Beruflich Dokumente
Kultur Dokumente
Chinese
Journal of
Natural
Medicines
doi: 10.3724/SP.J.1009.2011.00190
School of Medicine and Pharmacy, Key Laboratory of Marine Drugs, Ministry of Education, Ocean University of China, Qingdao
266003, China;
2
College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, China
Available online May 2011
[ABSTRACT] AIM: To study the chemical constituents of semi-mangrove plant Hibiscus tiliaceus. METHODS: The isolation and
purification of compounds were performed by silica gel, Sephadex LH-20 and HPLC, and their structures were determined by comparison of their physical and spectral data with the literatures. RESULTS: Ten compounds were isolated and identified as friedelin (1),
pachysandiol (2), glutinol (3), lupeol (4), germanicol (5), stigmast-4-en-3-one (6), stigmast-4, 22-dien-3-one (7), ergosta-4, 6, 8 (14),
22-tetraen-3-one (8), -sitosterol (9), and stigmasterol (10). CONCLUSION: Compounds 35 and 8 were isolated from this plant for
the first time.
[KEY WORDS] Hibiscus tiliaceus; Triterpenes; Steroids
[Document code] A
Introduction
Plant Material
The air-dried and powdered stems and barks of H. tiliaceus (11.0 kg) were extracted with industrial methanol three
times at room temperature. The extract was concentrated
under reduced pressure to generate a dark residue (336.0 g),
which was suspended in H2O and partitioned with petroleum
ether, ethyl acetate and n-butanol, yielding 83.0, 40.0 and
45.0 g of extraction fractions, respectively. Combined petroleum ether and ethyl acetate fraction based on TLC results.
Chin J Nat Med May 2011
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WANG Zhong-Zhao, et al. /Chinese Journal of Natural Medicines 2011, 9(3): 191193
Identification
WANG Zhong-Zhao, et al. /Chinese Journal of Natural Medicines 2011, 9(3): 191193
35.6 (C-8), 34.0 (C-22), 33.9 (C-2), 32.9 (C-6), 32.0 (C-7),
29.1 (C-25), 28.1 (C-16), 26.1 (C-23), 24.1 (C-15), 23.0
(C-28), 21.0 (C-11), 19.8 (C-26), 19.0 (C-27), 18.8 (C-21),
17.4 (C-19), 11.9 (C-29), 11.9 (C-18). Compound 6 was
identified as stigmast-4-en-3-one by comparison of the
physical and spectral data with the literature [10].
Compound 7 C29H46O, white needle, mp 115116 C.
ESI-MS m/z 410 [M]+. 1H NMR (600 MHz, CDCl3) : 5. 72
(1H, s, H-4), 5.15 (1H, dd, J = 15.4, 8.3 Hz, H-22), 5.02 (1H,
dd, J = 15.4, 8.8 Hz, H-23), 1.18 (3H, s, H-19), 1.01 (3H, d, J
= 6.6 Hz, H-21), 0.85 (3H, d, J = 6.1 Hz, H-27), 0.80 (3H, t, J
= 7.7 Hz, H-29), 0.80 (3H, d, J = 6.1 Hz, H-26), 0.72 (3H, s,
H-18). Compound 7 was identified as stigmast-4, 22-dien-3one by comparison of the physical and spectral data with the
literature [11].
Compound 8 C28H40O, yellow needle, mp 110113
C. ESI-MS m/z 392 [M]+. 1H NMR (600 MHz, CDCl3) :
6.61 (1H, d, J = 9.5 Hz, H-7), 6.03 (1H, d, J = 9.5 Hz, H-6),
5.74 (1H, s, H-4), 5.24 (2H, m, H-2223), 1.06 (3H, d, J =
6.7 Hz, H-21), 1.00 (3H, s, H-19), 0.96 (3H, s, H-18), 0.93
(3H, d, J = 6.8 Hz, H-28), 0.85 (3H, d, J = 8.0 Hz, H-27),
0.83 (3H, d, J = 7.1 Hz, H-26). Compound 8 was identified as
ergosta-4, 6, 8 (14), 22-tetraen-3-one by comparison of the
physical and spectral data with the literature [12].
Compound 9 C29H50O, white needle, mp 139140 C.
1
H NMR (600 MHz, CDCl3) : 5.35 (1H, d, J = 4.9 Hz, H-6),
3.52 (1H, m, H-3), 1.01 (3H, s, H-19), 0.92 (3H, d, J = 6.6 Hz,
H-21), 0.85 (3H, t, J = 7.2 Hz, H-29), 0.83 (3H, d, J = 6.6 Hz,
H-27), 0.81(3H, d, J = 6.1 Hz, H-26), 0.68 (3H, s, H-18).
Compound 9 was identified as -sitosterol by comparison of
the physical and spectral data with the literature [13].
Compound 10 C29H48O, white needle, mp 154156 C.
1
H NMR (600 MHz, CDCl3) : 5.35 (1H, m, H-6), 5.16 (1H,
dd, J = 15.4, 8.3 Hz, H-22), 5.02 (1H, dd, J = 15.4, 8.8 Hz,
H-23), 3.52 (1H, m, H-3), 1.02 (3H, d, J = 6.6 Hz, H-21),
1.01 (3H, s, H-19), 0.85 (3H, d, J = 6.6 Hz, H-26), 0.80 (3H, t,
J = 7.7 Hz, H-29), 0.80 (3H, d, J = 6.6 Hz, H-27), 0.70 (3H, s,
H-18). Compound 10 was identified as stigmasterol by comparison of the physical and spectral data with the literature [14].
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