David Lavie's research while affiliated with CUNY Graduate Center and other places

Publications (173)

Article
Hypericin is a potent virucidal agent with activity against a broad range of enveloped viruses and retroviruses. The effective virucidal activity emanates from a combination of photodynamic and lipophilic properties. Hypericin binds cell membranes (and, by inference, virus membranes) and crosslinks virus capsid proteins. This action results in a lo...
Article
In 14 species of Aegilops, four species of Triticum and two species of Hordeum, a complex of rare phenolic compounds was found and showed quantitative differences between the wild and domestic species. There was a dramatic reduction in the cultivars to about 5% of the amount of these phenolic constituents. In the wild species these phenolic compoun...
Article
pH dependent absorption and fluorescence spectra of hypericin 1 and its octahydroxy analogue 3 demonstrate their acidic properties, their deprotonation occuring in the ground and excited states from OH in the bay region and in the peri position to the carbonyl, respectively; the presence of the anion of 1 in the crystalline state is established by...
Article
Following attachment and entry of human immunodeficiency virus (HIV) into a host cell, the HIV genomic RNA is reverse transcribed to cDNA. This step may be inhibited by hypericin, a compound that induces alterations of the retroviral capsid. Incubation of HIV with hypericin rendered the virus noninfectious. The replication of HIV was blocked early;...
Article
The structure of a new chlorinated withanolide isolated from Withania somnifera chemotype III has been elucidated as 5α-chloro,6β,14α,17β,2OαF-tetrahydroxy-l-oxo-22R-witha-2,24-dienolide by 1H and 13CNMR and chemical ionization mass spectroscopy methods.
Chapter
Hypericin (Hy), 4,5,7,4′,5′,7′-hexahydroxy 2,2′dimethyl-meso naphthodian-throne, is a naturally occurring, polycyclic aromatic dianthraquinone (Figure 1). The molecule assumes a planar configuration and exhibits red fluorescence with an excitation peak at 495nm and emission peaks at 595nm and 645nm. It is a lipophilic compound soluble in polar orga...
Article
Hypericin, a polycyclic aromatic dianthroquinone, is a natural plant product with antiviral properties. We report here the development of a methodology for the extraction and quantitation of hypericin from plasma and biological fluids and the adaptation of a sensitive and selective method for detection of the compound by high-performance liquid chr...
Article
Administration of the aromatic polycyclic dione compounds hypericin or pseudohypericin to experimental animals provides protection from disease induced by retroviruses that give rise to acute, as well as slowly progressive, diseases. For example, survival from Friend virus-induced leukemia is significantly prolonged by both compounds, with hyperici...
Article
The structure and stereochemistry of a clerodane-type diterpene from Baccharis artemisioides which we have named bartemidiolide, 15,16-3α,4α-diepoxy-trans-cleroda-13(16),14-diene-20,12S-19,2β-diolide, have been determined by X-ray crystallographic analysis and spectroscopic data.
Article
Two aromatic polycyclic diones hypericin and pseudohypericin have potent antiretroviral activity; these substances occur in plants of the Hypericum family. Both compounds are highly effective in preventing viral-induced manifestations that follow infections with a variety of retroviruses in vivo and in vitro. Pseudohypericin and hypericin probably...
Article
The structure of a withanolide isolated from the hybrid of Withania somnifera chemotype III (Israel) by Indian I (Delhi) has been elucidated as (20R,22R)-5α,6α-epoxy-7α-17α,20-trihydroxy-1-oxo-witha-2,24-dienolide by X-ray single crystal analysis. This compound is the first example of a 5α,6α-epoxy-7α-hydroxy system among the withanolides, and thus...
Article
The structure of a new withanolide type isolated from Trechonaetes laciniata, having a hemiacetal ring system and a 5-member ring lactone has been elucidated by X-ray analysis as (23R)-5β,6β-epoxy-12β,17β-dihydroxy-1-oxo-12,22-hemiacetal-ergosta-2,24-dien-23,26-olide (trechonolide A). A second compound (trechonolide B) having at C-12 a β-methoxy gr...
Article
Eleven withanolides isolated from Withania somniferal. (Dun.) were analyzed on a C18 reversed-phase column. Good separation factors were obtained, especially when analysing the major component of the plant. The semi-quantitative determination of the main withanolides of chemotype III collected from four different locations (Yavne, Gedera, Farm-1 an...
Article
From the plant Jaborosa leucotricha a new withanolide 17α-hydroxy-5β,6β-epoxy-1-oxo-22R-witha-2,24-dienolide has been isolated and fully characterized.
Article
A new quaternary purine derivative isolated from the sea anemone Bunodosoma caissarum has been identified, by spectroscopic measurements and X-ray diffraction analysis, to be 3,9-dimethyl-6-methylimino-8-oxo-3,6,8,9-tetrahydropurine (caissarone) and isolated as the hydrochloride. The X-ray structure indicates that the exocyclic nitrogen is apparent...
Article
Two foliar applications of gibberellic acid (GA3, 250 mg l–1) enhanced the flowering in various clones of Papaver bracteatum. The most pronounced effects were obtained in late flowering clones in which GA3 increased significantly the number and weight of the capsules and thebaine yield per plant.
Article
The 13C NMR spectrum of the pentacyclic triterpene friedelin was fully assigned, taking into account signal multiplicities, correlations of the carbon lines with known proton resonances and Eu-induced shifts. This work clarifies the situation prevalent in the literature, in which three separate groups have published contradictory information. In ad...
Article
The structure of cordialin A has unambiguously been determined to be (24S)-24,25-epoxy-11α-hydroxydammar-20(22)en-23-one 3,19-hemiacetal by an X-ray analysis of its C(11) acetate. Crystals are orthorhombic, space group P212121, a= 6.431(4), b= 20.530(5), c= 21.777(8)Å, Z = 4. The ring conformations adopted are: for A, a very distorted boat; for B,...
Article
3-Oxo-friedelan-20α-oic acid, named as maytenonic (polpunonic) acid, has been isolated along with β-amyrin and sitosterol from Gymnosporia emarginata. 1H and 13C NMR signals have been assigned for the structure. X-ray analysis of the single crystal confirmed that the carboxylic acid is α-oriented at C-20 and the D/E rings of this D:A-friedo-oleanan...
Article
The structure of a new withanolide was elucidated as 3β,14α,2OαF,27-tetrahydroxy-1-oxo-20R,22R-witha-5,24-dienolide using chemical and spectroscopic methods. The structure was corroborated by comparative studies with known closely related withanolides. Sitosterol-β-d-glucoside was identified through chemical and spectroscopic means.
Article
An X-ray structure determination of methyl shoreate has shown that this compound has 20S,24R stereochemistry in the side chain. Ocotillone therefore possesses the same configuration, whereas eichlerianic acid and cabraleone must have 20S,24S stereochemistry. A previous wrong assignment is thereby corrected.
Article
Im Rahmen der Untersuchung der Struktur-Wirkungs- Beziehung des wird dieser zusammen mit den Verbindungen (V)-(VI) bei der bekannten Umsetzung der Säure (III) mit dem Alkohol (unzugänglich aus (I)] erhalten; dabei wird die neue Verbindung (VII) beobachtet.
Article
Within the framework of a synthetic project towards the preparation of the natural germination inhibitor 2,6-diaryl-3,7-dipxabicyclo[3.3.0]octane, several molecules with the same bicyclic skeleton were prepared and their 1H n.m.r. spectra are described in detail. For the symmetrical systems particularly, the spectra exhibited second-order features...
Article
The 13C NMR spectra of nine representative cucurbitacins have been analysed for signal assignment, by deduction and selective comparison. Detailed 1H NMR data have been provided.
Article
The structure of two new compounds, a withanolide and an ergostene derivative, are described and identified as 3β,14α,17β,20αF-tetrahydroxy-1-oxo-20S,22R-witha-5,24-dienolide ergosta-5,25-diene-3β,24ξ-diol. These are considered interesting intermediates in the biogenetic sequence leading to the formation of withanolides, the ergostene diol being a...
Article
Die Epoxidring?ffnung von Withanolid D (Ia) unter den im Formelschema angegebenen Bedingungen f?hrt zu den Produkten (II)+(III), (IV), (V) bzw. (VI) + (VII).
Article
Zwei neue Dammaran-Typ-Triterpene werden aus Cordia verbenacea DC isoliert und anhand IR- sowie 1H- und 13 C-NMR-spektroskopischer Daten als Cordialin A (Ia) und Cordialin B (Ib) identifiziert.
Article
The structure of a new naturally occurring steroidal lactone of the withanolide group isolated from Withania somnifera chemotype III has been elucidated as (20R,22R)-14α,2OαF-dihydroxy-1-oxowitha-2,5,16,24-tetraenolid. This compound is considered to be an intermediate in the biosynthesis of withanolide E, and is at the origin of the unusual α-orien...
Article
Two new dammarane-type triterpenes, cordialin A and B, isolated from Cordia verbenacea have been identified. They have in common a 3,19-hemiacetal group bridging ring A, and an 11α-hydroxy-group. They differ in the substitution pattern of the side-chain, the former having a 20(22)en-23-one system and a 24,25-epoxide group, while the latter bears a...
Article
The opening of the steroidal 5β,6β-epoxide group, with or without an adjacent 4β-hydroxy-group, was investigated under thermal conditions on a solid support, and in the presence of sodium chloride for several withanolides. The study was expanded with the compounds being treated with sulphuric acid in acetone at various concentrations and temperatur...
Article
Hybrid plants of Withania somnifera from cross-pollinations of either chemotypes II or III (Israel) and Indian I (Delhi) have been examined. From both hybrids, 14β-hydroxywithanone (5α,14β,17α-trihydroxy-6α,7α-epoxy-1-oxo-22R-witha-2,24-dienolide) has been identified. This compound is the first example of a 14β-substitution among withanolides. From...
Article
The chemical examination of Acnistus breviflorus afforded nine withanolides, four of which are new and were established as 2,3,24,25-tetrahydro-27-desoxywithaferin A (4β-hydroxy-5β,6β-epoxy-1-oxo-22 R-withanolide), 2,3-dihydro-27-desoxywithaferin A (4β-hydroxy-5β,6β-epoxy-22 R-witha-24-enolide), 5,6-desoxywithaferin A (4β,27-dihydroxy-1-oxo-22 R-wi...
Article
The structure of 1α,3β,20αF-trihydroxy-20R,22R-witha-5,24-dienolide, a new naturally occurring steroidal lactone of the withanolide g
Article
The structure of a new chlorinated withanolide isolated from the hybrid plants of Withania somnifera, chemotypes III (Israel) by Indian I, is established as the chlorohydrin of withanolide D (6α-chloro-4β,5β,20αF-trihydroxy-l-oxo-22R-witha-2,24-dienolide). Two other known chlorinated withanolides had been isolated from different sources and additio...
Article
The heritability and repeatability of various characters affecting thebaine and seed yields in Papaver bracteatum were estimated from parents and progeny families during two consecutive years of growth. Thebaine and seed yields per plant showed the lowest heritability and therefore low selection response. High selection responses were obtained for...
Article
Alpinigenine (1) was isolated in relatively large amount from a type of Papaver bracteatum Lindl. from Iran. Oxidation of this alkaloid with Jones reagent produced a lactone function and, unexpectedly, converted the NMe into an NCHO, present as a mixture of rotamers. Crystallization afforded one pure component, which equilibrated in solution within...
Article
14β-Hydroxywithanone (1), the first example of a 14β-substitution among withanolides, was isolated with Withania somnifera and its structure established by X-Ray analysis.
Article
Three new withanolides have been isolated from hybrids obtained by crossing a chemotype of Withania somnifera received from South Africa and chemotype II originating in Israel. The compounds have been characterized as 4β,20α-dihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-24-enolide, 20α-hydroxy-1,4-dioxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide, and 20α...
Article
Seven alkaloids were isolated from Papaver bracteatum Arya II, six of which: thebaine, 14β-hydroxycodeine, codeine, neopine, alpinigenine and protopine, have been previously found to be present in other types of this species. It is the first report of the isolation of O-methylflavinantine from P. bracteatum.
Article
Summary The naturally occurring lignan, monoepoxylignanolide (MEL) fromAegilops ovata L., inhibits germination of lettuce achenes (seeds) in incandescent light but not in the dark. The ‘action spectrum’ after preincubation of MEL in darkness shows inhibition in the regions of 399 nm and 712–804 nm, but after pretreatment with incandescent light inh...
Article
The structure of the hydrogenation product of barbatusin, a diterpenoid from Coleus barbatus Bentham has been revised on the basis of NMR and X-ray data. A geminal coupling of unusually high magnitude has been observed and analysed.
Article
2,6-Diaryl-3,7-dioxabicyclo[3,3,0]octan-8-one structures are assigned to two lignans isolated from Aegilops ovata L., by comparing their spectroscopic data to a synthetically prepared novel 2,4- and 2,6-diaryl monoepoxylignanolide. The possibility of differentiating between these two structural types is discussed and an X-ray analysis of the 2,4-di...
Article
A rapid method enabling a quantitative analysis of thebaine in capsules and latex of Papaver bracteatum has been devised, based on a TLC technique. This method was compared to the commonly used GLC procedure, and highly significant correlation coefficient (r = 0.90) and linear regression were found between the two methods. Values for concentrations...
Article
Ein aus Aegilops ovata isoliertes Lignan erwies sich als das 2,6-Diaryl-lignanolid (III), das zum NMR-spektroskopischen Identitätsvergleich durch Kondensation von Ferulasäure (I) mit Conyferylalkohol (II) dargestellt wurde.
Article
Thebaine yield components of capsules and roots of selected plants from one year old Arya I (Is) and two years old ARya II (Is) populations of Papaver bracteatum Lindl. were compared. A large chemical variation was found within each population but no marked differences were found between the selections from the two populations in thebaine content o...
Article
Two novel phenolic diglycerides have been isolated from Aegilops ovata together with scopoletin and p-coumaric acid. Spectroscopic evidence and a synthesis confirmed the proposed structures which are presented together with the CMR data for these diglycerides and related model compounds.
Article
Withaferin A and withanolide E, two steroidal lactones of plant origin were demonstrated to have specific immunosuppressive effects on human B and T lymphocytes as well as on mice thymocytes. E rosettes and EAC rosette formation by normal human T and B lymphocytes were inhibited by the two compounds at very low concentrations. The formation of mous...
Article
The structure of three diterpenoids from Coleus barbatus, Bentham (Labiatae) having a spirocyclopropyl side chain have been determined: they are barbatusin (1a), 3β-hydroxy-3-deoxybarbatusin (2) and cyclobutatusin (3a). The structures of 1a and 3a were established by X-ray diffraction analysis, and the latter compound has been shown to have an unus...
Article
Irradiation of the diterpenoid, barbatusin (2), produces dehydrocyclobutatusin (3), which contains a new four-membered ring; the structure of 3 was determined by x-ray methods.
Article
Several cholestane derivatives possessing rings A and B with the same substitution pattern as in the naturally occurring steroidal lactones of the withanolide group have been synthesised: 4β-hydroxycholesta-2,5-dien-1-one (10), 5,6β-epoxy-4β-hydroxy-5β-cholest-2-en-1-one (12), cholesta-2,5-dien-1-one (19), and 5,6β-epoxy-5β-cholest-2-en-1-one (21)....
Article
A synthetic approach has led to a revision of structure for the germination inhibitor of Aegilops ovata L., from which a second lignan of the same series has now been isolated and identified.
Article
Two compounds, tricin and a related new flavolignan have been isolated from Aegilops ovata L. dispersal units. Evidence leading to assignment of structure of this new compound is presented together with 1H and 13C‐NMR chemical shifts of related model compounds. These phenolics found together in the same plant species with a previously discovered li...
Article
Reciprocal crossbreeding between Withania somnifera chemotype III (Israel) and chemotype Indian I (Delhi) were performed. The F1 offspring of this cross was characterized by significant changes in the main steroidal lactone constituents of the parent plants. From the withaferin A (9) and the withanone (2) both present as major constituents in the p...
Article
In order to investigate the chemical behavior of pilocarpine, as well as the factors which determine its pharmacological activity, systematic and specific structural changes involving the lactone and imidazole moieties have been performed. Series of model compounds with cyclic or open-chain structures and a variety of N-3 bonded chains obtained fro...
Article
From Cabralea eichleriana DC. (Meliaceae) nine compounds having a dammarane skeleton have been isolated and identified. They are cabraleone 2, ocotillone 3, cabraleadiol 4a, cabralealactone 5, cabraleahydroxylactone 6a, eichlerianic acid 7a, shoreic acid 8a, dammarenolic acid 9a and eichlerialactone 10a. The only limonoid present is fissinolide1. C...
Article
Females of the mothEctomyelois ceratoniae prefer to oviposit on carobs,Ceratonia siliqua L., infested with the fungusPhomopsis sp. (Gothilf, 1964). An extract of the steam distillate of fungus-infested carobs was more effective in stimulating female moths to oviposit than was an extract of uninfested carobs. The extract of the fungus-infested carob...
Article
The mass spectra of α-, β- and γ-pyridine aldoximes and the respective O-methyl ethers were studied. The mass spectral behaviour of α-pyridine aldoxime is characterized by the elimination of NO, while the molecular ion of the γ-isomer expels H2 CN. In the case of the β-isomer the formation of the m/e 67 ion (C4H5N) in a concerted process is the mai...
Article
From Cabralea eichleriana seeds, the following compounds have been isolated: cabraleone, cabraleadiol, fissinolide, 3-deacetylfissinolide, gedunin, 7-deacetoxy-7-oxygedunin, 7-deacetoxy-7-hyd-roxygedunin, methyl angolensate, and three new compounds, 7-deacetoxy-7-hydroxyphotogedunin, cabralin, and isocabralin. Cabralin has also been obtained by pho...
Article
Seven steroidal lactones of the withanolide series have been isolated as minor constituents of the leaves of Withania somnifera Dun. (Solanaceae) chemotype I, along with the major component withaferin A. Structures have been assigned to the new compounds: withanolide N (17α,27-dihydroxy-1-oxo-20R,22R-witha-2,5,14,24-tetraenolide) (6a) and withanoli...
Article
The modifications taking place in the substitution pattern of organic molecules during cross breeding by pollination has been investigated. Through the process of hybridisation of different “chemotypes” of Withania somnifera (Solanaceae), changes have been observed among the substituents present in the steroidal lactones of the withanolide type whi...
Article
Chromatographic separation of the residue left after the separation of cucurbitacins D, E and I from the ethereal extracts of Ecballium elaterium L. (Cucurbitaceae) yielded five crystalline phenolics characterised as hydroquinone, 4-hydroxy acetophenone, 4-hydroxy-3-methoxy acetophenone (acetovanillone), 2-nitroquinol and 4-hydroxyphenyl-bisepoxy l...
Article
IT has been previously reported1 that the dispersal units of Aegilops ovata L. contain a germination inhibitor. Leachates of the hulls inhibited the germination of Lactuca achenes. This inhibition was considerably stronger in light than in darkness, an unusual feature, since all germination inhibitors already described inhibit the germination of La...
Article
The host extracts and their chemical components eliciting attraction and bite stimuli in Scolytus mediterraneus were investigated. The ether extract exhibited the highest activity as expressed by the number of holes on a Styropor disk impregnated with the extract. Taxifolin (V), pino-cembrin (I), and dihydrokaempferoi (III) showed high activity, wh...
Article
In addition to the previously reported cucurbitacins D and I (elatericins A and B) and various phenolics, the ethereal extract of the fruit juice of Ecballium elaterium L. has yielded six additional curcubitacins, which have been identified as cucurbitacins B (1b), L (4a), and R (dihydrocucurbitacin D)(2a), and anhydro-22-deoxo-3-epi-isocucurbitaci...
Article
The H–D exchange of methylene protons in a side-chain when situated between a positively charged N-atom (α–CH2) and a ketone function was studied in various pilocarpinium (N-methyl imidazolium) and hydroximinomethyl pyridiniums using NMR measurements. Structural factors which determine the course of the exchange are reported, and the role of the so...
Article
Nine new steroidal lactones of the withanolide series (withanolides E-M) have been isolated from the leaves of Withania somnifera Dun (Solanaceae) growing in the southern coastal plane of Israel. This population of W. somnifera constitutes a new chemotype and is designated as chemotype III. The following structures have been assigned to seven of th...
Article
Das durch direkte Methylenierung des Epoxycholestanons (I) nach bekanntem Verfahren erhältliche Methylenderivat (II) führt bei der Behandlung mit Tosylhydrazin und Na-boranat in Methanol zu einem Gemisch der Verbindungen (III) und (IV), während die Reduktion von (II) mit Li-alanat bzw. mit Na-boranat nur die Hydroxyderivate (V) bzw. (VI) liefert.
Article
Treatment of 1,2-epoxy-3-ketosteroids with tosylhydrazine and sodium borohydride in methanol lead to mixtures consisting of (i) ring A seco-acetylenic alcohols, (ii) methoxyhydrins formed by opening of the epoxide ring following the carbonyl reduction, and (iii) an epoxy-3,3-di- methylketal. For the corresponding 4-methylene derivative, the ring A...
Article
Résumé Dihydroelatericine A administré par voie buccale à des souris femelles au moins pendant deux semaines, empêche la fertilisation. L'éxamen histologique des ovaires démontre que la substance prévient l'ovulation.
Article
Seven compounds, namely, epoxyazadiradione (III), 6α-acetoxy-epoxyazadira-dione (VI), 6α-acetoxygedunin (Va), 6α-hydroxygedunin (Vb), 7-deacetoxy-7-oxogedunin (IVb), andirobin (VII), and methyl angolensate (VIII), were isolated from Carapa guianensis Aubl., three of which, VI, Va, and Vb are new compounds. The biogenetic implication of the isolatio...
Article
The title compound has been shown to be 6α,7α-epoxy-5α-hydroxy-1,12-dioxo-22R-witha-2,24-dienolide. This is the first natural 12-oxowithanolide isolated so far.