WO1983001065A1 - Nouvelles saponines steroides, leur procede d'extraction, et procede de preparation de 16-dehydropregnenolone a partir de ces nouvelles saponines - Google Patents

Nouvelles saponines steroides, leur procede d'extraction, et procede de preparation de 16-dehydropregnenolone a partir de ces nouvelles saponines Download PDF

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Publication number
WO1983001065A1
WO1983001065A1 PCT/JP1982/000384 JP8200384W WO8301065A1 WO 1983001065 A1 WO1983001065 A1 WO 1983001065A1 JP 8200384 W JP8200384 W JP 8200384W WO 8301065 A1 WO8301065 A1 WO 8301065A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
ompi
extraction
extract
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1982/000384
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Yakuhin Kogyo Kabushiki Kaisha Tokiwa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tokiwa Pharmaceutical Co Ltd
Original Assignee
Tokiwa Yakuhin Kogyo KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tokiwa Yakuhin Kogyo KK filed Critical Tokiwa Yakuhin Kogyo KK
Priority to DE8282902830T priority Critical patent/DE3269846D1/de
Publication of WO1983001065A1 publication Critical patent/WO1983001065A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring

Definitions

  • the present invention relates to a novel steroid saponin obtained from a plant belonging to the genus Eggplant, a method for extracting the same, and a method for producing 16-dehydropredanenolone or an ester thereof from the same.
  • de D predanenolone can be produced from Diosgenin, which is present in plants of the genus Chamonoimo.
  • diosgenin-containing plants produced in Japan, Dios eorea tokoro, and other plants have small rhizomes and a content of less than 1%.
  • D ioscorea composita (barl) aseo) is wild in Mexico.
  • barl barl
  • it since it is a wild plant, its reliability as a resource is poor. Therefore, there is concern about the shortage of diosgenin in the future, and it has been hoped that the production of 16-dehydromouth predanenolone from other raw materials will be opened.
  • the present inventors have searched for a plant containing steroid sapocon which is a raw material for producing 16-dehydropredanenolone, and as a result, have found that a plant of the genus Solanum belonging to the family Solanaceae (Solanace ae), in particular, a golden squirrel ( S olamm aculeatissimum Jacq.) Has the following structural formulas (XR-1) and (XR-1)
  • WiPO (2) a compound represented by the following structural formula (XR-2)
  • the compounds (XR-1) and (XR-2) can all be used for the production of 16-dehydropredanenone as well. Therefore, it is desirable to use them for the production of 16-dehydropredanenones without the need to separate them, but rather to extract and use them in the form of a mixture, the compound (XR-1) and ( The physical properties of XR-2) are as follows:
  • OMPI This is carried out by treating with a mineral acid such as hydrochloric acid, sulfuric acid or the like in ethanol, ethanol, isopropyl alcohol or a mixture thereof. It is desirable to use at least equimolar mineral acid.
  • the reaction is usually carried out by heating at a temperature of about 70'C for about 2 to 5 hours.
  • Marker degradation is performed by acetate lysis and chromic acid oxidation. '(Eg, ⁇ Facilities ⁇ and Fizza, “Stade,” p. 549, 1S59).
  • the acetolysis is carried out by reacting the above compound with an acetylating agent (acetic anhydride, acetyl chloride, 2,3-diacetoxypyridine, etc.).
  • an acetylating agent acetic anhydride, acetyl chloride, 2,3-diacetoxypyridine, etc.
  • an excess amount of the above acetylating agent is added in a solvent (acetic acid, pyridin, methanol, ethanol, or diisopropyl alcohol) at about 0 to 150 (preferably at room temperature to 110).
  • the reaction can be carried out in two stages by reacting for 2 to 15 hours and then reacting with acetic anhydride for about 18 hours at about 1 S5 in a sealed tube.
  • the mixture of the following compounds is considered to be fresh tiger by the first stage septal.
  • the second stage processing can be performed. This reaction is promoted by an acid (for example, toluenesulfonic acid) or a Lewis acid (for example, aluminum chloride). Further, an organic acid (for example, octanoic acid) can be used as a solvent. This reaction is considered to produce the following compound
  • reaction conditions are about 1 hour at room temperature to 22.
  • Anti-IS products such as adding water to the reaction solution
  • the extract was concentrated under reduced pressure to obtain about 70 g of the extract. If you need this n
  • the precipitated salt of the solution was filtered off, and the residue obtained by distilling off methanol (about 24 S ) was obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
PCT/JP1982/000384 1981-09-25 1982-09-24 Nouvelles saponines steroides, leur procede d'extraction, et procede de preparation de 16-dehydropregnenolone a partir de ces nouvelles saponines Ceased WO1983001065A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE8282902830T DE3269846D1 (en) 1981-09-25 1982-09-24 Novel steroid saponins, process for their extraction, and process for preparing 16-dehydropregnenolone therefrom

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP56/152488810925 1981-09-25
JP56152488A JPS5855500A (ja) 1981-09-25 1981-09-25 １６−デヒドロプレグネノロンの製造法

Publications (1)

Publication Number Publication Date
WO1983001065A1 true WO1983001065A1 (fr) 1983-03-31

Family

ID=15541570

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1982/000384 Ceased WO1983001065A1 (fr) 1981-09-25 1982-09-24 Nouvelles saponines steroides, leur procede d'extraction, et procede de preparation de 16-dehydropregnenolone a partir de ces nouvelles saponines

Country Status (5)

Country Link
US (1) US4482706A (enExample)
EP (1) EP0089377B1 (enExample)
JP (1) JPS5855500A (enExample)
DE (1) DE3269846D1 (enExample)
WO (1) WO1983001065A1 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5862200A (ja) * 1981-10-07 1983-04-13 Tokiwa Yakuhin Kogyo Kk １６−デヒドロプレグノロンの製造法
JP2562134B2 (ja) * 1986-09-19 1996-12-11 喜徳 喜谷 新規な白金−ステロイド錯体
US5808117A (en) * 1996-01-22 1998-09-15 Chowdhury; Pritish Kumar Process for the production of 16-Dehydropregenolone acetate form diosgenin
GB9923076D0 (en) * 1999-09-29 1999-12-01 Phytopharm Plc Sapogenin derivatives and their use
KR20070007214A (ko) * 1998-03-26 2007-01-12 파이토팜 피엘씨 알츠하이머병을 치료하기 위한 스밀라게닌 및안주로게닌-ｄ
GB9923078D0 (en) * 1999-09-29 1999-12-01 Phytopharm Plc Sapogenin derivatives and their use
GB9923077D0 (en) * 1999-09-29 1999-12-01 Phytopharm Plc Sapogenin derivatives and their use
GB0000228D0 (en) * 2000-01-06 2000-03-01 Phytopharm Plc Fluoro substituted sapogenins and their use
GB0107822D0 (en) * 2001-03-28 2001-05-23 Phytopharm Plc Sapogenin derivatives their synthesis and use methods based upon their use
US20050130948A1 (en) * 2002-03-27 2005-06-16 Daryl Rees Therapeutic methods and uses of sapogenins and their derivatives
CN102727501A (zh) * 2002-03-27 2012-10-17 菲特法姆股份有限公司 皂角苷配基及其衍生物的用途
JP2010535758A (ja) * 2008-01-04 2010-11-25 ビオスペクトルム，インコーポレイテッド ジオスゲニンを含む皮膚美白用組成物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5664000A (en) * 1979-10-29 1981-05-30 Osaka Chem Lab Novel saponin substance

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294785A (en) * 1963-07-29 1966-12-27 Schering Corp Novel process for the conversion of a sapogenin to a 16-dehydro steroid and intermediates produced thereby
GB1503388A (en) * 1975-07-01 1978-03-08 Inverni Della Beffa Spa Pharmaceutically active complexes and pharmaceutical compositions containing them
GB2019407B (en) * 1978-04-14 1982-10-06 Yamasa Shoyu Kk Glycosides of compounds of the 3-hydroxy oleanane series and their extraction from plants of genus periandra
DE2926463A1 (de) * 1978-07-05 1980-01-24 Roecar Holdings Nv Spiroketaline und ihre verwendung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5664000A (en) * 1979-10-29 1981-05-30 Osaka Chem Lab Novel saponin substance

Also Published As

Publication number Publication date
EP0089377A4 (en) 1984-11-23
DE3269846D1 (en) 1986-04-17
JPS5855500A (ja) 1983-04-01
EP0089377A1 (en) 1983-09-28
JPS6310160B2 (enExample) 1988-03-04
EP0089377B1 (en) 1986-03-12
US4482706A (en) 1984-11-13

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