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(New page: ==Phytosterols== {{Twocolumn| Most common phytosterols are campesterol, β-sitosterol, and stigmasterol. Soybean (''Glycine max'', Fabaceae)...)
 
(Phytosterols)
 
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==Phytosterols==
 
==Phytosterols==
 
{{Twocolumn|
 
{{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.
 +
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 plantsErgosterols 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]]).
 
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 +
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.]], [[: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 ([[: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。
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}}
  
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<center>
 +
{|
 +
! style="background-color:#fdd"| animal sterols
 +
! colspan="2" style="background-color:#dfd"| plant sterols
 +
|-
 +
| [[Image:cholestane.png]] || [[Image:campestane.png]] || [[Image:stigmastane.png]]
 +
|-
 +
| cholestane <br/>(cholesterol backbone)
 +
| campestane <br/>(campesterol backbone)
 +
| stigmastane <br/> (&beta;-sito and stigmasterol backbone)
 +
|-
 +
!
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! colspan="2" style="background-color:#ddf"| fungal sterols
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|-
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| || [[Image:ergostane.png]] || [[Image:poriferastane.png]]
 +
|-
 +
|
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| ergostane <br/>(ergosterol backbone)
 +
| poriferastane <br/> (poriferasterol backbone)
 +
|}
 +
</center>
 +
 +
==={{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.
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|
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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。
 +
植物ステロールを摂取するとコレステロール値を下げる効果があるので、植物ステロールを添加したマーガリンなども市販されています。
 +
ビタミンDもステロールの一種で、これは紫外線にあたることで皮膚内で合成されます。
 
}}
 
}}
  
 +
<references/>
  
 +
==={{Bilingual|Do plants contain animal sterols?|植物は動物ステロールも作る}}===
  
===Cardenolides (C23)===
 
 
{{Twocolumn|
 
{{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.
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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.
 +
<br/>
 +
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
 +
* ajugasterone from [[Species:Ajuga|''Ajuga chamaepitys'' and ''A. reptans'']], [[:Category:Lamiaceae|Lamiaceae]]
 +
* 20-hydroxyecdysone from [[Species:Serratula|''Serratula inermis'']], [[:Category:Asteraceae|Asteraceae]] and [[Species:Diploclisia|''Diploclisia glaucescens'']], [[:Category:Menispermaceae|Menispermaceae]]).
 
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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]]) の花粉はテストステロン(男性ホルモン)を含んでいます。
 +
<br/>
 +
昆虫の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:
 +
* 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
 +
* 20-ヒドロキシエクジソン ... キク科タムラソウ属 ([[Species:Serratula|''Serratula'']], [[:Category:Asteraceae|Asteraceae]]) やツヅラフジ科のDiploclisia ([[Species:Diploclisia|''Diploclisia'']], [[:Category:Menispermaceae|Menispermaceae]]) など
 
}}
 
}}
  
===Withanolides (C28)===
+
==Cardenolides (C23)==
 +
{{Twocolumn|
 +
The backbone of the foxglove [[Species:Digitalis|''Digitalis'']] ([[:Category:Plantaginaceae|Plantaginaceae]]) toxins 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.
 +
|
 +
 
 +
}}
 +
 
 +
{{Twocolumn|
 +
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.
 +
However, they are remarkably nontoxic to Lepidoptera, especially some species of Danaid butterfly <ref>Mebs D, Reuss E, Schneider M (2005) "Studies on the cardenolide sequestration in African milkweed butterflies (Danaidae)" [http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TCS-4FH0W41-2&_user=136130&_coverDate=04/30/2005&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1419399593&_rerunOrigin=google&_acct=C000010979&_version=1&_urlVersion=0&_userid=136130&md5=5e590ea4589343dedc6978d01fc177cc ''Toxicon'' 45(5):581-584]</ref>
 +
|
 +
}}
 +
 
 +
<references/>
 +
 
 +
===Distribution===
 +
{{Twocolumn|
 +
Cardenolides occur principally in the related families of [[:Category:Apocynaceae|Apocynaceae]] (including [[:Category:Asclepiadaceae|Asclepiadaceae]]).
 +
In the milkweed genus [[Species:Asclepias|Asclepias]], these compounds are secreted in the latex and almost every species contains these toxins.
 +
Other plant families such as [[:Category:Brassicaceae|Brassicaceae]], [[:Category:Moraceae|Moraceae]], [[:Category:Scrophulariaceae|Scrophulariaceae]], and some monocotyledons (e.g. [[Species:Urginea|Urginea]] in [[:Category:Liliaceae|Liliaceae]]) contain cardenolides.
 +
|
 +
}}
 +
 
 +
{{Twocolumn|
 +
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)==
 
{{Twocolumn|
 
{{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''.
 
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''.
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}}
 
}}
  
===Brassinolides (C28)===
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==Brassinolides (C28)==
 
{{Twocolumn|
 
{{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.
 
The configurations of C-2,3 and 5 are &alpha; in brassinolides whereas they are &beta; in ecdysteroids.
 
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|
 +
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。
 +
エルゴスタンが多く酸化された骨格をもち、酸素を含んだB環 (&epsilon;-ラクトン) が特徴です。
 +
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。
 +
}}
  
 +
{{Twocolumn|
 +
Brassinolides have anti-ecdysteroid activity: they delay imaginal moult when fed to the last instar of American cockroach (''Periplaneta americana'').
 +
|
 +
ブラシノライドは反エクジソン効果を持ちます。アメリカゴキブリの最終齢幼虫に食べさせると、脱皮が遅れることが知られています。
 
}}
 
}}

Latest revision as of 02:17, 4 August 2010

Contents

[edit] Phytosterols

Phytosterols contain extra methyl or ethyl group in the C-17 side chain. Most common phytosterols are campesterol, β-sitosterol, and stigmasterol. They occur both free and as 3-glucosides and all essential for membranes in higher plant. Less common are α-spinasterol (an isomer of stigmasterol) in spinach (Spinacia oleracea L., Chenopodiaceae) and alfalfa (Medicago sativa L., Fabaceae).
Some sterols are confined in lower plants. Ergosterols are found only in yeast and fungi, fucosterols are found in brown algae (Phaeophyceae) and in some higher plants, e.g. coconut (Cocos nucifera, Arecaceae).

animal sterols plant sterols
Cholestane.png Campestane.png Stigmastane.png
cholestane
(cholesterol backbone)
campestane
(campesterol backbone)
stigmastane
(β-sito and stigmasterol backbone)
fungal sterols
Ergostane.png Poriferastane.png
ergostane
(ergosterol backbone)
poriferastane
(poriferasterol backbone)

[edit] 植物ステロールと健康

Soybean (Glycine max, Fabaceae) is a rich source of phytosterols (about 0.1% of its weight), and is used for semi-synthesis of medicinal steroids [1]. Since dietary phytosterols reduce cholesterol levels, they are used as food additives such as for margarine [2]. Vitamin D is a family of sterol metabolites generated photochemically in our skin by UV irradiation.

  1. 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
  2. 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

[edit] 植物は動物ステロールも作る

Date palm seed (Phoenix dactylifera, Arecaceae) contains cholesterol and a trace amount of estrone (a female sex hormone). Estrone is also contained in seeds of pomegranate (Punica granatum, Punicaceae). The pollen of Scots pine (Pinus sylvestris, 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:

[edit] Cardenolides (C23)

The backbone of the foxglove Digitalis (Plantaginaceae) toxins 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.

Since Withering's report in 1785 [1], cardenolides have been extremely valuable clinically for congestive heart failure. However, they are remarkably nontoxic to Lepidoptera, especially some species of Danaid butterfly [2]

  1. Tröhler U (2007) Withering's 1785 appeal for caution when reporting on a new medicine. J R Soc Med 100(3): 155–156
  2. Mebs D, Reuss E, Schneider M (2005) "Studies on the cardenolide sequestration in African milkweed butterflies (Danaidae)" Toxicon 45(5):581-584

[edit] Distribution

Cardenolides occur principally in the related families of Apocynaceae (including Asclepiadaceae). In the milkweed genus Asclepias, these compounds are secreted in the latex and almost every species contains these toxins. Other plant families such as Brassicaceae, Moraceae, Scrophulariaceae, and some monocotyledons (e.g. Urginea in Liliaceae) contain cardenolides.

The 5α-configuration is found in Asclepias (e.g. aspecioside), whereas 5β-configuration is common in the foxglove Digitalis purpurea, 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).

[edit] Withanolides (C28)

Withanolides were found in the root of 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 [1]. The configuration of C-22 is usually R.

[edit] Brassinolides (C28)

Brassinolides are plant growth-promoting hormones isolated originally from Brassica napus, Brassicaceae (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 22R, 23R-diol are. The configurations of C-2,3 and 5 are α in brassinolides whereas they are β in ecdysteroids.

Brassinolides have anti-ecdysteroid activity: they delay imaginal moult when fed to the last instar of American cockroach (Periplaneta americana).


Cite error: <ref> tags exist, but no <references/> tag was found

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