Perkin I (original) (raw)
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Steroidal sapogenins LX. Survey of plants for steroidal sapogenins and other constituents
Journal of Pharmaceutical Sciences, 1961
This is a report of the chemical examination of the sixth 1,000 accessions in a survey of plants for steroidal sapogenins. Data are given for about 1,030 species in 128 families, practically all collected in the United States. I n Agaue a new record of 4.4% genin, mostly smilagenin, was established. The collections of Dioscoreu composita were uniformly high in diosgenin, with a new record of 10.1%.
Journal of the Brazilian …, 2005
A convenient pathway to obtain 3b-hydroxy-6-oxo-5a-steroids from 3b-acetoxy D5-steroids is reported; the methodology was applied to the synthesis of laxogenin (7), substance that behaves as a plant growth hormone. This is an alternative way to produce an important functionality found in many examples of naturally occurring steroids. The developed procedure uses inexpensive reagents and can be carried out in four steps. The oxidizing and acidic steps used in this methodology did not affect the labile spiroketal side chain present in diosgenin (16).
Journal of the Brazilian Chemical Society
A convenient pathway to obtain 3β-hydroxy-6-oxo-5α-steroids from 3β-acetoxy ∆5-steroids is reported; the methodology was applied to the synthesis of laxogenin (7), substance that behaves as a plant growth hormone. This is an alternative way to produce an important functionality found in many examples of naturally occurring steroids. The developed procedure uses inexpensive reagents and can be carried out in four steps. The oxidizing and acidic steps used in this methodology did not affect the labile spiroketal side chain present in diosgenin (16).
Due to the pressure of war work, the publication of our studies on the sapogenins of over three hundred plants from Mexico and United States will necessarily be delayed. In the present paper we are reporting some of our results in preliminary form. Earlier work on the biogenesis of the steroidal hormones and related compounds has focused our attention on this problem in both animals2 and plants. In the present paper we report the isolation and structures of thirteen new steroidal sapo-genins, thus more than doubling the number of these substances known. We have also found new sources for many of the previously known sapogenins. The extensive collections by the senior author were made possible only because of the kind and painstaking cooperation of the Botany Departments , Experimental Stations and Range Ecology Departments of the following Institutions : Texas A. and M
Steroidal Saponins with Plant Growth Stimulation Effects; Yucca schidigera as a Commercial Source
Plants
Plant growth-stimulation bioactivity of triterpenoid saponins is well known, especially for oleanane-type compounds. Nevertheless, a few phytotoxicity bioassays performed on some steroidal saponins have shown hormesis profiles and growth stimulation on Lactuca sativa roots. The focus of the work described here was on the use of the wheat coleoptile bioassay to evaluate plant growth stimulation, and on the search for a commercially available source of active saponins by bio-guided fractionation strategy. Selected saponins were tested and a cluster analysis showed that those saponins with a sugar chain of more than five units had a hormesis profile, while saponins with growth enhancement had fewer sugar residues. Two saponins showed similar activity to the positive control, namely the phytohormone indole-3-butyric acid (IBA). As a potential source of these metabolites, a commercial extract of Yucca schidigera used as a fertilizer was selected. Bio-guided fractionation led to the ident...
A unique immuno-stimulant steroidal sapogenin acid from the roots of Asparagus racemosus
Steroids, 2011
A new steroidal sapogenin molecule 1 having unique characteristics, 21-nor and unusual C19 carboxylic acid has been isolated from the roots of Asparagus racemosus. On the basis of chemical evidence, extensive spectroscopic analysis including two dimensional (2D) NMR and X-ray studies of single crystal, the structure of 1 was determined as (1S,2R,3S,8S,9S,10S,13S,14S,16S,17R,22R,25R)-21-nor-18,27␣dimethyl-1,2,3-trihydroxy-25-spirost-4-en-19-oic acid. 1 crystallizes in monoclinic space group P2 1 with a = 9.295(2), b = 11.238(2), c = 11.376(2)Å;ˇ= 91.993(4) • , Z = 2, D cal = 1.344 Mg/m 3 . The structure was solved by direct methods and refined by full-matrix least-squares procedure to a final R-value of 0.0561 for 4064 observed reflections. 1 was tested against the type of immune responses generated during treatment in normal and immune-suppressed animals and detailed biological activity evaluation suggests it to be a potent immunostimulator.
Steroidal Saponins fromDisporopsis pernyi
Helvetica Chimica Acta, 2004
Four new steroidal saponins, named disporosides A ± D (1 ± 4), corresponding to (3b,25R)-3- , have been isolated from the fresh rhizomes of Disporopsis pernyi, together with the three known compounds Ys-I, agavoside B, and (3b, -b-d-galactopyranosyl)oxy]-5a-spirostan-12-one. Their structures were elucidated by spectroscopic analyses, chemical transformations (acid hydrolysis), and comparison with literature data.
Barbourgenin, a New Steroidal Sapogenin from Agave sisalana Leaves
Journal of Natural Products, 1986
Hecogenin E (2 5R)-3 p-hydroxy-Saspirostan-12-one), an important precursor for the production of corticosteroids, is extracted from the sapogenin concentrate known as "coffee grounds," which is produced from the acid hydrolyzed juice of the leaves of Agave sisalana Perrine (Agavaceae). In addition to hecogenin, many different steroidal sapogenins have been isolated from either A. sisalana leaves or "coffee grounds" (1-3). From the latter we report the isolation of barbourgenin (l), which is a new dihy