Category:TP3P - Revision history

Adm: /* Phytosterols */

2010-08-03T17:17:11Z

‎Phytosterols

Adm: /* Phytosterols */

2010-08-03T17:15:32Z

‎Phytosterols

Adm: /* Brassinolides (C28) */

2010-08-03T17:07:26Z

‎Brassinolides (C28)

Adm: /* Brassinolides (C28) */

2010-08-03T07:23:54Z

‎Brassinolides (C28)

Adm: /* {{Bilingual|Do plants contain animal sterols?|植物は動物ステロールも作る}} */

2010-08-03T07:17:44Z

‎{{Bilingual|Do plants contain animal sterols?|植物は動物ステロールも作る}}

Adm: /* Phytosterols for Health */

2010-08-03T06:56:22Z

‎Phytosterols for Health

Adm: /* Phytosterols */

2010-08-03T06:38:14Z

‎Phytosterols

Adm at 06:27, 3 August 2010

2010-08-03T06:27:25Z

Adm at 05:17, 3 August 2010

2010-08-03T05:17:14Z

Adm: New page: ==Phytosterols== {{Twocolumn| Most common phytosterols are campesterol, β-sitosterol, and stigmasterol. Soybean (''Glycine max'', Fabaceae)...

2010-08-03T03:00:30Z

New page: ==Phytosterols== {{Twocolumn| Most common phytosterols are campesterol, β-sitosterol, and stigmasterol. Soybean (''Glycine max'', Fabaceae)...

New page

==Phytosterols==
{{Twocolumn|
Most common phytosterols are campesterol, β-sitosterol, and stigmasterol. Soybean ([[Species:Glycine|''Glycine max'']], [[:Category:Fabaceae|Fabaceae]]) is a rich source of phytosterols (about 0.1% of its weight), and is used for semi-synthesis of medicinal steroids <ref>Yamaya A, Endo Y, Fujimoto K, Kitamura K. “Effects of genetic variability and planting location on the phytosterol content and composition in soybean seeds” Food Chem 102(4): 1071-1075, 2006</ref>. Since dietary phytosterols reduce cholesterol levels, they are used as food additives such as for margarine <ref>Schiepers OJ, de Groot RH, van Boxtel MP, Jolles J, de Jong A, Lütjohann D, Plat J, Mensink RP “Consuming functional foods enriched with plant sterol or stanol esters for 85 weeks does not affect neurocognitive functioning or mood in statin-treated hypercholesterolemic individuals” J Nutr 139(7):1368-1373, 2009</ref>. Vitamin D is a family of sterol metabolites generated photochemically in our skin by UV irradiation.
|

}}

===Cardenolides (C23)===
{{Twocolumn|
The backbone of ''Digitalis'' glycosides with the androstane skeleton with a γ-lactone ring at C-17. Notable characters are its 14β-configuration in opposition to other steroids (the rings C/D are ''cis''), and the 20(22)-double bond. Their cardiac activity is well known.
|

}}

===Withanolides (C28)===
{{Twocolumn|
Withanolides were found in the root of [[Species:Withania|Withania Somnifera]], also known as Indian ginseng. Its backbone is a highly oxygenated ergostane with a γ-lactone ring linking C-22 and C-26 <ref>Iida, T et al. (1985) J. Lipid Res. 26,874</ref>. The configuration of C-22 is usually ''R''.
|
}}

===Brassinolides (C28)===
{{Twocolumn|
Brassinolides are plant growth-promoting hormones isolated originally from [[Species:Brassica|''Brassica napus'']] (rape). Its backbone is a highly oxygenated ergostane with the oxygen-expanded B-ring (ε-lactone). This lactone is not essential for plant growth activity (e.g. castasterone) but the 22''R'', 23''R''-diol are.
The configurations of C-2,3 and 5 are α in brassinolides whereas they are β in ecdysteroids.
|

}}

@@ Line 4: / Line 4: @@
 Most common phytosterols are campesterol, &beta;-sitosterol, and stigmasterol.  They occur both free and as 3-glucosides and all essential for membranes in higher plant. Less common are &alpha;-spinasterol (an isomer of stigmasterol) in spinach ([[Species:Spinacia|''Spinacia oleracea'' L.]], [[:Category:Chenopodiaceae|Chenopodiaceae]]) and alfalfa ([[Species:Medicago|''Medicago sativa'' L.]], [[:Category:Fabaceae|Fabaceae]]).
 <br/>
-Some sterols are confined in lower plants.  Ergosterols are found only in yeast and fungi, fucosterols are found in brown algae ([[:Category:Phaeophyceae|Phaeophyceae]]) and in some higher plants, e.g. coconut ([[Species:Cocos|''Cocos nucifera'']], [[:Category:Arecaceae|Arecaceae]].
+Some sterols are confined in lower plants.  Ergosterols are found only in yeast and fungi, fucosterols are found in brown algae ([[:Category:Phaeophyceae|Phaeophyceae]]) and in some higher plants, e.g. coconut ([[Species:Cocos|''Cocos nucifera'']], [[:Category:Arecaceae|Arecaceae]]).
+|
 植物ステロールの中でもっとも一般的なのが、カンペステロール、&beta;-シトステロール、スティグマステロールです。そのままか、3位の配糖体の形で存在し、高等植物の膜成分には必須の要素です。
-ほうれん草([[Species:Spinacia|''Spinacia oleracea'' L.]])やアルファルファ([[Species:Medicago|''Medicago sativa'' L.]])に含まれる&alpha;-スピナステロール （スティグマステロールの異性体）が含まれます。
+ほうれん草([[Species:Spinacia|''Spinacia oleracea'' L.]], [[:Category:Chenopodiaceae|Chenopodiaceae]])やアルファルファ([[Species:Medicago|''Medicago sativa'' L.]], [[:Category:Fabaceae|Fabaceae]])に含まれる&alpha;-スピナステロール （スティグマステロールの異性体）が含まれます。
 <br/>
-より下等な植物にのみ含まれるステロールもあります。エルゴステロールはイーストや真菌にのみ、フコステロールは褐藻や限られた高等植物（ココナツなど）に見出されます。
+より下等な植物にのみ含まれるステロールもあります。エルゴステロールはイーストや真菌にのみ、フコステロールは褐藻 ([[:Category:Phaeophyceae|Phaeophyceae]]) や限られた高等植物（ココナツなど [[Species:Cocos|''Cocos nucifera'']], [[:Category:Arecaceae|Arecaceae]]）に見出されます。
 }}

@@ Line 22: / Line 22: @@
 | campestane <br/>(campesterol backbone)
 | stigmastane <br/> (&beta;-sito and stigmasterol backbone)
 |}
 </center>
@@ Line 41: / Line 50: @@
 Date palm seed ([[Species:Phoenix|''Phoenix dactylifera'']], [[:Category:Arecaceae|Arecaceae]]) contains cholesterol and a trace amount of estrone (a female sex hormone). Estrone is also contained in seeds of pomegranate ([[Species:Punica|''Punica granatum'']], [[:Category:Punicaceae|Punicaceae]]).
 The pollen of Scots pine ([[Species:Pinus|''Pinus sylvestris'']], [[:Category:Pinaceae|Pinaceae]]) contains testosterone, the male sex hormone.
 A large number of ecdysones (insect moulting hormones) have been found in plants, and are called phytoecdysones. Examples are:
 * ecdysone from [[Species:Lychnis|Lychnis fulgens]], [[:Category:Caryophyllaceae|Caryophyllaceae]] and many ferns
@@ Line 46: / Line 56: @@
 * 20-hydroxyecdysone from [[Species:Serratula|''Serratula inermis'']], [[:Category:Asteraceae|Asteraceae]] and [[Species:Diploclisia|''Diploclisia glaucescens'']], [[:Category:Menispermaceae|Menispermaceae]]).
+|
-デーツ椰子 ([[Species:Phoenix|''Phoenix dactylifera'']], [[:Category:Arecaceae|Arecaceae]]) の種子はコレステロールや微量のエストロン（女性ホルモン）を含みます。エストロンはザクロ ([[Species:Punica|''Punica granatum'']], [[:Category:Punicaceae|Punicaceae]]) の種子にも含まれています。
+デーツ椰子 ([[Species:Phoenix|''Phoenix dactylifera'']], [[:Category:Arecaceae|Arecaceae]]) の種子はコレステロールだけでなく微量のエストロン（女性ホルモン）を含みます。エストロンはザクロ ([[Species:Punica|''Punica granatum'']], [[:Category:Punicaceae|Punicaceae]]) の種子にも含まれています。
-−
-ヨーロッパアカマツ ([[Species:Pinus|''Pinus sylvestris'']], [[:Category:Pinaceae|Pinaceae]]) の花粉にはテストステロン（男性ホルモン）が含まれています。
-脱皮ホルモンであるエクジステロイドは多くの植物にも含まれています。これらは植物エクジソンとも呼ばれます。例として:
+ヨーロッパアカマツ ([[Species:Pinus|''Pinus sylvestris'']], [[:Category:Pinaceae|Pinaceae]]) の花粉はテストステロン（男性ホルモン）を含んでいます。
 * エクジソン ... ナデシコ科センノウ属 ([[Species:Lychnis|''Lychnis'']], [[:Category:Caryophyllaceae|Caryophyllaceae]]) や多くのシダ類。
 * アジュガステロン ... シソ科キランソウ属 ([[Species:Ajuga|''Ajuga'']], [[:Category:Lamiaceae|Lamiaceae]]) など

@@ Line 100: / Line 100: @@
 このラクトン構造は植物の成長作用に関係ありませんが、22''R'', 23''R''にある二つの水酸基は重要です。
 C-2,3,5位の置換基は、ブラシノライドでは&alpha;位をとり、エクジステロイドでは&beta;位をとります。
 }}

@@ Line 91: / Line 91: @@
 }}
-===Brassinolides (C28)===
+==Brassinolides (C28)==
 {{Twocolumn|
-Brassinolides are plant growth-promoting hormones isolated originally from [[Species:Brassica|''Brassica napus'']] (rape).  Its backbone is a highly oxygenated ergostane with the oxygen-expanded B-ring (&epsilon;-lactone). This lactone is not essential for plant growth activity (e.g. castasterone) but the 22''R'', 23''R''-diol are.
+Brassinolides are plant growth-promoting hormones isolated originally from [[Species:Brassica|''Brassica napus'']], [[:Category:Brassicaceae|Brassicaceae]] (rape).  Its backbone is a highly oxygenated ergostane with the oxygen-expanded B-ring (&epsilon;-lactone). This lactone is not essential for plant growth activity (e.g. castasterone) but the 22''R'', 23''R''-diol are.
 The configurations of C-2,3 and 5 are &alpha; in brassinolides whereas they are &beta; in ecdysteroids.
+|
+ブラシノライドは、植物の成長ホルモンの一つでナタネ ([[Species:Brassica|''Brassica napus'']], [[:Category:Brassicaceae|Brassicaceae]]) で最初に見つかりました。
 }}

@@ Line 41: / Line 41: @@
 Date palm seed ([[Species:Phoenix|''Phoenix dactylifera'']], [[:Category:Arecaceae|Arecaceae]]) contains cholesterol and a trace amount of estrone (a female sex hormone). Estrone is also contained in seeds of pomegranate ([[Species:Punica|''Punica granatum'']], [[:Category:Punicaceae|Punicaceae]]).
 The pollen of Scots pine ([[Species:Pinus|''Pinus sylvestris'']], [[:Category:Pinaceae|Pinaceae]]) contains testosterone, the male sex hormone.
-A large number of ecdysones (insect moulting hormones) have been found in plants, and are called phytoecdysones (e.g. ecdysone from [[Species:Lychnis|Lychnis fulgens]], [[:Category:Caryophyllaceae|Caryophyllaceae]]) and many ferns, ajugasterone from [[Species:Ajuga|''Ajuga chamaepitys'' and ''A. reptans'']], [[:Category:Lamiaceae|Lamiaceae]], or 20-hydroxyecdysone from [[Species:Serratula|''Serratula inermis'']], [[:Category:Asteraceae|Asteraceae]] and [[Species:Diploclisia|''Diploclisia glaucescens'']], [[:Category:Menispermaceae|Menispermaceae]]).
+A large number of ecdysones (insect moulting hormones) have been found in plants, and are called phytoecdysones. Examples are:
+* ecdysone from [[Species:Lychnis|Lychnis fulgens]], [[:Category:Caryophyllaceae|Caryophyllaceae]] and many ferns
+|
 }}

@@ Line 25: / Line 25: @@
 </center>
-===Phytosterols for Health===
+==={{Bilingual|Phytosterols for Health|植物ステロールと健康}}===
 {{Twocolumn|
 Soybean ([[Species:Glycine|''Glycine max'']], [[:Category:Fabaceae|Fabaceae]]) is a rich source of phytosterols (about 0.1% of its weight), and is used for semi-synthesis of medicinal steroids <ref>Yamaya A, Endo Y, Fujimoto K, Kitamura K. (2006) “Effects of genetic variability and planting location on the phytosterol content and composition in soybean seeds” Food Chem 102(4): 1071-1075</ref>.  Since dietary phytosterols reduce cholesterol levels, they are used as food additives such as for margarine <ref>Schiepers OJ, de Groot RH, van Boxtel MP, Jolles J, de Jong A, Lütjohann D, Plat J, Mensink RP (2009) “Consuming functional foods enriched with plant sterol or stanol esters for 85 weeks does not affect neurocognitive functioning or mood in statin-treated hypercholesterolemic individuals” J Nutr 139(7):1368-1373</ref>.  Vitamin D is a family of sterol metabolites generated photochemically in our skin by UV irradiation.
@@ Line 35: / Line 35: @@
 <references/>
 ==Cardenolides (C23)==

@@ Line 14: / Line 14: @@
 <center>
 {|
 |-
 | [[Image:cholestane.png]] || [[Image:campestane.png]] || [[Image:stigmastane.png]]
@@ Line 27: / Line 29: @@
 Soybean ([[Species:Glycine|''Glycine max'']], [[:Category:Fabaceae|Fabaceae]]) is a rich source of phytosterols (about 0.1% of its weight), and is used for semi-synthesis of medicinal steroids <ref>Yamaya A, Endo Y, Fujimoto K, Kitamura K. (2006) “Effects of genetic variability and planting location on the phytosterol content and composition in soybean seeds” Food Chem 102(4): 1071-1075</ref>.  Since dietary phytosterols reduce cholesterol levels, they are used as food additives such as for margarine <ref>Schiepers OJ, de Groot RH, van Boxtel MP, Jolles J, de Jong A, Lütjohann D, Plat J, Mensink RP (2009) “Consuming functional foods enriched with plant sterol or stanol esters for 85 weeks does not affect neurocognitive functioning or mood in statin-treated hypercholesterolemic individuals” J Nutr 139(7):1368-1373</ref>.  Vitamin D is a family of sterol metabolites generated photochemically in our skin by UV irradiation.
+|
+大豆 ([[Species:Glycine|''Glycine max'']], [[:Category:Fabaceae|Fabaceae]]) は植物ステロールが豊富で (重量のおよそ0.1%)、医薬品のステロイド合成用に使われます。
 }}

@@ Line 1: / Line 1: @@
 ==Phytosterols==
 {{Twocolumn|
-Most common phytosterols are campesterol, &beta;-sitosterol, and stigmasterol.  Soybean ([[Species:Glycine|''Glycine max'']], [[:Category:Fabaceae|Fabaceae]]) is a rich source of phytosterols (about 0.1% of its weight), and is used for semi-synthesis of medicinal steroids <ref>Yamaya A, Endo Y, Fujimoto K, Kitamura K. “Effects of genetic variability and planting location on the phytosterol content and composition in soybean seeds” Food Chem 102(4): 1071-1075, 2006</ref>.  Since dietary phytosterols reduce cholesterol levels, they are used as food additives such as for margarine <ref>Schiepers OJ, de Groot RH, van Boxtel MP, Jolles J, de Jong A, Lütjohann D, Plat J, Mensink RP “Consuming functional foods enriched with plant sterol or stanol esters for 85 weeks does not affect neurocognitive functioning or mood in statin-treated hypercholesterolemic individuals” J Nutr 139(7):1368-1373, 2009</ref>.  Vitamin D is a family of sterol metabolites generated photochemically in our skin by UV irradiation.
+Phytosterols contain extra methyl or ethyl group in the C-17 side chain.
+|
 }}
 ==Cardenolides (C23)==
@@ Line 15: / Line 40: @@
 {{Twocolumn|
-When used in small doses, they are extremely valuable clinically for congestive heart failure.
+Since Withering's report in 1785 <ref>Tröhler U (2007) Withering's 1785 appeal for caution when reporting on a new medicine. [http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1809157/ ''J R Soc Med'' 100(3): 155–156]</ref>, cardenolides have been extremely valuable clinically for congestive heart failure.
+|
 }}
 ===Distribution===

@@ Line 7: / Line 7: @@
 {{Twocolumn|
-The backbone of ''Digitalis'' glycosides with the androstane skeleton with a &gamma;-lactone ring at C-17. Notable characters are its 14&beta;-configuration in opposition to other steroids (the rings C/D are ''cis''), and the 20(22)-double bond. Their cardiac activity is well known.
+The 5&alpha;-configuration is found in Asclepias  (e.g. aspecioside), whereas 5&beta;-configuration is common in the foxglove [[Species:Digitalis|Digitalis purpurea]], [[:Category:Plantaginaceae|Plantaginaceae]] (e.g. digoxin).  In some Asclepias, sugars are attached to the two hydroxyl groups at C-2 and C-3 position to form cyclic bridges (e.g. asclepin, calactin).
+|
 }}
-===Withanolides (C28)===
+==Withanolides (C28)==
 {{Twocolumn|
 Withanolides were found in the root of [[Species:Withania|Withania Somnifera]], also known as Indian ginseng.  Its backbone is a highly oxygenated ergostane with a &gamma;-lactone ring linking C-22 and C-26 <ref>Iida, T et al. (1985) J. Lipid Res. 26,874</ref>. The configuration of C-22 is usually ''R''.