(±)9, 10-dihydroxy-Δ 6a(10a)-tetrahydrocanabinol and (±)8, 9-dihydroxy-Δ 6a(10a)-tetrahydrocannabinol: 2 new cannabinoids fromCannabis sativa L.

Summary The structures of 2 new polyhydroxylated cannabinoids, (±)9, 10-dihydroxy- ^6a(10a)-tetrahydorcannabinol and (±)8, 9-dihydroxy- ^6a(10a)-tetrahydrocannabinol, obtained from a hexane extract of an IndianCannabis variant were determined by spectral means and correlation with cannabinol.Acknowledgments. Supported by contract No. HSM-42-70-109 from the National Institute on Drug Abuse and the Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi. The authors are grateful to Mrs Glenda Lewis (Research Institute) for running the gas chromatographic analyses and to Mr C. Versluis (Analytical Chemistry Laboratory, University Of Utrecht, The Netherlands) for recording an element list of both compounds.Cannabis Herbarium specimens are stored in the herbarium, Department of Pharmacology, School of Pharmacy, University of Mississippi, University, MS 38677, USA.     

ß-Cannabispiranol: A new non-cannabinoid phenol from cannabis sativa L.

Summary An ethanol extract of Cannabis sativa L. afforded upon partitioning and repeated chromatography a new non-cannabinoid phenol [7-hydroxy-5-methoxy-spiro-(cyclohexane-1, 1-indan)-4\-ol](IIIa), named -cannabispiranol.Acknowledgments. Supported by contract HSM-42-70-109 and grant DA-00928-01 from the National Institute on Drug Abuse as well as the Research Institute of Pharmaceutical Sciences. The authors are grateful to Mrs Glenda Lewis for running the GC analyses and to Dr Stephen Billets for running the Mass Spectra. Cannabis Herbarium specimens are stored in the Herbarium, Department of Pharmacognosy, School of Pharmacy, University of Mississippi, USA.     

Constituents ofCannabis sativa L. XXI: Estrogenic activity of a non-cannabinoid constituent

Summary A non-cannabinoid phenol (4,4,dihydroxy-5-methoxybibenzyl) increased uterine weight in prepubescent female rats, suggesting non-cannabinoids contribute to the estrogenic effects ofCannabis.Acknowledgments. This research was supported by Contract 271-78-3527 from the National Institute on Drug Abuse and by the Research Institute of Pharmaceutical Sciences, University of Mississippi. The authors are grateful to Karen S. Tomaszewski for technical assistance.     

Biomimetic synthesis of cannabispiran

Summary Total synthesis of cannabispiran (1) was accomplished by a biomimetic-type cyclization of the bibenzyl2, using K₃Fe(CN)₆ or MoOCl₄.Acknowledgment. Supported in part by the Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi.     

Enantiomeric cannabinoids: stereospecificity of psychotropic activity

Summary The 1,1-dimethylheptyl homolog of (–)-(3R,4R)-7-hydroxy-delta-6-tetrahydrocannabinol (compoundII) is highly psychotropic in mice, rats and pigeons. The (+)-(3S,4S) enantiomer (III) was found to be psychotropically inactive at doses up to several thousand times those of the ED₅₀ of (II).We thank Dr A. Breuer and Mrs H. Amsalem for help with the syntheses. The research reported above was supported in Tucson by NIH grant NS 15441; in Uppsala by grants from the Swedish Medical Research Council (5757) and the Swedish Council for the Planning and Coordination of Research (84/2082); in Jerusalem by the Szold Foundation.Presented in part at a meeting at the US National Institute on Drug Abuse, Washington, D.C., October 1986, see NIDA Research Monographs79 (1987) 15.     

Buffalo α S1-casein; its terminal residues and amino acid composition

Summary BuffaloaS₁-casein was treated with carboxypeptidase-A to determine the C-terminal amino acid residue, which was — leucine-tryptophan. The Sakaguchi reagent was used to confirm arginine as the N-terminal amino acid. The colored p-phenylazophenyl thiohydantions of tryptophan and arginine released from C- and N-terminals respectively were quantitatively estimated and from this molecular weights of buffaloaS₁ casein were calculated and found to be 26,300 and 26,100 respectively.Acknowledgment. We are thankful to Prof. B. K. Bachhawat, Indian Institute of Chemical Biology, for encouragement. We also thank Prof. S. K. Mukherjee, Bose Institute, for amino acid analysis. Part of this work was completed when the authors were at the University of Kalyani, West Bengal.     

Squalene and other unsaturated hydrocarbons,inBryocladia cuspidata

Summary By gas chromatography-electron impact mass spectrometry the red algaBryocladia cuspidata, was found to contain n-pentadecane and n-heptadecane. Gas chromatography-chemical ionization mass spectrometry indicated the presence of squalene as well as a C₂₁ pentaene and a C₂₁ hexaene, tentatively identified as 1,6,9,12,15-heneicosapentaene and 1,6,9,12,15,18-heneicosahexaene.Acknowledgments. This study was supported in part by a grant (AI 04769) from the National Institute of Allergy and Infectious Diseases. S.C. on leave of absence from the University of Catania, thanks the National Research Council of Italy for a Fellowship (1974–1975).     

A potent attractant of zoospores ofAphanomyces cochlioides isolated from its host,Spinacia oleracea

A highly potent attractant of zoospores ofAphanomyces cochlioides, a causal fungus of the root rot disease of spinach (Spinacia oleracea), was isolated from spinach roots, and its structure was determined by spectroscopic evidence and chemical synthesis as cochliophilin A (5-hydroxy-6,7-methylenedioxyflavone,1). A chromosorb particle prepared by soaking in solution of1 showed a potent attracting activity toward the zoospores using concentrations of1 above 10^–9 or 10^–10 M.     

Lymphatic metastasis of tumour; persistent transport of cells

Summary A model of lymphatic metastasis established by injecting Walker rat carcinoma cells into the rat footpad was used to study the output of tumour cells from the footpad. The lymphatic efferent from the footpad was cannulated in a group of rats with advanced neoplasm; it was shown that the output of tumou cells was continuou over periods up to 90 min and ranged from 10²–10⁵ cells/min.Acknowledgment. This work was supported by a grant from the National Cancer Institute of Canada to C.R.F. and I.C. We are grateful to Mrs W. Kao and Mr I. Etches for meticulous technical help and to the Photographic Section, Department of Pathology for illustrations. Dr V.S. Gupta of Veterinary Physiology, University of Saskatchewan supplied the tumour for transplantation.     

Cannabiripsol: a novel Cannabis constituent.

Cannabiripsol [(-) (6aR, 9S, 10S, 10aR)9,10-dihydroxy-hexahydrocannabinol] (1), a new cannabinoid was isolated from a South African Cannabis variant. The structure was determined by spectral means and by synthesis.     

ZNS-aktive Phenylpropylamine vonCatha edulis FORSK. (Celastraceae) kenyanischer Herkunft

Summary The phenylpropylamine fraction ofCatha edulis FORSK. grown in Kenya has been investigated. The major components have been found to be (S)-(–)--aminopropiophenone (1), (+)-norpseudoephedrine (2) and(–)-norephedrine (3). Quantitative ratios of1, 2, 3 in tissues of different age are discussed.

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ZNS-aktive Phenylpropylamine vonCatha edulis FORSK. (Celastraceae) kenyanischer Herkunft

     

Two new kaempferol 3,7-diglycosides and kaempferitrin in the fernAsplenium trichomanes

Summary The fronds of the fernAsplenium trichomanes contain kaempferol 3,7-dirhamnoside (1) and the new compounds kaempferol 3-O-a-rhamnoside-7-O-a-arabinoside (2) and kaempferol 3-O-a-arabinoside-7-O-a-rhamnoside (3). The presence of the above flavonoids has been shown by spectroscopic methods and chemical degradations.Acknowledgments. The author thanks Prof. H. Wagner (Institut für pharmazeutische Arzneimittellehre der Universität München, München) for a sample of kaempferol 3,7-dirhamnoside, Dr K. R. Markham (Chemistry Division, D.S.I.R., Petone, New Zealand) for a gift of pectinase and Mr A. D'Urso (Botanic Institute, University of Catania) for help in acquiring the plant material.     

Characterization of the host-specific toxins produced byHelminthosporium sacchari,the causal organism of eyespot disease of sugarcane

Summary Investigation of the host-specific toxin complex fromH. sacchari has led to the isolation of 3 isomeric glycosidic components C₃₉H₆₄O₂₂, each active at 2×10^–11 moles. The 3 isomers consist of 4 galactose units linked to an aglycone residue C₁₅H₂₄O₂.Acknowledgments. The Boyce Thompson-Cornell group thanks J.F. Rissler, University of Maryland, A.K. Bose, Stevens Institute of Technology, R. Barker and A. Serriani, Cornell University, and C. Grinnalds and J. Golay, Boyce Thompson Institute for help with various aspects of this work. Supported in part by a grant to V.M. from the US Department of Agriculture (8100720). The Zürich group thanks Dr G.A. Strobel, Department of Botany and Microbiology, Montana State University, Bozeman, for supplying a potent toxin-producing strain (M 36), a susceptible clone of sugarcane (51 NG 97), and a reference sample of helminthosporoside, Dr. K. Hostettmann and Mme M. Hostettmann-Kaldas, Pharmazeutisches Institut ETH Zürich, for assistance in developing the DCC separation and Sandoz A.G., Basel, for financial support.     

Temperature dependence of neurotransmitter release in the antarctic fishPagothenia borchgrevinki

Summary The quantal contents of endplate potentials from extraocular muscles of an antarctic fishPagothenia borchgrevinki were measured over a range of temperatures. Quantal release was maximal at about 5°C but showed little dependence on temperature between –2°C and 10°C. Above 10°C quantal content declined until release ceased about 18°C. In view of the fact that the ambient temperature at which these fish live is constant at –1.9°C, the results suggest thatPagothenia borchgrevinki is only partially adapted to its environment despite 25 million years acclimatization.The authors wish to thank the staff of New Zealand's Scott Base, Antarctica, without whose cooperation the work would have been impossible. Mr J. Quinn of the Auckland University Physiology Department gave invaluable assistance with computing and electronics and the Antarctic Division of the New Zealand Department of Scientific and Industrial Research provided transportation and logistic support. The project was financially supported by the New Zealand University Grants Committee and the Auckland University Research Committee. S.P. was a Senior Fellow of the N.Z. Medical Research Council.     

Zur Stereochemie der Propandioldehydrase-Reaktion

Summary Propanedioldehydrase is shown to convert both (+)-(S)-2-²H-propanediol,3, and (–)-(R)-1-²H₂-propanediol,5, to specimens of deuterated propion-aldehyde, for which the (S)-configuration has been established. Thus, in the propanedioldehydrase reaction migration of hydrogen atoms from C–1 to C–2 always occurs with inversion of configuration.     

On the association between lysogeny and carcinogenicity in nitroquinolines and related compounds

Zusammenfassung In einer Serie von 16 Nitroquinolinen und verwandten Substanzen wurde eine gute Übereinstimmung zwischen Phageninduktion inEscherichia coli C-600 und Karzinogenese nachgewiesen.

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Supported by grants No. C-6516 and FR-05526 from the National Cancer Institute and Contract NO. PH 86-66-169 from the Division of Air Pollution, U.S.P.H.S. We thank Dr.Y. Kawazoe of the National Cancer Center Research Institute, Tokyo, for his generous gift of the compounds tested.     

Evidence that two species of aphid ingest food through an open stylet sheath

Zusammenfassung Myzus persicae undAcyrthosiphon pisum nehmen beim Saugen an Saccharoselösungen Kohlenstoffteilchen bis zu einem Durchmesser von 0,5–1 auf (ungefähre Weite des Nahrungskanals der Stechborsten). Demnach muss die um die Stechborsten ausgebildete Speichelscheide am Ende offen sein. BeiA. pisum konnte beobachtet werden, dass grössere Kohlenstoffteilchen an der Stechborstenspitze das Saugen deutlich behindern, was durch Bewegungen der Stechborsten und erneute Speichelabgabe behoben werden konnte.

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The contribution of this author was made while on sabbatical leave from the Waite Institute, University of Adelaide (South Australia), and supported in part by Public Health Service Training Grant No. 5T1-AI-218, from the National Institute of Allergy and Infectious Diseases (USA).     

A simple gas liquid chromatography procedure for determination of cannabinoidic acids inCannabis sativa L.

Résumé La chromatographie gazeuse des extraits de la marihuana donne la quantité complète de chaque composant cannabinoïque; tandis que la silylation des extraits précédant la chromatographie gazeuse, fournit des informations indépendentes sur les formes acides et non acides de chaque composant cannabinoïque.

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Department of Pharmacognosy, School of Pharmacy, University of Mississippi, research supported by National Institute of Mental Health, Contract No. HSM-42-70-109.     

Insect antifeedant terpenes,hot-tasting to humans

Summary Four dialdehyde sesquiterpenoids (1–4) isolated from East AfricanWarburgia plants exhibit powerful antifeeding activity for larvae of the armyworms,Spodoptera exempta andS. littoralis. The hotness of these sesquiterpenes is associated with this activity. The specific absolute stereochemistry of these antifeedants appears to govern the hotness of the taste.The authors are grateful to Proff. K. Nakanishi, A.S. Kende and T. Kubota for their interest and valuable discussion. Succulatal was provided by Dr. Y. Asakawa. This work was initiated during the stay of I.K. at the International Center of Insect Physiology and Ecology, Nairobi, Kenya. We also thank Mr A. Chapya for technical assistance.     

Hemolymph proteins in an ascitic condition,induced by lethal1(3)gl tumorous tissue inDrosophila hydei

Summary Drosophila hydei larvae homozygous for the gene1(3)gl may survive to the age of 3 weeks, become bloated and be incapable of metamorphosis. Wild-type flies after the injection of a fragment of the1(3)gl disc, which has been previously culture in vivo for 40–500 days, also become bloated (ascitic reaction). In the hemolymph of both the advanced1(3)gl larvae and ascitic adult hosts the accumulation of a specific protein is observed.Acknowledgments. This work was supported by the Swiss National Science Foundation under Grant No.3.792-0.76 and the Georges und Antoine Claraz-Schenkung. We thank Prof. H. Gloor, University of Geneva, and Prof. P.S. Chen, University of Zürich, for advice and criticism.