Nest cell lining of the solitary beeHylaeus bisinuatus (Hymenoptera: Colletidae)

The nest cell lining ofHylaeus bisinuatus (Hymenoptera: Colletidae) was shown by high-resolution solidstate [¹³C]NMR to be composed of lipid polymer and protein. The lipid polymer was shown by reduction and subsequent GC/MS analysis to be comprised of -hydroxy fatty acids (C₂₀, C₂₂, C₂₄ and C₂₆) and fatty alcohols (C₁₆ to C₃₀). The protein portion of the lining had a silk-like amino acid composition.     

A reinvestigation of the chemistry of the Dufours gland of the formicine ant,Anoplolepis custodiens

The components of individual Dufours glands excised fromAnoplolepis custodiens workers were analysed by GC-MS. In addition to then-alkanes andn-alkenes previously reported² in these glands, primary alcohols (C₁₉-C₂₂), secondary alcohols (C₂₀-C₂₃), 2-ketones (C₂₀-C₂₃) and possibly carboxylate ethyl esters (C₁₉ and C₂₁) were identified as components of these glands. It seems possible that these high-boiling compounds are used by the workers in laying trails on the hot sandy surfaces of their characteristic habitat and in lining of the inner walls of nests, but no standard compounds have been available to us for any behavioral studies.     

Secretion of the Dufour gland of the antNothomyrmecia macrops (Hymenoptera:Formicidae)

Summary The Dufour gland of the primitive Australian antNothomyrmecia macrops contains microgram quantities in total of linear alkanes and alkenes from C₁₃ to C₃₀ with heptadecene the major component (66%). In all, 50 substances, including methyl-branched hydrocarbons, aldehydes and acetates, -farnesene and -springene in low nanogram amounts, were identified by gas chromatography-mass spectrometry.     

Chemical defense in the three European species ofCrematogaster ants

The composition of the Dufour gland of the antC. scutellaris has been reinvestigated by gas chromatography/mass spectrometry. The major components of the gland are (2E,5E,12Z)-4-oxoheneicosa-2,5,12-trien-1-ol acetate (1a) its ¹⁴ and ¹⁶ double bond isomers (1b and1c), and the corresponding (Z,Z)-dienes5a and5b, all containing an acetylated C₂₁ chain. The previously proposed structures1d, 1e, and5c, which are based on an homologous acetylated C₂₃ chain, correspond to minor derivatives present in the gland. Traces of acetylated C₁₉ homologs, tentatively identified as1g-1i, have also been found. The Dufour gland contents of the two other EuropeanCrematogaster species have also been studied.C. auberti is very similar toC. scutellaris in producing mainly1a, 1b and1c, together with the same higher and lower homologs, but it lacks the dienic derivatives5, whereasC. sordidula contains essentially the acetylated C₁₉ compounds1g, 1h, and1i, accompanied by acetylated C₁₇ homologs.     

Hydrolysis of isoprenyl diphosphates with the acid phosphatase fromCinnamomum camphora

Direct observations of the enzymatic hydrolysis of C₁₀ acyclic allylic isoprenyl diphosphates by an acid phosphatase from the leaves ofCinnamomum camphora (camphor tree) were made using¹H and³¹P NMR spectrometers. The measurements indicated that the allylic primary diphosphates, geranyl diphosphate and neryl diphosphate, were hydrolyzed to their corresponding alcohols in a sequential manner via their corresponding monophosphates, whereas the allylic tertiary diphosphate, linalyl diphosphate, was hydrolyzed only to its corresponding monophosphate.     

The sterols of two hadromerida sponges

Summary Sterols were extracted and identified from 2 marine sponges,Aaptos aaptos andSuberites domuncula. The sponges contained conventional C₂₆–C₃₀ sterols with a saturated ring system. Minor amounts of cholest-7-en-3-ol and cholesterol were also present. Cholestanol and 24-ethylcholestanol were the major components of the sterol mixtures.We thank Prof. L. Boniforti (Istituto Superiore di Sanità, Roma) for CG-MS analysis, Prof. R. Pronzato (Istituto di Zoologia dell'Università di Genova) for identifying the sponges and A. Senatore for G.C. measurements. This research was supported by grants of Ministero P.I. and C.N.R.     

Synthesis and metabolism of vertebrate-type steroids by tissues of insects: A critical evaluation

Summary This review covers the synthesis and the metabolism of vertebrate-type steroids (progesterone, testosterone, estradiol, corticosteroids) by insect tissues and discusses the significance of the reactions for insect physiology. Biosynthesis of vertebrate-type steroids from cholesterol hitherto has been demonstrated in only two insect species, i.e. the water beetleAcilius sulcatus (Coleoptera) and the tobacco hornwormManduca sexta (Lepidoptera). InAcilius, steroid synthesis is associated with exosecretion (chemical defense). Nothing, however, is known about a physiological role of the C₂₁ steroid conjugate present in ovaries and eggs ofManduca. No synthesis of vertebrate-type steroids was observed in any other insect investigated to date. Most metabolic conversions of steroids by insects concerned oxidoreduction of oxygen groups (hydroxysteroid dehydrogenase activity) and (polar and apolar) conjugate formation. All important enzymatic steps involved in synthesis and catabolism, as known from studies with tissues of vertebrates, were not, or hardly observed. The conclusion is drawn that typical vertebrate-type (C₂₁, C₁₉ and C₁₈) steroids probably do not act as physiologically active substances in insects.     

Alkaloid biosynthesis

Zusammenfassung Es wird eine neue Theorie der Alkaloidbiosynthese vorgeschlagen, die alle Alkaloidtypen vereinigt. Die Grundidee dieser Theorie beruht auf der Überlegung, dass die Alkaloide eher mit Kohlehydraten als mit Aminosäuren genetisch verwandt sind. Alle Strukturtypen der Alkaloide sind hypothetisch teilbar in C₄, C₆-C₁, C₆-C₂ und C₆-C₃-Fragmente, und können daher in Beziehung zum Davis-Sprinson-Schema, welches die Biosynthese aromatischer Naturstoffe behandelt, gebracht werden.

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From a lecture, entitledAlkaloid Biosynthesis, presented on October 8, 1958, as one of a series of ten lectures onRecent Advances in the Chemistry of Natural Products sponsored by the New York Section of the American Chemical Society during fall of 1958.     

The isolation,culture and organ differentiation from mesophyll protoplasts ofMollugo nudicaulis Lam., a C4 species

Summary Isolation and culture of mesophyll protoplasts fromMollugo nudicaulis, a C₄ species, is reported. Protoplasts developed into callus with root formation. However, no shoot was differentiated. This work was carried out as a part of our overall objective of inducing somatic fusion between the protoplasts of C₃ and C₄ species ofMollugo.     

Vincanorin und Vincarein,zwei neue Alkaloide ausVinca minor L.

Summary The isolation of two new alkaloids fromVinca minor L. (Apocynaceae) is described. Vincarein, C₂₁H₂₄N₂O₄, and Vincanorin, C₁₉H₂₂N₂O, both probably belong to the group of indol alkaloids.     

Instar-specific defensive secretions of stink bugs (Heteroptera: Pentatomidae)

Defensive secretions (allomones) from first-instar nymphs of stink bugs in the subfamily Pentatominae contain (E)-4-oxo-2-decenal as a major constituent, whereas this compound is absent from later instars. In contrast, first instars ofEdessa meditabunda (Edessinae) produce allomones like those of later instars. The C₆ and C₈ (E)-4-oxo-2-alkenals are common, characteristic exocrine compounds of nymphal and adult Heteroptera, but (E)-4-oxo-2-decenal is previously unknown as a major natural product for which a biological role has yet to be established.     

Über Inhaltsstoffe ausPetasites officinalis Moench I. Petasin und die Petasolester B und C

Summary Three spasmolytically active substances which contain no nitrogen, namely petasin and the petasolesters B and C, were isolated fromPetasites officinalis Moench. They are all esters of the same C₁₅-alcohol. Petasin is an ester of angelic acid, whereas the petasolesters B and C are derivates of a new acid containing sulphur, the-methylmercapto-acrylic acid.     

Chemical analysis of the pheromone blends produced by males and females of the neotropical moth,Mocis megas (Guénée) (Lepidoptera,Noctuidae, Catocalinae)

Summary Pheromonal secretions produced by females and males of the noctuid moth,Mocis megas (Guénée) have been analyzed by gas chromatography and mass spectrometry (EI (electron impact) and CI (chemical ionization)). The female sex pheromone was a blend of (Z,Z,Z) 3,6,9 heneicosatriene (55%) and (Z,Z) 3,6-cis-9S, 10R-epoxyheneicosadiene (45%). Male secretion produced at the level of a prothoracic organ was a blend of two unsaturated major hydrocarbons: (Z,Z) 6,9 heneicosadiene, (64%) and (Z,Z,Z) 3,6,9 heneicosatriene (24%) and C₁₉, C₂₀ and C₂₂ homologues (total ratio 12%), as minor components. The trienic hydrocarbon was present in both sexes. The behavioral role of this male secretion has not yet been elucidated.     

The C4-dicarboxylate transport system ofRhizobium meliloti and its role in nitrogen fixation during symbiosis with alfalfa (Medicago sativa)

TheRhizobium meliloti C₄-dicarboxylate transport (Dct) system is essential for an effective symbiosis with alfalfa plants. C₄-dicarboxylates are the major carbon source taken up by bacteroids. Genetic analysis of Dct^– mutant strains led to the isolation of thedct carrier genedctA and the regulatory genesdctB anddctD. The carrier genedctA is regulated in free-living cells by the alternative sigma factor RpoN and the two-component regulatory system DctB/D. In addition, DctA is involved in its own regulation, possibly by interacting with DctB. In bacteroids, besides the DctB/DctD system an additional symbiotic activator is thought to be involved indctA expression. Further regulation ofdctA in the free-living state is reflected by diauxic growth of rhizobia, with succinate being the preferred carbon source. The tight coupling of C₄-dicarboxylate transport and nitrogen fixation is revealed by a reduced level of C₄-dicarboxylate transport in nitrogenase negative bacteroids.     

Structure and stereochemistry of coccuvine (Cocculus laurifolius DC)

Summary Coccuvine C₁₇H₁₉NO₂, m.p. 137–38°, a new alkaloid fromCocculus laurifolius DC has been assigned the structure and stereochemistry as (I) on the basis of spectroscopic studies and chemical correlation.     

Furodendin,a C22 degraded terpene from the spongePhyllospongia dendyi

Summary The structure of furodendin (5), a minor secondary metabolite of the spongePhyllospongia dendyi, has been solved by spectral methods. Furodendin is probably derived, biosynthetically, by elimination of a C₃ unit from a C₂₅ geranyl-farnesol precursor.Acknowledgment. We thank Dr C. Evans for sponge identification, RRIMP Museum number FN 1516/000.     

The determination of volatile aldehydes in gases and vapours

Zusammenfassung Es wird eine neue Methode vorgeschlagen, Acetaldehyd, Propionaldehyd und Butyraldehyd in Gegenwart von CH₄, C₂H₆, C₃H₈, C₂H₄, C₃H₆, C₂H₂, CO₂, CO, N₂, H₂ und O₂ quantitativ zu bestimmen. Die Methode besteht darin, das Gasgemenge mit Hilfe eines Orsatschen Apparates durch eine bei 20°C gesättigte, Chromtrioxyd und Schwefelsäure enthaltende Natriumsulfatlösung zu schicken, welche die oben genannten Aldehyde selektiv absorbiert.     

Zur Kenntnis der Blattlipide vonAcer platanoides L. während der herbstlichen Vergilbung

Summary The lipids of green and yellow leaves ofAcer platanoides L. have been investigated. Yellow leaves were found to contain phytyl linolenate, a further example of the formation of esters containing terpenoid alcohols and unsaturated fatty acids in yellow autumn leaves. The determination af squalene in leaves of the same tree showed an increase of squalene content during the whole season and the autumn colouration. Regarding the leaf lipids we conclude autumn colouration to be characterized by 3 facts: (1) Lipid degradation, (2) formation of esters and (3) accumulation of lipid intermediates.     

Zur Bildung von Carbonylverbindungen in Fetten nach Einwirkung von Elektronenstrahlen

Summary Investigations of the formation of carbonyl compounds in fats subjected to electron rays (100 Mrad) have been reported. More than 20 different substances can be determined by gasliquid-chromatography. The splitting of the ester-C-O-C-bonds is mostly accompanied by a fracture of the fatty acid chain and carbonyl compounds with 6 to 12 C-atoms are essentially formed (aldehydes mostly up to 9 C-atoms). A relatively high concentration of unsaturated C₉-ketones and a small amount of ketones with more than 13 C-atoms has been found in irradiated tripalmitin and palmitic acid. None of these higher compounds could be detected in unsaturated oils, which contain more C₁₁- and C₁₂-ketones.     

Toxic substances produced byFusarium. VII. Control of fusarial wilt of safflower by root exudates and extractives ofRuellia tuberosa

Summary Exudates and extractives of roots ofRuellia tuberosa, containing 2,6-dimethoxyquinone, acacetin and a C₁₆-quinone, have been shown to produce significant protective and curative actions againstFusarium oxysporum-incited wilt of safflower. The potentiality of the root extractives as a foliar fungicide is appraised.