2018 Springer Science+Business Media, LLC
Chemistry of Natural Compounds, Vol. 54, No. 3, May, 2018
A NEW POLYUNSATURATED LIPID FROM Tetrastigma hemsleyanum
and Shengan Tang
From the petroleum ether extract of Tetrastigma hemsleyanum, a new polyunsaturated lipid, (9R)-hydroxy-
-dihydroxypropyl ester (1), was isolated and its structure was established
on the basis of IR, MS, and extensive NMR spectroscopic analysis.
Keywords: Tetrastigma hemsleyanum, polyunsaturated lipid, structural elucidation.
Tetrastigma hemsleyanum Diels et Gilg, known as “Sanyeqing” in China, belongs to the genus Tetrastigma Planch.,
family Vitaceae and is mainly distributed in the south of Yangtze River in China. The root of the plant is commonly used as
herbal medicine for heat-clearing, toxicity-removing, phlegm dispelling, pain relief, and for promoting blood circulation .
Research on the bioactivities of the extract from the roots of Tetrastigma hemsleyanum has focused on anticancer, liver
protection, and anti-inflammatory activities [2–5]. Phytochemical investigations of the roots of this species revealed the presence
of several flavonoids, terpenoids, as well as organic acids [6–8]. Hence, we report herein the extraction, isolation, and structure
elucidation of a new polyunsaturated fatty acid glyceride obtained from the roots of Tetrastigma hemsleyanum.
(9R)-Hydroxy-(10E,12Z,15Z)-octadecatrienoic-2c,3c-dihydroxypropyl ester (1) was isolated as a yellow solid. Its
molecular formula C
was established by the HR-ESI-MS spectrum (m/z 369.2637 [M + H]
, calcd for C
369.2641), representing four degrees of unsaturation. The
H NMR spectrum of compound 1 (Table 1) revealed one methyl
signal at G 0.93 (3H, t, J = 7.5 Hz), six oxygenated protons [G 4.04 (1H, dd, J = 4.0, 11.1 Hz), 3.95–4.02 (1H, m), 3.90 (1H, dd,
J = 6.4, 11.1 Hz), 3.60–3.69 (1H, m), 3.39–3.47 (2H, m)], and six olefinic protons [G 6.44 (1H, dd, J = 11.6, 15.0 Hz), 5.96 (1H,
t, J = 10.5 Hz), 5.66 (1H, dd, J = 6.1, 15.0 Hz), 5.26–5.40 (3H, m)]. The
C NMR and DEPT spectra showed 21 carbon
signals, involving one methyl, 11 methylenes, eight methines, and one quaternary carbon. From the
C NMR spectra
(Table 1), the presence of one ester carbonyl (G 174.5) and three disubstituted C=C bonds (G 138.5, 131.7, 128.7, 128.3, 126.7,
123.5) was determined. The
C NMR spectral data of 1 were similar to literature values  except for an additional
glyceryl group, indicating that 1 was a polyunsaturated monoacylglycerol.
The gross structure of 1 was established on the basis of extensive 2D NMR analysis. From the
H COSY spectrum,
two long-range correlation systems were identified, including H-2/-3/-4/-5/-6/-7/-8/-9/-10/-11/-12/-13/-14/-15/-16/-17/-18, as
well as H-1c/-2c/-3c, which were assembled with the assistance of the polyunsaturated monoacylglycerol skeleton of 1 by
elucidating the HMBC spectrum. In the HMBC spectrum, the proton signals at G 4.04 (H-1ca) and 3.90 (H-1cb) correlated with
the carbon signal at G 174.5; thus, the glyceryl group was assigned at positions C-1c, C-2c, and C-3c. Therefore, the chemical
structure of 1 was determined as shown (Fig. 1).
1) Department of Pharmaceutical Science, Beijing Hospital, National Center of Gerontology, No.1 DaHua Road,
Dong Dan, 100730, Beijing, P. R. China; 2) Research Center of Basic Medical Sciences, Tianjin Key Laboratory on Technologies
Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University,
300070, Tianjin, P. R. China, e-mail: email@example.com; firstname.lastname@example.org. Published in Khimiya Prirodnykh
Soedinenii, No. 3, May–June, 2018, pp. 364–365. Original article submitted August 29, 2016.