Components of Podophyllin. Vi. Isolation of Two New Compounds From Podophyllum Emodi Wall

Nadkarni, Moreshwar V.; Maury, Priscilla B.; Hartwell, Jonathan L.

doi:10.1021/ja01121a527

Cited by 12 publications

(5 citation statements)

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“…7432), based on a method described by Nadkarni et al (1953). The resin (7 g) was dissolved in 30 ml of the eluens ethanol:toluene (1:1) and was chromatographed on a column (12.5 x 3.0 cm) packed with silica gel (Merck GF254).…”

Section: Synthesis Of the Substrate Desoxypodophyllotoxinmentioning

confidence: 99%

The production of podophyllotoxin and its 5-methoxy derivative through bioconversion of cyclodextrin-complexed desoxypodophyllotoxin by plant cell cultures

Uden

Bouma²,

Waker³

et al. 1995

Plant Cell Tiss Organ Cult

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The bioconversion of the lignan desoxypodophyllotoxin by cell suspensions of Linumflavum and of Podophyllum hexandrum was investigated. The apolar substrate could be easily dissolved in the culture medium at a concentration of 2 mM by complexation with dimethyl-/~-cyclodextrin. Growth parameters of the cell suspensions were not affected by either the addition of cyclodextrin itself, or when cyclodextrin-complexed desoxypodophyllotoxin was present in the medium. The complexed lignan disappeared from the medium within 7 days for both cell cultures. Cellularly only small amounts of desoxypodophyllotoxin were found. After feeding of desoxypodophyllotoxin, the cell culture of L. flavum accumulated 5-methoxypodophyllotoxin and 5-methoxypodophyllotoxin-/~-D-glucoside.After 7 days a total maximal content of 2.38% on a dry weight basis of 5-methoxypodophyllotoxin was formed, corresponding with 249 mg 1-l suspension. The highest bioconversion percentage of 52.3% was found at day 14.The desoxypodophyllotoxin-fed culture of P. hexandrum accumulated podophyllotoxin and its fl-D-glucoside with a maximal content of 2.87% on a dry weight basis after 9 days, corresponding with 192 mg 1-1 suspension. The highest bioconversion percentage of 33.2% was also found at day 9.

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Section: Synthesis Of the Substrate Desoxypodophyllotoxinmentioning

confidence: 99%

The production of podophyllotoxin and its 5-methoxy derivative through bioconversion of cyclodextrin-complexed desoxypodophyllotoxin by plant cell cultures

Uden

Bouma²,

Waker³

et al. 1995

Plant Cell Tiss Organ Cult

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“…Demethylpodophyllotoxin Demethylpodophyllotoxin has been found only from one source, the resin from Podophyllum emodi Wall. (233). The resin was extracted with alcohol, treated with benzene, and the solution chromatographed on activated alumina.…”

Section: Ho/vxchmentioning

confidence: 99%

“…The structure of demethylpodophyllotoxin was readily established by elemental analysis, by methoxyl determination (233), and by methylation with diazomethane to podophyllotoxin: Like podophyllotoxin, demethylpodophyllotoxin is isomerized with alkaline reagents by inversion of the carbon atom carrying the carboxyl group. This change gives rise to demethylpicropodophyllin and its derivatives (232) The position of the phenolic hydroxyl group was determined by permanganate oxidation of the ethyl ether of demethylpicropodophyllin to the ethyl ether of syringic acid, a compound already known: Demethylpodophyllotoxin was tested in tumor-bearing mice and was found to produce hemorrhage and necrosis in Sarcoma 37 (401).…”

Section: Ho/vxchmentioning

confidence: 99%

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The Naturally Occurring Lignans

Hearon¹,

MacGregor²

1955

Chem. Rev.

106

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“…At the end of 2010, 59 lignans, including compound 1 and its analogues 2 – 59 , were successively isolated from various plants (Table ), such as Podophyllum hexandrum (Figure ), Podophyllum peltatum , Podophyllum versipelle , Diphylleia cymosa , Diphylleia cymosa, Juniperus communis , Juniperus sabina (Figure ), Justicia procumbens , Cleistanthus collinus , Sinopodophyllum emodi , Linum flavum , Dysosma versipellis , Phyllanthus piscatorum , Hyptis verticillata , Bursera morelensis , Bursera fagaroides , Bursera graveolens , and Commiphora incise …”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Chemistry and Biology of Podophyllotoxins

Xiang

Che

2017

Chemistry A European J

181

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Podophyllotoxin and its related aryltetralin cyclolignans belong to a family of important products that exhibit various biological properties (e.g., cytotoxic, insecticidal, antifungal, antiviral, anti-inflammatory, neurotoxic, immunosuppressive, antirheumatic, antioxidative, antispasmogenic, and hypolipidemic activities). This Review provides a survey of podophyllotoxin and its analogues isolated from plants. In particular, recent developments in the elegant total chemical synthesis, structural modifications, biosynthesis, and biotransformation of podophyllotoxin and its analogues are summarized. Moreover, a deoxypodophyllotoxin-based chemosensor for selective detection of mercury ion is described. In addition to the most active podophyllotoxin derivatives in each series against human cancer cell lines and insect pests listed in the tables, the structure-activity relationships of podophyllotoxin derivatives as cytotoxic and insecticidal agents are also outlined. Future prospects and further developments in this area are covered at the end of the Review. We believe that this Review will provide necessary information for synthetic, medicinal, and pesticidal chemistry researchers who are interested in the chemistry and biology of podophyllotoxins.

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Components of Podophyllin. Vi. Isolation of Two New Compounds From Podophyllum Emodi Wall

Cited by 12 publications

References 1 publication

The production of podophyllotoxin and its 5-methoxy derivative through bioconversion of cyclodextrin-complexed desoxypodophyllotoxin by plant cell cultures

The production of podophyllotoxin and its 5-methoxy derivative through bioconversion of cyclodextrin-complexed desoxypodophyllotoxin by plant cell cultures

The Naturally Occurring Lignans

Recent Advances in the Chemistry and Biology of Podophyllotoxins

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