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- Title
Stereochemical assignment of three new benzylisoquinoline alkaloids from Phaeanthus vietnamensis by NMR study combined with CD spectroscopy.
- Authors
Tu, Duong Ngoc; Hoang, Nguyen Huy; Diep, Nguyen Thi; Van Khanh, Ho; Quyet, Nguyen; Dung, Phan Tien; Ebel, Rainer; Tai, Bui Huu; Cuong, Nguyen The; Tuyen, Nguyen Van; Kiem, Phan Van; Nhiem, Nguyen Xuan
- Abstract
The HMBC correlations (Figure 2) between H-4 ( I i SB H sb 2.53 and 2.75) and C-3 ( I i SB C sb 47.3)/C-4a ( I i SB C sb 126.3)/C-5 ( I i SB C sb 111.3)/C-8a ( I i SB C sb 128.9), between H-5 ( I i SB H sb 6.51) and C-4 ( I i SB C sb 25.7)/C-7 ( I i SB C sb 146.5)/C-8a ( I i SB C sb 128.9), and between H-8 ( I i SB H sb 6.12) and C-1 ( I i SB C sb 64.7)/C-4a ( I i SB C sb 126.3)/C-6 ( I i SB C sb 147.3) indicated the presence of an isoquinoline alkaloid unit. The second benzyl unit was determined as 3-hydroxy-4-methoxycarbaldehydebenzene by HMBC corelations from H-7' ( I i SB H sb 9.81) to C-1' ( I i SB C sb 131.7)/C-2' ( I i SB C sb 120.6)/C-6' ( I i SB C sb 130.0), from H-6' ( I i SB H sb 7.76) to C-1' ( I i SB C sb 131.7)/C-2' ( I i SB C sb 120.6)/C-4' ( I i SB C sb 158.3)/C-7' ( I i SB C sb 192.3), and from methoxy protons ( I i SB H sb 3.93) to C-4' ( I i SB C sb 158.3). The HMBC correlations between H-10/H-14 ( I i SB H sb 7.01) and C- I i ( I i SB C sb 40.5)/C-9 ( I i SB C sb 134.0)/C-12 ( I i SB C sb 156.0), between H-11/H-13 ( I i SB H sb 6.85) and C-12 ( I i SB C sb 156.0), and between H- I i ( I i SB H sb 2.79 and 3.18) and C-1 ( I i SB C sb 64.9)/C-8a ( I i SB C sb 128.8)/C-9 ( I i SB C sb 134.0)/C-10/C-14 ( I i SB C sb 130.9) indicated the presence of I p i -hydroxybenzyl moiety at C-1 of isoquinoline.
- Subjects
ISOQUINOLINE alkaloids; METHOXY group; SPECTROMETRY; CHEMICAL formulas; THIN layer chromatography; NORMAL-phase chromatography; ALKALOIDS
- Publication
Magnetic Resonance in Chemistry, 2021, Vol 59, Issue 11, p1160
- ISSN
0749-1581
- Publication type
Article
- DOI
10.1002/mrc.5203