CN105705018B - (s,s)‑开环异落叶松树脂酚二葡糖苷和(r,r)‑开环异落叶松树脂酚二葡糖苷的制备 - Google Patents
(s,s)‑开环异落叶松树脂酚二葡糖苷和(r,r)‑开环异落叶松树脂酚二葡糖苷的制备 Download PDFInfo
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- CN105705018B CN105705018B CN201480041131.2A CN201480041131A CN105705018B CN 105705018 B CN105705018 B CN 105705018B CN 201480041131 A CN201480041131 A CN 201480041131A CN 105705018 B CN105705018 B CN 105705018B
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- 0 C*CO[C@@]1[C@@](Oc2cc(CC[C@](CO)[C@](Cc(cc3*=C)ccc3O)CO[C@@]([C@@](*)[C@]3O)O[C@](CO)[C@]3O)cc(OC)c2O)IO[C@](CO)[C@@]1O Chemical compound C*CO[C@@]1[C@@](Oc2cc(CC[C@](CO)[C@](Cc(cc3*=C)ccc3O)CO[C@@]([C@@](*)[C@]3O)O[C@](CO)[C@]3O)cc(OC)c2O)IO[C@](CO)[C@@]1O 0.000 description 8
- QOWCBKMQPRAPGD-UHFFFAOYSA-N CC1C(C2)C2(C)CCC1 Chemical compound CC1C(C2)C2(C)CCC1 QOWCBKMQPRAPGD-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Toxicology (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711326022.7A CN107955046A (zh) | 2013-06-10 | 2014-06-10 | 开环异落叶松树脂酚二葡糖苷的制备 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361833258P | 2013-06-10 | 2013-06-10 | |
| US61/833,258 | 2013-06-10 | ||
| PCT/US2014/041636 WO2014200964A1 (en) | 2013-06-10 | 2014-06-10 | Preparation of (s,s)-secoisolariciresinol diglucoside and (r,r)-secoisolariciresinol diglucoside |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711326022.7A Division CN107955046A (zh) | 2013-06-10 | 2014-06-10 | 开环异落叶松树脂酚二葡糖苷的制备 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105705018A CN105705018A (zh) | 2016-06-22 |
| CN105705018B true CN105705018B (zh) | 2018-01-12 |
Family
ID=52022698
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711326022.7A Pending CN107955046A (zh) | 2013-06-10 | 2014-06-10 | 开环异落叶松树脂酚二葡糖苷的制备 |
| CN201480041131.2A Active CN105705018B (zh) | 2013-06-10 | 2014-06-10 | (s,s)‑开环异落叶松树脂酚二葡糖苷和(r,r)‑开环异落叶松树脂酚二葡糖苷的制备 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711326022.7A Pending CN107955046A (zh) | 2013-06-10 | 2014-06-10 | 开环异落叶松树脂酚二葡糖苷的制备 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US10030040B2 (enExample) |
| EP (2) | EP3488697A1 (enExample) |
| JP (3) | JP6321788B2 (enExample) |
| KR (1) | KR102270124B1 (enExample) |
| CN (2) | CN107955046A (enExample) |
| AU (1) | AU2014278362B2 (enExample) |
| CA (1) | CA2920346A1 (enExample) |
| CY (1) | CY1120759T1 (enExample) |
| DK (1) | DK3007557T3 (enExample) |
| ES (1) | ES2691845T3 (enExample) |
| HR (1) | HRP20181663T1 (enExample) |
| HU (1) | HUE040022T2 (enExample) |
| IL (2) | IL243029B (enExample) |
| LT (1) | LT3007557T (enExample) |
| PL (1) | PL3007557T3 (enExample) |
| PT (1) | PT3007557T (enExample) |
| RS (1) | RS57846B1 (enExample) |
| SI (1) | SI3007557T1 (enExample) |
| SM (1) | SMT201800575T1 (enExample) |
| TR (1) | TR201815423T4 (enExample) |
| WO (1) | WO2014200964A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10030040B2 (en) * | 2013-06-10 | 2018-07-24 | The Trustees Of The University Of Pennsylvania | Preparation of (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside |
| CA2950744A1 (en) * | 2014-05-30 | 2015-12-03 | The Trustees Of The University Of Pennsylvania | Use of secoisolariciresinol diglucosides (sdgs) and related compounds for protection against radiation and chemical damage |
| US11197876B2 (en) | 2014-05-30 | 2021-12-14 | The Trusiees Of The University Of Pennsylvania | Effects of LGM2605 on a primate model of asthma |
| US20170258821A1 (en) | 2014-05-30 | 2017-09-14 | The Trustees Of The University Of Pennsylvania | USE OF SECOISOLARICIRESINOL DIGLUCOSIDES (SDGs) AND RELATED COMPOUNDS FOR PROTECTION AGAINST RADIATION AND CHEMICAL DAMAGE |
| JP2018528208A (ja) * | 2015-09-01 | 2018-09-27 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | 放射線損傷からの保護のためのセコイソラリシレシノールジグルコシド(sdg)および関連化合物の使用 |
| ES2969209T3 (es) | 2016-06-07 | 2024-05-17 | Univ Pennsylvania | Composiciones y métodos para proteger órganos de lesiones por isquemia/reperfusión asociadas con el trasplante |
| KR20200016372A (ko) | 2017-06-12 | 2020-02-14 | 리그나메드, 엘엘씨 | (s,s)-세코이소라리시레시놀 디글루코시드 및 (r,r)-세코이소라리시레시놀 디글루코시드의 제조 방법 |
| CN110283218A (zh) * | 2019-06-24 | 2019-09-27 | 暨南大学 | 提高木酚素油溶性的改性方法 |
| CN111233944B (zh) * | 2020-03-25 | 2023-02-28 | 宝鸡市辰光生物科技有限公司 | 一种同时制备分离四种木脂素类成分的高效液相方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101117641A (zh) * | 2007-07-27 | 2008-02-06 | 大连医诺生物有限公司 | 开环异落叶松树脂酚二葡萄糖苷的制备方法 |
| CN102050848A (zh) * | 2009-11-01 | 2011-05-11 | 桂林莱茵生物科技股份有限公司 | 一种亚麻木酚素的制备方法 |
| EP2514426A1 (en) * | 2009-12-15 | 2012-10-24 | Consejo Superior De Investigaciones Científicas (CSIC) | Compounds having anti-inflammatory activity |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3065925B2 (ja) * | 1996-01-30 | 2000-07-17 | 日清製油株式会社 | 活性酸素種消去剤及び退色防止剤 |
| US6911330B1 (en) * | 1998-04-24 | 2005-06-28 | Washington State University Research Foundation | Recombinant secoisolariciciresinol dehydrogensase, and methods of use |
| FI110868B (fi) * | 2001-01-22 | 2003-04-15 | Maa Ja Elintarviketalouden Tut | Menetelmä sekoisolarisiresinolidiglykosidin (SDG) eristämiseksi ja puhdistamiseksi pellavansiemenistä |
| US20030060420A1 (en) | 2001-09-14 | 2003-03-27 | Rick Heintzman | Process for extraction and stabilization of phytoestrogens from flaxseed and product therefrom |
| EP1490380B1 (en) | 2002-04-02 | 2010-07-14 | Lignan Research, LLC | Aprocess for recovering secoisolariciresinol diglycoside from de-fatted flaxseed |
| JP2006347978A (ja) * | 2005-06-17 | 2006-12-28 | Nippon Flour Mills Co Ltd | 抗肥満剤及びこれを含む食品並びにペットフード |
| JP2007308469A (ja) * | 2005-11-11 | 2007-11-29 | Nippon Flour Mills Co Ltd | リグナンを有効成分とする男性用抗肥満剤 |
| CN100395253C (zh) * | 2006-05-12 | 2008-06-18 | 中国科学院山西煤炭化学研究所 | 一种由亚麻籽制备开环异落叶松树脂酚二葡萄糖苷的方法 |
| JP2010057367A (ja) * | 2008-09-01 | 2010-03-18 | Nitto Boseki Co Ltd | 魚肉の褐変防止剤および褐変防止方法 |
| CA2808746A1 (en) * | 2010-08-20 | 2012-02-23 | Federation Des Producteurs Acericoles Du Quebec | Sugar plant derived by-products and methods of production thereof |
| CN102558252A (zh) | 2010-12-31 | 2012-07-11 | 西安天一生物技术有限公司 | 一种亚麻木酚素的生产工艺 |
| US10030040B2 (en) * | 2013-06-10 | 2018-07-24 | The Trustees Of The University Of Pennsylvania | Preparation of (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside |
-
2014
- 2014-06-10 US US14/897,181 patent/US10030040B2/en active Active
- 2014-06-10 SM SM20180575T patent/SMT201800575T1/it unknown
- 2014-06-10 EP EP18183923.4A patent/EP3488697A1/en not_active Withdrawn
- 2014-06-10 EP EP14811683.3A patent/EP3007557B1/en active Active
- 2014-06-10 HU HUE14811683A patent/HUE040022T2/hu unknown
- 2014-06-10 PT PT14811683T patent/PT3007557T/pt unknown
- 2014-06-10 TR TR2018/15423T patent/TR201815423T4/tr unknown
- 2014-06-10 CN CN201711326022.7A patent/CN107955046A/zh active Pending
- 2014-06-10 KR KR1020167000483A patent/KR102270124B1/ko active Active
- 2014-06-10 AU AU2014278362A patent/AU2014278362B2/en not_active Ceased
- 2014-06-10 ES ES14811683.3T patent/ES2691845T3/es active Active
- 2014-06-10 CN CN201480041131.2A patent/CN105705018B/zh active Active
- 2014-06-10 JP JP2016519582A patent/JP6321788B2/ja not_active Expired - Fee Related
- 2014-06-10 PL PL14811683T patent/PL3007557T3/pl unknown
- 2014-06-10 CA CA2920346A patent/CA2920346A1/en not_active Abandoned
- 2014-06-10 SI SI201430924T patent/SI3007557T1/sl unknown
- 2014-06-10 HR HRP20181663TT patent/HRP20181663T1/hr unknown
- 2014-06-10 WO PCT/US2014/041636 patent/WO2014200964A1/en not_active Ceased
- 2014-06-10 DK DK14811683.3T patent/DK3007557T3/en active
- 2014-06-10 LT LTEP14811683.3T patent/LT3007557T/lt unknown
- 2014-06-10 RS RS20181236A patent/RS57846B1/sr unknown
-
2015
- 2015-12-10 IL IL243029A patent/IL243029B/en active IP Right Grant
-
2018
- 2018-04-04 JP JP2018072178A patent/JP6513853B2/ja not_active Expired - Fee Related
- 2018-07-23 US US16/042,866 patent/US10870670B2/en active Active
- 2018-10-16 CY CY181101054T patent/CY1120759T1/el unknown
-
2019
- 2019-04-10 JP JP2019074548A patent/JP6785335B2/ja active Active
- 2019-09-24 IL IL26962219A patent/IL269622A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101117641A (zh) * | 2007-07-27 | 2008-02-06 | 大连医诺生物有限公司 | 开环异落叶松树脂酚二葡萄糖苷的制备方法 |
| CN102050848A (zh) * | 2009-11-01 | 2011-05-11 | 桂林莱茵生物科技股份有限公司 | 一种亚麻木酚素的制备方法 |
| EP2514426A1 (en) * | 2009-12-15 | 2012-10-24 | Consejo Superior De Investigaciones Científicas (CSIC) | Compounds having anti-inflammatory activity |
Non-Patent Citations (2)
| Title |
|---|
| Biosynthetic Pathway to the Cancer Chemopreventive SecoisolariciresinolDiglucoside-Hydroxymethyl Glutaryl Ester-Linked Lignan Oligomers in Flax (Linum usitatissimum) Seed;Joshua D. Ford等;《J. Nat. Prod.》;20011013;第64卷;第1388-1397页 * |
| Investigation of in vitro and in vivo antioxidant potential of secoisolariciresinol diglucoside;Sadiq S. Moree,J. Rajesha;《Mol Cell Biochem》;20121030;第373卷;第179-187页 * |
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