Search PubMed⌕ Search

Biomedical subjects

M C Wani

Publications and source records attributed to M C Wani.

At least 73 records · Page 4Linked to original sources
PubMed1977

Synthesis, antifertility activity, and protein binding affinity of 7(8 leads to 11 alpha)abeo steroids.

A series of 7(8 leads to 11 alpha)abeo steroids was synthesized by a modification of the previously described total synthesis of this class of compounds and evaluated for biological activity. In general, there was a marked reduction in the relative binding affinities of these compounds for the rabbit uterus estrogen and progestin receptor proteins. None of the compounds which were subjected to uterotropic, antiuterotropic, postcoital, progestational, antiprogestational, or antiandrogenic assays showed any significant activity.

Animals↗
PubMed1976

Isolation and chemical characterization of antitumor agents from plants.

This paper reviews methods which have evolved at the Research Triangle Institute during the last 15 years for the isolation and characterization of antitumor agents from plants. The isolation procedures stress mild, nonchemical methods. Solvent partition and the Craig Counter Current Distribution are used during the early stages of fractionation. Subsequent purification involves many types of chromatography: adsorption, partition, thin-layer, preparative thin layer, gel-exclusion, and medium- and high-pressure liquid chromatography. The pure compound is crystallized from a suitable solvent. The fractionation is monitored with in vitro and in vivo bioassays. Physical methods used for structure determination are: ultraviolet, infrared, and nuclear magnetic resonance spectrometry, and X-ray crystallography.

Alkaloids↗
PubMed1975

Flavonoids. 8. Synthesis and antifertility and estrogen receptor binding activities of coumarins and delta3-isoflavenes.

A series of coumarins and delta3-isoflavenes was prepared. Although antifertility activity was shown by all of these compounds, the required dosage in mice varied from 13.5 mug/kg/day to 50 mg/kg/day. The most potent compounds were the 2-methyl-4-ethylisoflavenes, two of which (2a and 2b) were about equipotent with DES on a molar basis. They were followed by the 2,2-dimethylisoflavenes, the 2-unsubstituted isoflavene, and the coumarins. The most active compounds possessed an acetoxy group at C-7 and an oxygen function at C-4'. Presence of fluorine at C-4' or diethylaminoethoxy at C-M decreased the antifertility activity. The uterotropic activity followed the same trends as the antifertility activity with some evidence for the separation of the two effects in the 2,2-dimethylisoflavene series. Based on a limited study it appears that two phenolic hydroxyl groups are required for the presence of good estrogen receptor binding activity. An apparent lack of correlation between the estrogen binding activity and uterotropic or antifertility effects is probably explained by in vivo metabolism.

Animals↗
PubMedDate not supplied

Plant antitumor agents, 19. Novel triterpenes from Maprounea africana.

Four new pentacyclic triterpenes have been isolated from Maprounea africana. These triterpenes are members of the previously unknown urs-12-en-29-oic acid series. The structures of these compounds were deduced from spectral and chemical evidence. The parent compound, maprounic acid, was identified as 3B-hydroxyurs-12-en-29-oic acid. The remaining three triterpenes were identified as maprounic acid 3-p-hydroxybenzoate, 7 beta-hydroxymaprounic acid 3-p-hydroxybenzoate, and 2 alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate. Of the four triterpenes, only the 7 beta-hydroxy derivative exhibited in vivo P-388 activity.

Acetylation↗
PubMedDate not supplied

Plant antitumor agents, 21. Flavones, coumarins, and an alkaloid from Sargentia greggii.

Investigation of the MeOH extracts of Sargentia greggii (Rutaceae) led to the isolation of two known flavones, zapotin and 5,6,2'-trimethoxyflavone, and a new flavone, 5,6,2',3',4',6'-hexamethoxyflavone (1), whose structure was established by spectral data and confirmed by total synthesis. In addition, two known coumarins, 3-(alpha,alpha-dimethylallyl) herniarin and seselin, and a new coumarin, O-geranylosthenol (3), have been isolated from this plant. The structure of 3 was deduced from spectral data. Although the crude extracts displayed KB activity, none of the crystalline compounds were significantly active.

Alkaloids↗
PubMedDate not supplied

Plant antitumor agents, 27. Isolation, structure, and structure activity relationships of alkaloids from Fagara macrophylla.

The known alkaloids nitidine chloride [1] and 6-oxynitidine [2] and a new compound 6-methoxy-5,6-dihydronitidine [3] have been isolated from Fagara macrophylla. Compound 3 was the major product and was shown to be an artifact. The alkaloids 1 and 3 have been interconverted by treatment of 1 under basic conditions or 3 under acidic conditions. On sublimation 1 and 3 formed 8,9-dimethoxy-2,3-methylenedioxybenzo[c]phenanthridine [4] which could then be converted to 5,6-dihydronitidine [5]. The alkaloids 1 and 3 are about equipotent in P-388 mouse leukemia, giving high T/C values of 240-260% at doses of 30-50 mg/kg. The other compounds were inactive. The structural requirement for antitumor activity in the phenanthridine series is the ability to form a C-6 iminium ion.

Alkaloids↗
PubMedDate not supplied

Indoles in edible members of the Cruciferae.

Antimutagenic fractions from collards yielded indole-3-carboxaldehyde [4] and traces of indole-3-acetonitrile [2]. The compounds had no antimutagenic activity. An analytical procedure for various indoles in plants was developed based on reversed-phase hplc. The indoles studied included the 3-carbinol 1, the acetonitrile 2, the carboxaldehyde 4, the 3-carboxylic acid 5, and the 3-acetic acid 6. Many Cruciferae and non-Cruciferae were analyzed. The latter did not contain measurable quantities of these compounds. In the case of the Cruciferae--with the exception of collards, which consistently indicated the presence of the aldehyde 4--major indole found was the nitrile 2. Although a particularly careful search for the carbinol 1 was conducted, only trace levels were noted. A review of the literature indicates that the content and occurrence of this indole in plants have been heavily overestimated. Because of the low levels found in the Cruciferae, our studies indicate that the role of the compound as a dietary factor may be questionable.

Chromatography, High Pressure Liquid↗