Effect of a Marine Algal Constituent on the Growth of Lettuce and Rice Seedlings

Kubo, Isao; Ochi, Masamitsu; Shibata, Kozo; Hanke, Frederick J.; Nakatsu, Tetsuo; Tan, Kah-Siew; Taniguchi, Makoto; Kamikawa, Tadao; Yamagiwa, Yoshiro; Arizuka, Mitsuo; Wood, William F.

doi:10.1021/np50067a005

Cited by 26 publications

(21 citation statements)

References 4 publications

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“…Reaction of alcohols 6, 14, and 15 with Me 2 SO 4 in the presence of NaH gave benzyl methyl ethers 16 [23], 17, and 18 [22], respectively, in high yields (96, 96, and 94%, resp.). O-Demethylation of 16, 17, and 18 with BBr 3 in CH 2 Cl 2 at 0 -258 under N 2 , followed by addition of MeOH for deactivation of excess BBr 3 at 0 -608, afforded MeOCH 2 -substituted benzene-diols 19 [24], 20, and 21 [25], respectively, in high yields in a one-pot reaction (Scheme 2). Conclusions.…”

Section: H-and 13mentioning

confidence: 99%

Total Synthesis of the Biologically Active, Naturally Occurring 3,4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol and Regioselective O‐Demethylation of Aryl Methyl Ethers

Akbaba

Balaydın

Goksu

et al. 2010

Helvetica Chimica Acta

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.tr) 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol (2), a natural product, has been synthesized for the first time starting from (3-bromo-4,5-dimethoxyphenyl)methanol (5) in five steps and with an overall yield of 34%. The reaction of some methoxymethyl-substituted aryl methyl ethers with BBr 3 , followed by the addition of MeOH, afforded the corresponding methoxymethyl-substituted arylphenols in high yields.

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Section: H-and 13mentioning

confidence: 99%

Total Synthesis of the Biologically Active, Naturally Occurring 3,4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol and Regioselective O‐Demethylation of Aryl Methyl Ethers

Akbaba

Balaydın

Goksu

et al. 2010

Helvetica Chimica Acta

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“…Syntheses of phenols ( 5 and 15 ) and bromophenols ( 13 , 14 and 16) were performed in two steps. The first step was the synthesis of their derivatives with methoxides 6–12 because phenolic OH groups in reactions were usually protected as arylmethylethers 5, 10, 15, 17, 70–73. The second step was the demethylation of the corresponding compounds.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antioxidant Properties of (3,4‐Dihydroxyphenyl)(2,3,4‐trihydroxyphenyl)methanone and Its Derivatives

Çetinkaya

Göçer

Menzek

et al. 2011

Archiv der Pharmazie

114

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(3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone (5) and its two derivatives with bromine were synthesized from reactions such as bromination and demethylation of (3,4-dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone (6). The Wolf-Kishner reduction product (9) of 6 and its three derivatives with bromine were obtained. 4-(3,4-Dihydroxybenzyl)benzene-1,2,3-triol and its dibromide derivative (16) were also synthesized from 9 and the corresponding dibromide derivative. The in vitro antioxidant activities of nine new compounds synthesized in these reactions were determined by analyzing the radical scavenging activities of bromophenols for 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 1,1-diphenyl-2-picryl-hydrazyl (DPPH), N,N-dimethyl-p-phenylenediamine (DMPD), and the superoxide anion radical (O(2)(·-)) and examining the total reducing power through Fe(3+)-Fe(2+) transformation, FRAP and CUPRAC assays and the ferrous ions (Fe(2+)) chelating activities. Moreover, the results of these activities were compared to those of standard antioxidant compounds such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol, and trolox. The results showed that the synthesized bromophenols had effective antioxidant power. The phenol 5 with two phenolic rings and five phenolic hydroxyl groups was the most potent antioxidant and radical scavenger. In conclusion, the new compounds are promising molecules to be used owing to their potential antioxidant properties.

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“…2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether has shown antioxidant and antimicrobial activity (Lim et al, 2000). An investigation of the biological activities of a-O-methyllanosol isolated from the extracts of the red algae Odonthalia washingtoniensis and Odonthalia floccosa revealed that it exhibits a stimulating effect on the growth and elongation of lettuce and rice seedlings in in vitro and in vivo systems (Kubo et al, 1990).…”

Section: Halogenated Phenols In Marine Algaementioning

confidence: 99%

“…Bibliography: 1 Whitfield et al, (1999); 2 Kladi et al, (2003); 3 Weinstein et al, (1975); 4 Lim et al, 2000;5 Glombitza and Stoffelen, (1972); 6 Craigie and Gruenig, (1967); 7 Katsui et al, (1967); 8 Stoffelen et al, (1972); 9 Pedersen et al, (1974); 10 Chantraine et al, (1973); 11 Chevolot-Magueur et al, (1976); 12 De Nanteuil and Mastagli, (1981); 13 Kubo et al, (1990); 14 Blackman and Matthews, (1982).…”

Section: -Bromo-45-dihydroxybenzyl Alcoholmentioning

confidence: 99%

Volatile halogenated metabolites from marine red algae

2004

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A significant number of halogenated low molecular weight metabolites have exhibited an impressive array of biological properties ranging from antimicrobial to insecticidal activities. Studies on the natural products chemistry of the red seaweeds were recently stimulated by the discovery of the acyclic monoterpene halomon, which exhibits selective antitumor activity in the National Cancer Institute's human tumor and disease oriented in vitro screen.The present review is a taxonomy based compilation of the available literature on the halogenated volatile metabolites (C 1 -C 10 ) produced by red seaweeds, with a short description of the reported ecological and pharmaceutical activities. The review begins with a presentation of simple halogenated hydrocarbons and phenols, showing their wide occurrence in rhodophyta, along with a description of simple halogenated lipids in some of the most frequently investigated red algae species and finally focuses on the chemical composition of individual red algae species.

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Effect of a Marine Algal Constituent on the Growth of Lettuce and Rice Seedlings

Cited by 26 publications

References 4 publications

Total Synthesis of the Biologically Active, Naturally Occurring 3,4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol and Regioselective O‐Demethylation of Aryl Methyl Ethers

Total Synthesis of the Biologically Active, Naturally Occurring 3,4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol and Regioselective O‐Demethylation of Aryl Methyl Ethers

Synthesis and Antioxidant Properties of (3,4‐Dihydroxyphenyl)(2,3,4‐trihydroxyphenyl)methanone and Its Derivatives

Volatile halogenated metabolites from marine red algae

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