每周分子Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

Molecule of the Week:

Narciclasine

每周分子: 水仙环素

水仙环素又被称为石蒜西定醇，是在石蒜科孤挺花属植物中发现的一种羟基异喹啉生物碱。石蒜科孤挺花属中最著名的是水仙，水仙环素因此而得名。水仙花和长寿花属于水仙属。

1967年，Circolo医院（位于意大利布斯托-阿西齐奥）的Giovanni Ceriotti，Luigi Spandrio和Annivale Gazzaniga从水仙中分离出了水仙环素。在当时，水仙环素被认为可以抑制细胞分裂。到21世纪早期，水仙环素已被确认为是一种抗肿瘤药物。

2016年，歌德大学(德国美因河畔法兰克福)的Robert Fürst就水仙环素的抗肿瘤和抗炎研究写了综述。目前，还没有对水仙环素进行人体临床试验。

水仙环素微溶于水。但是在2003年，亚利桑那州立大学的GeorgeR. Petit和他的同事们在水仙环素两个相邻的羟基间合成了一个环状磷酸盐。他们称这种产物为narcistatin (CAS登记号为496963-44-1)，水溶性更强（4克/升），是有价值的水仙环素前药。

水仙环素速览

CAS 登记号	29477-83-6
摩尔质量	307.26 g/mol
分子式	C₁₄H₁₃NO₇
外观	白色至类米色
熔点	246 ºC
水溶性	Slight

水仙环素危害信息

GHS 分类*: 生殖细胞突变，1B类
H340—可致基因缺陷

【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SciFinder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。

Narciclasine, also known as lycoricidinol, is an isocarbostyril alkaloid found in the Amaryllidaceae (amaryllis) family of flowering plants. One notable genus of the family is Narcissus, from which narciclasine gets its name. Daffodils and jonquils are members of the Narcissus genus.

In 1967, Giovanni Ceriotti, Luigi Spandrio, and Annivale Gazzaniga at Circolo Hospital (Busto Arsizio, Italy) isolated narciclasine from Narcissus varieties. At that time, it was known to inhibit cell division. By the early 2010s, narciclasine was an established antitumor agent.

In 2016, Robert Fürst at Goethe University (Frankfurt am Main, Germany) reviewed the antitumor and anti-inflammatory findings on narciclasine. At present, no clinical trials on narciclasine have been conducted on humans.

Narciclasine is sparingly soluble in water. But in 2003, George R. Petit and colleagues at Arizona State University (Tempe) synthesized a cyclic phosphate at two of the adjacent hydroxyl groups of narciclasine. The product, which they called narcistatin (CAS Reg. no. 496963-44-1), is much more water-soluble (4 g/L), making it a valuable prodrug for narciclasine.

Narciclasine fast facts

CAS Reg. No.	29477-83-6
Molar mass	307.26 g/mol
Empirical formula	C₁₄H₁₃NO₇
Appearance	White to off-white powder
Melting point	246 ºC
Water solubility	Slight

Narciclasine hazard information

GHS classification*: germ cell mutagenicity, category 1B
H340—May cause genetic defects

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

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 SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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