Glucosidation of 2-hydroxy- and 5-hydroxy-1,4-naphthoquinone

Steinerová, N.; Cudlín, J.; Ванек, З.

doi:10.1135/cccc19802684

Cited by 11 publications

(3 citation statements)

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“…2-Hydroxy-1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone were glucosidized and their acetylated glucosides were tested for their immunosuppressive and immunostimulative properties. It was found that their activity was comparable with clinically used preparation [10]. Naphthoquinones as aglycones have a wide range of biological properties, they are known for their phytotoxicity, extracts from Impatiens noli-tangere L., Impatiens glandulifera Royle and Impatiens parviflora DC.…”

Section: Introductionmentioning

confidence: 99%

Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

et al. 2013

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Methanolic extract from lyophilized roots of Impatiens glandulifera Royle was analyzed by high performance liquid chromatography using DAD and FLD detection and this revealed one dominant highly fluorescent very unstable substance. The stability of this derivative is strongly dependent on the plant material drying procedure and extraction procedure used. The structure of the substance was established as 1,2,4-trihydroxynaphthalene-1-O-glucoside (THNG) according LC-MS and NMR measurements. When lyophilized plant material was extracted with methanol an almost four times higher amount of THNG was found in the extract, compared to the amount of 2-hydroxy-1,4-naphthoquinone obtained, while in the case of the same lyophilized plant material extracted with water there was no THNG in the extract. The main compounds in this case was 2-hydroxy-1,4-naphthoquinone. In the plant material dried at the laboratory temperature and extracted by methanol there are only traces of THNG.

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Section: Introductionmentioning

confidence: 99%

Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

et al. 2013

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“…The compounds were reported to be effective in vivo against rat tumor Walker 256 carcinosarcoma, mouse lymphocytic leukemia P-388, and Ehrlich ascitic tumor [2,3]. Since that time synthesis, isolation and cytotoxic, antitumor, immunomodulatory, and antifungal properties of O-glycosides of natural products juglone, lapachol, lawsone, shikonin, and related 1,4-naphthoquinones were reported [4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

“…Juglone derivatives possessing acetylated sugar moiety (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) are significantly more active than that possessing sugar moiety with free hydroxyl groups (15, 16).…”

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confidence: 99%

Antileukemic Properties and Structure-Activity Relationships of O- and SGlycosylated Derivatives of Juglone and Related 1,4-Naphthoquinones

Fedorov¹

2011

TOGLYJ

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Glycosylated derivatives of physiologically active natural compound juglone and related 1,4-naphthoquinones are known as antifungal, immunomodulatory, and antitumor substances. However, their antileukemic properties and structure-activity relationships have been studied insufficiently. Antileukemic effects and structure-activity relationships (SAR) of the 50 1,4-naphthoquinone derivatives were examined using HL-60 human promyelocytic leukemia cells and MTS method of the study of cell viability. As was shown, the substances inhibited viability of HL-60 cells at the wide range of concentrations. SAR study revealed the structure peculiarities which lead to increase or decrease of the antileukemic activity of the compounds studied. In conclusion, O-or S-glycosylated derivatives of juglone and related 1,4-naphthoquinones have potential for development of the new antileukemic agents and should be further investigated.

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ChemInform Abstract: GLUCOSIDATION OF 2‐HYDROXY‐ AND 5‐HYDROXY‐1,4‐NAPHTHOQUINONE

Steinerová¹,

Cudlín²,

Ванек³

1981

Chemischer Informationsdienst

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Glucosidation of 2-hydroxy- and 5-hydroxy-1,4-naphthoquinone

Cited by 11 publications

References 0 publications

Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

Antileukemic Properties and Structure-Activity Relationships of O- and SGlycosylated Derivatives of Juglone and Related 1,4-Naphthoquinones

ChemInform Abstract: GLUCOSIDATION OF 2‐HYDROXY‐ AND 5‐HYDROXY‐1,4‐NAPHTHOQUINONE

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