ω-异硫氰甲基长叶烯的合成、结构表征及抑藻活性

doi:10.3969/j.issn.0253-2417.2021.02.014

林产化学与工业 ›› 2021, Vol. 41 ›› Issue (2): 103-109.doi: 10.3969/j.issn.0253-2417.2021.02.014

ω-异硫氰甲基长叶烯的合成、结构表征及抑藻活性

王梦竹¹(), 蓝虹云¹^,², 黄道战¹^,²^,*(), 朱茂茂¹, 邹虹³

1. 广西民族大学化学化工学院, 广西南宁 530008
2. 广西林产化学与工程重点实验室, 广西南宁 530008
3. 广西民族大学医院, 广西南宁 530006

收稿日期:2020-08-16 出版日期:2021-04-28 发布日期:2021-05-08
通讯作者: 黄道战 E-mail:wmz19941109@163.com;huangdaozhan@gxun.edu.cn
作者简介:黄道战, 教授, 硕士生导师, 研究领域为林产资源化学加工利用; E-mail: huangdaozhan@gxun.edu.cn
王梦竹(1994-), 女, 河北保定人, 硕士生, 主要从事林产精细化学品开发及应用研究; E-mail: wmz19941109@163.com
基金资助:
广西自然科学基金项目(2017GXNSFAA198027);广西创新驱动发展重大专项子课题(桂科AA17204087-21);广西科技基地和人才专项(桂科AD18126005)

Synthesis, Structurally Characterization and Alga Inhibiting Activity of ω-Isothiocyanomethyl Longifolene

Mengzhu WANG¹(), Hongyun LAN¹^,², Daozhan HUANG¹^,²^,*(), Maomao ZHU¹, Hong ZOU³

1. College of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530008, China
2. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, China
3. Hospital of Guangxi University for Nationalities, Nanning 530006, China

Received:2020-08-16 Online:2021-04-28 Published:2021-05-08
Contact: Daozhan HUANG E-mail:wmz19941109@163.com;huangdaozhan@gxun.edu.cn

摘要/Abstract

摘要：

以正己烷为溶剂，在加热回流条件下，ω-氯甲基长叶烯（Ia）与硫氰酸铅进行取代反应，选择性合成具有低刺激性气味的ω-异硫氰甲基长叶烯（Ib）。采用高分辨率质谱、傅里叶红外吸收光谱、紫外吸收光谱、¹H与¹³C核磁共振谱对目标化合物的化学结构进行表征确证。高分辨质谱确定了其分子式为C₁₇H₂₅NS，傅里叶红外吸收光谱、紫外-可光吸收光谱、¹H NMR与¹³C NMR分别证实了NCS结构和长叶烯结构的存在。化合物Ib兼具长叶烯和异硫氰酸甲酯的分子结构，可归属于异硫氰酸烯丙酯类化合物。通过96孔板二倍稀释法抑藻活性试验的评价，得到化合物Ib能够抑制斜生栅藻和中肋骨条藻的生长，其最小抑制质量浓度分别为62.5和31.25 mg/L左右，抑藻活性明显优于化合物Ia、长叶烯和异硫氰酸甲酯。

关键词: 长叶烯, ω-氯甲基长叶烯, 硫氰酸铅, 异硫氰酸烯丙酯, 抑藻活性

Abstract:

ω-Isothiocyanomethyl longifolene(Ib) with low irritating odor was selectively synthesized by substitution reaction of lead thiocyanate and ω-chloromethyl longifolene(Ia) under reflux heating with hexane as solvent. The final product was characterized through HRMS, FT-IR, UV, ¹H NMR and ¹³C NMR. The molecular formula of C₁₇H₂₅NS was determined by HRMS, and the presence of N=C=S structure and long-leaf alkene structure was confirmed by FT-IR, UV spectroscopy and ¹H NMR and ¹³C NMR spectroscopy, respectively. Compound Ib could be regarded as an allyl isothiocyanate compound, containing longifolene and methyl isothiocyanate molecule structure moiety. The algae inhibitory activity of compound Ib was evaluated by 96-well plate two-fold dilution assay. It was obtained that compound Ib was able to inhibit the growth of Scenedesmus obliquus and Skeletonema sp. with the MIC of about 62.5 and 31.2 mg/L, respectively, and the algae inhibitory activity was significantly better than that of compound Ia, longleafene and methyl isothiocyanate.

Key words: longifolene, ω-chloromethyl longifolene, lead thiocyanate, allyl isothiocyanate, alga inhibiting activity

中图分类号:

TQ35

王梦竹, 蓝虹云, 黄道战, 朱茂茂, 邹虹. ω-异硫氰甲基长叶烯的合成、结构表征及抑藻活性[J]. 林产化学与工业, 2021, 41(2): 103-109.

Mengzhu WANG, Hongyun LAN, Daozhan HUANG, Maomao ZHU, Hong ZOU. Synthesis, Structurally Characterization and Alga Inhibiting Activity of ω-Isothiocyanomethyl Longifolene[J]. Chemistry and Industry of Forest Products, 2021, 41(2): 103-109.

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ω-异硫氰甲基长叶烯的合成、结构表征及抑藻活性

Synthesis, Structurally Characterization and Alga Inhibiting Activity of ω-Isothiocyanomethyl Longifolene

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