Thiarubrines: Novel Dithiacyclohexadiene Polyyne Photosensitizers from Higher Plants

Ellis, Shona; Balza, Felipe; Constabel, Peter; Hudson, J. B.; Towers, G.H.N.

doi:10.1021/bk-1995-0616.ch014

Cited by 16 publications

(16 citation statements)

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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: 99%

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: 99%

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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“…80 kcal mol -1 6a. Exposure of 1a to visible light, leading to desulfurization, results in enhanced biological activity …”

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confidence: 99%

Photochemistry of Thiarubrine A and Other 1,2-Dithiins: Formation of 2,6-Dithiabicyclo[3.1.0]hex-3-enes

et al. 1996

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“…Another known strategy of the regnum Plantae against the toxic sunlight is the concentration of PSs in special glands (e.g., hypericin in dark glands of Hypericum perforatum [123]) or resin canals (e.g., thiarubins in resin canals of the outer cortex of Ambrosia [124][125][126] or in the roots of Chaenactis douglasii [127]). Representatives of the regnum Fungi are-in this regard-not as intensively studied.…”

Section: What We Know From Phototoxic Plants and What We Might Extrapmentioning

confidence: 99%

Does the chemistry of fungal pigments demand the existence of photoactivated defense strategies in basidiomycetes?

Siewert

2021

Photochem Photobiol Sci

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The well-known photosensitizers hypericin, harmane, and emodin are typical pigments of certain mushroom species—is this a coincidence or an indication towards a photoactivated defense mechanism in the phylum Basidiomycota? This perspective article explores this hypothesis by cross-linking the chemistry of fungal pigments with structural requirements from known photosensitizers and insights from photoactivated strategies in the kingdom Plantae. Thereby, light is shed on a yet unexplored playground dealing with ecological questions, photopharmaceutical opportunities, and biotechnological potentials.

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Thiarubrines: Novel Dithiacyclohexadiene Polyyne Photosensitizers from Higher Plants

Cited by 16 publications

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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

Photochemistry of Thiarubrine A and Other 1,2-Dithiins: Formation of 2,6-Dithiabicyclo[3.1.0]hex-3-enes

Does the chemistry of fungal pigments demand the existence of photoactivated defense strategies in basidiomycetes?

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