CN110283224A - 一种罗汉果甜苷v的半合成方法 - Google Patents
一种罗汉果甜苷v的半合成方法 Download PDFInfo
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- CN110283224A CN110283224A CN201910643082.4A CN201910643082A CN110283224A CN 110283224 A CN110283224 A CN 110283224A CN 201910643082 A CN201910643082 A CN 201910643082A CN 110283224 A CN110283224 A CN 110283224A
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- China
- Prior art keywords
- momordica glycoside
- momordica
- glycoside
- hydrogenation reaction
- catalyst
- 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.)
- Granted
Links
- 229930182470 glycoside Natural products 0.000 title claims abstract description 82
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 82
- 235000009815 Momordica Nutrition 0.000 title claims abstract description 80
- 241000218984 Momordica Species 0.000 title claims abstract description 80
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 241001409321 Siraitia grosvenorii Species 0.000 claims abstract description 10
- 235000011171 Thladiantha grosvenorii Nutrition 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- VCRYGHPVKURQMM-UHFFFAOYSA-N methane;platinum Chemical compound C.[Pt] VCRYGHPVKURQMM-UHFFFAOYSA-N 0.000 claims description 3
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 239000000287 crude extract Substances 0.000 claims description 2
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 claims description 2
- 244000269722 Thea sinensis Species 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000013459 approach Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930189775 mogroside Natural products 0.000 description 4
- 238000010812 external standard method Methods 0.000 description 3
- TVJXHJAWHUMLLG-UHFFFAOYSA-N mogroside V Natural products CC(CCC(OC1OC(COC2OC(CO)C(O)C(O)C2OC3OC(CO)C(O)C(O)C3O)C(O)C(O)C1O)C(C)(C)O)C4CCC5(C)C6CC=C7C(CCC(OC8OC(COC9OC(CO)C(O)C(O)C9O)C(O)C(O)C8O)C7(C)C)C6(C)C(O)CC45C TVJXHJAWHUMLLG-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- ZYZJWAJOTPNVPI-ZVBSCDOUSA-N cucurbitane Chemical compound C([C@H]1[C@]2(C)CC[C@@H]([C@]2(CC[C@]11C)C)[C@H](C)CCCC(C)C)CC2[C@H]1CCCC2(C)C ZYZJWAJOTPNVPI-ZVBSCDOUSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 229930182493 triterpene saponin Natural products 0.000 description 2
- GHBNZZJYBXQAHG-KUVSNLSMSA-N (2r,3r,4s,5s,6r)-2-[[(2r,3s,4s,5r,6r)-6-[[(3s,8s,9r,10r,11r,13r,14s,17r)-17-[(2r,5r)-5-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-3-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H](CC[C@@H](C)[C@@H]1[C@]2(C[C@@H](O)[C@@]3(C)[C@H]4C(C([C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]6[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O6)O)O5)O)CC4)(C)C)=CC[C@H]3[C@]2(C)CC1)C)C(C)(C)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GHBNZZJYBXQAHG-KUVSNLSMSA-N 0.000 description 1
- CGGWHBLPUUKEJC-HRTKKJOOSA-N (3S,8R,9R,10R,13R,14S,17R)-17-[(2R,5R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-hydroxy-6-methylheptan-2-yl]-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one Chemical compound C[C@H](CC[C@@H](O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(C)(C)O)[C@H]1CC[C@@]2(C)[C@H]3CC=C4[C@@H](CC[C@H](O[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O)[C@H]5O)C4(C)C)[C@]3(C)C(=O)C[C@]12C CGGWHBLPUUKEJC-HRTKKJOOSA-N 0.000 description 1
- CGGWHBLPUUKEJC-UHFFFAOYSA-N 11-oxomogroside V Natural products C1CC2(C)C3CC=C(C(C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)C(CO)O5)O)O4)O)CC4)(C)C)C4C3(C)C(=O)CC2(C)C1C(C)CCC(C(C)(C)O)OC(C(C(O)C1O)OC2C(C(O)C(O)C(CO)O2)O)OC1COC1OC(CO)C(O)C(O)C1O CGGWHBLPUUKEJC-UHFFFAOYSA-N 0.000 description 1
- 206010010219 Compulsions Diseases 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003648 triterpenes Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
Description
Claims (7)
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CN201910643082.4A CN110283224B (zh) | 2019-07-16 | 2019-07-16 | 一种罗汉果甜苷v的半合成方法 |
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CN110283224A true CN110283224A (zh) | 2019-09-27 |
CN110283224B CN110283224B (zh) | 2020-08-28 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303232A (zh) * | 2020-03-31 | 2020-06-19 | 湖南华诚生物资源股份有限公司 | 一种通过乙酰化反应制备罗汉果苷v的方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101018802A (zh) * | 2004-07-13 | 2007-08-15 | 三菱化学株式会社 | 甾类化合物的制备方法 |
WO2014086842A1 (en) * | 2012-12-04 | 2014-06-12 | Evolva Sa | Methods and materials for biosynthesis of mogroside compounds |
CN106279339A (zh) * | 2016-08-09 | 2017-01-04 | 湖南华诚生物资源股份有限公司 | 一种高纯度罗汉果苷v的分离纯化方法 |
CN106350564A (zh) * | 2015-07-20 | 2017-01-25 | 中国科学院天津工业生物技术研究所 | 罗汉果醇合成途径中萜类化合物及其糖基化产物的合成方法 |
CN109678921A (zh) * | 2017-11-28 | 2019-04-26 | 华东师范大学 | 一种熊去氧胆酸的制备方法 |
CN109912676A (zh) * | 2019-03-07 | 2019-06-21 | 华东师范大学 | 一种3β-熊去氧胆酸的制备方法 |
-
2019
- 2019-07-16 CN CN201910643082.4A patent/CN110283224B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101018802A (zh) * | 2004-07-13 | 2007-08-15 | 三菱化学株式会社 | 甾类化合物的制备方法 |
WO2014086842A1 (en) * | 2012-12-04 | 2014-06-12 | Evolva Sa | Methods and materials for biosynthesis of mogroside compounds |
CN106350564A (zh) * | 2015-07-20 | 2017-01-25 | 中国科学院天津工业生物技术研究所 | 罗汉果醇合成途径中萜类化合物及其糖基化产物的合成方法 |
CN106279339A (zh) * | 2016-08-09 | 2017-01-04 | 湖南华诚生物资源股份有限公司 | 一种高纯度罗汉果苷v的分离纯化方法 |
CN109678921A (zh) * | 2017-11-28 | 2019-04-26 | 华东师范大学 | 一种熊去氧胆酸的制备方法 |
CN109912676A (zh) * | 2019-03-07 | 2019-06-21 | 华东师范大学 | 一种3β-熊去氧胆酸的制备方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303232A (zh) * | 2020-03-31 | 2020-06-19 | 湖南华诚生物资源股份有限公司 | 一种通过乙酰化反应制备罗汉果苷v的方法 |
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GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A semi synthetic method of Mogroside V Effective date of registration: 20210422 Granted publication date: 20200828 Pledgee: CITIC Bank Changsha branch Pledgor: HUNAN HUACHENG BIOTECH, Inc. Registration number: Y2021980002898 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20231127 Granted publication date: 20200828 Pledgee: CITIC Bank Changsha branch Pledgor: HUNAN HUACHENG BIOTECH, Inc. Registration number: Y2021980002898 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A semi synthetic method of mogroside V Granted publication date: 20200828 Pledgee: Agricultural Bank of China Limited Changsha Wangcheng District sub branch Pledgor: HUNAN HUACHENG BIOTECH, Inc. Registration number: Y2024980000707 |