Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1983-04-20
1984-11-13
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 5, 536181, 2603974, C07J 1700
Patent
active
044827067
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
FIELD OF THE INVENTION
The present invention relates to novel steroid saponins obtained from plants belonging to Solanaceae, extraction of the said steroid saponins and process for preparing 16-dehydropregnenolone or its ester from the said steroid saponins.
BACKGROUND OF THE INVENTION
Said 16-dehydropregnenolone is a compound having the following formula: ##STR1## and is useful as an intermediate for preparing various sexual hormones, corticoids, oral contraceptive drugs etc. It is known that 16-dehydropregnenolone is prepared from diosgenin which is contained mainly in plants of the genus Dioscorea. However, Dioscorea tokoro and some other analogous species, which are the diosgenin containing plants growing in Japan, are not satisfactory source of supply for diosgenin because their rhizomes are poor and contents of diosgenin are less than only 1%. The chief source of diosgenin at the present time is Dioscorea composita (barbasco) which is a naturally growing species in Mexico. However, this species is not reliable source because it is a wild plant. It has therefore been felt anxious about deficiency of diosgenin source and found necessary to develop a novel preparative method for 16-dehydropregnenolone from other source.
DISCLOSURE OF THE INVENTION
As a result of an extensive study searching for steroid saponin containing plants which may be a source for the preparation of 16-dehydropregnenolone carried out by the present inventors, it has now been discovered that Solanum species belonging to Solanaceae, typically Solanum aculeatissimum Jacq., contains steroid saponin compounds represented by formulae (XR-1) and (XR-2) described later in a high content, that these compounds can be successfully extracted, and that 16-dehydropregnenolone can be prepared using these compounds as starting materials.
According to the invention, there are provided (1) a compound represented by the following formula (XR-1): ##STR2## (2) a compound represented by the following formula (XR-2): ##STR3## (3) a process for extracting the compounds (XR-1) and (XR-2) which comprises extracting a plant belonging to the Solanum genus and containing the compounds (XR-1) and (XR-2) with water or an organic solvent and separating the compounds (XR-1) and (XR-2) contained in the extract, and (4) a process for preparing 16-dehydropregnenolone or lower aliphatic acid ester thereof which comprises hydrolyzing the compound (XR-1) or (XR-2), subjecting the obtained product to Marker's degradation and treating the obtained product with water, a lower alcohol or a lower aliphatic acid.
In the process for extracting the compounds (XR-1) and (XR-2), it is preferable to use water or a hydrophilic organic solvent, especially water, a lower alcohol (such as for example, methanol, ethanol, propanol etc.) or a mixture thereof. The compounds (XR-1) and (XR-2) can be obtained in an isolated state, or as a mixture of these two compounds, by treating the said extract, or extract (organic phase) obtained by extracting the concentrate of the said extract with other solvent (for example, a mixture of water: butanol=1:1), with the conventional means such as concentration, crystallization, recrystallization, chromatography, solvent-partition etc. Since both the compounds (XR-1) and (XR-2) can be used for preparing 16-dehydropregnenolone in the same way, it is not necessary to separate these two compounds and it is more preferable to use as a mixture of the two compounds.
The compounds (XR-1) and (XR-2) have the following physical properties when they are isolated.
XR-1
colorless needles
m.p.: 196.degree.-204.degree. C.
angle of rotation: [.alpha]sub.D.sup.27 =-28.4.degree. (c=1.02, pyridine)
FD-MS (m/Z): 1069
IR .nu..sub.max.sup.KBr (cm.sup.- 1): 3400
CMR (d.sub.5 -py.)
.delta.(ppm)=15.03, 16.11, 18.25, 18.40, 19.33, 21.04, 24.31, 30.06, 31.63, 32.16, 32.16, 33.09, 33.77, 37.04, 37.48, 38.56, 38.85, 39.83, 40.46, 50.22, 56.42, 61.35, 62.42, 62.62, 69.25, 70.28, 71.55, 72.18, 72.18, 72.48, 72.48, 73.60, 73.89, 75.11, 76.28, 77.21, 77.75, 78.1
REFERENCES:
patent: 4101652 (1978-07-01), Bonati
patent: 4265886 (1981-05-01), Pegel
patent: 4320225 (1982-03-01), Hashimoto et al.
Murakami Kotaro
Tomimatsu Toshiaki
Brown Johnnie R.
Peselev Elli
Tokiwa Yakuhin Kogyo Kabushiki Kaisha
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