2018 Springer Science+Business Media, LLC
Chemistry of Natural Compounds, Vol. 54, No. 3, May, 2018
A NEW APORPHINE ALKALOID FROM THE STEMS
OF Liriodendron chinense
C. Y. Chen,
C. L. Kao,
W. J. Li,
H. C. Chen,
and H. T. Li
A new aporphine alkaloid, liriodenchine (1), along with 13 known compounds, including three aporphine
alkaloids, liriodenine (2), (–)-anonaine (3), and (–)-norstephalagine (4); three lignans, (+)-syringaresinol
(5), (+)-yangambin (6), and (+)-eudesmin (7); and seven benzenoids, p-hydroxybenzoic acid (8),
p-hydroxybezaldehyde (9), vanillic acid (10), vanillin (11), syringic acid (12), syringaldehyde (13), and
3,4,5-trimethoxybenzoic acid (14), were isolated from the leaves of Liriodendron chinense (Magnoliaceae).
These compounds were characterized and identified by physical and spectral evidence.
Keywords: Liriodendron chinense, Magnoliaceae, aporphine, liriodenchine, alkaloid.
Liriodendron is a genus of two species of characteristically large deciduous trees in the magnolia family (Magnoliaceae).
Two species of Liriodendron are known extent. Liriodendron tulipifera is native to eastern North America, while L. chinense
is native to China and Vietnam. Both species often grow to great size, sometimes exceeding 32 m or 100 feet in height. In
Hupeh, a province of China, L. chinense is called “Wo-Chang-Chiu” which means goose foot. This refers to the shape of its
leaves . Recently, we reported seven alkaloids, two sesquiterpene lactones, two lignans, three benzenoids, one cyclitol, and
one steroid from the leaves of this plant . To further understand the chemotaxonomy and to continue searching for biologically
and chemically novel agents from Magnoliaceous plants [3–15], the stems of L. chinense were chosen for further phytochemical
investigation. The MeOH extract of the plant was subjected to solvent partitioning and chromatographic separation to afford
14 pure substances. The chemical constituents of the plant L. chinense were separated by column and thin-layer chromatography.
Investigation of the MeOH extract of the stems has led to the isolation of 14 compounds: one new aprophine:
liriodenchine (1); three known aporphine alkaloids, liriodenine (2) , (–)-anonaine (3) , and (–)-norstephalagine (4)
; three lignans, (+)-syringaresinol (5) , (+)-yangambin (6) , and (+)-eudesmin (7) ; and seven benzenoids,
p-hydroxybenzoic acid (8) , p-hydroxybezaldehyde (9) , vanillic acid (10) , vanillin (11) , syringic acid (12)
, syringaldehyde (13) , and 3,4,5-trimethoxybenzoic acid (14) . These compounds were obtained and characterized
by comparison of their physical and spectral data (UV, IR, NMR, and MS) with values obtained in the literature. In this paper,
we report the isolation and structural elucidation of liriodenchine (1).
1) Department of Nutrition and Health Sciences, Fooyin University, Kaohsiung, Taiwan, e-mail: firstname.lastname@example.org;
2) Tzu Hui Institute of Technology, Pingtung County, Taiwan; 3) Department of Nursing, Fooyin University, Ta-Liao, 83102,
Kaohsiung, Taiwan; 4) Department of Medical Laboratory Science and Biotechnology, Fooyin University, Kaohsiung, Taiwan,
e-mail: email@example.com. Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 432–433. Original
article submitted November 24, 2016.