Reserpine: A Challenge for Total Synthesis of Natural Products

Bioactivity-guided fractionation of cranberry fruit was used to determine the identity of triterpenoid esters from Vaccinium macrocarpon, which inhibit tumor cell growth and may play a role in cancer prevention. In our previous study, a fraction from whole fruit exhibited tumor cell growth inhibition in vitro. The major components of this fraction were isolated by chromatographic separation of ethyl acetate extracts, purified by semipreparative HPLC, and identified by NMR as cis- (1) and trans- (2) isomers of 3-O-p-hydroxycinnamoyl ursolic acid. These triterpenoid esters have not been previously reported in Vaccinium fruit. Bioassay of the purified triterpene cinnamates in tumor cell lines in vitro showed slightly greater activity of compound 1 in most cell lines, with GI(50) values of approximately 20 microM in MCF-7 breast, ME180 cervical and PC3 prostate tumor cell lines. Quercetin was slightly less active than 1, while cyanidin-3-galactoside exhibited much lower cytotoxicity, with GI(50) greater than 250 microM in all cell lines. Phenylboronic acid (3) was also isolated from the fruit but showed insignificant antitumor activity.

Identification of triterpene hydroxycinnamates with in vitro antitumor activity from whole cranberry fruit (Vaccinium macrocarpon).

Carbachol-induced bladder mast cell activation: augmentation by estradiol and implications for interstitial cystitis

Dynorphin (1–13): Analgesia, hypothermia, cross-tolerance with morphine and β-endorphin

Light and electron microscopic analysis of adenovirus-infused ileal loops disclosed virus particles within the tubulo-vacuolar apparatus of absorptive cells. Tissue observed from five-minute loops contained virus particles largely within apical tubules and vesicular profiles. Similar particles were observed within cisternae and supranuclear vacuoles as well as within apical tubules in tissue samples from 10- and 15-minute loops. Loops maintained for 30 minutes demonstrated virions predominantly in the supranuclear vacuole of each absorptive cell. In no instance was a virion seen free within the cytoplasm or nucleus and none was apparent elsewhere in the mucosa. It appears that absorptive cells of the ileum are capable of sequestering exogenous virions and conveying them to established lysosomal bodies in the supranuclear cytoplasm. Here they may be either stored or degraded, thus impeding their progress to other intra- or extracellular locations. The possible significance of these findings is discussed in detail, and it is proposed that sequestration of ingested virions by the tubulo-vacuolar apparatus of the ileal absorptive cell may serve some protective function in the developing neonate. It is suggested that direct infusion of “purified” virus into intestinal loop preparations is an efficient means of observing virus-intestinal cell interactions in the living animal. This experimental model might prove effective in future studies of viral infection in the intestine, particularly if it is combined with both serological and morphological methods.

Uptake of adenovirus by intestinal absorptive cells of the suckling rat. II. The neonatal jejunum.

Reactions of phthalide and 6-chlorophthalide with sodium salts of thiophenols gaveo-(phenylmercaptomethyl)benzoic acids (III), which were cyclized by the action of polyphosphoric acid to 6, 11-dihydrodibenz(b,e)-thiepin-11-ones (1). These ketones were treated with 3-di-methylaminopropylmagnesium chloride and other basic Grignard reagents and the products (IV) dehydrated to a series of 11-(aminoalkylidene)-6,11-dihydrodibenz(b,e)-thiepins (V), the hydrochlorides of which show psychotropic activity.

Derivate des 6,11-Dihydrodibenz(b,e)thiepins, eine neue Gruppe von psychotropen Substanzen

Resolution during total synthesis of reserpine

A series of cyclohexylamine derivatives methylated both on nitrogen atom and in position 1, 2 and 6 of the cyclohexane ring have been prepared. Some of them showed considerable hypotensive and ganglioplegic activity. The most interesting compound is N,N,1,2,2-pentamethylcyclohexylamine (‘penhexamine’) whose activity compares favourably with mecamylamine or dimecamine.

Polymethylcyclohexylamine — neue, hypotensiv wirksame substanzen

Two notes on the last stages of a DL reserpine synthesis

5-Fluortryptamin und weitere neue Bz-substituierte Tryptamine

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