Diterpenoids from Rosmarinus officinalis L. and their nitric oxide inhibitory activity
Cite this paper: Vietnam J. Chem., 2021, 59(2), 229-234
Article
DOI: 10.1002/vjch.202000161
Diterpenoids from Rosmarinus officinalis L. and their nitric oxide
inhibitory activity
Le Thi Huyen*, Le Thi Oanh
VNU University of Science, Vietnam National University, Hanoi,
19 Le Thanh Tong, Hoan Kiem, Hanoi 10000, Viet Nam
Submitted September 17, 2020; Accepted February 4, 2021
Abstract
One icetexane diterpenoid, demethylsalvicanol (1) and four abietane diterpenoids, sageone (2), 20-deoxocarnosol
(3), 11,12,20-trihydroxy-abieta-8,11,13-triene (4), and 7α-ethoxyrosmanol (5) were isolated from the n-hexane layer of
the leaves and twigs of Rosmarinus officinalis L. Chemical structures of compounds were identified by ESI-MS, 1D-,
2D-NMR spectra and by comparison of the spectral data in the literature. Compounds 1-5 were evaluated anti-
inflammatory activity by inhibitory NO production, LPS stimulated on RAW 264.7 cells. At a concentration of 100 µM,
compound 4 exhibited inhibitory percentage of 34.7±1.8 %, meanwhile compounds 1-3 and 5 showed cytotoxic effect.
After dilution to concentration of 20 µM, except compound 1 and 2, compounds 3-5 did not show cytotoxic effect.
Their NO inhibitory productions were ranging from 20.5±2.4 % to 26.7±1.9 %. Compounds 1, 3 and 4 have been
reported for the first time from the Rosmarinus genus.
Keywords. Rosmarinus officinalis, icetexane diterpenoid, abietane diterpenoid, nitric oxide inhibitor.
1. INTRODUCTION
Ecology and Biological Resources, Vietnam
Academy of Science and Technology). A voucher
Rosmarinus officinalis L. (family Lamiaceae) is a specimen (RO.19.01) was stored at Faculty of
shrub, woody, perennial herbs with fragrant Chemistry, VNU University of Science.
evergreen needle-like leaves that found primarily in
the Mediterranean region and widely spread in
2.2. General experimental procedures
been used as a herbal medicine since ancient times The general experimental procedures and
measurement techniques are as the same as
described in Ref. [21].
components have been identified as diterpenoids,
2.3. Extraction and separation
phytochemical study of this plant has not been
The dried ground leaves and twigs of R. officinalis
studied yet in Vietnam. This paper reported the
(2.0 kg) were grinded into fine powder and extracted
isolation,
structure
elucidation
and
anti-
with methanol (3 times 5 L) in ultrasonic extractor
for 2 h each. After removal of the solvent under
reduced pressure, the to get the residue was 160.0
g. Warm water (2 L, 50 oC) was added to this extract
and then successively partitioned by solvents with
increasing polarity n-hexane, EtOAc to obtain the
n-hexane (ROH, 36.0 g), EtOAc (ROE, 85.0 g) and
aqueous layer (ROW, 35.0 g) after evaporating
solvents in vacuo under reduced pressure to
dryness.
inflammatory activity of five diterpenoids from the
n-hexane extract of the leaves and twigs of R.
officinalis.
2. MATERIALS AND METHODS
2.1. Plant materials
The leaves and twigs of R. officinalis were collected
in Ha Giang, Vietnam in January 2019, and
identified by Dr. Nguyen The Cuong, Institute of
229 Wiley Online Library © 2021 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH
Vietnam Journal of Chemistry
Le Thi Huyen et al.
Figure 1: Chemical structures of compounds 1-5
The ROH fraction was carried out by a silica gel
Sageone (2): Colorless amorphous powder; ESI-
1
column eluting with a n-hexane increasing amounts MS m/z: 301.18 [M+H]+, C19H24O3; MW: 300; H-
and 13C-NMR (CDCl3) data, see table 1.
of EtOAc (100:0 0:1, v/v) to yield fractions H1–
20-Deoxocarnosol (3): Colorless amorphous
powder; ESI-MS m/z: 317.21 [M+H]+, C20H28O3;
MW: 316; 1H- and 13C-NMR (CDCl3) data, see table 1.
11,12,20-Trihydroxy-abieta-8,11,13-triene (4):
Colorless amorphous powder; ESI-MS m/z: 319.22
H7. H2 fraction was then separated on a silica gel
column and eluted with a gradient mobile phase n-
hexane-acetone (100:0 0:1, v/v) to give fractions,
H2A – H2E. H2A fraction (776.9 mg) was
chromatographed by an RP-18 column eluting with
acetone-H2O (2.5:1, v/v) to give fractions, H3A-
H3E. H3C was separated on an RP-18 column
eluting with acetone- H2O (2.0:1, v/v) which
afforded compound 2 (3.0 mg). Compounds 3 (10.0
mg) and 4 (17.6 mg) were obtained from H3D
fraction using RP-18 column (solvent eluents of
acetone-H2O, 2.0:1, v/v). H2C fraction (887.0 mg)
was separated by an RP-18 column using acetone-
H2O (2.0:1, v/v) as mobile phase to obtain fractions,
H4A-H4C. Fraction H4C was further separated by
an RP-18 column washing with acetone-H2O (1.5:1,
v/v) giving 1 (21.0 mg). Fraction H2E (1.725 g) was
loaded on an RP-18 column eluting with acetone-
H2O (2.5:1, v/v) to give five fractions, H5A-H5E.
H5C was further purified on RP-18 column, eluted
with acetone-H2O (2.0:1, v/v), a compound labeled
as 5 (27.2 mg) was obtained in pure state.
1
[M+H]+, C20H30O3; MW: 318; H- and 13C-NMR
(CDCl3), data, see table 2.
7α-ethoxyrosmanol (5): Colorless amorphous
powder; ESI-MS m/z: 375.23 [M+H]+, C22H30O5;
1
MW: 374; H- and 13C-NMR (CDCl3) data, see
table 2.
2.4. Inhibition of nitric oxide production
Inhibition of NO production in LPS-stimulated
3. RESULTS AND DISCUSSION
Compound 1 was appeared as a colorless amorphous
powder. Its ESI-MS had a pseudo-molecular ion
peak at m/z 319.23 [M+H]+, calculating to molecular
1
formula of C20H30O3. The H NMR and HSQC
Demethylsalvicanol (1): Colorless amorphous
powder; ESI-MS m/z: 319.23 [M+H]+, C20H30O3;
MW: 318; 1H- and 13C-NMR (CDCl3) data, see table 1.
spectra of 1 indicated the signals of two tertiary
methyl groups at δH 0.85 and 0.92 (each 3H, s), an
isopropyl group at δH 1.21, 1.23 (each, 3H, d, J = 7.0
Vietnam Journal of Chemistry
Diterpenoids from Rosmarinus officinalis L…
Hz), and δH 3.18 (1H, m), an aromatic proton at δH HMBC correlations from H-14 (δH 6.56)/H-15 to C-
6.56 (1H, s), and a pair of doublets at δH 2.55 and 12 (δC 140.9). From the above data, compound 2
3.05 (each, 1H, d, J = 14.5 Hz). The 13C NMR was identified to be 20-deoxocarnosol, an abietane
spectrum of 1 revealed signals of 20 carbons which diterpenoid previously reported from Coleus
were classified by DEPT spectrum as seven non- barbatus.[17]
protonated carbons, three methines, six methylenes,
Compound 3 was isolated as a colorless
1
and four methyl carbons. Of these, the signals at δC amorphous powder. H-NMR spectrum of 3 showed
21.5, 22.3 and 27.2 were assigned to the isopropyl the presence of four tertiary groups at δH 1.24, 1.23,
group; six carbon signals ranging from δC 117.2 to 1.27, 1.27 and one aromatic proton at δH 6.58 (s, H-
142.6 together with a singlet aromatic proton signal 14). The 13C-NMR and HSQC spectra displayed
at δH 6.56 were assigned to a pentasubtituted signals of 19 carbons, including a ketone group at δC
aromatic ring. The above evidence leds suggestion 202.1 which appeared to be conjugated with a tetra-
that compound 1 was a diterpenoid type icetexane
by 2D-NMR spectra. The important HMBC
substituted olefin (δC 116.5 and 175.6). Therefore,
the structure of 3 was determined to be sageone, a
nor-diterpene compound isolated from Salvia
officinalis.[18]
correlations of
1
were shown in figure 2.
Consequently, structure of 1 was established to be
demethylsalvicanol, an icetexane diterpenoid previously
isolated from Salvia broussonetii.[16]
Compound 4 was appeared as a white
amorphous powder. Its ESI-MS had a pseudo-
molecular ion peak at m/z 319.22 [M+H]+ together
with 13C NMR analysis which was determined its
Compound 2 was obtained as a colorless
amorphous powder. It had a molecular formula
C20H28O3 which was suggested from a pseudo-
molecular ion peak [M+H]+ at m/z 317.18 in the ESI-
1
molecular formula of C20H30O3. The H and 13C
NMR spectra of 4 were quite similar to those of 2
except for the replacement of an oxygenated methine
(δH 4.71/δC 71.1) in 2 instead of a methylene group
(δH 2.85/δC 32.0) in 4. In addition, molecular
formula of 4 (C20H30O3) had more two hydrogen
than that of 2 (C20H28O3). These clear findings
implied that the structure of 4 was similar to 2
except for the absence of ether bridge between C-7
and C-20 in compound 4. The remaining NMR
signals of 4 were assigned by analysis of HSQC and
HMBC spectra as mentioned in compound 2. From
above spectral findings and comparison with the
NMR data of 11,12,20-trihydroxy-abieta-8,11,13-
triene - the compound previously isolated from
Salvia mellifera,[19] compound 4 was identified as
11,12,20-trihydroxy-abieta-8,11,13-triene.
Compound 5 was obtained as an yellow
amorphous powder. It showed identical signals with
those of compound 2 except the chemical shift of a
carbonyl group at δC 129.3 (C-20) and the presence
of ethoxy group in compound 5 (δC 66.2 and 15.8).
Comparison of the NMR data of 5 with those
published in the literatures, 5 was identified as 7α-
ethoxyrosmanol.[20]
To evaluate NO inhibitory production on RAW
264.7 cells, LPS-stimulated, all compounds were
sceened for cytotoxic activity at concentrations of
100 and 20 µM. All compounds showed cell
viability over than 80% at the concentration of 20
µM was further chosen for evaluating NO inhibitory
production. As the results, compounds 1-5 showed
weak inhibitory activity inhibitory rates ranging
from 20.5±2.4 % to 51.6±1.5 %. L-NMMA was
used as a positive control with NO inhibitory values
13
1
MS and in consistent with C NMR data. H NMR
and HSQC spectra of 2 also showed the presence of
two tertiary methyl groups at δH 0.85 and 1.14; each
3H, s), an isopropyl group at δH 1.24 (d, J = 7.0 Hz),
1.26 (d, J = 7.0 Hz) and 3.10 (1H, m), an aromatic
proton signal at δH 6.61 (s), and a pair of doublets at
δH 3.08 and 4.31 (d, J = 8.5 Hz) was due to H-20.
The 13C NMR spectrum of 2 showed 20 carbon
resonances coresponding to seven non-protonated
carbons, four methines, five methylenes, and four
methyl carbons. Of these, three carbon signals at δC
21.5, 22.3 and 27.2 were assigned for an isopropyl
group; six carbon signals ranging from δC 112.5 to
139.9 together with a singlet aromatic proton signal
at δH 6.61 suggested of a pentasubtituted aromatic
ring; two oxygen bearing carbons at δC 68.8 and
71.7. The NMR data of 2 were similar to the
corresponding data of 20-deoxocarnosol[17] (Table
1). In addition, the HMBC correlations between H-
18 (δH 0.85) and C-3 (δC 41.3)/C-4 (δC 34.0)/C-5 (δC
43.2)/C-19 (δC 21.3) and between H-19 (δH 1.14)
and C-3/C-4/C-5/C-18 (δC 33.0) confirmed both two
angular methyl groups at C-4; the HMBC
correlations from H-16 (δH 1.24)/H-17 (δH 1.26) to
C-13 (δC 131.9)/C-15 (δC 27.3) and from H-15 (δH
3.10) to C-12 (δC 141.5)/C-13 (δC 132.8)/C-16 (δC
21.5)/C-17 (δC 22.3) indicated the location of
isopropyl group at C-13 of the aromatic ring. The
NMR data of ring C of 2 with those of 20-
deoxocarnosol were found to match, identifying the
two hydroxyl groups were at C-11 and C-12 , which
were further confirmed by the observation of the
Vietnam Journal of Chemistry
Le Thi Huyen et al.
of 82.2±2.5 % at the concentration of 20 µM.
Table 1: NMR spectral data of 1-3 and reference compounds
1
2
3
C
1
,a
a,b
,a
a,b
,a
a,b
#δC
δC
δHa,c (mult., J in Hz)
$δC
δC
δHa,c (mult., J in Hz) %δC
δC
δHa,c (mult., J in Hz)
2.59 (m)
41.6 41.3 1.50 (m)/1.80 (m)
202.1 202.1 -
30.1
35.1 2.69 (dd, 7.0, 12.0) 19.0
35.7 1.94 (t, 7.0)
37.2
31.1
2.12 (brd, 13.5)
2
3
4
18.7 18.6 1.41 (m)/1.80 (m)
42.3 42.3 1.27 (m)/1.40 (m)
35.1
35.6
37.2
19.1 1.62 (m)
41.3 1.28 (m)/1.56 (m)
34.0 -
41.2
33.9
34.4 34.4
-
-
1.46 (ddd, 1.5, 5.5,
11.5)
30.8 30.2 1.57 (m)/2.03 (m)
71.1 71.1 4.71 (dd, 1.5, 3.0)
5
6
7
58.1 58.2 1.32 (dd, 12.5, 2.5) 175.8 175.6 -
43.0
43.2
24.3 24.3 1.15 (m)/2.00 (m)
36.0 36.1 2.64 (dd, 12.0, 14.0)
2.73 (dd, 7.5, 14.0)
27.4 27.4 2.53 (t, 7.5)
28.4 28.4 2.39 (t, 7.5)
8
9
136.4 136.1 -
120.3 121.1 -
127.5 127.5 -
130.3 130.3 -
116.5 116.5 -
139.9 140.0 -
143.2 143.3 -
133.1 133.1 -
116.5 116.6 6.58 (s)
132.9 133.3 -
127.5 127.6 -
10 71.3 71.9
11 142.6 142.6 -
12 140.4 141.5 -
13 132.4 132.8 -
14 117.5 117.9 6.56 (s)
15 27.2 27.2 3.18 (m)
16 21.5 21.5 1.23 (d, 7.0)
17 22.3 22.3 1.21 (d, 7.0)
18 32.2 32.2 0.85 (s)
19 22.8 22.9 0.92 (s)
-
39.9
40.1 -
140.9 139.0 -
139.3 140.9 -
132.2 131.9 -
112.2 112.5 6.61 (s)
27.1
22.4
22.4
26.1
26.1
27.2 3.29 (m)
22.4 1.24 (d, 6.5)
22.4 1.23 (d, 6.5)
26.2 1.27 (s)
27.1
22.7
22.7
32.0
21.2
27.3 3.10 (m)
22.6 1.24 (d, 7.0)
22.7 1.26 (d, 7.0)
33.0 0.85 (s)
26.2 1.27 (s)
21.3 1.14 (s)
3.08 (d, 8.5)/4.31 (d,
8.5)
20 41.6 41.6 2.57 (s)/3.03 (s)
68.5
68.6
Measured in a)CDCl3, b)125 MHz, c)500 MHz. #)δC of demethylsalvicanol,[16]
$)δC of sageone[18],%)δC of 20-deoxocarnosol.[17]
Figure 2: The key HMBC correlations of compounds 1-5
Vietnam Journal of Chemistry
Diterpenoids from Rosmarinus officinalis L…
Table 2: The 1H- and 13C-NMR data of compounds 4-5 and reference compounds
4
5
C
a
*δC
a,b
a
a,b
δC
δHa,c (mult., J in Hz)
&δC
δC
δHa,c (mult., J in Hz)
1.97 (ddd, 1.5, 5.5, 11.5)/3.18 (brd,
14.0)
1
31.4
31.3 1.22 (m)/3.21 (m)
27.4 27.2
2
3
4
18.9
41.4
33.6
18.9 1.43 (m)/1.67 (m)
41.1 1.26 (m)/1.50 (m)
19.0
38.0
31.4
50.9
75.3
75.7
19.0 1.53 (m)/1.64 (m)
38.0 1.20 (m)/1.43 (m)
31.4
33.6
-
-
5
6
52.7
19.0
52.7 1.41 (m)
19.0 1.63 (m)/1.70 (m)
32.0 2.85 (m)
50.9 2.28 (s)
75.4 4.35 (d, 3.0)
75.8 4.66 (d, 3.0)
7
32.0
8
130.0
127.5
44.0
130.1
-
-
-
-
-
-
126.6 126.7
124.6 124.4
-
-
-
-
-
-
9
127.5
44.0
10
11
12
13
14
15
16
17
18
19
47.0
47.1
142.1
142.2
132.5
118.9
27.2
142.1
142.1
132.4
118.9 6.52 (s)
27.2 3.20 (m)
22.6 1.22 (d, 6.5)
22.3 1.23 (d, 6.5)
33.9 0.88 (s)
142.7 142.4
141.4 141.9
134.6 135.0
120.8 120.6 6.77 (s)
27.2
22.2
22.3
22.0
31.3
27.3 3.10 (m)
22.2 1.20 (d, 7.0)
22.4 1.21 (d, 7.0)
22.0 0.92 (s)
22.5
22.2
33.8
22.8
22.8 0.97 (s)
31.4 1.01 (s)
3.93 (d, 9.5) / 4.47
(d, 9.5)
20
67.3
67.2
179.1 179.3
-
-CH2CH3
-CH2CH3
66.2
15.8
66.2 3.85 (m)
15.8 1.32 (t, 6.5)
Measured in a)CDCl3, b)125 MHz, c)500 MHz. *)δC of 11,12,20-trihydroxy-abieta-8,11,13-triene[19] &)δC of 7α-ethoxyrosmanol.[20]
,
Table 3: Inhibitory effects of compounds 1-5 in the LPS induced NO production in RAW 264.7 cells
Compounds
Concentration (µM)
Inhibition (%)
43.6±1.9
Cell viability (%)
97.8±1.1
34.5±0.9
103.8±1.8
17.9±1.4
99.8±2.4
6.6±3.1
20
100
20
100
20
100
20
100
20
1
51.6±1.5
26.7±1.9
26.7±1.4
20.5±2.4
82.2±2.5
2
3
4
5
102.8±2.7
78.5±2.2
96.8±3.0
10.1±2.1
95.2±2.1
100
20
L-NMMAa
a)Positive control.
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Acknowledgement. This research is funded by the
Vietnam National University, Hanoi (VNU) under
project number QG.19.11.
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H. Lee, J. Park, J. Kim, H. S. Lee. Abietane
Corresponding author: Le Thi Huyen
VNU University of Science, Vietnam National University, Hanoi
19, Le Thanh Tong, Hoan Kiem, Hanoi 10000, Viet Nam
E-mail: lethihuyen@hus.edu.vn.
6 trang
18/04/2022
920
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