2018 Springer Science+Business Media, LLC
Chemistry of Natural Compounds, Vol. 54, No. 3, May, 2018
SECONDARY METABOLITES FROM THE ROOTS
OF Cinnamomum macrostemon
C. Y. Chen,
C. L. Kao,
W. J. Li,
H. C. Yeh,
S. C. Huang,
and H. T. Li
Cinnamomum macrostemon Hayata is a medium-sized evergreen tree; it is endemic in Taiwan and distributed at
medium altitudes throughout the island . In the course of screening for biologically and chemically novel agents from
Formosan Lauraceous plants, C. macrostemon Hayata was chosen for further phytochemical investigation. Its branchlets
appear to be erect, slender, and glabrous, and it buds with nine imbricate seales, scales with brown hairs in winter. Leaves
appear to be chartaceous, somewhat polished above, dull beneath, ovate-lanceolate to oblong-lanceolate, 10–15 cm long, 3–4 cm
wide, acuminate to obtuse apex, acute or suddenly acute at base, with three main veins, nerves finely prominent on both sides,
not fragrant when crushed; petioles appear to be 1 cm long and are widely furrowed above . Previously, we isolated 12
compounds, including two fatty acids, one coumarin, four benzenoids, two steroids, one triterpenoid, one lignan, and one
dibenzocycloheptene from the twigs of this plant . The roots of this plant are also being studied and published for the first
time. In continuation of a program toward studies in chemotaxonomy from Formosan Lauraceous plant , an MeOH extract
of its roots was subjected to solvent partitioning and chromatographic separation to afford 12 pure substances. These compounds,
including three coumarins, coumarin (1) , isoscopoletin (2) , and scopoletin (3) ; two steroids,
-sitostenone (4) 
-sitosterol (5) ; two benzenoids, cinnamic acid (6)  and eugenol (7) ; two lignans, (+)-yangambin (8)  and
(+)-syringaresinol (9) ; three novel dibenzocycloheptenes, tenuifolin (10) , reticuol (11) , and subamol (12) ,
were isolated from the roots of C. macrostemon.
The roots of Cinnamomum macrostemon Hayata were collected from Pinglin Hsiang, Taipei County, Taiwan, in
November 2009. Plant material was identified by Dr. Fu-Yuan Lu (Department of Forestry and Natural Resources, College of
Agriculture, National Chiayi University). A voucher specimen (Cinnamo. 9) was deposited in the School of Medical and
Health Sciences, Fooyin University, Kaohsiung, Taiwan. The air-dried leaves of C. macrostemon (2.3 kg) were extracted with
MeOH (10 L u 5) at room temperature, and a MeOH extract (90.3 g) was obtained upon concentration under reduced pressure.
The residue was placed on a silica gel column and eluted with CHCl
gradually enriched with MeOH to afford four fractions.
Fraction 1 (3.11 g) eluted with n-hexane–acetone (30:1) was further purified by silica gel column chromatography using the
same solvent system to obtain coumarin (1) (8 mg), isoscopoletin (2) (5 mg), and scopoletin (3) (10 mg). Fraction 2 (5.84 g)
eluted with n-hexane–acetone (20:1) was further separated using silica gel column chromatography and purified by preparative
TLC (thin layer chromatography) to yield
-sitostenone (4) (16 mg),
-sitosterol (5) (75 mg), cinnamic acid (6) (6 mg),
and eugenol (7) (34 mg). Fraction 3 (4.18 g) was purified by silica gel chromatography (CH
–MeOH, 15:1) to give
(+)-yangambin (8) (6 mg) and (+)-syringaresinol (9) (8 mg). Fraction 4 (15.23 g) eluted with CH
–MeOH (10:1) was
further purified by silica gel column chromatography using the same solvent system to obtain three novel dibenzocycloheptenes,
tenuifolin (10) (3 mg), reticuol (11) (6 mg), and subamol (12) (9 mg). These compounds were obtained and characterized by
comparison of their physical and spectral data with values obtained in the literature [4–14].
Coumarin (1). Colorless oil. UV (MeCN, O
, nm): 260, 330. IR (neat, Q
): 1730, 1630 .
Isoscopoletin (2). White needles (EtOAc), mp 184–186qC. UV (MeCN, O
, nm): 260, 315. IR (neat, Q
3400 (OH), 1720 (C=O), 1630 .
1) School of Medical and Health Sciences, Fooyin University, Kaohsiung, Taiwan, e-mail: firstname.lastname@example.org,
email@example.com; 2) Tzu Hui Institute of Technology, Pingtung County, Taiwan; 3) Department of Nursing, Fooyin University,
Ta-Liao, 83102, Kaohsiung Taiwan; 4) Department of Creative Product Design, College of Design, Ling Tung University,
40852, Taichung, Taiwan . Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 477–478. Original
article submitted August 31, 2016.