JPH029590B2 - - Google Patents
Info
- Publication number
- JPH029590B2 JPH029590B2 JP57025519A JP2551982A JPH029590B2 JP H029590 B2 JPH029590 B2 JP H029590B2 JP 57025519 A JP57025519 A JP 57025519A JP 2551982 A JP2551982 A JP 2551982A JP H029590 B2 JPH029590 B2 JP H029590B2
- Authority
- JP
- Japan
- Prior art keywords
- tocopherol
- extract
- leaves
- ethanol
- hexane
- 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.)
- Expired - Lifetime
Links
- 229930003799 tocopherol Natural products 0.000 claims description 15
- 239000011732 tocopherol Substances 0.000 claims description 15
- 235000019149 tocopherols Nutrition 0.000 claims description 11
- 229930003802 tocotrienol Natural products 0.000 claims description 11
- 239000011731 tocotrienol Substances 0.000 claims description 11
- 235000019148 tocotrienols Nutrition 0.000 claims description 11
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 229940068778 tocotrienols Drugs 0.000 claims description 10
- 241001133760 Acoelorraphe Species 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 244000099147 Ananas comosus Species 0.000 claims description 5
- 235000007119 Ananas comosus Nutrition 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims 1
- 125000002640 tocopherol group Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 229940087168 alpha tocopherol Drugs 0.000 description 10
- 229960000984 tocofersolan Drugs 0.000 description 10
- 235000004835 α-tocopherol Nutrition 0.000 description 10
- 239000002076 α-tocopherol Substances 0.000 description 10
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 description 6
- 235000010382 gamma-tocopherol Nutrition 0.000 description 6
- 239000002478 γ-tocopherol Substances 0.000 description 6
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 6
- 240000000111 Saccharum officinarum Species 0.000 description 5
- 235000007201 Saccharum officinarum Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OTXNTMVVOOBZCV-UHFFFAOYSA-N 2R-gamma-tocotrienol Natural products OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000234295 Musa Species 0.000 description 4
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000010384 tocopherol Nutrition 0.000 description 4
- 229960001295 tocopherol Drugs 0.000 description 4
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 4
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 3
- OTXNTMVVOOBZCV-YMCDKREISA-N gamma-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CCc2c1 OTXNTMVVOOBZCV-YMCDKREISA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 3
- 235000019145 α-tocotrienol Nutrition 0.000 description 3
- 239000011730 α-tocotrienol Substances 0.000 description 3
- 235000019150 γ-tocotrienol Nutrition 0.000 description 3
- 239000011722 γ-tocotrienol Substances 0.000 description 3
- OTXNTMVVOOBZCV-WAZJVIJMSA-N γ-tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-WAZJVIJMSA-N 0.000 description 3
- FGYKUFVNYVMTAM-UHFFFAOYSA-N (R)-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3t,7t,11-trienyl)-chroman-6-ol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 229940064063 alpha tocotrienol Drugs 0.000 description 2
- 229940066595 beta tocopherol Drugs 0.000 description 2
- FGYKUFVNYVMTAM-YMCDKREISA-N beta-Tocotrienol Natural products Oc1c(C)c2c(c(C)c1)O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CC2 FGYKUFVNYVMTAM-YMCDKREISA-N 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 235000010389 delta-tocopherol Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FGYKUFVNYVMTAM-MUUNZHRXSA-N epsilon-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-MUUNZHRXSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 235000007680 β-tocopherol Nutrition 0.000 description 2
- 239000011590 β-tocopherol Substances 0.000 description 2
- 235000019151 β-tocotrienol Nutrition 0.000 description 2
- 239000011723 β-tocotrienol Substances 0.000 description 2
- FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 description 2
- 239000002446 δ-tocopherol Substances 0.000 description 2
- 235000019144 δ-tocotrienol Nutrition 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 1
- ODADKLYLWWCHNB-UHFFFAOYSA-N 2R-delta-tocotrienol Natural products OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- BTNBMQIHCRIGOU-UHFFFAOYSA-N delta-tocotrienol Natural products CC(=CCCC(=CCCC(=CCCOC1(C)CCc2cc(O)cc(C)c2O1)C)C)C BTNBMQIHCRIGOU-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002871 fertility agent Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011729 δ-tocotrienol Substances 0.000 description 1
- ODADKLYLWWCHNB-LDYBVBFYSA-N δ-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-LDYBVBFYSA-N 0.000 description 1
- 150000003790 δ-tocotrienols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
Description
【発明の詳細な説明】
本発明はパーム、バナゝ、パイナツプル及びサ
トウキビ等の葉に含まれるトコフエロール類及び
トコトリエノール類の分離方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating tocopherols and tocotrienols contained in leaves of palm, banana, pineapple, sugarcane, etc.
トコフエロール類はビタミンＥ活性を有し、動
物の抗不妊薬として利用されてきたが、最近油脂
食品の酸化防止、成人病の予防、老化の防止等の
作用が明らかになり、食品添加物、医薬品、栄養
食品及び化粧品等への需要が急速に増大してい
る。 Tocopherols have vitamin E activity and have been used as anti-infertility drugs for animals, but recently it has been revealed that they can prevent the oxidation of oil and fat foods, prevent adult diseases, and prevent aging. , demand for nutritional foods, cosmetics, etc. is rapidly increasing.
本発明者らはパーム、バナゝ、パイナツプル及
びサトウキビ等の葉を粉砕又は細断後乾燥するか
又はしないで、アルコール、エーテル、ケトン等
の有機溶剤を単独又は混合したもので抽出する
か、これらの有機溶剤と水不溶性有機溶剤との混
合溶剤を用いて抽出することにより、トコフエロ
ール類並びにトコトリエノール類を分離し得るこ
とを見出した。さらに、この抽出物について、低
温分別、シリカ、アルミナ、イオン交換樹脂等を
用いる吸着処理並びに分子蒸留等を単独又は組合
せて用いることにより、トコフエロール類並びに
トコトリエノール類を濃縮し得ることを見出し、
本発明を完成した。 The present inventors crushed or shredded the leaves of palm, banana, pineapple, sugarcane, etc., with or without drying, and extracted them with an organic solvent such as alcohol, ether, or ketone alone or in a mixture thereof. It has been found that tocopherols and tocotrienols can be separated by extraction using a mixed solvent of an organic solvent and a water-insoluble organic solvent. Furthermore, it has been discovered that tocopherols and tocotrienols can be concentrated in this extract by using low-temperature fractionation, adsorption treatment using silica, alumina, ion exchange resin, etc., and molecular distillation, etc., alone or in combination,
The invention has been completed.
本発明におけるトコフエロール類はα―トコフ
エロール、β―トコフエロール、γ―トコフエロ
ール及びδ―トコフエロール等である。また、ト
コトリエノール類はα―トコトリエノール、β―
トコトリエノール、γ―トコトリエノール及びδ
―トコトリエノール等である。これらの８種の成
分のうち、δ―トコフエロール、α―、β―及び
δ―トコトリエノールは少量成分であり、ビタミ
ンＥ活性の最も強いα―トコフエロール及びγ―
トコフエロールが主成分として含まれている。 Tocopherols in the present invention include α-tocopherol, β-tocopherol, γ-tocopherol, and δ-tocopherol. In addition, tocotrienols include α-tocotrienol, β-
Tocotrienol, γ-tocotrienol and δ
-Tocotrienols, etc. Among these eight components, δ-tocopherol, α-, β-, and δ-tocotrienol are minor components, and α-tocopherol and γ-tocopherol have the strongest vitamin E activity.
Contains tocopherol as the main component.
本発明の出発物質はパーム、バナゝ、パイナツ
プル及びサトウキビの葉で、生育中並びに収穫後
の葉を含むものであり、例えば果実を収穫する時
に切り取つた葉及びサトウキビを収穫する時に刈
取つた葉もあげられる。 The starting materials of the present invention are palm, banana, pineapple and sugarcane leaves, including both growing and harvested leaves, such as leaves cut when harvesting fruit and leaves cut when harvesting sugarcane. can give.
本発明によれば、メタノール、エタノール、イ
ソプロパノール等のアルコール、エチルエーテ
ル、イソプロピルエーテル等のエーテル、アセト
ン、メチルエチルケトン等のケトン、ギ酸メチ
ル、ギ酸エチル、酢酸メチル、酢酸エチル等のカ
ルボン酸エステル、石油エーテル、ヘキサン、ヘ
プタン、ベンゼン、トルエン、キシレン等の炭化
水素及びクロロホルム、塩化メチレン、塩化エチ
レン等のハロゲン化炭化水素等の有機溶剤を単独
又は混合物を抽出溶剤として用いて葉を抽出処理
することにより、トコフエロール類並びにトコト
リエノール類を含む抽出物が得られる。 According to the present invention, alcohols such as methanol, ethanol and isopropanol, ethers such as ethyl ether and isopropyl ether, ketones such as acetone and methyl ethyl ketone, carboxylic acid esters such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, petroleum ethers By extracting the leaves using organic solvents such as hydrocarbons such as hexane, heptane, benzene, toluene, and xylene, and halogenated hydrocarbons such as chloroform, methylene chloride, and ethylene chloride, alone or in combination as extraction solvents, An extract containing tocopherols and tocotrienols is obtained.
本発明における抽出物を有機溶剤の存在下で低
温分別を行い、可溶部にトコフエロール類並びに
トコトリエノール類の濃縮物が得られる。 The extract in the present invention is subjected to low-temperature fractionation in the presence of an organic solvent, and a concentrate of tocopherols and tocotrienols is obtained in the soluble portion.
また、本発明における抽出物を無極性有機溶剤
に溶解し、アルミナ又はシリカを充填したカラム
に流し、続いて、アルコール、エーテル、ケト
ン、エステル、芳香族化合物、無極性有機溶剤及
び有機塩素化物等を単独又は混合溶液として流
し、後者の流出区分から溶剤を除去して、残留物
中にトコフエロール及びトコトリエノール濃縮物
を得ることができる。上記方法のアルミナ又はシ
リカの代りに、イオン交換体をカラムにつめ、こ
れに抽出物の有機溶剤の溶液を流し、続いて酸性
の有機溶剤を流して得られる区分を水洗、蒸留
後、残留物中にトコフエロール類及びトコトリエ
ノール類の濃縮物を得ることができる。 In addition, the extract in the present invention is dissolved in a nonpolar organic solvent and passed through a column packed with alumina or silica, and then alcohol, ether, ketone, ester, aromatic compound, nonpolar organic solvent, organic chloride, etc. alone or as a mixed solution, and the solvent can be removed from the latter effluent section to obtain tocopherol and tocotrienol concentrates in the residue. Instead of alumina or silica in the above method, an ion exchanger is packed in a column, and an organic solvent solution of the extract is poured into the column, followed by an acidic organic solvent.The resulting section is washed with water, and after distillation, the residue is Concentrates of tocopherols and tocotrienols can be obtained therein.
さらに、本発明における抽出物を10-2〜10-3mm
Hg以下の真空度で分子蒸留を行い、190℃〜230
℃で留出する区分を回収して、トコフエロール類
及びトコトリエノール類の濃縮物を得ることがで
きる。 Furthermore, the extract in the present invention is 10 -2 to 10 -3 mm
Molecular distillation is performed at a vacuum level below Hg, and the temperature is 190℃~230℃.
The fraction distilled at °C can be collected to obtain a concentrate of tocopherols and tocotrienols.
以下実施例により本発明を詳細に説明する。 The present invention will be explained in detail below with reference to Examples.
実施例 １
パームの葉２Kg（水分42％）を細断した後、ヘ
キサン、エタノール（Ｖ／Ｖ、１：１）混合溶液
を用い、室温22〜24℃で抽出した。抽出物102ｇ
を得た。この抽出物にエタノール800mlを加え、
よく振りまぜた後、−20℃に冷却し、可溶部を分
別した。可溶部からエタノールを留去し、残留物
15ｇを得た。この残留物(1)はα―トコフエロール
81000μｇ／ｇ、β―トコフエロール350μｇ／ｇ、
γ―トコフエロール4240μｇ／ｇ、γ―トコトリ
エノール200μｇ／ｇ、合計85790μｇ／ｇを含有
していた。Example 1 After 2 kg of palm leaves (water content 42%) were shredded, they were extracted at room temperature of 22 to 24°C using a mixed solution of hexane and ethanol (V/V, 1:1). 102g extract
I got it. Add 800ml of ethanol to this extract,
After shaking well, the mixture was cooled to -20°C and the soluble portion was separated. Distill ethanol from the soluble part and remove the residue.
Obtained 15g. This residue (1) is α-tocopherol
81000 μg/g, β-tocopherol 350 μg/g,
It contained 4240 μg/g of γ-tocopherol, 200 μg/g of γ-tocotrienol, and 85790 μg/g in total.
実施例 ２
サトウキビの葉１Kg（水分73％）を細断した
後、ヘキサン、エタノール（Ｖ／Ｖ、１：１）混
合溶液を用い、室温20〜22℃で抽出した。抽出物
15ｇを得た。この抽出物にエタノール200mlを加
え、よくかきまぜた後、−20℃に冷却し、可溶部
を分別した。可溶部からエタノールを留去し、残
留物３ｇを得た。この残留物はα―トコフエロー
ル12000μｇ／ｇ及びγ―トコフエロール4500μ
ｇ／ｇ、合計16500μｇ／ｇを含有していた。Example 2 1 kg of sugarcane leaves (moisture 73%) were shredded and extracted at room temperature of 20 to 22° C. using a mixed solution of hexane and ethanol (V/V, 1:1). extract
Obtained 15g. After adding 200 ml of ethanol to this extract and stirring well, it was cooled to -20°C and the soluble portion was separated. Ethanol was distilled off from the soluble portion to obtain 3 g of residue. This residue contains 12000μg/g of α-tocopherol and 4500μg/g of γ-tocopherol.
g/g, a total of 16,500 μg/g.
実施例 ３
実施例３で得られた残留物(1)10ｇを50mlのエタ
ノールに溶解し、これをOH型塩基性陰イオン交
換樹脂アンバーライトIRA401を径５cm、長さ100
cmのガラス製クロマト管に50cmの高さに充填した
層に流し、トコフエロール類及びトコトリエノー
ル類を吸着させた後、300mlのヘキサンを流して、
中性物質を流去した。次に５％酢酸エタノール
200mlを流し、流出後から溶剤を留去するとトコ
フエロール濃縮物0.8ｇ（純度65％）が得られた。Example 3 10 g of the residue (1) obtained in Example 3 was dissolved in 50 ml of ethanol, and this was mixed into an OH type basic anion exchange resin Amberlite IRA401 with a diameter of 5 cm and a length of 100 mm.
After adsorbing tocopherols and tocotrienols, pour 300 ml of hexane into a glass chromatography tube packed at a height of 50 cm.
Neutral substances were washed away. Next, 5% acetic ethanol
200 ml of the solution was poured, and the solvent was distilled off after the flow, yielding 0.8 g of tocopherol concentrate (purity 65%).
実施例 ４
パイナツプルの葉１Kg（水分45％）を細断した
後、アセトンを用い室温23〜24℃で抽出した。抽
出物45.2ｇを得た。この抽出物をエタノール400
mlに溶解後、−20℃で冷却し、可溶部を分取した。
可溶部からエタノールを留去し、残留物8.6ｇを
得た。この残留物はα―トコフエロール48000μ
ｇ／ｇ、γ―トコフエロール12800μｇ／ｇ、α
―トコトリエノール650μｇ／ｇ、γ―トコトリ
エノール1100μｇ／ｇ、合計62550μｇ／ｇを含有
していた。Example 4 After 1 kg of pineapple leaves (water content 45%) were shredded, they were extracted with acetone at room temperature of 23 to 24°C. 45.2g of extract was obtained. Add this extract to 400 ml of ethanol
ml, cooled at -20°C, and collected the soluble portion.
Ethanol was distilled off from the soluble portion to obtain 8.6 g of residue. This residue contains α-tocopherol 48,000μ
g/g, γ-tocopherol 12800μg/g, α
-Tocotrienol 650μg/g, γ-tocotrienol 1100μg/g, total 62550μg/g.
実施例 ５
バナゝの葉20Kg（水分65％）を細断した後、ヘ
キサン・エタノール（Ｖ／Ｖ、１：１）混合溶液
を用い、室温24〜25℃で抽出した。この抽出液は
α―トコフエロール22000μｇ、γ―トコフエロ
ール1060μｇ、合計23060μｇを含有していた。Example 5 After cutting 20 kg of banana leaves (65% moisture) into pieces, they were extracted at room temperature of 24 to 25°C using a mixed solution of hexane and ethanol (V/V, 1:1). This extract contained 22,000 μg of α-tocopherol, 1,060 μg of γ-tocopherol, and a total of 23,060 μg.
実施例 ６
パームの葉４Kg（水分48％）をローラーを用い
て圧片した後細断し、ヘキサン―エタノール
（Ｖ／Ｖ、１：１）、混合溶液12を加え、一夜室
温22〜24℃に放置後、抽出液を分別した。抽出物
186ｇを得た。この抽出物にメタノール１を加
え、よく振りまぜた後、０℃に冷却し、可溶部を
分別した。可溶部からメタノールを留去し、残留
物48ｇを得た。Example 6 4 kg of palm leaves (moisture 48%) were crushed using a roller and then shredded, 12 pieces of a mixed solution of hexane-ethanol (V/V, 1:1) was added, and the mixture was kept at room temperature 22-24°C overnight. After being left to stand, the extract was separated. extract
Obtained 186g. After adding methanol 1 to this extract and shaking it well, it was cooled to 0°C and the soluble portion was separated. Methanol was distilled off from the soluble portion to obtain 48 g of residue.
残留物20ｇに精製パーム油20ｇを加え、分子蒸
留を行い、５×10-3mmHgで、第１留分（〜190
℃）、第２留分190〜200℃、第３留分200℃〜220
℃、残留分の４区分に分別した。それぞれの区分
のトコフエロール含有量は第１区分23.5％、第２
区分8.1％、第３区分2.5％、残留分0.6％であつ
た。 Add 20g of refined palm oil to 20g of the residue, perform molecular distillation, and reduce the first fraction (~190
℃), 2nd distillate 190-200℃, 3rd distillate 200℃-220
It was separated into four categories: temperature and residual content. The tocopherol content in each category is 23.5% for the first category and 23.5% for the second category.
The content was 8.1% in Category 3, 2.5% in Category 3, and 0.6% residual.
実施例 ７
パームの葉（水分42％）2.3Kgを細断し、室温
（22〜24℃）において、ヘキサン―エタノール
（１：１、Ｖ／Ｖ）混合溶媒で抽出を行なうと、
抽出物116ｇが得られた。この抽出物に５のヘ
キサン―エタノール（１：１、Ｖ／Ｖ）混合溶媒
あるいは５のヘキサンを加えてよく撹拌する。
次に、上記混合物を大量の温水で洗い、水溶性の
物質を除去する。充分に乾燥した後、−20℃に冷
却し、ヘキサン可溶部を分取した。このヘキサン
可溶部をシリカカラム（Bio Sil Ａ、100〜200メ
ツシユ）を通し、ひき続いてヘキサンで溶出する
と、最初に炭化水素類が溶出され、次に、α―ト
コフエロールが溶出された。得られたα―トコフ
エロール画分は2.5ｇで、α―トコフエロール濃
度は68.4％であり、α―トコフエロールの回収率
は83.3％であつた。Example 7 2.3 kg of palm leaves (water content 42%) were shredded and extracted with a hexane-ethanol (1:1, V/V) mixed solvent at room temperature (22-24°C).
116 g of extract was obtained. A mixed solvent of 5 hexane-ethanol (1:1, V/V) or 5 hexane is added to this extract and stirred well.
The mixture is then washed with plenty of warm water to remove water-soluble substances. After sufficiently drying, the mixture was cooled to -20°C, and the hexane-soluble portion was separated. When this hexane-soluble portion was passed through a silica column (Bio Sil A, 100-200 mesh) and subsequently eluted with hexane, hydrocarbons were eluted first, and then α-tocopherol was eluted. The α-tocopherol fraction obtained was 2.5 g, the α-tocopherol concentration was 68.4%, and the recovery rate of α-tocopherol was 83.3%.
Claims (1)
エロール類並びにトコトリエノール類を分離する
方法において、核植物の葉を有機溶剤を単独又は
混合物で用いて、抽出処理することを特徴とする
トコフエロール及びトコトリエノールの分離方
法。1. A method for separating tocopherols and tocotrienols in palm leaves and pineapple leaves, which comprises extracting nuclear plant leaves using an organic solvent alone or in a mixture. Method.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2551982A JPS58144382A (en) | 1982-02-19 | 1982-02-19 | Separation of tocopherol and tocotrienol |
| GB08303777A GB2117381B (en) | 1982-02-19 | 1983-02-11 | Vitamin e extraction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2551982A JPS58144382A (en) | 1982-02-19 | 1982-02-19 | Separation of tocopherol and tocotrienol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58144382A JPS58144382A (en) | 1983-08-27 |
| JPH029590B2 true JPH029590B2 (en) | 1990-03-02 |
Family
ID=12168302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2551982A Granted JPS58144382A (en) | 1982-02-19 | 1982-02-19 | Separation of tocopherol and tocotrienol |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58144382A (en) |
| GB (1) | GB2117381B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010155829A (en) * | 2008-12-05 | 2010-07-15 | Shonan Institute For Medical & Preventive Science | Anti-androgenic agent, prostate hypertrophy inhibitor and androgen dependent hair loss inhibitor, each containing whole grass of bananas, except their fruits, as effective ingredient |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3424614A1 (en) * | 1983-07-05 | 1985-01-17 | Kuraray Co., Ltd., Kurashiki, Okayama | METHOD FOR PRODUCING AN EXTRACT |
| US4603142A (en) * | 1984-06-01 | 1986-07-29 | Wisconsin Alumni Research Foundation | Cholesterol lowering method of use |
| DE3582904D1 (en) * | 1984-08-02 | 1991-06-27 | Henkel Corp | CLEANING TOCOPHEROLS BY EXTRACTION. |
| AU618791B2 (en) * | 1988-03-16 | 1992-01-09 | Bioindustry Development Centre | Production of high concentration tocopherols and tocotrienols from palm oil by-product |
| US5217992A (en) * | 1989-10-04 | 1993-06-08 | Bristol-Myers Squibb Company | Tocotrienols in the treatment of hypercholesterolemia, hyperlipidemia and thromboembolic disorders |
| HUT63158A (en) * | 1990-05-23 | 1993-07-28 | Lipogenics Inc | Process for obtaining tokotrienols, tokoferols and tokotrienol-like compounds and pahrmaceutical compositions comprising same as active ingredient |
| FR2669032B1 (en) * | 1990-11-14 | 1993-04-23 | Cecchi Georges | PROCESS FOR THE MANUFACTURE OF A PREPARATION OF D-ALPHA-TOCOPHEROL. |
| US5985344A (en) * | 1997-09-02 | 1999-11-16 | The Ricex Company | Process for obtaining micronutrient enriched rice bran oil |
| US6706898B2 (en) * | 1998-01-29 | 2004-03-16 | Archer-Daniels-Midland Company | Methods for separating a tocopherol from a tocopherol-containing mixture |
| EP0941671B1 (en) | 1998-03-12 | 2015-09-09 | International Flavors & Fragrances Inc. | Taste agent from Saccharum Officinarum, process for preparing it, products containing it |
| ATE340618T1 (en) * | 1999-01-25 | 2006-10-15 | Dsm Ip Assets Bv | METHOD FOR PRODUCING AN OIL-LOADED ADSORPTION AGENT |
| JP5312731B2 (en) * | 2006-08-30 | 2013-10-09 | 株式会社ノエビア | Topical skin preparation |
| US20100291006A1 (en) * | 2007-10-05 | 2010-11-18 | Horizon Science Pty Ltd | Natural Preservatives and Antimicrobial Agents |
| MY157650A (en) * | 2008-03-06 | 2016-07-15 | Nova Lab Sdn Bhd | Extract from oil palm leaves comprising phenolic acids |
| EP2411033B1 (en) | 2009-03-24 | 2015-03-04 | Universiti Putra Malaysia | Anti-diabetic nutraceutical composition from palm leaf extract |
| EP2672832B1 (en) | 2011-02-08 | 2020-03-25 | The Product Makers (Australia) Pty Ltd | Sugar extracts |
| EP2890467B1 (en) | 2012-08-28 | 2019-09-25 | The Product Makers (Australia) Pty Ltd | Extraction method |
| US10350259B2 (en) | 2013-08-16 | 2019-07-16 | The Product Makers (Australia) Pty Ltd | Sugar cane derived extracts and methods of treatment |
| US20150259370A1 (en) * | 2014-03-11 | 2015-09-17 | Ecotech Development LLC | Integrated process extraction of pineapple biomass into fibers and natural products |
-
1982
- 1982-02-19 JP JP2551982A patent/JPS58144382A/en active Granted
-
1983
- 1983-02-11 GB GB08303777A patent/GB2117381B/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ALSTRACTS * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010155829A (en) * | 2008-12-05 | 2010-07-15 | Shonan Institute For Medical & Preventive Science | Anti-androgenic agent, prostate hypertrophy inhibitor and androgen dependent hair loss inhibitor, each containing whole grass of bananas, except their fruits, as effective ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58144382A (en) | 1983-08-27 |
| GB2117381A (en) | 1983-10-12 |
| GB8303777D0 (en) | 1983-03-16 |
| GB2117381B (en) | 1985-07-10 |
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