Bioassay Directed Fractionation of Petroleum Ether Extract of Aerial Parts of Ceriops tagal: Isolation of Lupeol as the Nematicidal Agent against Cyst Nematode Heterodera zeae

Abstract

Plant parasitic cyst nematode Heterodera zeae is a pest, causing substantial economic losses in agriculture. Organic pesticides, based on plant products have emerged as eco-benign nematicidal agents. Ceriops tagal is a well-known marine medicinal plant which has not been evaluated against any nematode. Petroleum ether extract of the aerial parts of the plant (CTP), exhibited promising activity against infective stage larvae of H. zeae. On subjecting to classical solvent-solvent separation, it afforded petroleum ether soluble (CTP-S), methanol soluble (CTPMS-1, CTPMS-2) and insoluble (CTPM-IN-2) fractions, which exhibited activity against the cyst nematode within 24 h exposure. GC, GC/MS and HR-ESI-MS analyses of CTPMS-1 and CTPMS-2 fractions resulted in the identification of a number of compounds, including pentacyclic triterpenoids, lupeol (1), betunal (2), betulin (3), lupenone (4), betulonaldehyde (5), betulonic acid (7), methyl 3-acetoxy-27-O-(3,4-dihydroxy-Ecinnamoyl)-20(29)-lupen-28-oate (8) and β-amyrin, along with phenylpropanoid esters, fatty acids and their derivatives, benzamide, and indole derivatives. CTPM-IN-2 which mainly contained lupeol (1) exhibited maximum nematicidal activity, with 91 % and 93 % mortality of the larvae of H. zeae, after exposure for 72 h at the concentration of 0.5 % and 1 %, respectively. Its fractionation and purification through column chromatography resulted in the isolation and identification of four lupane-type triterpenoids 1, 3, 4 and betulinic acid (6). One of its most abundant column fractions CC-9-18 (145 mg) which exhibited substantial activity, with 81 % mortality at the lowest concentration of 0.125 % after 48 h of incubation mainly contained lupeol. It seems lupeol, a wide spread bio-privileged triterpenoid is the nematicidal principle of the plant as its authentic sample showed LC 50 value of 0.061 after 72 h exposure. It is for the first time that nematicidal activity is reported for any part of C. tagal and that of lupeol against H. zeae. Pentacyclic triterpenoids 1-8 are biosynthetically related. Of the twenty-four compounds isolated or identified in the present investigation only five constituents 1, 3, 6, 7 and palmitic acid have been isolated previously from C. tagal.

Biochemometry identifies ostruthin as pluripotent antimicrobial and anthelmintic agent from masterwort

“… 21 A growing number of research articles aims to identify new anthelmintics from natural sources. 22 , 23 , 24 , 25 , 26 Plant extracts are an important source of new chemical scaffolds with valuable applications for drug discovery. 27 , 28 , 29 , 30 However, the search for bioactive compounds from complex mixtures (i.e., crude extracts) remains a Herculean task.…”

Fermentation, bioactivity and molecular identification of endophytic fungi isolated from mangrove Ceriops tagal

“…This bark species has been used in traditional medicine to treat hemorrhage (Bandaranayake 1998). Phytochemical analysis revealed that C. tagal is rich in gallic acid, quercetin (Sachithanandam et al 2022), terpenoids (Biswas et al 2021;Zhang et al 2021;Ahmad et al 2022), and steroids (Egra et al 2023). These compounds have been shown to have various potential therapeutic applications, including antitumor (Ni et al 2018;Sachithanandam et al 2022), antibacterial (Chacha et al 2008;Egra et al 2023), antioxidant (Sachithanandam et al 2022;Egra et al 2023), antihyperglycemic, analgesic, anti-inflammatory (Biswas et al 2023), diuretic (Biswas et al 2021), immunosuppressant (Zhang et al 2021), and nematocidal (Ahmad et al 2022) activities.…”

“…Phytochemical analysis revealed that C. tagal is rich in gallic acid, quercetin (Sachithanandam et al 2022), terpenoids (Biswas et al 2021;Zhang et al 2021;Ahmad et al 2022), and steroids (Egra et al 2023). These compounds have been shown to have various potential therapeutic applications, including antitumor (Ni et al 2018;Sachithanandam et al 2022), antibacterial (Chacha et al 2008;Egra et al 2023), antioxidant (Sachithanandam et al 2022;Egra et al 2023), antihyperglycemic, analgesic, anti-inflammatory (Biswas et al 2023), diuretic (Biswas et al 2021), immunosuppressant (Zhang et al 2021), and nematocidal (Ahmad et al 2022) activities. For instance, vomifoliol, a sesquiterpene isolated from the hypocotyls extracts of C. tagal, displayed an immunosuppressant effect by inhibiting the dephosphorylation of NFAT1 and the proliferation of Jurkat cells (Zhang et al 2021).…”