Alkaloids from the Bulbs of Boophone disticha

Abstract

Boophone disticha is widely used in South African traditional medicine. Several of its biological properties can be corroborated via its alkaloid constituents. Previous research on this plant led to the isolation of several alkaloids, mainly of the crinane alkaloid group of the Amaryllidaceae. In the present study, one new compound 1- O-acetylbuphanamine (1) and four known crinane alkaloids were isolated chromatographically from the ethanol extract of the bulbs of B. disticha. Their structures were determined via spectroscopic methods, including 1D and 2D NMR, ESI-MS, HRMS and IR data.

Chemical Principles of Boophone, Nerine, Crossyne, Clivia, Cryptostephanus, Haemanthus and Scadoxus of the South African Amaryllidaceae and Their Biological Properties

“…Chemotypically, nine Amaryllidaceae alkaloid groups were identified during this period including, the galanthamine (1), phenanthridone (such as narciclasine 2), lycorane (such as lycorine 3), crinane (such as crinamine 4), belladine (5), ismine (6), tazettine (7), homolycorine (8) and montanine (9) groups (Figure 2) [5,6]. Unrepresented were the trisphaeridine (10), bicolorine (11), cherylline (12), cliviahaksine (13), augustamine (14) and cripowellin (such as cripowellin A 15) groups [5,6]. The biological properties amongst others described included, antimicrobial, anti-inflammatory, antioxidant, antitumoral and antimutagenic effects [5,6].…”

“…There was also an increase (up to 19 %) in the proportion of HeLa cells with sub-G1 amounts of DNA (apoptotic cells) following a 24 h treatment with distichamine (35) at its highest tested concentration (20 M) [13]. A fresh bulb EtOH extract of B. disticha afforded the -crinane alkaloids undulatine (33), buphanisine (36), buphanamine (37), 3-O-acetylnerbowdine (38) and 1-O-acetylbuphanamine (39), the last of which was determined to be a novel compound [14]. Interestingly, the first four of these alkaloids were prior shown to be isolates of the plant [8].…”

“…Interestingly, the first four of these alkaloids were prior shown to be isolates of the plant [8]. 1-O-Acetylbuphanamine (39) is unique in the sense that it possesses an acetyl moiety in its structure, which distinguishes it from its parent compound buphanamine (37) [14]. Both compounds, like distichamine (35) does, also reflect the C-ring double bond in the unusual C-2/C-3 position [14].…”

“…1-O-Acetylbuphanamine (39) is unique in the sense that it possesses an acetyl moiety in its structure, which distinguishes it from its parent compound buphanamine (37) [14]. Both compounds, like distichamine (35) does, also reflect the C-ring double bond in the unusual C-2/C-3 position [14]. It is more common in crinane alkaloids to have the double bond attached at the C-1 and C-2 carbons, as in buphanisine (36) [4].…”

“…Alkaloid principles of Boophone, Nerine, Crossyne, Clivia, Haemanthus and Scadoxus and their biological activities. Boophone disticha lycorine (3), buphandrine(32), undulatine (33), 3-epibuphanisine (34), distichamine(35), buphanisine(36), buphanamine (37), 3-O-acetylnerbowdine (38), 1-O-acetylbuphanamine (39), crinamidine(40), nerbowdine (41), 3epicrinine(42) buphandrine (weak activity against HeLa cells, IC50 >50 M) distichamine (good activity against HeLa cells, IC50 2.2 M) lycorine, buphanisine, 3-O-acetylnerbowdine (ligands for antidiabetic drug targets including, GCK, DPP4 and AMY2A)[12][13][14][15][16] …”