Christia vespertilionis (L.f.) Bakh. f. is an ornamental plant with unique butterfly-shaped leaves, hence its vernacular name “butterfly wing” or “rerama” in Malay. In Malaysia, the green-leafed variety of this plant has gained popularity in recent years due to testimonial reports by local consumers of its medicinal uses, which include treatment for cancer. Despite these popular uses, there is very limited information on the phytochemistry of the leaf of this plant, presenting a significant gap in the cheminformatics of the plant species. Herein, we report a substantially detailed phytochemical profile of the leaf metabolome of the green-leafed variety of C. vespertilionis, obtained by deploying an untargeted tandem mass spectrometry-based molecular networking approach. The detailed inspection of the molecular network map generated for the leaf metabolome enabled the putative identification of 60 metabolites, comprising 13 phenolic acids, 20 flavonoids, 2 benzyltetrahydroisoquinoline-type alkaloids, 4 hydroxyjasmonic acid derivatives, 2 phenethyl derivatives, 3 monoacylglycerols, 4 fatty acid amides, 2 chlorophyll derivatives, 4 carotenoids, 2 organic acids, 1 nucleoside, and 3 amino acids. Flavonoids are the major class of metabolites that characterize the plant leaves. Employing a mass-targeted isolation approach, two new derivatives of apigenin-6-C-β-glucoside, the major constituents of the plant leaf, were successfully purified and spectroscopically characterized as apigenin-6-C-β-glucoside 4′-O-α-apiofuranoside (28) and apigenin-6-C-β-[(4″,6″-O-dimalonyl)-glucoside] 4′-O-α-apiofuranoside (47). This work provides further information on the chemical space of the plant leaf, which is a prerequisite to further research towards its valorization as a potential phytopharmaceutical product.

Clitorea ternatea has been used in Ayurvedic medicine as a brain stimulant to treat mental illnesses and mental functional disorders. In this study, the metabolite profiles of crude C. ternatea root extract (CTRE), ethyl acetate (EA), and 50% aqueous methanol (50% MeOH) fractions were investigated using ultrahigh-performance liquid chromatography–diode array detector–tandem mass spectrometry (UHPLC–DAD–MS/MS), while their effect on the stress-like behavior of zebrafish, pharmacologically induced with reserpine, was investigated. A total of 32 compounds were putatively identified, among which, a series of norneolignans, clitorienolactones, and various flavonoids (flavone, flavonol, isoflavone, and isoflavanone) was found to comprise the major constituents, particularly in the EA and 50% MeOH fractions. The clitorienolactones, presently unique to the species, were present in both the free and glycosylated forms in the roots. Both the EA and 50% MeOH fractions displayed moderate effects on the stress-induced zebrafish model, significantly decreasing freezing duration and elevating the total distance travelled and average velocity, 72 h post-treatment. The results of the present study provide further evidence that the basis for the use of C. ternatea roots in traditional medicine to alleviate brain-related conditions, such as stress and depression, is attributable to the presence of clitorienolactones and the isoflavonoidal constituents.

Christia vespertilionis or butterfly wings is a traditional medicinal plant used to treat, among others, colds and bronchitis. The plant was also reported to be a remedy for cancer, with several products based on the plant becoming commercially available, raising some safety concerns on its consumption. The present study was carried out to assess the toxic and teratogenic effects of the plant on the embryonic development of zebrafish (Danio rerio) as the animal model. Zebrafish embryos were exposed to 50, 100, 200, 400, and 800 μg/mL of the methanolic leaf extract of C. vespertilionis, starting from 5 to 120 hours post-fertilization (hpf). The median lethal concentration (LC50) value of the extract was determined to be 419.84 μg/mL, which is within the safety limit stipulated by the Organisation for Economic Co-operation and Development (OECD) guideline. However, results from the teratogenicity evaluation revealed multiple signs of developmental defects in embryos exposed to 200 μg/mL and higher concentrations of the extract. The magnitude of the defects was observed to be concentration-dependent. Moreover, no hatching and spontaneous movement of tail coiling were observed at 400 and 800 μg/mL concentrations due to the delayed growth and early mortality, respectively. A significant reduction in heartbeat rate was also reported for the surviving embryos at the 400 μg/mL test concentration. The present study has provided preliminary results on the potentially toxic and teratogenic effects of the extract at high concentrations.