Berberine, a main secondary metabolite isolated from Tali kuning (Tinospora dissitiflora Diels), an indigenous medicinal plant from Manokwari, Papua, Indonesia

Abstract

Tali kuning (Tinospora dissitiflora Diels) is a lying, climbing liana, with yellow stem, belonging to family Menispermaceae.The indigenous people of Papua are using this plant extracts for herbal medicine used for, either preventing or combating malaria symptoms. This practice is still the main option, when the malaria drugs and modern health treatments are difficult to be achieved due to geographical and transportation reasons. Malaria symptoms are very complicated, ranging from higher in fever but feeling cold, the tongue feels very bitter taste, and food could not be swollen into the stomach due to feeling vomiting. With respect to the malaria herbage, the bioactivity of Tali kuning (Tinospora dissitiflora Diels) mainly from Manokwari, best to our knowledge has not been investigated yet. This paper describes the isolation, and structural elucidation of main secondary metabolites isolated from Tali kuning (Tinospora dissitiflora Diels). 10 isolated TK (except TK5) were analyzed with NMR, and eight (8) TK spectra (1-H-NMR, 13-C-NMR) were confirmed, ranging from TK1, TK2, TK4, TK6, TK7, TK8, TK9, and TK11.The spectra (UV, 1-H-NMR, 13-C-NMR, MS) of 8 TK compounds were identified by comparing with those spectra data available on the published literature. The UV spectrum of 8 isolated compounds revealed that all compound have a similar pattern, having  max at nm: 222, 226, 234, 236, 264, and 347, suggesting that these signals are berberine. Surprisingly, all 7 TK (except TK6) recorded from LC-EI MS/MS spectra had the molecular ion peak at 335.95 m/z, and high resolution EI-MS at 336 m/z confirmed the molecule formula of berberine (C20H17NO4). Furthermore, NMR spectra of 7 TK (except TK6) strongly indicated the presence of two methoxyl groups (-OCH3) at C-9, C-10, and a dioxymethylene (O-CH2-O-) connected C2 to C3. These spectra, also, confirmed that 7 TK are having Quartenary Protoberberine Alkaloid (QPA) Skeleton. The 8 isolated of TK have predominantly yellow color, except for TK 7, which is brown. Grycova et al., (2007) reported that QPA are characterized by bright color, ranging from yellow to orange. These color appearances depend on many variables, such as methods of crystallization, purification, both, or solvent pH. It is concluded that the main secondary metabolite of tali kuning (tinospora dissitiflora dields) is protoberberine (having protoberberine skeleton) and it is reported the first time isolated from this plants. In addition, the work on other secondary metabolites and the biological performances of these plant metabolites are in progress.