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Chemistry and Industry of Forest Products ›› 2021, Vol. 41 ›› Issue (2): 103-109.doi: 10.3969/j.issn.0253-2417.2021.02.014

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

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

  1. 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


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

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