Documente Academic
Documente Profesional
Documente Cultură
DOI 10.1007/s11418-009-0376-y
NOTE
Received: 3 August 2009 / Accepted: 23 October 2009 / Published online: 4 December 2009
The Japanese Society of Pharmacognosy and Springer 2009
known compounds have been isolated for the first time from
the Lygodiaceae. Here, we report the structural characterization of these compounds by spectroscopic analysis.
Introduction
Lygodium japonicum (Thunb.) Sw., belonging to the
Lygodiaceae family and that only has Lygodium [1], is
endemic to Southern China and the southwestern area of
China and commonly called zuo zhuan hui teng. This plant
species is a perennial plant, and roots of several species of
this genus are used in Chinese traditional medicine to treat
hepatitis and dysentery [2]. Chemical studies on the genus
have been reported and have revealed the presence of flavones, phenolic acids and steroidal glycosides [3, 4]. As our
chemical studies on the medicinal plants in China aimed at
searching biologically active compounds, we researched the
roots of Lygodium japonicum (Thunb.) Sw., which resulted
in the isolation of a new naphthoquinone, 6-hydroxy-2-isopropyl-7-methyl-1,4-naphthoquinone. Moreover, three
L. Chen G. Zhang (&) J. He C. Pan W. Mi Q. Wang
School of Traditional Chinese Materia Medica,
Shenyang Pharmaceutical University,
110016 Shenyang, China
e-mail: zhangguogang824@hotmail.com
J. Guan
College of Applied Chemistry, Shenyang Institute of Chemical
Technology, 110142 Shenyang, China
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Table 1 1H and 13C NMR data for compound 1 (300 and 75 MHz, in
DMSO-d6)
Position
HSQC
HMBC
dH, mult,
J in Hz
dC
1
183.5
156.6
131.6
185.2
110.3
160.9
131.8
129.5
124.1
10
CH3-7
6.68 (1H)
C2/C11
7.30 (1H)
C4/C9/C6
7.77 (1H)
C10/C7(CH3)/
C1/C6
131.7
16.2
2.24 (3H, s)
C6/C8
11
26.6
3.09 (1H, m)
C12 and
C13/C2/C1/C3
12 and 13
21.4
1.12 (6H, d,
J = 6.8)
C11/C2
CH(CH3)2
H
HO
O
5
10
H
3
2
H3C
8
H
H
CH 3
1
O
CH3
Experimental
General
Melting points were determined on an X4-A micro-melting
point apparatus and were uncorrected. ESIMS spectra
were measured on an Agilent 1100 LC-MSD-Trap-SL, and
HRESIMS spectra were measured on an Bruker Daltonics MicroTOFQ. NMR spectra were measured on a
Bruker ARX-600 and 300 NMR spectrometer with tetramethylsilane (TMS) as the internal reference and chemical
shifts are expressed in d (ppm). UV spectra were recorded
on a Shimadzu UV-2201 spectrometer. IR spectra were
recorded on a Bruker IFS-55 spectrophotometer. TLC was
performed on silica gel GF254 (1040 lm; Qingdao,
China). Separation were performed by Semiprep-HPLC
named Shimadzu SPD-10A apparatus equipped with UV
detector under ODS column (i.d. 10 mm 9 200 mm).
Plant material
Lygodium japonicum (Thunb.) Sw. (Lygodiaceae), roots
collected in Anhui province of China, were identified by
asso-Prof. Jincai Lu. A voucher was deposited in the Traditional Chinese medica of Shenyang Pharmaceutical
University.
Extraction and isolation
Air-dried roots of Lygodium japonicum (Thunb.) Sw.
(4 kg) were crushed and extracted twice under reflux with
70% EtOH. Evaporation of the solvent under reduced
pressure delivered the 70% EtOH extract (around 280 g).
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