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Podophyllotoxone Sale

(Synonyms: 鬼臼脂毒酮) 目录号 : GC64705

Podophyllotoxone 是从八角莲根中分离得到的,具有抗癌活性。Podophyllotoxone 能够抑制 tubulin 微管蛋白聚合。

Podophyllotoxone Chemical Structure

Cas No.:477-49-6

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5 mg
¥4,050.00
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10 mg
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产品描述

Podophyllotoxone is isolated from the roots of Dysosma versipellis and has anti-cancer activities.Podophyllotoxone is able to inhibit the tubulin polymerization[1].

Podophyllotoxone inhibits human prostate cancer cells PC3 and DU145 growth with IC50 values of 14.7 and 20.6 µM[1].

[1]. Juan Li , et al. Absolute Configuration of Podophyllotoxone and Its Inhibitory Activity Against Human Prostate Cancer Cells. Chin J Nat Med. 2015 Jan;13(1):59-64.

Chemical Properties

Cas No. 477-49-6 SDF Download SDF
别名 鬼臼脂毒酮
分子式 C22H20O8 分子量 412.39
溶解度 DMSO : 100 mg/mL (242.49 mM; Need ultrasonic) 储存条件 4°C, away from moisture and light
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1 mg 5 mg 10 mg
1 mM 2.4249 mL 12.1244 mL 24.2489 mL
5 mM 0.485 mL 2.4249 mL 4.8498 mL
10 mM 0.2425 mL 1.2124 mL 2.4249 mL
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Research Update

Absolute configuration of Podophyllotoxone and its inhibitory activity against human prostate cancer cells

Chin J Nat Med 2015 Jan;13(1):59-64.PMID:25660289DOI:10.1016/S1875-5364(15)60007-3.

Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L(-1), respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.

Comprehensive study of Anthriscus sylvestris lignans

Phytochemistry 2021 Dec;192:112958.PMID:34560578DOI:10.1016/j.phytochem.2021.112958.

Wild chervil (Anthriscus sylvestris) is a widespread, wild-growing herbaceous plant from Apiaceae family, known for high content of lignans related to podophyllotoxin, and thus representing a promising new source for their industrial isolation. The data on detailed chemical profile of A. sylvestris lignans are still lacking. By combining fractionation with non-targeted LC-DAD-ESI-MS/MS metabolite profiling, we have identified, fully or tentatively, 46 lignans, 12 of which were never reported in A. sylvestris and 19 in any biological source. The dominant lignans were found to be nemerosin, yatein, deoxypodophyllotoxin, podophyllotoxin, Podophyllotoxone and guayadequiol. In addition to well-known dibenzylbutyrolactones, aryltetralins and 7-oxygenated aryltetralins, we found several oxygenated lignan classes previously undescribed in A. sylvestris - 7-hydroxy, 7-oxo and 8-hydroxydibenzylbutyrolactones, a 7'-oxotetrahydrofuran and a 7-hydroxyarylnaphthalene. To facilitate future rapid classification and identification of lignans in raw extracts, UV, MS and NMR spectral features of different lignan classes are described.

Quantitative HPLC-UV Study of Lignans in Anthriscus sylvestris

Molecules 2022 Sep 17;27(18):6072.PMID:36144804DOI:10.3390/molecules27186072.

Wild chervil (Anthriscus sylvestris) is a wild-growing plant from the Apiaceae family, used as a food in Europe and eastern Asia. Due to its high content of lignans known to possess anti-inflammatory, antiproliferative, antiviral and other activities, it represents a potential functional food. However, quantitative data on lignans are still scarce and limited to deoxypodophyllotoxin, nemerosin and yatein. In this paper, a newly developed and validated reverse-phase HPLC-UV method was used to evaluate the content of 14 lignans in both aerial parts and roots of A. sylvestris. The most abundant root components were found to be deoxypodophyllotoxin (2.0-42.8 mg/g), nemerosin (2.0-23.4 mg/g), yatein (1.1-18.5 mg/g), Podophyllotoxone (0.7-20.5 mg/g), guaiadequiol (0.8-8.3 mg/g) and dimethylmatairesinol (0.1-5.2 mg/g). Despite the high intra-population variability, a general trend of an increased lignan content during plant development could be observed in the root samples, whereas an opposite trend was observed in the herb samples. A validation study indicated that some of the investigated compounds-7-oxoaryltetralins and dibenzylbutyrolactones-have low stability and require cold storage in the dark. Furthermore, dibenzylbutyrolactones were confirmed to undergo a fast cis-trans isomerization; therefore, only the total content of these isomers should be reported.

Toxicity and Larvicidal Activity of Podophyllum-Based Lignans Against Aedes aegypti (Diptera: Culicidae)

J Med Entomol 2017 Jan;54(1):159-166.PMID:28082643DOI:10.1093/jme/tjw130.

Aedes aegypti L. (Diptera: Culicidae) is a mosquito species that has adapted to urban environments and is the main vector of dengue viruses. Because of the increasing incidence of dengue, a more environmentally acceptable insecticide needs to be found. Natural products have been and continue to be an important source of leading compounds that can be modified in order to develop new drugs. The lignan family of natural products includes compounds with a diverse spectrum of biological activity. Podophyllotoxin and its related lignans represent an exciting class of natural products that can be targeted at different types of biological activity and are therefore worth exploring further. This study had the aim of evaluating the larvicidal activity of an ethanolic extract from the rhizomes and roots of Podophyllum hexandrum (PM-3) and its isolated lignans, Podophyllotoxone (1) and desoxypodophyllotoxin (2), on the larvae of the mosquito vector Ae. aegypti. The PM-3 extract and the compounds (1) and (2) were dissolved in a mixture of acetone and dimethylsulfoxide at final concentrations of 1, 10, 30, 50, 100, and 200 μg/ml. After dilution, the solutions were applied (μg/ml) to the larvae-rearing medium. Overall, the ethanolic extract from the rhizomes and roots of P. hexandrum and the compounds (1) and (2) showed larvicidal activity against the larvae of Ae. aegypti According to the results from this study, it can be concluded that Podophyllotoxone (1) and desoxypodophyllotoxin (2) exhibited significant toxicity toward Ae. aegypti larvae.

Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR

Phytochemistry 2011 Dec;72(17):2172-9.PMID:21889175DOI:10.1016/j.phytochem.2011.08.009.

The aryltetralin lignan deoxypodophyllotoxin is much more widespread in the plant kingdom than podophyllotoxin. The latter serves as a starting compound for the production of cytostatic drugs like etoposide. A better insight into the occurrence of deoxypodophyllotoxin combined with detailed knowledge of its biosynthestic pathway(s) may help to develop alternative sources for podophyllotoxin. Using HPLC combined with electrospray tandem mass spectrometry and NMR spectroscopy techniques, we found nine lignans and five related structures in roots of Anthriscus sylvestris (L.) Hoffm. (Apiaceae), a common wild plant in temperate regions of the world. Podophyllotoxone, deoxypodophyllotoxin, yatein, anhydropodorhizol, 1-(3'-methoxy-4',5'-methylenedioxyphenyl)1-ξ-methoxy-2-propene, and 2-butenoic acid, 2-methyl-4-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]-, (2E)-3-(7-methoxy-1,3-benzodioxol-5-yl)-2-propen-1-yl ester, (2Z)- were the major compounds. α-Peltatin, podophyllotoxin, β-peltatin, isopicropodophyllone, β-peltatin-a-methylether, (Z)-2-angeloyloxymethyl-2-butenoic acid, anthriscinol methylether, and anthriscrusin were present in lower concentrations. α-Peltatin, β-peltatin, isopicropodophyllone, Podophyllotoxone, and β-peltatin-a-methylether have not been previously reported to be present in A. sylvestris. Based on our findings we propose a hypothetical biosynthetic pathway of aryltetralin lignans in A. sylvestris.