Biochemical Systematics and Ecology 93 (2020) 104159

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Biochemical Systematics and Ecology

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Monoterpenoid indole alkaloids from Kopsia hainanensis Tsiang

Ting He a, 1, Yu-Dan Wang a, b, 1, Fang-Ru Li a, Shu-Yue He a, Qi-Min Cui a, Ya-Ping Liu c,
Tian-Rui Zhao a, **, Gui-Guang Cheng a, *
a
Faculty of Agriculture and Food, Kunming University of Science and Technology, Kunming, 650500, China
b
Engineering Research Center of Biopolymer Functional Materials of Yunnan, Yunnan Minzu University, Kunming, 650500, China
c
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences Kunming, 650201, China

A R T I C L E I N F O A B S T R A C T

Keywords: A phytochemical investigation on the twigs and leaves of Kopsia hainanensis Tsiang resulted in the isolation and
Kopsia hainanensis Tsiang identification of 18 alkaloids, including two sarpagine type alkaloids (1 and 2), five eburnane type alkaloids
Apocynaceae (3–7), three aspidofractinine type alkaloids (8–10), one vincadine type alkaloid (11), three akuammiline type
Alkaloids
alkaloids (12–13 and 15), one corynanthean type alkaloid (14), two ajmalicine-like type alkaloids (16 and 17),
Chemotaxonomy
and one aspidospermine type alkaloid (18). The new structure of compound 1 was elucidated by means of
spectroscopic analysis, including HRESIMS, and 1D and 2D NMR experiments. Compounds 1–2, 4–5, 7, and
10–17 are herein reported for the first time from this plant, while the compounds 1, 2, 7, and 12–17 have not
been previously recorded in the Kopsia genus. The chemotaxonomic significance and distribution of these
monoterpenoid indole alkaloids in Kopsia genus are discussed.

1. Subject and source
The genus Kopsia, belonging to the family Apocynaceae, contains
approximately 30 species, which are widely distributed in tropical and
subtropical regions of Asia (Allorge et al., 1994). There are 4 species
distributed in China, including Kopsia hainanensis Tsiang, Kopsia offici­
nalis Tsiang, Kopsia fruticosa Ker, and Kopsia lancibracteolata Merr. (Feng
et al., 1984). K. hainanensis is a shrub (http://www.theplantlist.org/t
pl1.1/record/kew-106330), and used as a Traditional Chinese Medi­
cine in the treatment of rheumatism, sore throat and so on (Yang et al.,
2012). The twigs and leaves of K. hainanensis were collected from
Xishuangbanna prefecture, Yunnan province of China, in July 2018, and
identified by a coauthor, Dr. Yaping Liu. A voucher specimen has been
deposited at the Faculty of Agriculture and Food, Kunming University of
Science and Technology with a voucher number Cheng-2018070201.
2. Previous work
Previous phytochemical investigations revealed that the
K. hainanensis are good sources of indole alkaloids with biological ac­
tivity (Zhu et al., 1986; Kam and Tan, 1990; Kam et al., 1993b; Varea
et al., 1993; Kam and Sim, 1998; Kam and Choo, 2004a; Midleton, 2004;
Lai et al., 2012). In addition, some triterpenoids and flavonoids were
also isolated from species of Kopsia (Yang et al., 2012). To the best of our
knowledge, there are currently few reports on the chemical constituents
of K. hainanensis.
3. Present study
The air-dried sample of K. hainanensis (10 kg) was extracted with
MeOH (30 L, 48 h) four times at room temperature and then concen­
trated under reduced pressure to give a crude extract (1.1 kg). The crude
extract was partitioned between ethyl acetate (EtOAc) and acidic
aqueous including 0.5% hydrochloric acid solution (pH 2–3). The
aqueous acidic phase was adjusted to pH 9–10 with 5% aqueous
ammonia, and then partitioned with EtOAc (1:1, v/v) for three times to
obtain a crude alkaloidal extract (80 g). The crude alkaloidal extract was
chromatographed on silica gel column using a gradient of CHCl3/MeOH
(1:0–0:1) to afford six fractions (A-E). Fraction A (3 g) was further
applied to a silica gel column chromatography (CC) using petroleum
ether-acetone (20:1–1:1) eluent to yield three subfractions A-1-A-3.
Subfraction A-1 was separated by RP-18 CC (MeOH–H2O, 10:90–80:20),

* Corresponding author.
** Corresponding author.
E-mail addresses: food363@163.com (T.-R. Zhao), ggcheng@kust.edu.cn (G.-G. Cheng).
1
These authors contributed equally to this work.

https://doi.org/10.1016/j.bse.2020.104159
Received 22 May 2020; Received in revised form 5 July 2020; Accepted 5 September 2020
Available online 17 September 2020
0305-1978/© 2020 Elsevier Ltd. All rights reserved.
T. He et al.
and then separated by semi-preparative RP-HPLC with acetonitrile-H2O
as eluent (60:40–70:30) to yield compound 3 (10 mg), compounds 2 (16
mg) and 11 (5 mg). Subfraction A-3 was subjected to a silica gel CC using
a petroleum ether-acetone gradient (15:1–1:1) to yield compound 4 (8
mg). Fraction B (8 g) was subjected to a silica gel CC using petroleum
ether-acetone (10:1–1:1) eluent to yield two subfractions B-1-B-2. Sub­
fraction B-1 was further applied to a silica gel CC using a petroleum
ether-acetone gradient (8:1–3:1) to yield compound 14 (8 mg). Sub­
fraction B-2 was separated by semi-preparative RP-HPLC with acetoni­
trile-H2O as eluent (60:40–70:30) to yield 12 (12 mg) and 9 (20 mg).
Fraction C (15 g) was separated by RP-18 CC (MeOH–H2O, 10:90–80:20)
Fig. 1. Structures of compounds 1–18.
2
Biochemical Systematics and Ecology 93 (2020) 104159
to obtain four subfractions C-1-C-4. Subfraction C-1 was further applied
to a silica gel column with petroleum ether-acetone (10:1–1:1) and then
separated by semi-preparative RP-HPLC with acetonitrile-H2O (50:50)
to yield 8 (10 mg), 10 (10 mg), and 13 (20 mg). Subfraction C-3 was
separated by semi-preparative RP-HPLC with acetonitrile-H2O (50:50)
to yield 5 (9 mg) and 6 (20 mg). Fraction D (4 g) was separated by RP-18
CC (MeOH–H2O, 10:90–80:20) to obtain five subfractions D-1-D-5.
Subfraction D-2 was further applied to a silica gel CC with chloroform-
acetone (10:1–1:1) eluent to yield 7 (5 mg). Subfraction D-3 was sepa­
rated by semi-preparative RP-HPLC with a gradient of acetonitrile-H2O
(40:60–70:30) to yield 15 (18 mg) and 16 (10 mg). Subfraction E (10.5
T. He et al. Biochemical Systematics and Ecology 93 (2020) 104159

g) was separated by RP-18 CC (MeOH–H2O, 10:90–50:50) to obtain vincadiffine (2) (Achenbach et al., 1994), (− )-eburnamenine (3) (Yang
three subfractions E-1-E-3. Subfraction E-1 was further applied to a silica et al., 2016), O-methy-vincanol (4) (Yang et al., 2016), O-methyl-16-­
gel CC with chloroform-methanol (10:1–1:1) and then separated by epi-vincanol (5) (Zeches et al., 1984), (+)-eburnamine (6) (Kam et al.,
semi-preparative RP-HPLC with a gradient of acetonitrile-H2O (40:60) 1992), melohenine B (7) (Feng et al., 2009a), kopsinine (8) (Feng et al.,
to yield 1 (12 mg) and 17 (7 mg). Subfraction E-3 was separated on a 1984), (2β,5β)-aspidofractinin-16-ol (9) (He et al., 2006), aspido­
preparative RP-HPLC with a gradient of MeOH–H2O (30:70–60:40) to fractinine (10) (Nogueira et al., 2014), quebrachamine (11) (Santosa
give 18 (10 mg) (Fig. 1). et al., 2008), 5-methoxystrictamine (12) (Zhou et al., 2005), picralinal
Compound 1 was obtained as a white amorphous powder. The mo­ (13) (ABE et al., 1989), fluorocarpamine (14) (Atta-Ur-Rahman et al.,
lecular formula, C22H26N2O5, was established by a quasi-molecular ion 1989), pleiomalicine (15) (Tan et al., 2010), dihydrocorynantheol (16)
at m/z 399.1904 [M + H]+ (calcd for 399.1914) in the positive HRESIMS (Robert et al., 1983), corynantheol (17) (Quetin-Leclercq et al., 1991),
spectrum, indicating eleven indices of hydrogen deficiency. The IR and leuconolam (18) (Atta-Ur-Rahman et al., 1995) (see Fig. 1).
spectrum suggested the presence of hydroxy (3442 cm− 1), carbonyl
(1720 cm− 1), ester carbonyl (1635 cm− 1), and aromatic ring (1465 and
3.1. Spectral data of compound 1
1383 cm− 1) groups, respectively. The 1H NMR spectrum displayed sig­
nals for two methyls at δH 1.62 (3H, d, J = 6.2 Hz) and 2.42 (3H, s), one
methoxy at δH 3.15 (3H, s), three aromatic protons at δH 6.95 (1H, d, J = Compound 1: white amorphous powder; [α]25 D -75 (c 0.1, CH3OH); UV
1.2 Hz), 6.80 (1H, dd, J = 8.4, 1.2 Hz) and 7.16 (1H, d, J = 8.4 Hz). Its (c 0.1, CH3OH) λmax (log ε): 202 (3.26), 230 (3.04), and 320 (3.07) nm;
13
C NMR and DEPT spectra exhibited 22 carbon signals assignable for IR (KBr) cm− 1: 3442, 2922, 1720, 1635, 1465, 1434, 1383, and 1046
two methyls (δC 11.9 and 42.0), one methoxy groups (δC 48.7), four cm− 1; 1H and 13C NMR data, see Table 1; HRESIMS m/z 399.1904 (calcd
methylenes (δC 18.2, 43.0, 50.8, and 68.2), six methines (δC 32.0, 58.3, for C22H26N2O5 [M + H]+, 399.1914).
103.3, 112.9, 117.1, and 119.8) and nine quaternary carbons (δC 52.5,
117.5, 128.9, 131.8, 135.6, 136.3, 150.9, 172.6, and 189.2). The full 4. Experimental
assignment of the 1H and 13C NMR spectroscopic data was confirmed by
the analysis of HSQC and HMBC spectra. The 1H and 13C NMR data The HRESIMS data were recorded on an Agilent G6230 TOF MS.
(Table 1) of compound 1 were similar to those of vincadiffine (Achen­ Optical rotations were measured on a JASCO P-1020 polarimeter. The IR
bach et al., 1994) except for the presence of a hydroxyl group in the spectra were obtained by a Bruker FT-IRTensor 27 spectrophotometer
aromatic benzene ring of 1. The key HMBC correlations from δH 6.95 with KBr pellets. UV spectra were obtained using a Shimadzu UV-2401A
(1H, d, H-9) to δC 150.9 (s, C-10), 117.1 (d, C-11) and 131.8 (s, C-13), spectrometer. The 1D and 2D NMR spectra were recorded on a Bruker
from δH 6.80 (1H, dd, H-11) to δC 103.3 (d, C-9), 150.9 (s, C-10), 112.9 AV-400, 600 MHz and DRX-500 MHz spectrometer with TMS as an in­
(d, C-12) and 131.8 (s, C-13) and from 7.16 (1H, d, H-12) to δC 128.9 (s, ternal standard. Chemical shifts (δ) were expressed in ppm with refer­
C-8) and 150.9 (s, C-10) confirmed that the hydroxyl group was located ence to the solvent signals. Methanol and acetonitrile were of HPLC
at C-10 (Fig. 2). This assumption was also verified by the increase of 16 grade. All solvents used in column chromatography were distilled.
Da in the HRESIMS spectrum. Other parts of 1 were identical to those of
vincadiffine, which were supported by detailed analysis of 2D NMR 5. Chemotaxonomic significance
spectra of 1. Thus, the structure of compound 1 was established and
named as 10-hydroxy-vincadiffine. Indole alkaloids are the characteristic secondary metabolites in
The structural characterization of compounds 2–18 was performed species of Kopsia (Kam and Lim, 2008). In this research, 18 mono­
by 1D and 2D NMR, MS, and comparison with reported data in the terpenoid indole alkaloids were isolated and characterized from the
literature. These compounds were unambiguously identified as twigs and leaves of K. hainanensis. Compounds 1 and 2 are two sarpagine
type alkaloids, and reported from K. hainanensis for the first time.
Compound 2 has been previously reported from Tabernaemontana
Table 1
glandulosa (Stapf) Pichon (Achenbach et al., 1994) and Ervatamia chi­
The 1H and13C NMR spectroscopic data of compound 1 in DMSO‑d6 (δ in ppm, J
nensis (Merr.) Tsiang (Guo et al., 2012). Notably, four eburnane type
in Hz).
1 13
alkaloids (3–6) with a 6/5/6/6/6 pentacyclic ring skeleton system are
Position H NMR C NMR
isolated from K. hainanensis. Compounds 3 and 6 have been previously
2 135.6 C reported from Kopsia larutensis King & Gamble (Kam et al., 1993a).
3 189.2 C Compounds 4 and 5 are reported from K. hainanensis for the first time,
5 3.51, overlap 58.3 CH
6a 3.52, overlap 18.2 CH2
but have been previously reported from Kopsia jasminiflora Pit. (Kitajima
6b 3.16, m et al., 2014), Melodinus henryi Craib (Feng et al., 2010) and Melodinus
7 117.5 C hemsleyanus diels (Wang et al., 2019a). Compound 7 is an alkaloid with a
8 128.9 C 6/9/6/6 tetracyclic ring system, regarded as a key intermediate from
9 6.95, d (1.2) 103.3 CH
indole to quinoline alkaloids, and was firstly reported from Melodinus
10 150.9 C
11 6.80, dd (8.4, 1.2) 117.1 CH henryi Craib (Feng et al., 2009a).
12 7.16, d (8.4) 112.9 CH Compounds 8–10 are three aspidofractinine type alkaloids, while
13 131.8 C compound 10 is reported from K. hainanensis for the first time. In
14 3.35, overlap 43.0 CH2 addition, Compound 8 has been previously reported from species of
15 3.48, overlap 32.0 CH
16 52.5 C
Kopsia, such as K. officinalis (Yang et al., 2017), K. jasminiflora Pit
17a 3.67, overlap 68.2 CH2 (Kitajima et al., 2014). and K. hainanensis (Yang et al., 2012), whereas 9
17b 3.36, overlap has been reported from Kopsia officinalis (He et al., 2006) and
18 1.62, d (6.2) 11.9 CH3 K. hainanensis (Yang et al., 2012). Compound 11 is reported from
19 5.42, q (6.2) 119.8 CH
K. hainanensis for the first time, but has been previously reported from
20 136.3 C
21a 2.87, d (13.2) 50.8 CH2 other species of Kopsia, such as K. jasminiflora (Kitajima et al., 2014).
21b 3.66, d (13.2) and K. officinalis (Feng et al., 1983). Compounds 12–13 and 15 are three
22 172.6 C akuammiline type alkaloids and compounds 12–13 are reported from
OCH3 3.15, s 48.7 CH3 K. hainanensis for the first time. Compound 12 has been previously re­
N–CH3 2.42, s 42.0 CH3
ported from Alstonia scholaris (L.) R. Br (Cai et al., 2008; Feng et al.,

3
T. He et al.
Fig. 2. Key HMBC (
2009b). and Melodinus fusiformis Champ. ex Benth. (Zhou et al., 2012).
Compound 13 has been generally reported from species of Alstonia
(Rastogi et al., 1970; Chen et al., 1986; Zhou et al., 2005; Cai et al.,
2008; Feng et al., 2009b) and also reported from Rhazya orientalis
(Decne.) A.DC. (Evans et al., 1968), Hunteria zeylanica (Retz.) Gardner
ex Thwaites (Lavaud et al., 1982), and Melodinus hemsleyanus Diels (Guo
and Zhou, 1993). Compound 15, an alkaloid-carbamic acid derivative,
was firstly reported from Alstonia angustifolia Wall. ex A.DC. (Tan et al.,
2010). Compound 14 is a corynanthean type alkaloid and is reported
from K. hainanensis for the first time, but has been previously reported
from species of Alstonia (Jacquier et al., 1980; Ghedira et al., 1988; Kam
et al., 2004b) and Tabernaemontana (Abaul et al., 1989; Shi et al., 2019).
Compounds 16 and 17 are two ajmalicine-like type alkaloids and are
firstly isolated from K. hainanensis. Compound 16 has been previously
reported from Mitragyna parvifolia (Roxb.) Korth. (Shellard and
Houghton, 1973), Hunteria zeylanica (Retz.) Gardner ex Thwaites (Ara­
mbewela and Khuong-Huu, 1981), and Rhazya stricta Decne. (Zaman,
1986). Meanwhile, Compound 17 has been previously reported from
Pterotaberna inconspicua (Stapf) Stapf (Morfaux et al., 1982), Rauwolfia
cumminsii Stapf. (Iwu and Court, 1978a, 1978b), and Rauwolfia mom­
basiana Stapf. (Iwu and Court, 1978c). Compound 18 has been previ­
ously reported from other species of Kopsia, such as Kopsia griffithii King
& Gamble (Kam et al., 1999), Kopsia officinalis (Wang et al., 2019b),
Kopsia jasminiflora Pit. (Kitajima et al., 2014), Kopsia singapurensis Ridl
(Subramaniam et al., 2008). and K. hainanensis (Yang et al., 2012).
This study has enriched the chemical compositions of K. hainanensis.
Notably, compounds 1, 2, 7, and 12–17 have not been previously
recorded in the Kopsia genus, which could be used as chemotaxonomic
markers to differentiate K. hainanensis from other species of Kopsia.
These results indicated that K. hainanensis shares relatively similar but
largely different chemotaxonomic chemical composition compared to
other species of Kopsia. Therefore, a further research needs to be un­
dertaken on the chemistry of species of Kopsia to fully evaluate the
systematic importance of these compounds.
Biochemical Systematics and Ecology 93 (2020) 104159
) correlations of compound 1.
Declaration of competing interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
the work reported in this paper.
Acknowledgements
This research was supported by the Applied Basic Research Project of
Yunnan Province in China (Grant numbers No.2018FB036 and
2017FD121), the open program of State Key of Phytochemistry and
Plant Resources in West China (P2018-KF08), the National Natural
Science Foundation of China (Grant numbers 31872676), and the Key
Laboratory Training Program of Yunnan University of Traditional Chi­
nese Medicin of China (Grant No.2017DG006).
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://doi.
org/10.1016/j.bse.2020.104159.
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