Correct structures of Diels–Alder adducts from the natural cyclolignan thuriferic acid and its 8-epimer

López-Pérez, Jose Luis; Abad, Antonio; Olmo, Esther del; Feliciano, Arturo San

doi:10.1016/j.tet.2005.11.068

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…Compound 1a was identified as isopicropodophyl- H-NMR data of compound 1a corresponded to those in the literature (Dewick & Jackson 1981). Coelution of compound 1a on RP-HPLC with standard isopicropodophyllone further confirmed its identity (Ló pez- Péreza et al 2006). Although isopicropodophyllone (1a) can be synthetically prepared from podophyllotoxin, it requires a two-step reaction: oxidation using pyridinium dichromate (PDC)/CH 2 Cl 2 , and epimerization in AcOH to afford a mixture containing isopicropodophyllone (1a), but with a yield of only ca.…”

Section: Isolation and Structural Determination Of Compound 1asupporting

confidence: 70%

Biotransformation of podophyllotoxin byHordeum vulgarecell suspension cultures

Teng

McManus²,

Mau

et al. 2007

Biocatalysis and Biotransformation

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Hordeum vulgare cell suspension cultures were used to modify podophyllotoxin (1). One major product (1a) and one minor product (1b) were detected in both the culture medium and cells. To optimize the yield of compound 1a, we showed that:(1) the optimal concentration of added podophyllotoxin (1) was 33 mg L (1 ; higher concentrations caused cell toxicity; (2) the stage of the cell cycle (lag/log/stationary) at which podophyllotoxin was added only marginally affected the yield of compound 1a; the optimal addition time was after lag phase, in which the yield of compound 1a reached ca. 76%, and (3) biotransformation of podophyllotoxin (1) was relatively slow; podophyllotoxin fed at 4 days after subculture resulted in yields of compound 1a of ca. 56, 64 and 76% after an additional 3, 6 and 10 days of incubation, respectively. Product 1a was purified and identified as isopicropodophyllone (1a) based on MS and NMR data.

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Section: Isolation and Structural Determination Of Compound 1asupporting

confidence: 70%

Biotransformation of podophyllotoxin byHordeum vulgarecell suspension cultures

Teng

McManus²,

Mau

et al. 2007

Biocatalysis and Biotransformation

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“…The starting podophyllotoxin ( 1a ) was isolated from commercial Podophyllum resin and transformed into podophyllotoxone 1d through a well documented and previously reported procedure . The desired hybrid pinacol derivatives of podophyllotoxins 4 – 17 were synthesized through McMurry type condensations − of podophyllotoxone ( 1d ) with a variety of carbonyl compounds including several aldehydes and ketones (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimitotic and Tubulin Interaction Profiles of Novel Pinacol Derivatives of Podophyllotoxins

et al. 2012

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Several pinacol derivatives of podophyllotoxins bearing different side chains and functions at C-7 were synthesized through reductive cross-coupling of podophyllotoxone and several aldehydes and ketones. While possessing a hydroxylated chain at C-7, the compounds retained their respective hydroxyl group with either the 7α (podo) or 7β (epipodo) configuration. Along with pinacols, some C-7 alkylidene and C-7 alkyl derivatives were also prepared. Cytotoxicities against neoplastic cells followed by cell cycle arrest and cellular microtubule disruption were evaluated and mechanistically characterized through tubulin polymerization inhibition and assays of binding to the colchicine site. Compounds of the epipodopinacol (7β-OH) series behaved similarly to podophyllotoxin in all the assays and proved to be the most potent inhibitors. Significantly, 7α-isopropyl-7-deoxypodophyllotoxin (20), without any hydroxyl function, appeared as a promising lead compound for a novel type of tubulin polymerization inhibitors. Experimental results were in overall agreement with modeling and docking studies performed on representative compounds of each series.

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“…As shown in Scheme , a series of pinacol and olefin derivatives of podophyllotoxin 293 – 310 was obtained through the McMurry reaction of podophyllotoxone ( 7 ) with various aldehydes or ketones. The dihydro derivative 311 was produced by the Pd‐catalyzed hydrogenation of 308 .…”

Section: Structural Modifications Of Podophyllotoxin and Deoxypodophymentioning

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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Correct structures of Diels–Alder adducts from the natural cyclolignan thuriferic acid and its 8-epimer

Cited by 7 publications

References 19 publications

Biotransformation of podophyllotoxin byHordeum vulgarecell suspension cultures

Biotransformation of podophyllotoxin byHordeum vulgarecell suspension cultures

Synthesis and Antimitotic and Tubulin Interaction Profiles of Novel Pinacol Derivatives of Podophyllotoxins

Recent Advances in the Chemistry and Biology of Podophyllotoxins

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