Photoactive antiviral and cytotoxic activities of synthetic thiophenes and their acetylenic derivatives

Hudson, James B.; Graham, Elizabeth; Miki, N.; Towers, G.H.N.; Hudson, L.; Rossi, Renzo; Carpita, Adriano; Neri, Dario

doi:10.1016/0045-6535(89)90080-5

Cited by 60 publications

(25 citation statements)

References 17 publications

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“…They are characterized by having an intense red color and photo-labile structure. These compounds have shown toxicity against a wide range of organisms including bacteria (Chan et al, 1975;Towers et al, 1985), fungi (Towers et al, 1993;Ellis et al, 1995), viruses (Hudson et al, 1989), insects (Iyengar et al, 1987;Guillet et al, 1997), nematodes (Bakker et al, 1979) and mammals (Troung et al, 1997). The mode of action of thiarubrines is believed to be through production of DNAcleaving reactive oxygen species (Wang and Koreeda, 1998).…”

Section: Introductionmentioning

confidence: 97%

Polyacetylenes accumulation in Ambrosia maritima hairy root and cell cultures after elicitation with methyl jasmonate

Zid

Orihara

2005

Plant Cell Tiss Organ Cult

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Three lines of hairy root culture of Ambrosia maritima induced by Agrobacterium rhizogenes ATCC15834 were established. Thiarubrine A, thiarubrine A epoxide, thiarubrine A diol and their precursor pentayneene were produced by the hairy roots after elicitation with methyl jasmonate, the common signal molecule in the plant defense and development. Thiarubrine A diol was the main form detected in the medium. Maximum yield was achieved when the 13-day-old hairy root cultures were exposed to 40 lM methyl jasmonate for 72 h. Callus and cell suspension cultures were established and maintained on Murashige and Skoog medium supplied with a-naphthylacetic acid (NAA) and kinetin. When the cell suspension cultures were elicited with methyl jasmonate, pentayneene was the only polyacetylene produced. The yield of pentayneene in hairy root cultures was much higher (9.6 times) than that of cell suspension cultures.Abbreviations: DEPT -distortionless enhancement by polarization transfer; FAB-MS -fast atom bombardment mass spectroscopy; HMBC -heteronuclear multiple bond correlation; MeJ -methyl jasmonate

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Section: Introductionmentioning

confidence: 97%

Polyacetylenes accumulation in Ambrosia maritima hairy root and cell cultures after elicitation with methyl jasmonate

Zid

Orihara

2005

Plant Cell Tiss Organ Cult

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“…These compounds have been found to show nematocidal [1], insecticidal [2], antibacterial [3], antifungal [4], antiviral [5], and antioxidant activity [6]. Moreover, furan and thiophene derivatives occur in boiled and cooked beef.…”

Section: Introductionmentioning

confidence: 99%

Thermochemical and thermophysical study of 2-thiophenecarboxylic acid hydrazide and 2-furancarboxylic acid hydrazide

Silva

Amaral

Santos

2008

The Journal of Chemical Thermodynamics

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“…A. maritima hairy roots accumulated the polyacetylenes thiarubrine A, thiarubrine A epoxide, thiarubrine A diol and pentayneene after elicitation with 40 μM methyl jasmonate for 72 hrs at day 13 of the culture period. These compounds showed toxicity against microorganisms (Hudson et al 1989, Towers et al 1993, insects (Guillet et al 1997) and nematodes (Bakker et al 1997). It was proposed that the biosynthesis of these polyacetylenes in A. maritima hairy roots proceeds via a catabolic pathway involving linoleic acid (AbouZid and Orihara 2007).…”

Section: Introductionmentioning

confidence: 99%

Increase in Lipoxygenase Activity in Hairy Roots of Ambrosia maritima after Elicitation with Methyl Jasmonate

AbouZid

Orihara

2013

Plant Tissue Cult. & Biotech.

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Hairy roots of Ambrosia maritima L. were cultured in MS in the dark. Time course production was studied for pentayneene and thiarubine A after addition of 40 μM methyl jasmonate to the 13-day-old hairy roots. The levels of pentayneene and thiarubrine A showed maximum increase after 72 hrs adding methyl jasmonate. Lipoxygenase activity was increased in the hairy roots elicited with 40 μM methyl jasmonate. The increase in activity was 28-fold higher than control cultures 24 hrs after elicitor addition. The increase in enzyme activity was concomitant with the increase in pentayeneene, the precursor for polyacetylene biosynthesis. N-propyl gallate, a potent in vivo and in vitro lipoxygenase inhibitor, reduced polyacetylene production by the hairy roots at concentration of 100 μM. It is suggested that lipoxygenase may be at least partially involved in polyacetylene biosynthesis in A. maritima hairy roots.

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Photoactive antiviral and cytotoxic activities of synthetic thiophenes and their acetylenic derivatives

Cited by 60 publications

References 17 publications

Polyacetylenes accumulation in Ambrosia maritima hairy root and cell cultures after elicitation with methyl jasmonate

Polyacetylenes accumulation in Ambrosia maritima hairy root and cell cultures after elicitation with methyl jasmonate

Thermochemical and thermophysical study of 2-thiophenecarboxylic acid hydrazide and 2-furancarboxylic acid hydrazide

Increase in Lipoxygenase Activity in Hairy Roots of Ambrosia maritima after Elicitation with Methyl Jasmonate

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