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: Sambunigrin

每周分子：苯乙腈葡糖苷

苯乙腈葡糖苷也被称为(S)-野樱甙，是在接骨木的叶子和其他部分产生的一种氰苷。在一些蔷薇科属树(P. japonica和P. serotina)中能够发现其非对映体(R)-野樱甙。

1905年，法国著名的研究员——里昂科学学院的药剂师/植物学家Jean Louis Léon Guignard和巴黎Laënnec医院的化学家/药剂师Émile Bourquelot——各自从S. nigraleaves中分离出了苯乙腈葡糖苷。他们的研究还表明，在酶的降解作用下，从1公斤的新鲜叶子中可以产生多达126毫克的氰化氢(HCN)(请参阅“危害信息”)。

关于S. nigra的好消息是，它的花朵和成熟的浆果中不含苯乙腈葡糖苷。在许多非处方产品中都含有S. nigra的水果提取物，这些非处方产品旨在支持免疫系统，帮助缓解感冒症状，并对抗一些革兰氏阳性和革兰氏阴性细菌。但这些用途都尚未得到美国食品药品监督管理局(FDA)的批准。2011年，FDA对堪萨斯州的一家公司采取了法律行动，该公司声称，其接骨木果汁产品可以预防某些疾病，并可用于治疗某些疾病。

苯乙腈葡糖苷信息速览

CAS登记号	99-19-4
分子式	C₁₄H₁₇NO₆
摩尔质量	295.29 g/mol
外观	白色粉末
熔点	151–152 ºC
水溶性	28 g/L (预测)

苯乙腈葡糖苷危害信息

GHS分类*：非危险物质或混合物

* 化学品分类及标记全球协调制度。尽管在一项安全数据表上有这种分类，但许多报告表明，当植物中含有苯乙腈葡糖苷的部分被摄入时，该化合物在肠道中会被水解为HCN，因此如果人们吞食了苯乙腈葡糖苷，它将对人体产生伤害。

【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。

Sambunigrin, also referred to as (S)-prunasin, is a cyanogenic glycoside that is produced in the leaves and other parts of the elderberry plant Sambucus nigra. Its diastereomer (R)-prunasin is found in some species of Prunus trees, including P. japonica (Japanese bush cherry) and P. serotina (wild black cherry).

In 1905, working independently, prominent French researchers—pharmacist/botanist Jean Louis Léon Guignard at the Faculty of Sciences of Lyon and chemist/pharmacist Émile Bourquelot at Laënnec Hospital in Paris—isolated sambunigrin from S. nigraleaves. They also showed that, upon enzymatic degradation, as much as 126 mg of hydrogen cyanide (HCN) is produced from 1 kg of fresh leaves. (See also the hazard information box.)

The good news about S. nigra is that its flowers and ripe berries do not contain sambunigrin. Extracts from the fruit are contained in a wide range of over-the-counter products that purport to support the immune system, help relieve cold symptoms, and combat some Gram-positive and Gram-negative bacteria. But none of these uses has yet been approved by the US Food and Drug Administration. In 2011, the FDA took legal action against a Kansas company that claimed that its elderberry juice product prevented certain illnesses and could be used to treat certain diseases.

Sambunigrin fast facts

CAS Reg. No.	99-19-4
Empirical formula	C₁₄H₁₇NO₆
Molar mass	295.29 g/mol
Appearance	White powder
Melting point	151–152 ºC
Water solubility	28 g/L (est.)

Sambunigrin hazard information

GHS classification*: not a dangerous substance or mixture

*Globally Harmonized System of Classification and Labeling of Chemicals. Despite this classification in at least one safety data sheet, many reports indicate that when plant parts that contain sambunigrin are ingested, the compound hydrolyzes to HCN in the gut, making sambunigrin hazardous if it is swallowed.

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