Synthesis of Naturally Occurring Rubilactone, Mollugin, and Dihydromollugin of <i>Rubia cordifolia</i>

Ho, Li‐Kang; Yu, Hai-Chin; Ho, Chen-Ta; Don, Ming‐Jaw

doi:10.1002/jccs.200100014

Cited by 13 publications

(4 citation statements)

References 10 publications

(9 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pyranoxanthones 6-8 were obtained by dehydrogenation of the respective dihydropyranoxanthones 3-5 with DDQ in refluxing dry dioxane [ 5 ]. While dihydropyranoxanthone 3 gave pyranoxanthone 6 , dihydropyranoxanthone 4 afforded pyranoxanthone 7 ( Scheme 1 a) and dihydropyranoxanthone 5 gave pyranoxanthone 8 ( Scheme 1 b) in 67, 41 and 25% yield, respectively.…”

Section: Resultsmentioning

confidence: 99%

Antitumor Activity of Some Prenylated Xanthones

et al. 2009

View full text Add to dashboard Cite

Pyranoxanthones 6-8 were obtained by dehydrogenation of the respective dihydropyranoxanthones 3-5 with DDQ in dry dioxane. Two prenylated xanthones 10,11 were obtained from the reaction of 1-hydroxyxanthone (9) with prenyl bromide in alkaline medium, or by condensation of xanthone 9 with isoprene in the presence of orthophosphoric acid. The structural elucidation of the two new compounds 6,11, as well as an update of data for the already described prenylated derivatives 7,8,10 were accomplished by IR, UV, HRMS and NMR (1H, 13C, HSQC and HMBC) techniques. The effect of the prenylated xanthone derivatives on the in vitro growth of human tumor cell lines MCF-7 (breast adenocarcinoma) and NCI-H460 (non-small cell lung cancer) is also reported. Compounds 10 and 11 have been found to exhibit a moderate growth inhibitory activity against the MCF-7 cell line.

show abstract

Section: Resultsmentioning

confidence: 99%

Antitumor Activity of Some Prenylated Xanthones

et al. 2009

View full text Add to dashboard Cite

show abstract

“…Finally, it was found that mollugin could be obtained in 81% yield by using a DDQ oxidation of dihydromollugin (2) in toluene, which is an improved oxidation procedure compared to the literature. 9 In summary, in this report, the present synthetic strategies for mollugin are based upon the observation of possible biosynthetic precursors. Two alternative precursors were presented and this resulted in two different approaches.…”

Section: Methodsmentioning

confidence: 99%

Efficient Syntheses of Mollugin

Habonimana¹,

Claessens²,

Kimpe³

2006

Synlett

View full text Add to dashboard Cite

Two different strategies are presented to synthesize mollugin, based upon a close investigation of possible natural precursors. The best total synthesis of mollugin, a natural product isolated from rubiaceous herbs, is achieved in an overall yield of 61% starting from 1,4-dihydroxynaphthalene-2-carboxylic acid. The key reaction is the prenylation and spontaneous pyran ring formation. Subsequent oxidation of the intermediate 3,4-dihydromollugin with DDQ afforded mollugin.

show abstract

“…Mollugin was synthesized according to the method reported by Ho et al [14]. Oxomollugin used for the NO production inhibitory activity was prepared from 1 according to the method reported by Lumb et al [16].…”

Section: Experimental Section Materialsmentioning

confidence: 99%

“…Thus, we chemically synthesized mollugin by the method reported by Ho et al [14] in order to investigate and analyze the action of mollugin.…”

Section: Introductionmentioning

confidence: 99%

Oxomollugin, a potential inhibitor of lipopolysaccharide-induced nitric oxide production including nuclear factor kappa B signals

et al. 2015

View full text Add to dashboard Cite

Mollugin, a naphthoquinone derivative, was reported to possess various biological activities such as anti-inflammatory and anti-tumor activity. Mollugin isolated from Rubia tinctorum roots inhibited lipopolysaccharide-induced nitric oxide (NO) production in RAW264.7 macrophages. However, mollugin synthesized for further investigation of its anti-inflammatory mechanism showed weak activity in addition to unstable assay results. From the result of analysis on a degradation product of mollugin, oxomollugin was found to be the main active substance of mollugin degradation, showing a potent inhibitory activity on NO-production including nuclear factor kappa B signals.

show abstract

Synthesis of Naturally Occurring Rubilactone, Mollugin, and Dihydromollugin of Rubia cordifolia

Cited by 13 publications

References 10 publications

Antitumor Activity of Some Prenylated Xanthones

Antitumor Activity of Some Prenylated Xanthones

Efficient Syntheses of Mollugin

Oxomollugin, a potential inhibitor of lipopolysaccharide-induced nitric oxide production including nuclear factor kappa B signals

Contact Info

Product

Resources

About