Effect of Rhodanine and 2(5<i>H</i>)-Thiophenone in Green Algae and Liverwort Cells

Abstract

Rhodanine (2-thioxo-4-thiazolidinone) and 2(5H)-thiophenone inhibit germination and root growth of several plants. Using Scenedesmus acutus and Marchantia polymorpha L., these compounds were assayed with respect to degradation of chlorophyll, light-induced ethane formation and growth inhibition to determine the action mechanism. Chlorophyll reduction and growth inhibition of liverwort cells were quantitatively correlated with light-induced ethane formation of Scenedesmus in the presence of these compounds. Furthermore, we found that rhodanine itself decreased the chlorophyll content in liverwort cells and produced ethane with Scenedesmus cells in the light although no protoporphyrin IX (PPIX) accumulated. Diuron did not influence ethane formation with these two compounds as is observed with peroxidizing herbicides like oxyfluorfen. Apparently, rhodanine prevents PPIX accumulation by AFM.

Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties

“…The IC 50 value of the unsubstituted rhodanine related to PET inhibition in spinach chloroplasts was previously determined by Muro et al [ 14 ] using spinach chloroplasts. However, the IC 50 value of approximately 1 mmol/L which was obtained for rhodanine during the normal 1 min assay decreased to 0.1 mmol/L when the assay was done after illumination for 3 min, indicating possible chemical modification of the compound.…”

“…The inhibition of photosynthetic electron transport by rhodanine (IC 50 ≈ 1 mmol/L) was observed by Muro et al [ 14 ]. In another study, rhodanine and rhodanine- N -acetic acid strongly inhibited growth of Daucus carota L. var.…”

“…Rhodanine represents an important scaffold in drug discovery [ 5 ], and the influence of its derivatives on plant physiology has been well documented, too [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. 5-Arylalkylidenerhodanines [ 7 ] and 3-arylrhodanines [ 9 ] were patented as potential herbicides, and 5-(5-barbiturilidene)rhodanine inhibited growth of algae in water at relatively low concentrations [ 8 ].…”

A calorimetric and computational study on the thermochemistry of 2-(5H)-furanone and 2-(5H)-thiophenone

“…b Enthalpic differences between the experimental [53] and computed values are given in parentheses. and 2-(5H)-thiophenone (reactions (2) to (4)), when the estimated values of D f H m for dihydro-2-(3H)-thiophenone (reactions (14) to (17)) and 2-cyclopenten-1-one (reactions (18) to (21)), calculated in this work (reported in table 7) are employed, one can suggest that the estimated values for dihydro-2-(3H)-thiophenone and 2-cyclopenten-1-one are reliable and can be used with confidence.…”

“…The design and synthesis of a number of thiolactomycin analogues were reported by Jones et al, as potential anti-malarial and anti-trypanosomal agents [16]. The 2-(5H)-thiophenone has shown herbicidal activity [17] and the naphthalenylmethyl thiophenones have antihyperglycemic activity [18]. Moreover, substituted derivatives of both 2-(5H)-furanone and 2-(5H)-thiophenone have been used as endothelin antagonists [19].…”