Dimeric 1,4-benzoquinone derivatives and a resorcinol derivative from Ardisia gigantifolia

The present communication is, in effect, a discussion of the results obtained in the investigation of citrinin, and described in the preceding memoir (Part XIV ); these results, combined with some few further observations, appear to afford a key to the constitution of the substance. In considering this matter, it is convenient to start with the dihydric phenol, C 9 H 12 O 2 (I) (p. 290), which was obtained by fusing either of the isomeric products A or B (p. 283) with potassium hydroxide. This dihydric phenol has the composition of a dihydroxypropylbenzene, but the relative position of the hydroxyl groups and the arrangement of the alkyl side-chain or chains is unknown. The colour reaction with ferric chloride is, however, in agreement with the view that the substance is a resorcinol derivative, rather less well in harmony with the catechol hypothesis, and is hardly reconcilable with the assumption of a quinol nucleus.

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Ardisiphenol D, a resorcinol derivative identified fromArdisia brevicaulis, exerts antitumor effect through inducing apoptosis in human non-small-cell lung cancer A549 cells

Pharmaceutical Biology ◽

10.3109/13880209.2013.869231 ◽

2014 ◽

Vol 52 (7) ◽

pp. 797-803 ◽

Cited By ~ 2

Author(s):

Feng Zhao ◽

Yuan Hu ◽

Chuanke Chong ◽

Minghui Lu ◽

Liping Chen ◽

...

Keyword(s):

Lung Cancer ◽

Small Cell Lung Cancer ◽

Cell Lung Cancer ◽

Antitumor Effect ◽

A549 Cells ◽

Small Cell ◽

Small Cell Lung ◽

Resorcinol Derivative

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Targeting multiple cannabinoid anti-tumour pathways with a resorcinol derivative leads to inhibition of advanced stages of breast cancer

British Journal of Pharmacology ◽

10.1111/bph.12803 ◽

2014 ◽

Vol 171 (19) ◽

pp. 4464-4477 ◽

Cited By ~ 35

Author(s):

Ryuichi Murase ◽

Rumi Kawamura ◽

Eric Singer ◽

Arash Pakdel ◽

Pranamee Sarma ◽

...

Keyword(s):

Breast Cancer ◽

Advanced Stages ◽

Resorcinol Derivative

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Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5-alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

Phytotherapy Research ◽

10.1002/ptr.3256 ◽

2011 ◽

Vol 25 (2) ◽

pp. 271-276 ◽

Cited By ~ 5

Author(s):

Paula López ◽

Graciela Ferraro ◽

Claudia Anesini

Keyword(s):

Antioxidant Activity ◽

Resorcinol Derivative

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Calorimetric Study On The Interactions Of 5-n-Heptadec(en)Yiresolcinols From Cereal Grains With Zwitterionic Phospholipid (DPPC)

Zeitschrift für Naturforschung C ◽

10.1515/znc-1991-5-614 ◽

1991 ◽

Vol 46 (5-6) ◽

pp. 423-427 ◽

Cited By ~ 7

Author(s):

Andrzej B. Hendrich ◽

Arkadiusz Kozubek

Keyword(s):

Transition Temperature ◽

Heat Content ◽

Half Width ◽

Cereal Grains ◽

Aliphatic Chain ◽

Calorimetric Study ◽

Main Transition ◽

Resorcinol Derivative ◽

Thermotropic Properties ◽

Transition Heat

The effect of two 5-n-alk(en)ylresorcinol* (17:1 and 17:0) homologs at the concentrations of 5 - 20% on the thermotropic properties of dipalmitoylphosphatidylcholine in hydrated bilayers has been studied. The effect is different, depending on unsaturation of the aliphatic chain of resorcinol derivative. Saturated homologue ( 5 - 2 0 m ol% ) induces disappearance of the pretransition , increase of the main transition temperature and a half-width of the sition peak. Unsaturated homologue shifts pretransition towards higher temperatures, and similarly to the saturated one increases transition half-width but decreases the transition temperature, decreases the transition heat content and induces some phase separation

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A Novel Resorcinol Derivative from the Leaves of Piper betle

Chemistry of Natural Compounds ◽

10.1007/s10600-017-2070-8 ◽

2017 ◽

Vol 53 (4) ◽

pp. 611-613 ◽

Cited By ~ 2

Author(s):

Akhtar Atiya

Keyword(s):

Piper Betle ◽

Resorcinol Derivative

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Synthesis of Resorcinol Derivatives and their Effects on Melanin Production

Cosmetics ◽

10.3390/cosmetics7030055 ◽

2020 ◽

Vol 7 (3) ◽

pp. 55

Author(s):

Yoshihiro Tokudome ◽

Tsuyoshi Hoshi ◽

Sayaka Mori ◽

Ichiro Hijikuro

Keyword(s):

Inhibitory Effect ◽

Melanoma Cells ◽

Tyrosinase Activity ◽

Melanin Production ◽

Skin Whitening ◽

Alkyl Chains ◽

Murine Melanoma ◽

Resorcinol Derivative ◽

Melanin Contents ◽

Murine Melanoma Cells

Several resorcinol derivatives were synthesized and their effects on the survival rate of B16 murine melanoma cells, melanin production, and tyrosinase activity were investigated with an aim to evaluate their skin whitening effect. Twelve resorcinol derivatives were synthesized by esterification with three functional groups (L-ascorb-6-yl, ethyl, and glyceryl) linked via four alkyl chains of varying lengths (n = 2–5) at the 4-position. The structures of the 12 resorcinol derivatives were confirmed by Nuclear Magnetic Resonance (NMR). The derivatives were added to B16 murine melanoma cells and the melanin contents in the cells and culture medium were measured. To measure the tyrosinase activity, the substrate L-DOPA was added to a mushroom-derived tyrosinase solution, and the inhibition of the tyrosinase activity was determined. At 10 µM, the resorcinol derivatives did not affect the survival of the B16 murine melanoma cells, but the melanin content was reduced. At 1 µM, the derivatives significantly inhibited the tyrosinase activity in the mushroom-derived tyrosinase solution. A plot of the inhibitory effect on melanin production against the cLogP value for each resorcinol derivative indicated that the highest inhibition occurred at a cLogP value of approximately 2. Therefore, these resorcinol derivatives are expected to serve as effective skin whitening agents.

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