Ketone components in the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca, and pheromonal activity of synthetic ketones

Two active fractions were found during the isolation of contact sex pheromone of female elytra of the white‐spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae), in addition to fraction of hydrocarbons that had previously been identified. One fraction was essential to evoke a series of precopulatory behaviors of males toward a glass dummy when coated together with the hydrocarbon blend. The other fraction enhanced this activity when added to the mixture. From the latter synergistic fraction, we isolated five novel compounds and identified them as 10‐heptacosanone, (Z)‐18‐heptacosen‐10‐one, (18Z,21Z)‐heptacosa‐18,21‐dien‐10‐one, (18Z,21Z,24Z)‐heptacosa‐18,21,24‐trien‐10‐one, and 12‐heptacosanone by GC‐MS and NMR analyses. A blend of four of these synthetic ketones, without 12‐heptacosanone, in the ratio and concentration found in female elytra extract (250 : 400 : 1000 : 180 ng FE^?1) showed greater synergistic effect than the natural fraction containing the ketones. This effect was canceled out by further addition of 12‐heptacosanone (100 ng FE^?1), which was still comparable to the effect of the natural ketone fraction.     

The identification of 24-methylene-24,25-dihydrolanosterol and other possible ergosterol precursors in Phycomyces blakesleeanus and Agaricus campestris

The following sterols have been isolated from the fungi, Phycomyces blakesleeanus and Agaricus campestris: ergosterol, lanosterol, 24-methylene-24,25-dihydrolanosterol and episterol. 4,4-Dimethyl-5α-ergosta-8.24(28)-dien-3β-ol and 4α-methyl-5α-ergosta-8,24(28)-dien-3β-ol have been tentatively identified. Evidence for the incorporation of label from l-methionine-[methyl-¹⁴C] into some of these sterols in P. blakesleeanus has been obtained. The significance of these sterols in ergosterol biosynthesis is discussed.     

Metabolism of 24-dihydrolanosterol in Ochromonas malhamensis and Chlorella ellipsoidea

24-Dihydrolanosterol-[2-³H] was converted to cholesterol in Chlorella ellipsoidea but ergost-5-enol, poriferasterol, clionasterol were not labelled. The absence of the necessary 24(25) double bond precursor eliminates the possibility of C₂₈ and C₂₉ sterol synthesis. However, it was confirmed that 24-dihydrolanosterol was metabolized by Ochromonas malhamensis to give cholesterol, brassicasterol, and poriferasterol.     

The 220 MHz NMR spectra of phytosterols

The 220MHz NMR spectra of forty two steroids are reported. Eight pairs of C-24 epimers (24α- and 24β) and two pairs of double bond isomers (cis and trans) can be distinguished by this technique. The influence of substituents, solvents and stereochemistry on methyl group chemical shifts is discussed.     

A new δ-lactone from the flowers of Grewia asiatica

The structure of 3, 21, 24 trimethyl-5,7-dihydroxyhentriacontanoic acid δ-lactone, a new δ-lactone, isolated from the flowers of Grewia asiatica has been deduced on the basis of physico-chemical studies.     

Cytochemical studies on the localization of methanol oxidase and other oxidases in peroxisomes of methanol-grown Hansenula polymorpha

The localization of methanol oxidase activity in cells of methanol-limited chemostat cultures of the yeast Hansenula polymorpha has been studied with different cytochemical staining techniques. The methods were based on enzymatic or chemical trapping of the hydrogen peroxide produced by the enzyme during aerobic incubations of whole cells in methanol-containing media. The results showed that methanol-dependent hydrogen peroxide production in either fixed or unfixed cells exclusively occurred in peroxisomes, which characteristically develop during growth of this yeast on methanol. Apart from methanol oxidase and catalase, the typical peroxisomal enzymes d-aminoacid oxidase and l--hydroxyacid oxidase were also found to be located in the peroxisomes. Urate oxidase was not detected in these organelles. Phase-contrast microscopy of living cells revealed the occurrence of peroxisomes which were cubic of form. This unusual shape was also observed in thin sections examined by electron microscopy. The contents of the peroxisomes showed, after various fixation procedures, a completely crystalline or striated substructure. It is suggested that this substructure might represent the in vivo organization structure of the peroxisomal enzymes.     

Localization of the human prealbumin gene to chromosome 18

A human liver cDNA library was screened using an oligonucleotide probe based on the amino acid sequence of human prealbumin. The cDNA insert of one positive clone was sequenced and found to contain the entire coding sequence of human prealbumin plus untranslated 5' and 3' regions. This cDNA was used to probe DNA from a panel of mouse/human somatic cell hybrids. Only those hybrids containing human chromosome 18 showed the human-specific hybridization pattern, thereby localizing the human prealbumin gene to this chromosome.     

Four new and other 4α-methylsterols in the seeds of Solanaceae

Four new 4α-methylsterols in the seeds of Solanaceae were identified as 31-norlanost-9(11)-enol, 24-methyl-31-norlanost-9(11)-enol, 4α,24-dimethylcholesta-7,24-dienol and 4α-methyl-24-ethylcholesta-7,24-dienol. The other 4α-methylsterols identified in the seeds were 31-norcycloartanol, 31-norcycloartenol, cycloeucalenol, 31-norlanost-8-enol, 31-norlanosterol, obtusifoliol, 4α,14α,24-trimethylcholesta-8,24-dienol, 4α-methylcholest-8-enol, lophenol, 24-methyllophenol, 24-ethyllophenol, gramisterol and citrostadienol. The distribution of these seventeen 4α-methyl- sterols in the seeds of eight species of the Solanaceae was determined.     

The conversion of 5α-lanost-24-ene-3β,9α-diol and parkeol into poriferasterol by the alga Ochromon as malhamensis

The 4,4-dimethylsterols 4α-lanost-24-ene-3β,9α-diol-[2-³H₂] and parkeol-[2-³H₂] were synthesized from lanosterol and subsequently incubated with cultures of Ochromonas malhamensis. 5α-Lanost-24-ene-3β,9α-diol was converted into poriferasterol with three times the efficiency of parkeol. Clionasterol was also found to be labelled from both parkeol and 5α-lanost-24-ene-3β,9α-diol. No significant incorporation of radioactivity into sterols was obtained after feeding 5α-lanost-24-ene-3β,9α-diol to higher plants, the chlorophyte alga Trebouxia, yeast or a cell free homogenate of rat liver.     

Ultrastructural changes in rat adrenal cortical cells after chronic stimulation with β1–24-corticotropin

Summary Adult rats were given 15 daily subcutaneous injections either of synthetic ^1–24-corticotropin or of the corresponding placebo (controls) and were sacrificed 1 h after the final injection. In stimulated animals, the adrenal glands were increased in weight as compared to those of controls. Stereological analysis at light microscopic level of the outer zona fasciculata cells showed moderate volumetric increases of nuclei, cytoplasm and capillaries and a marked volumetric increase of lipid droplets in stimulated animals. Stereologic analysis of electron micrographs confirmed the marked increase in relative volume and surface density of lipid droplets, while volume fractions alone were increased for the Golgi apparatus and decreased for the endoplasmic reticulum and mitochondria. Biochemical analysis of the whole adrenal gland showed that the corticotropin injections produced a moderate increase in protein concentration, a marked increase in triglycerides and no appreciable changes in either phospholipid or cholesterol concentrations. The synthetic polypeptide therefore appears to have stimulating trophic effects on adrenal cortical cells, as shown by the increase in protein and cell size. However, it depresses the activity of the two types of organelle, endoplasmic reticulum and mitochondria, which have a major functional role in steroid synthesis. The increase of lipid droplets was interpreted as being primarily due to neutral fat accumulation, and secondarily to a diminished utilization of cholesterol for steroid synthesis. These findings suggest that, using this regime of administration, synthetic ^1–24 corticotropin, unlike native ACTH, inhibits steroid synthesis.