Two new stemona alkaloids fromStemona tuberosaLour.

Abstract

Two new pyrrolo[1,2-α]azepine-type stemona alkaloids, named as tuberostemonoxirine (1) and 9α-epi-tuberospironine (2), were isolated from the roots of Stemona tuberosa. The structures and relative configurations of new compounds were established on the basis of extensive spectroscopic evidences, especially 1D and 2D NMR and HR-MS experiments.

Furfural Derivatives and Phenolic Constituents in Stemona tuberosa Lour

“…The structures of the isolates were established by analysis of the extensive spectroscopic data (such as HR-ESI-MS, 1D/2D NMR, ORD, and ECD). Among them, compound 1 represents a previously undescribed furfural derivative, and the other twentyfive known compounds (2-26) were identified as 1,4-difuranyl-2,3dihydroxy-1,4-butanedione (2), [8] tuberostemonoxonine (3), [9] didehydrotuberostemonine A (4), [10] N-(4-hydroxyphenethyl)acetamide (5), [11] aurantiamide (6), [12] aurantiamide acetate (7), [13] stilbostemin B 3'-O-β-D-glucopyranoside (8), [14] trans-resveratrol 3-O-β-D-glucopyranoside (9), [15] daidzin (10), [16] rutin (11), [17] emodin-8-O-β-Dglucopyranoside (12), [18] psoralen (13), [19] isopsoralen ( 14), [20] isoacteoside (15), [21] 3,5-dihydroxy-1-(3,4-dihydroxyphenyl)-7-(4hydroxyphenyl)heptane ( 16), [22] (+)-syringaresinol (17), [23] (+)-syringaresinol-4-O-β-D-glucoside (18), [24] hydroxybenzaldehyde (19), [25] 3-hydroxy-4-methoxybenzoic acid (20), [26] 4-methoxybenzoic acid (21), [27] 4-hydroxybenzonic acid ( 22), [28] 1,2,4-benzenetriol (23), [29] caffeic acid (24), [17] 4-hydroxycinnamic acid (25), [30] and protocatechuic acid (26), [31] Analysis of the 1D NMR, HMQC, and HMBC data allowed the overall assignments of the NMR data of 1 as listed in Table 1. Further, NOESY correlations between H 3 -11 and H-2/H-5/H-7, and between H-5 and H-7, indicated that H-2, H 3 -11, H-5, and H-7 were at a relatively close distance in space, or oriented in the same direction.…”

Isolation and Bioactivities of Stemona Alkaloid: A Review

“…72 Stemona-lactams R ( 137 ) with a hydroxy group at C10 was obtained from the roots of Stemona tuberosa (Figure 5). 26 Yuea et al 27 found 9 a - epi -tuberospironine ( 138 ) from the roots of Stemona tuberosa (Figure 5). Hu et al 73 achieved 3 novel croomine group alkaloids, stemtuberlines C-E ( 139 - 141 ), from the roots of Stemona tuberosa (Figure 5).…”

“…Schinnerl et al 23 obtained tuberostemonine N (26) from a mixture of Stemona species (Figure 3). In 2008, Lin et al 24 discovered tridehydrotuberostemonine, 9α-bisdehydrotuberostemonine (27), and 9α-bisdehydrotuberostemonine A (28), from the roots of Stemona tuberosa collected from Yunnan Province (Figure 3). 9α-Bisdehydrotuberostemonine A was the first sample of tuberostemonine-type alkaloid with an opened ring E, while 9α-bisdehydrotuberostemonine possesses a pyrrole ring.…”

“…Tuberostemonoxirine (34) containing an epoxy ring was obtained from the roots of Stemona tuberosa. 27 Lai et al 28 reported the isolation and structure determination of stenines A (35) and stenine B (36) from the roots of Stemona sessilifolia (Figure 3). Both compounds do not have a lactone ring at C3 and stenine A (35) contains an N-oxide structure.…”

New Stemona alkaloids from the roots of Stemona tuberosa

“…sessilifolia and S . tuberosa , respectively. In our ongoing search for AChE‐inhibiting natural compounds, five new Stemona alkaloids ( 1–5 ) of the miscellaneous group according to Pilli's classification, or tuberostemonine group according to Greger's classification, were isolated from the EtOH extract of the roots of S. tuberosa .…”