JPH0278679A - Riboflavin derivative - Google Patents
Riboflavin derivativeInfo
- Publication number
- JPH0278679A JPH0278679A JP23046888A JP23046888A JPH0278679A JP H0278679 A JPH0278679 A JP H0278679A JP 23046888 A JP23046888 A JP 23046888A JP 23046888 A JP23046888 A JP 23046888A JP H0278679 A JPH0278679 A JP H0278679A
- Authority
- JP
- Japan
- Prior art keywords
- vitamin
- acid
- reaction
- formula
- concentrated
- 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.)
- Pending
Links
- 150000003287 riboflavins Chemical class 0.000 title claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 9
- ZHEHPTDHYQQKJR-DRZSPHRISA-N (2s,3s,4s)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentanoic acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O ZHEHPTDHYQQKJR-DRZSPHRISA-N 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000011541 reaction mixture Substances 0.000 abstract description 3
- 159000000000 sodium salts Chemical class 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 12
- 229930003270 Vitamin B Natural products 0.000 description 10
- 235000019156 vitamin B Nutrition 0.000 description 10
- 239000011720 vitamin B Substances 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 6
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- -1 alkali metal salt Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000013598 vector Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 241000180097 Chattonella Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000222480 Schizophyllum Species 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000021468 vitamin B8 Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、ビタミンＢ、酸活性を有する新規なリボフラ
ビン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to vitamin B, a novel riboflavin derivative with acid activity.
従来の技術
担子菌（Ｂａｓｉｄｉｏｍｙｃｅｔｅｓ）の一種である
スエヒロタケ（Ｓｃｈｉｚｏｐｈｙｌｌｕｍ ｃｏｍｍ
ｕｎｅ）によって産出されるフラビン誘導体である次式
（Ｉ″）：−Ｃ−ＯＨ
−Ｃ−ＯＨ
−Ｃ−ＯＨ
で表わされる７、８−ジメチル−１０−（２，３，４−
トリヒドロキシ−４−カルボキシブチル）イソアロキサ
ジン（以下、ビタミンＢ、酸という。）は、種々の微生
物で生理活性を示すだけでなく［タチバナ（Ｓ、 ’ｌ
’ ２ｃｈ １ｂａｎａ）、ムラカミ（Ｔ 、Ｍｕｒａ
ｋａｗａｉ）、モレキュラー・アンド・セルラー・バイ
オケミストリー（Ｍｏｌｅｃｕｌａｒ ａｎｄ Ｃｅ１
ｌｕｌａｒ Ｂ ｉｏｃｈｅｍ、）、第５１巻、第１４
９頁（１９８３年）］、赤潮の本体をなすシャトネラ・
アンチイカの生育を極めて低濃度（１ｍｇ／Ｑ）で著し
く阻害することが知られている［古城、立花、醗酵工学
、第６３巻（第２号）、第１３７頁（１９８５年）］。Conventional technology Schizophyllum comm, a type of Basidiomycetes,
7,8-dimethyl-10-(2,3,4-
Trihydroxy-4-carboxybutyl) isoalloxazine (hereinafter referred to as vitamin B, acid) not only shows physiological activity in various microorganisms [Tachibana (S, 'l
'2ch 1bana), Murakami (T, Mura
kawai), Molecular and Cellular Biochemistry (Molecular and Ce1)
lular Biochem,), Volume 51, No. 14
9 (1983)], Chattonella, which forms the main body of red tide.
It is known that the growth of anti-squid is significantly inhibited at extremely low concentrations (1 mg/Q) [Koshiro, Tachibana, Fermentation Engineering, Vol. 63 (No. 2), p. 137 (1985)].
明が解決しようとする課題
本発明は、このようなビタミンＢＪ活性を有する新規な
リボフラビン誘導体を提供する為になされたものである
。SUMMARY OF THE INVENTION The present invention has been made to provide a novel riboflavin derivative having such vitamin BJ activity.
即ち、本発明は、次式（Ｉ）ニ
−Ｃ−０Ｂ
−Ｃ−ＯＨ
−Ｃ−ＯＨ
（式中、Ｍはアルカリ金属原子を示す）で表わされるリ
ボフラビン誘導体に関する。That is, the present invention relates to a riboflavin derivative represented by the following formula (I) -C-0B-C-OH-C-OH (wherein M represents an alkali metal atom).
一般式（１）において、Ｍはアルカリ金属原子、好まし
くはナトリウム原子もしくはカリウム原子を示す。In general formula (1), M represents an alkali metal atom, preferably a sodium atom or a potassium atom.
式（Ｉ）で表わされる化合物（以下、ビタミンＢ！酸ア
ルカリ金属塩という。）の製造方法は特に限定的ではな
いが、好適な方法は、ビタミンＢ、酸を例えば水酸化ナ
トリウムまたは水酸化カリウムで中和させる方法である
。The method for producing the compound represented by formula (I) (hereinafter referred to as vitamin B! acid alkali metal salt) is not particularly limited, but a preferred method is to use vitamin B and an acid such as sodium hydroxide or potassium hydroxide. This is a method of neutralizing it.
この場合、通常、ビタミンＢ、酸は、０．１−１００
ｍｍｏｌ／１２の水溶液として使用し、反応温度は、室
温〜８０℃とする。In this case, vitamin B and acid are usually 0.1-100
It is used as an aqueous solution of mmol/12, and the reaction temperature is from room temperature to 80°C.
ビタミンＢ２酸アルカリ金属塩の水に対する溶解性は、
ビタミンＢ２酸に比べて著しく高い。The solubility of vitamin B2 acid alkali metal salt in water is
It is significantly higher than vitamin B2 acid.
以下、本発明を実施例によって説明する。Hereinafter, the present invention will be explained by examples.
実施例１
ビタミンＢ２酸２００１１９（４，９Ｘ Ｉ Ｏ−’！
１１０１）を４１２の水に溶解させ、濃縮器で約ｌＱに
濃縮後、攪拌器を備えた反応容器（２ａ）内に入れ、光
を遮断した状態で、攪拌下、室温で、水酸化ナトリウム
水溶液（０，０１Ｎ）４８．０ｍ１２（４，８Ｘ Ｉ
Ｏ−’ｍｏｌ）を添加した。この場合のｐＨは７．５３
（２５℃）であり、添加後、反応を３時間行った。Example 1 Vitamin B2 acid 200119 (4,9X IO-'!
1101) in 412 of water, concentrated to about 1Q in a concentrator, placed in a reaction vessel (2a) equipped with a stirrer, and dissolved in an aqueous sodium hydroxide solution under stirring at room temperature while blocking light. (0,01N) 48.0m12 (4,8X I
O-'mol) was added. In this case the pH is 7.53
(25°C), and the reaction was carried out for 3 hours after the addition.
反応混合物は、約１００−に濃縮し、限外濾過後、更に
、濾液を凍結乾燥機でフリーズドライすることによって
、ビタミンＢ！酸ナトリウム塩を１９６．４１１９（４
，３Ｘ ｌ Ｏ−’１１０１）得た（収率８７゜８％）
。The reaction mixture was concentrated to about 100% and after ultrafiltration, the filtrate was freeze-dried in a freeze dryer to obtain vitamin B! acid sodium salt to 196.4119 (4
, 3X l O-'1101) was obtained (yield 87°8%)
.
生成物のＵＶスペクトル、■Ｒスペクトル、’Ｈ−ＮＭ
ＲＺベクトルＨよび”Ｃ−ＮＭＲＺベクトルをそれぞれ
第１図〜第４図に示す。UV spectrum of product, ■R spectrum, 'H-NM
The RZ vector H and the "C-NMRZ vector are shown in FIGS. 1 to 4, respectively.
実施例２
ビタミンＢ、酸２００＋ｍ９（４，９Ｘ １０−’ｍｏ
ｌ）を、４Ｑの水に溶解させ、実施例１と同様の装置、
操作で水酸化カリウム水溶液（０，０１Ｎ）４ＬＯ■ａ
（４，８Ｘ ｌ Ｏ−’ｍｏｌ）を添加した。この場合
のｐＨは７．５５（２５℃）であり、添加後、反応を３
時間行った。Example 2 Vitamin B, acid 200+m9 (4,9X 10-'mo
l) in 4Q of water, and using the same apparatus as in Example 1,
Potassium hydroxide aqueous solution (0,01N) 4LO■a by operation
(4,8X 1 O-'mol) was added. The pH in this case was 7.55 (25°C), and after the addition, the reaction was
Time went.
反応混合物を実施例１と同様の処理に付すことによって
、ビタミンＢ、酸カリウム塩を２２０．１１１９（４、
６Ｘ ｌ Ｏ−’ｍｏｌ）得た（収率９３．９％）。By subjecting the reaction mixture to the same treatment as in Example 1, vitamin B, acid potassium salt was obtained at 220.1119 (4,
6X 1 O-'mol) (yield 93.9%).
生成物のＵＶスペクトル、ＩＲスペクトル、’Ｈ−ＮＭ
Ｒスペクトルおよび”Ｃ−ＮＭＲスペクトルをそれぞれ
第５図〜第８図に示す。Product UV spectrum, IR spectrum, 'H-NM
The R spectrum and the C-NMR spectrum are shown in FIGS. 5 to 8, respectively.
発明の効果
本発明によるビタミンＢ、酸アルカリ金属塩は、ビタミ
ンＢ８酸に比べて著しく高い水に対する溶解性を有し、
医薬品の分野等において有用なだけでなく、赤潮の防除
剤としても利用可能な化合物である。Effects of the Invention The vitamin B acid alkali metal salt according to the present invention has significantly higher solubility in water than vitamin B8 acid,
This compound is not only useful in the pharmaceutical field, but can also be used as a red tide control agent.
第１図〜第４図はそれぞれビタミンＢ、酸ナトリウム塩
のＵＶスペクトル、ＩＲスペクトル、’Ｈ−ＮＭＲスペ
クトノ呟”Ｃ−ＮＭＲＸベクトルを示すチャートである
。
第５図〜第８図はそれぞれビタミンＢ、酸カリウム塩の
ＵＶスペクトル、ＩＲスペクトル、′Ｈ−ＮＭＲスペク
トルおよび”Ｃ−ＮＭＲスペクトルを示すチャートであ
る。Figures 1 to 4 are charts showing the UV spectra, IR spectra, and 'H-NMR spectra' C-NMRX vectors of vitamin B and acid sodium salts, respectively. 1 is a chart showing a UV spectrum, an IR spectrum, a 'H-NMR spectrum and a 'C-NMR spectrum of the acid potassium salt.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23046888A JPH0278679A (en) | 1988-09-14 | 1988-09-14 | Riboflavin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23046888A JPH0278679A (en) | 1988-09-14 | 1988-09-14 | Riboflavin derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0278679A true JPH0278679A (en) | 1990-03-19 |
Family
ID=16908299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23046888A Pending JPH0278679A (en) | 1988-09-14 | 1988-09-14 | Riboflavin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0278679A (en) |
-
1988
- 1988-09-14 JP JP23046888A patent/JPH0278679A/en active Pending
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