Abstract
An effective method was developed for the preparative separation and purification of monoterpenoid indole alkaloid epimers from Ervatamia yunnanensis Tsiang using a combination of pH-zone-refining counter-current chromatography and preparative high-performance liquid chromatography. With this method, two pairs of MIA epimers including ervatamine (72 mg, 1), 20-epi-ervatamine (27 mg, 4), dregamine (95 mg, 2), tabernaemontanine (129 mg, 3), along with two MIAs, apparicine (112 mg, 5) and isovoacangine (15 mg, 6), were successfully purified from 2.1 g crude extract of E. yunnanensis, each with a purity of over 95% as determined by HPLC. The structures of the MIAs were identified by ESI-MS, 1D, and 2D NMR.
Highlights
IntroductionMonoterpenoid indole alkaloids (MIAs) are an important group of alkaloids in plants that are mainly elaborated by the plants of the Apocynaceae, Rubiaceae, and Loganiaceae families [1]
Monoterpenoid indole alkaloids (MIAs) are an important group of alkaloids in plants that are mainly elaborated by the plants of the Apocynaceae, Rubiaceae, and Loganiaceae families [1].These alkaloids originating from the condensation of tryptophan with secologanin have attracted significant interests of synthetic organic chemists due to their structural diversity and complicated biosynthesis [2,3,4,5]
Which always led to poor separation effect, low recovery, and a requirement of high quantities of solvents
Summary
Monoterpenoid indole alkaloids (MIAs) are an important group of alkaloids in plants that are mainly elaborated by the plants of the Apocynaceae, Rubiaceae, and Loganiaceae families [1]. These alkaloids originating from the condensation of tryptophan with secologanin have attracted significant interests of synthetic organic chemists due to their structural diversity and complicated biosynthesis [2,3,4,5]. The conventional methods for the separation of MIA epimers were often based on repeated column chromatography, which always led to poor separation effect, low recovery, and a requirement of high quantities of solvents It is Molecules 2019, 24, 1316; doi:10.3390/molecules24071316 www.mdpi.com/journal/molecules which always led to poor separation effect, low recovery, and a requirement of high quantities of solvents. It is necessary to develop an effective method to separate and purify large necessary an effective method to separate andpharmacological purify large quantities of MIA epimers with quantities to ofdevelop
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