudomonas aeruginosa, vancomycin-resistant Enterococcus faecalis (VRE) and methicillin-resistant Staphylococcus aureus (MRSA) with IC values in the range of 2.95-8.59μg/mL. Compounds 4 and 5 showed significant antimicrobial activities against C. neoformans, MRSA and Staphylococcus aureus with IC values in the range of 1.06-2.60μg/mL. Additionally, significant antimalarial activities of tripteryols A-B (1-2) against chloroquine-sensitive D6 and resistant W2 clones of Plasmodium falciparum were observed and none of the compounds 1-5 were cytotoxic to Vero cells.

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Tripterygium wilfordii: An inspiring resource for rheumatoid arthritis treatment

Zhang

Mao

et al. 2020

Medicinal Research Reviews

126

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Tripterygium wilfordii Hook F (TwHF)‐based therapy is among the most efficient and crucial therapeutics for the treatment of rheumatoid arthritis (RA), which indicates that TwHF is a potential source of novel anti‐RA drugs. However, accumulating studies have observed that TwHF‐based therapy induces multi‐organ toxicity, which prevents the wide use of this herb in clinical practice, although several recent studies have attempted to reduce the toxicity of TwHF. Notably, our research group developed a “Clinical Practice Guideline for Tripterygium Glycosides/Tripterygium wilfordii Tablets in the Treatment of Rheumatoid Arthritis” (No. T/CACM 1337‐2020) approved by the China Association of Chinese Medicine to standardize the clinical application of TwHF‐based therapy and thus avoid adverse effects. Although great strides have been made toward the characterization of TwHF‐based therapy and revealing its underlying pharmacological and toxicological mechanisms, several crucial gaps in knowledge remain as potential barriers to enhance its therapeutic effects on the premise of safety assurance. This review offers a global view of TwHF, ranging from its chemical constituents, quality control, clinical observations, and underlying pharmacological mechanisms to toxic manifestations and mechanisms. We focus on the important and emerging aspects of this field and highlight the major challenges and strategies for using novel techniques and approaches to gain new insights into unresolved questions. We hope that this review will improve the understanding of TwHF application and draw increasing interdisciplinary attention from clinicians that practice both Chinese and Western medicine, basic researchers, and computer scientists.

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Two Prenylated and C-methylated Flavonoids from Tripterygium wilfordii Hook. F. (Celastraceae)

Cited by 5 publications

References 0 publications

Simultaneous Quantification of 18 Bioactive Constituents in Tripterygium wilfordii Using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry

Simultaneous Quantification of 18 Bioactive Constituents in Tripterygium wilfordii Using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry

Prenylated flavonoids from the stems and roots of Tripterygium wilfordii

Tripterygium wilfordii: An inspiring resource for rheumatoid arthritis treatment

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