每周分子 | Molecule of the Week

Original ACS 美国化学会 ACS美国化学会 2023-03-12

收录于合集 #每周分子 142个

点击上方， 订阅话题 ，不错过每周分子！

每周分子：佛手柑素

Molecule of the Week: Bergamottin

佛手柑素是呋喃香豆素类化合物。呋喃香豆素是一类存在于许多植物种子和果实中的有机化合物，尤其是芸香科(柑橘类水果)和伞形科(芹菜、胡萝卜等)植物。顾名思义，呋喃香豆素的中心结构由一个呋喃环与双环香豆素类结构稠合而成。

补骨脂素和当归素是未发生取代的呋喃香豆素类化合物，其中呋喃环和香豆素环分别成线性和角度稠合。佛手柑素及其氧化产物6'，7' -二羟基佛手柑素(DHB)和6'，7' -环氧佛手柑素是在补骨脂素的5位连接有香叶醇衍生侧链的补骨脂素衍生物。佛手柑素得名于佛手柑(Citrus bergamia) ，由维也纳大学的Ernst Späth和Paul Kainrath于1937年从佛手柑油中首次分离获得。

佛手柑素在许多人的生命中起着重要作用。它与DHB共同抑制细胞色素P450酶CYP3A，从而减缓或阻止洛伐他汀(lovastatin)、辛伐他汀(simvastatin)、阿托伐他(atorvastatin)汀等“他汀”类药物的代谢，从而减少体内胆固醇载体——低密度脂蛋白(LDL)的形成。佛手柑素在葡萄柚中含量尤为丰富，这就是为什么建议在服用他汀类药物时不要食用葡萄柚或葡萄柚汁。

氧化的佛手柑素和西柚的其他成分也会抑制他林洛尔(talinolol)的传输，talinolol是P-糖蛋白的底物，P-糖蛋白是一种重要的细胞膜成分，可以从细胞中清除外来物质。要了解更多关于佛手柑素及其衍生物的信息，请参见Science Direct：

https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/bergamottin

佛手柑素信息速览

CAS 登记号	7380-40-7
CAS SciFinder命名	7H-Furo[3,2-g][1]benzopyran-7-one,4-{[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy}-
分子式	C₂₁H₂₂O₄
摩尔质量	338.40 g/mol
外观	白色晶体或粉末
熔点	55–56 °C
水溶性	≈10mg/L (est.)

佛手柑素危害信息

GHS分类：皮肤致敏，类别1
H317-可能引起皮肤过敏反应

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的CAS SciFinderⁿ中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

Furanocoumarins are organic compounds found in the seeds and fruits of many species of plants, notably in the families Rutaceae (citrus fruits) and Apiaceae (celery, carrots, and others). As the name suggests, the central structure of furanocoumarins consists of a furan ring fused to a two-ring coumarin system.

Psoralen and angelicin are unsubstituted furanocoumarins in which the furan and coumarin rings are fused in linear and angular orientations, respectively. Bergamottin and its oxidation products 6′,7′-dihydroxybergamottin (DHB) and 6′,7′-epoxybergamottin are psoralen derivatives that have geraniol-derived side chains attached at the 5-position. Bergamottin is named after the bergamot orange (Citrus bergamia); it was first isolated from bergamot oil in 1937 by Ernst Späth and Paul Kainrath at the University of Vienna.

Bergamottin plays a role in the lives of many people. It and DHB inhibit the cytochrome P450 enzyme CYP3A, thereby slowing or preventing the metabolism of lovastatin, simvastatin, atorvastatin, and other “statin” drugs that decrease the formation of low-density lipoprotein (LDL) carriers of cholesterol in the body. Bergamottins are particularly abundant in grapefruit, which is why statin labels advise against consumption of the fruit or its juice close to the time the drugs are taken.

The oxidized bergamottins and other grapefruit ingredients also inhibit the transport of talinolol, a substrate for P glycoprotein, an important cell membrane component that removes foreign substances from cells. For more information on bergamottin and its derivatives, see this Science Direct entry:

https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/bergamottin

Bergamottinfast facts

CAS Reg. No.	7380-40-7
SciFinder nomenclature	7H-Furo[3,2-g][1]benzopyran-7-one,4-{[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy}-
Empirical formula	C₂₁H₂₂O₄
Molar mass	338.40 g/mol
Appearance	white crystals or powder
Melting point	55–56 °C
Watersolubility	≈10 mg/L (est.)

Bergamottinhazard information

Skinsensitization, category 1
H317-Maycause an allergic skin reaction

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using CAS SciFinderⁿ. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

往期回顾：

每周分子Molecule of the Week：无穷烯

每周分子Molecule of the Week：克林霉素

每周分子Molecule of the Week：羟基马桑毒素

每周分子Molecule of the Week：甲酸

每周分子Molecule of the Week：三氯吡氧乙酸

每周分子Molecule of the Week：柠檬酸

每周分子Molecule of the Week：八甲基环四硅氧烷

每周分子Molecule of the Week：胍丁胺

每周分子Molecule of the Week：雌四醇

每周分子Molecule of the Week：丙戊酸

每周分子Molecule of the Week：二硫化钯