Isolation and Characterization of Stemphylin, a Chromone Glucoside from Stemphylium botryosum

A phytotoxic compound was isolated from a liquid culture medium of Stemphylium botryosum, a pathogen of lettuce. The toxin is an amorphous yellow solid with absorbance maxima at 218, 268, and 427.5 nm and exhibits a bathochromic shift in alkaline pH. It has a molecular weight of 370 and an empirical formula of C(17)H(22)O(9). Glucose and aromatic pigments are detected after acid hydrolysis. Based on its spectral and chemical properties, the proposed structure of the toxin is 3-hydroxy- 2,2-dimethyl-5-alpha-d-glucopyranoside-2,3-dihydrochromone, and it has been given the trivial name stemphylin. A linear relationship exists between lesion area and amount of toxin applied to a young lettuce leaf. The relationship between toxin production and the development of disease symptoms is discussed.     

Isolation and phytotoxicity of a metabolite from Curvularia eragrostidis and characterisation of its modes of action

Digitaria sanguinalis is a widespread troublesome weed distributed all over the world. Curvularia eragrostidis QZ‐2000 is a potential candidate for biocontrol of D. sanguinalis. A phytotoxic metabolite from the culture filtrate of this fungus was extracted by ethyl acetate, isolated by bioassay‐guided column chromatography and thin layer chromatography on silica gel, characterised by ultra violet, infrared ray (IR), mass spectrometry (MS), ¹H‐nuclear magnetic resonance (NMR) and ¹³C‐NMR spectral data analyses and identified as α,β‐dehydrocurvularin. The phytotoxin significantly inhibited seed germination of D. sanguinalis from 43 to 688 μM. The EC₅₀ value of seed germination was 152 μM. The EC₅₀ values of elongation of radicle and coleoptile were 102 and 172 μM, respectively. α,β‐dehydrocurvularin caused extensive necrosis on leaves of many notorious weeds at 688 μM, while maize and soybean were insensitive to it. Therefore, α,β‐dehydrocurvularin was regarded as a non‐host‐selective phytotoxin. At concentrations of 172–688 μM, α,β‐dehydrocurvularin caused a decrease in chlorophyll content. α,β‐dehydrocurvularin had stronger impacts on chlorophyll A fluorescence, photophosphorylation and Mg²⁺‐ATPase activity at higher concentrations. These results suggest that α,β‐dehydrocurvularin affected the photosynthetic capacity. In the present study, α,β‐dehydrocurvularin significantly inhibited mitosis of root tip cells. It supports that the α,β‐dehydrocurvularin has potential for development as a natural bioherbicide.     

The Chemistry of Ilexol. I.

Ilexol, a new triterpenoid alcohol isolated from the barks of several species of the Genus Ilex, has now been oxidized with chromium trioxide to yield a ketone, designated as ilexone of C₃₀H₄₈O, m.p. 239.5–240.5°, and – 68.74°, which gives oxirne of m. p. 256.5–257.5°, 2,4-dinitrophenylhydrazone of m.p. 260–261°, and positive Zimmermann test.

On reduction with sodium and ethanol as well as with lithium aluminum hydride, it has been shown that ilexone is regenerated to yield an alcohol proved to be identical with natural ilexol.

On reduction according to the procedure of Huang-Minion, ilexone has been shown to yield an oxygen-free compound, designated as ilexene of C₃₀H₅₀, and m.p. 241–242°.

It seems most likely that ilexol might be a triterpenoid alcohol of C₃₀H₄₉OH, an alcoholic hydroxyl group of which is secondary in nature, and moreover attached at C–3 in its molecule.     

Developing classification in action: I. Human infants

Human infants’ developing manipulatory transformations involved in classifying objects from ages 6 to 24 months were investigated. Infants’ manipulations develop from predominantly serial one-at-a-time acts with one object to predominantly parallel two-at-a-time acts with two objects. This shift is marked by increasingly overt transformational consequences for the objects manipulated. When infants construct parallel transformations they are initially different. With age they are increasingly identical or reciprocal. Also during this age period, as the number of objects manipulated at the same time increases, so does the frequency with which infants coordinate them. At the same time, the kind of objects infants manipulate simultaneously changes. Six-month-olds manipulate different objects when acting on more than one object at a time. By age 12 months, infants switch to manipulating identical objects at the same time, indicating that they are beginning to construct identity classes. Since this development occurs about a half year before human infants develop any substantial naming behavior, the origins of classification cannot depend on this linguistic development     

Diacridines: bifunctional intercalators. I. Chemistry, physical chemistry and growth inhibitory properties.

The synthesis, as well as the rationale for synthesis of diacridines, double intercalators, as potential inhibitors of nucleic acid synthesis is presented. The syntheses of (9-acridyl)-putrescine and -spermine, and bis(-9-acridyl)-putrescine, -spermidine, -spermine diamines and of bis(6-chloro-2-methoxy-9-acridyl)-putrescine and -spermine diamines, all substituted on the terminal NH2 groups are described. In addition, the homologous series of diacridines connected by the amino groups of the diamines NH2(CH2)nNH2 (where n = 2,3,4,6,8,10,12,14,16,18) to the C-9 of the diacridines has been synthesized. The chemical properties of these compounds as well as their molecular relationship to DNA are presented. The effect of the double intercalators on the Tm of DNA and of (A)n - (U)n, (dA)n - (dT)n, (G)n - (C)n and on (dG)n - (dC)n have been determined. The double acridine intercalators produce a much greater increase of the Tm of these nucleic acids than do the single acridine intercalators. They also profoundly affect the Tm of DNA in physiological salt concentrations; under these latter conditions the single intercalators have no effect. The relationship between the length of the chain connecting the two acridine rings and the inhibition of the growth of P-388 cells in vitro and vivo is presented. Their growth inhibitory properties appear, in general, to parallel their intercalative abilities.     

Inert dust insecticides: Part I. Mechanism of action

The mode of action of inert dust insecticides on the grain weevil ( Calandra granaria L.) has been investigated by determination of mortality-time curves and by a detailed study of the influence of dusts on the water relations of the insects. It has been found that dusts do not depend for their action on any chemical reactivity, some highly inert substances such as diamond and carborundum being very effective. A physical process is therefore indicated.
Dusts do not penetrate into the respiratory system, and although large amounts are ingested these seem to have little harmful effect.
It has been demonstrated that effective dusts increase the rate of evaporation of water from insects to the air, and that the relative killing powers of different dusts run parallel with their capacities for promoting evaporation. The results are in harmony with the view (proposed by earlier workers) that inert dusts kill insects by inducing death by desiccation.