123.130.221.191：建立内容为“{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 402020819 | ImageFile = Ergosterol structure.svg | ImageSize = 250px | IUPACName…”的新页面

2021-07-21T16:08:23Z

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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402020819
| ImageFile = Ergosterol structure.svg
| ImageSize = 250px
| IUPACName = ergosta-5,7,22-trien-3β-ol
| OtherNames =
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392539
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z30RAY509F
| InChIKey = DNVPQKQSNYMLRS-APGDWVJJBI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DNVPQKQSNYMLRS-APGDWVJJSA-N
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1232562
| CASNo = 57-87-4
| CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-352-7
| PubChem = 444679
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16933
| SMILES = O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4
| InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
| MeSHName = Ergosterol
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>28</sub>H<sub>44</sub>O
| MolarMass = 396.65 g/mol
| ExactMass = 396.339216
| Appearance =
| Density =
| MeltingPt = 160.0 °C
| BoilingPt = 250.0 °C
}}
| Section3 = {{Chembox Hazards
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}}
'''麦角固醇'''<ref>[http://www.term.gov.cn/pages/homepage/result2.jsp?id=334522&subid=10001798&subject=%E6%BF%80%E7%B4%A0%E4%B8%8E%E7%BB%B4%E7%94%9F%E7%B4%A0&subsys=%E7%94%9F%E7%89%A9%E5%8C%96%E5%AD%A6%E4%B8%8E%E5%88%86%E5%AD%90%E7%94%9F%E7%89%A9%E5%AD%A6] 全国科学技术名词审定委员会</ref>（{{lang-en|Ergosterol}}，又称为'''[[麦角]][[甾醇]]'''）是从[[真菌类]][[酵母]]与[[麦角菌]]中发现的一种[[植物固醇]]。在[[紫外线]]照射下可被转化为[[维生素D2]]。它是酵母和[[真菌]][[细胞膜]]的组成部分，功能与动物细胞膜中的[[胆固醇]]相同。对于素食者说，麦角固醇是唯一的[[维生素D]]食物来源，不过人体内可从胆固醇合成维生素D。

==应用==

===真菌检测===

麦角固醇由真菌合成，虽然有在草如[[黑麦]]<ref>{{cite journal | pmid = 21919518 | year = 2011 | last1 = Jäpelt | first1 = RB | last2 = Didion | first2 = T | last3 = Smedsgaard | first3 = J | last4 = Jakobsen | first4 = J | title = Seasonal variation of provitamin D2 and vitamin D2 in perennial ryegrass (Lolium perenne L.) | volume = 59 | issue = 20 | pages = 10907–12 | doi = 10.1021/jf202503c | journal = Journal of agricultural and food chemistry}}</ref>和紫[[花苜蓿]]（包括[[苜蓿]]芽），并在植物的花，如[[啤酒花]]<ref>{{cite journal | pmid =17760411 | year =2007 | last1 =Magalhães | first1 =PJ | last2 =Carvalho | first2 =DO | last3 =Guido | first3 =LF | last4 =Barros | first4 =AA | title =Detection and quantification of provitamin D2 and vitamin D2 in hop (Humulus lupulus L.) by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry | volume =55 | issue =20 | pages =7995–8002 | doi =10.1021/jf071308d | journal =Journal of agricultural and food chemistry}}</ref>中发现麦角固醇的报告，然而，目前认为这些麦角固醇来自污染植物的真菌。因此，麦角固醇的检测技术可用于检测草，谷物，和进料系统中的真菌。<ref>http://wwww.aslo.org/lo/toc/vol_46/issue_3/0573.pdf</ref><ref>{{cite journal | pmid =2400324 | year =1990 | last1 =Müller | first1 =HM | last2 =Schwadorf | first2 =K | title =Ergosterol as a measure for fungal growth in feed. 2. Ergosterol content of mixed feed components and mixed feed | volume =40 | issue =4 | pages =385–95 | journal =Archiv fur Tierernahrung}}</ref>

麦角固醇也可以用来作为在土壤中真菌生物量的一个指标，尽管其会缓慢降解，但如果将样本储存于冰点以下的黑暗环境，[[降解速度]]会减慢甚至停止。

===[[抗真菌药物]]靶点===

由于麦角固醇只在真菌[[细胞]]中发挥生物功能，因此可作为抗真菌药物的作用靶点。麦角固醇也存在与一些[[单细胞生物]]，如[[非洲锥虫病|非洲昏睡症]][[病原体]][[锥虫]]<ref>{{cite journal |author=Roberts CW, McLeod R, Rice DW, Ginger M, Chance ML, Goad LJ |title=Fatty acid and sterol metabolism: potential antimicrobial targets in apicomplexan and trypanosomatid parasitic protozoa |journal=Mol. Biochem. Parasitol. |volume=126 |issue=2 |pages=129–42 |year=2003 |month=February |pmid=12615312 |doi=10.1016/S0166-6851(02)00280-3}}</ref>的细胞膜，这是相关药物用于治疗该病的理论依据。

例如抗真菌药物[[两性霉素B]]，其与[[霉菌]]细胞膜上的麦角固醇结合，造成细胞膜通透性的改变，导致真菌细胞内的成分，主要是钾离子和氢离子，及其他成份如[[氨基酸]]、[[蛋白质]]等泄漏到膜外，破坏真菌正常[[代谢]]及抑制生长，细胞产生裂解而造成霉菌[[细胞死亡]]。<ref>常用药物手册中华书局(香港)有限公司周自永王世祥</ref>其用于抵抗真菌或[[原虫]][[感染]]，由于与胆固醇也有一定的亲和性而对人体产生[[副作用]]，现一般已被其它更安全的药物取代。

[[咪康唑]]，[[伊曲康唑]]和[[克霉唑]]则抑制真菌细胞从{{en-link|羊毛甾醇|lanosterol|羊毛甾醇}}到麦角固醇的合成，转化过程中与[[羊毛甾醇]]4号碳上两个甲基的消除相关的酶被抑制，从而实现抗真菌作用。

===潜在用途===

有研究显示麦角固醇可能具有抗[[肿瘤]]特性。<ref name="Yazawa2000">{{cite journal
| author = Yazawa Y, Yokota M, Sugiyama K.
| title = Antitumor promoting effect of an active component of Polyporus, ergosterol and related compounds on rat urinary bladder carcinogenesis in a short-term test with concanavalin A
| journal = Biol Pharm Bull
| volume = 11
| pages = 1298–1302
| publisher =
| location =
| year = 2000
| doi = 10.1248/bpb.23.1298
| pmid = 11085355
| issue = 11
}}</ref><ref name="Takaku2001">{{cite journal |pmid=11340091 |year=2001 |last1=Takaku |first1=T |last2=Kimura |last3=Okuda |title=Isolation of an antitumor compound from Agaricus blazei Murill and its mechanism of action |volume=131 |issue=5 |pages=1409–13 |journal=The Journal of nutrition |first2=Y |first3=H}}</ref>

==[[毒性]]==

麦角固醇粉对[[皮肤]]，眼睛和[[呼吸道]]有刺激性。大量摄入可引起{{en-link|高血钙症|hypercalcemia|高血钙症}}，长时间的高血钙症会导致钙盐在软组织，特别是[[肾脏]]中沉积。<ref>[http://fscimage.fishersci.com/msds/28224.htm Material Safety Data Sheet], Fisher Scientific</ref>

==参考文献==

{{reflist|2}}

== 外部链接 ==
* [http://ptcl.chem.ox.ac.uk/MSDS/ER/ergosterol.html Safety (MSDS) data for ergosterol] Oxford University (2005)

{{维生素}}
{{胆固醇与甾体中间产物}}
{{植物固醇}}

[[Category:细胞生物学]]

[[Category:固醇]] [[Category:营养学]] [[Category:维生素D]]
==参考来源==
*[http://zh.wikipedia.org/wiki/%E9%BA%A6%E8%A7%92%E5%9B%BA%E9%86%87 维基百科-麦角固醇]

麦角固醇 - 版本历史

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