High-Value-Added Utilization of Turpentine:Screening of Anti-Influenza Virus Agents fromβ-Pinene Derivatives

Turpentine is a renewable and resourceful forest product.The deep processing and utilization of turpentine,particularly its primary componentβ-pinene,has garnered widespread attention.This study aimed to synthesize 40 derivatives ofβ-pinene,including nopinone,3-cyanopyridines of nopinone,myrtanyl acid,myrtanyl acylthioureas,and myrtanyl amides.We assessed the antiviral activities of theseβ-pinene derivatives against influenza virus A/Puerto Rico/8/34(H1N1)using the 3-(4,5-dimetylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method.Theβ-pinene derivatives were used before and after cellular infection with the influenza virus to evaluate their preventive and therapeutic effects against the H1N1 virus.The results showed that only compound 10o exhibited a preventive effect against the H1N1 virus with a half-maximal inhibitory concentration(IC50)value of 47.6μmol/L.Among the compounds,4e,4i,and 4l demonstrated therapeutic effects against cellular infection,with compound 4e displaying the most potent therapeutic effect(IC50=17.5μmol/L),comparable to the positive control ribavirin.These findings indicated that certainβ-pinene derivatives exhibited in vitro antiviral activity against the H1N1 influenza A virus,warranting further investigation as potential anti-influenza agents.

Synthesis and Antioxidant Activity of(E)ω-Formylcamphene-Based Thiazole Hydrazone Derivatives

(E)ω-formylcamphene was synthesized fromα-pinene,the main component of turpentine,and then reacted with thiosemicarbazide to obtain(E)ω-formylcamphene thiosemicarbazide 3,which was reacted with 14α-bromoace-tophenone compounds to obtain 14(E)ω-formylcamphene thiazole hydrazone compounds 5a–5n;the yields were all above 80%.The structures of the target compounds were characterized by IR,^(1)H-NMR,^(13)C-NMR,and HR-MS analyses.Then,500,250,125,62.5,and 31.25 mg/L drug solutions were prepared.Free radical scavenging experi-ments of 1,1-diphenyl-2-picrylhydrazyl(DPPH)and 2,2-bis(3-ethyl-benzothiazole-6-sulfonic acid)diammonium salt(ABTS)were carried out with Trolox and L-ascorbic acid as the control samples.The scavenging rates of 14 compounds for DPPH and ABTS free radicals were obtained;the IC_(50) values of scavenging free radicals were fitted using SPSS software.The results show that 14(E)ω-formylcamphene-based thiazole hydrazone compounds exhibited good scavenging effects on the two free radicals,especially when the concentration of the drug solution was 125 and 62.5 mg/L;most compounds exceeded the scavenging efficiency of Trolox and L-ascorbic acid.

Preparation of Amide-Containing Insecticidal Derivatives from the Renewable Natural Productβ-Pinene

The preparation of bioactive derivatives from the renewable natural product pinene is a hot research topic in the deep processing and utilization of pinene.In this study,β-pinene was used to develop novel molecules as a promising new precursor of insecticide.A series of amide-containing derivatives ofβ-pinene were synthesized and characterized.The insecticidal activities of these derivatives against Mythimna separate and Semiaphis heraclei were tested.The structure characterization results showed that the characterization data of amide-containing derivatives were in full agreement with their proposed structures.The insecticidal activities evaluation results indicated that amide-containing derivatives exhibited weak insecticidal activity against Mythimna separate,but exhibited moderate to good insecticidal activity against Semiaphis heraclei.After testing for 72 h,the corrected mortality against Semiaphis heraclei of compounds 5c,5e,5f,5 h,5j,and 5 m was 100%at 1000 mg/L.The structure-activity relationship analysis results showed that the introduction of an amide group into the structure of derivatives improved their insecticidal activity against Semiaphis heraclei.Meanwhile,the amide-containing derivatives containing the F and NO_(2) substituted benzene ring might improve their insecticidal activity against Semiaphis heraclei.This study will be helpful for the high value-added utilization of the natural renewable resourceβ-pinene and the development of novel insecticides.

Synthesis and anticancer activity of(+)-nopinone-based 2-amino-3-cyanopyridines

Twelve(+)-nopinone-based 2-amino-3-cyanopyridines 4a-1 were synthesized from(–)-β-pinene.The structures of these compounds were characterized by FT-IR,1H NMR,and ESI-MS.All the compounds were tested for their anticancer activity against lung cancer cell line A549,gastric cancer cell line MKN45 and breast cancer cell line MCF7 by MTT method,respectively.The results showed that compounds 4f,4j and 4k had promising anticancer activity against these cancer cell lines,in particular,compound 4f exhibited broad-spectrum and highly efficient anticancer activity against cell lines A549,MKN45 and MCF7 with IC50 of 23.78,67.61 and 53.87μmol·L^(-1),respectively.The preliminary analysis of the structure activity relationship implied that the Br or Cl substituted group of the benzene ring in these derivatives significantly contributed to the anticancer activity.