JPH0557994B2 - - Google Patents

Info

Publication number: JPH0557994B2
Authority: JP; Japan
Prior art keywords: cystanoside; water; hydrogen atom; formula; solvent
Prior art date: 1985-02-19
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.): Expired - Lifetime

Application number

JP60029335A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61189290A (ja

Inventor

Hiromi Kobayashi

Hiroko Karasawa

Seigo Fukushima

Toshio Myase

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.)

YOMEISHU SEIZO KK

Original Assignee

YOMEISHU SEIZO 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.)

1985-02-19

Filing date

1985-02-19

Publication date

1993-08-25

1985-02-19 Application filed by YOMEISHU SEIZO KK filed Critical YOMEISHU SEIZO KK

1985-02-19 Priority to JP60029335A priority Critical patent/JPS61189290A/ja

1986-08-22 Publication of JPS61189290A publication Critical patent/JPS61189290A/ja

1993-08-25 Publication of JPH0557994B2 publication Critical patent/JPH0557994B2/ja

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
YDDMELPLARDERH-UHFFFAOYSA-N cistanoside Natural products CC1OC(OC2C(O)C(OCCc3ccc(O)c(OC(=O)C)c3)OC(COC4OC(CO)C(O)C(O)C4O)C2OC(=O)C=Cc5ccc(O)c(O)c5)C(O)C(O)C1O YDDMELPLARDERH-UHFFFAOYSA-N 0.000 claims description 15
-1 β-D-glucopyranosyl Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
238000000605 extraction Methods 0.000 claims description 9
239000004952 Polyamide Substances 0.000 claims description 8
238000004440 column chromatography Methods 0.000 claims description 8
239000000284 extract Substances 0.000 claims description 8
235000013372 meat Nutrition 0.000 claims description 8
229920002647 polyamide Polymers 0.000 claims description 8
239000011347 resin Substances 0.000 claims description 8
229920005989 resin Polymers 0.000 claims description 8
238000001179 sorption measurement Methods 0.000 claims description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000003495 polar organic solvent Substances 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
238000005194 fractionation Methods 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
238000000746 purification Methods 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
239000000287 crude extract Substances 0.000 description 9
230000000694 effects Effects 0.000 description 7
229930185474 acteoside Natural products 0.000 description 5
229910003460 diamond Inorganic materials 0.000 description 5
239000010432 diamond Substances 0.000 description 5
238000010828 elution Methods 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
FBSKJMQYURKNSU-ZLSOWSIRSA-N acteoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O FBSKJMQYURKNSU-ZLSOWSIRSA-N 0.000 description 4
FBSKJMQYURKNSU-UKQWSTALSA-N acteoside I Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)C=Cc4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O FBSKJMQYURKNSU-UKQWSTALSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
229930182470 glycoside Natural products 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
QFRYQWYZSQDFOS-UHFFFAOYSA-N verbascoside Natural products CC1OC(COC2C(O)C(COC3OC(C(O)C(O)C3O)C(=O)O)OC(Oc4cc(O)cc5OC(=CC(=O)c45)c6ccc(O)c(O)c6)C2O)C(O)C(O)C1O QFRYQWYZSQDFOS-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
230000002180 anti-stress Effects 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
239000012156 elution solvent Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
241000411851 herbal medicine Species 0.000 description 3
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229930015704 phenylpropanoid Natural products 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
ALERZNQPBWWLMW-UHFFFAOYSA-N 2''-acetylacteoside Natural products OC1C(O)C(O)C(C)OC1OC1C(OC(C)=O)C(OCCC=2C=C(O)C(O)=CC=2)OC(CO)C1OC(=O)C=CC1=CC=C(O)C(O)=C1 ALERZNQPBWWLMW-UHFFFAOYSA-N 0.000 description 2
APXLKFCQWDJADY-VSALRCHLSA-N 2'-acetylacteoside Natural products C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)C=Cc4ccc(O)c(O)c4)[C@H](OC(=O)C)[C@H](O)[C@H]1O APXLKFCQWDJADY-VSALRCHLSA-N 0.000 description 2
WKQLGHCWJNLUKK-UHFFFAOYSA-N Cistanoside C Natural products C1=C(O)C(OC)=CC=C1CCOC1C(O)C(OC2C(C(O)C(O)C(C)O2)O)C(OC(=O)C=CC=2C=C(O)C(O)=CC=2)C(CO)O1 WKQLGHCWJNLUKK-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
RLGRBYHBNWLGER-CNMJWYMJSA-N [(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate Chemical compound C1=C(O)C(OC)=CC(CCO[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)[C@H](OC(=O)\C=C\C=3C=C(OC)C(O)=CC=3)[C@@H](CO)O2)O)=C1 RLGRBYHBNWLGER-CNMJWYMJSA-N 0.000 description 2
KJJKGAYHJMZKLA-DBDAIDROSA-N [(2r,3r,4s,5r,6r)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-3-yl] (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1CO[C@@H]1[C@@H](OC(C)=O)[C@H](OCCC=2C=C(O)C(O)=CC=2)O[C@H](CO)[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 KJJKGAYHJMZKLA-DBDAIDROSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
RLGRBYHBNWLGER-UHFFFAOYSA-N cistanoside D Natural products C1=C(O)C(OC)=CC(CCOC2C(C(OC3C(C(O)C(O)C(C)O3)O)C(OC(=O)C=CC=3C=C(OC)C(O)=CC=3)C(CO)O2)O)=C1 RLGRBYHBNWLGER-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
ZMYQRHSOVRDQDL-NSWBACJASA-N leucosceptoside A Natural products COc1cc(C=CC(=O)O[C@@H]2[C@@H](CO)O[C@@H](OCCc3ccc(O)c(O)c3)[C@H](O)[C@H]2O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)ccc1O ZMYQRHSOVRDQDL-NSWBACJASA-N 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
235000020995 raw meat Nutrition 0.000 description 2
210000003296 saliva Anatomy 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
241000201308 Boschniakia Species 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
241000076824 Cistanche ambigua Species 0.000 description 1
241000336291 Cistanche deserticola Species 0.000 description 1
241000336315 Cistanche salsa Species 0.000 description 1
241000985690 Cistanche sinensis Species 0.000 description 1
MQDZZCJYWRZONM-UHFFFAOYSA-N Cistanoside A Natural products COc1ccc(CCOC2OC(COC3OC(CO)C(O)C(O)C3O)C(OC(=O)C=Cc4ccc(O)c(O)c4)C(OC5OC(C)C(O)C(O)C5O)C2O)cc1O MQDZZCJYWRZONM-UHFFFAOYSA-N 0.000 description 1
208000019914 Mental Fatigue Diseases 0.000 description 1
241000204801 Muraenidae Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940076810 beta sitosterol Drugs 0.000 description 1
LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
QXMNTPFFZFYQAI-IMDKZJJXSA-N beta-sitosterol 3-O-beta-D-glucopyranoside Natural products CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]5C[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(C)C QXMNTPFFZFYQAI-IMDKZJJXSA-N 0.000 description 1
PJWPOUFMMWFJOL-UHFFFAOYSA-N beta-sitosterol-beta-D-glucoside Natural products CCC(CCC(C)C1CCC2C3C=CC4CC(CCC4(C)C3CCC12C)OC5OC(CO)C(O)C(O)C5O)C(C)C PJWPOUFMMWFJOL-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
NPJICTMALKLTFW-OFUAXYCQSA-N daucosterol Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CC[C@@H](CC)C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O NPJICTMALKLTFW-OFUAXYCQSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000029087 digestion Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
208000037805 labour Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
229950005143 sitosterol Drugs 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1

Landscapes

Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)

JP60029335A 1985-02-19 1985-02-19 新規なシスタノサイド類及びその製法 Granted JPS61189290A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60029335A JPS61189290A (ja)	1985-02-19	1985-02-19	新規なシスタノサイド類及びその製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60029335A JPS61189290A (ja)	1985-02-19	1985-02-19	新規なシスタノサイド類及びその製法

Publications (2)

Publication Number	Publication Date
JPS61189290A JPS61189290A (ja)	1986-08-22
JPH0557994B2 true JPH0557994B2 (de)	1993-08-25

Family

ID=12273361

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60029335A Granted JPS61189290A (ja)	1985-02-19	1985-02-19	新規なシスタノサイド類及びその製法

Country Status (1)

Country	Link
JP (1)	JPS61189290A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104262414B (zh) *	2014-09-17	2017-03-22	中国科学院过程工程研究所	一种从肉苁蓉中制备苯乙醇苷、甘露醇、低聚糖浆及多糖的方法
CN104650161A (zh) *	2014-12-30	2015-05-27	新疆医科大学	肉苁蓉苷a标准品的半制备液相色谱方法

1985
- 1985-02-19 JP JP60029335A patent/JPS61189290A/ja active Granted

Also Published As

Publication number	Publication date
JPS61189290A (ja)	1986-08-22

Legal Events

Date	Code	Title	Description
2004-07-13	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-02-19	EXPY	Cancellation because of completion of term

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