Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents

Abstract

A series of novel genipin glycoside derivatives incorporating 11 glycosidic moieties at either the 1 or 10 position of genipin were designed and synthesized. These compounds exhibited moderate to excellent inhibitory activities against tobacco mosaic virus. Especially, the in vitro and in vivo activities of compounds 6e, 7c, 7d, 7f, 7h, and 7i were comparable to that of ribavirin. In particular, compound 7c, the mannosyl derivative of genipin at the 10 position, showed the best activity. The series of genipin glycosyl derivatives also displayed fungicidal activities against 14 kinds of phytopathogenic fungi, especially for Rhizoctonia cerealis and Sclerotinia sclerotiorum. Moreover, compound 6h exhibited good insecticidal activity against diamondback moth; compounds 7b, 7c, and 7g exhibited moderate insecticidal activity against three kinds of Lepidoptera pests (oriental armyworm, cotton bollworm, and corn borer); and compound 7e showed excellent larvacidal activities against mosquito.

Novel Findings regarding the Bioactivity of the Natural Blue Pigment Genipin in Human Diseases

“…Genipin has also shown therapeutic and preventive potential in blocking white spot syndrome virus (WSSV) by inhibiting Bax inhibitor-1 gene expression; it also inhibited WSSV replication when applied at concentrations of 6.25 to 50 mg/kg by decreasing the expression of STAT (signal transducer and activator of transcription) in crayfish and shrimp [ 50 ]. In addition, genipin glycoside derivatives have also been found to have antiviral and antifungal activities [ 51 ].…”

Management and Risk in the Frame of Ipm with Biological Control Methods

“…). It can be used some new compounds -glycosilated genidipin and derivatives which can be used against VMT, against fungi (Sclerotinia, Rhizoctonia, and so on) and insecticidal activity (Xia et al, 2018).…”

Design, Synthesis and Evaluations of New 10‐Triazolyl‐1‐methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells

“…Genipin is widely used in the pharmaceutical industry for cross‐linking in biopolymer synthesis as a drug delivery agent . Recently, structural modifications of genipin have been found to improve potency or as a template for synthesis of novel bioactive compounds . Among the modified genipin analogues reported to date, only a few have described possible analogues that could hold anticancer potential over the parent compound.…”