Two new triterpenoid saponins: telephiifoliosides A and B from the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq

Article abstract of DOI:10.1080/14786419.2021.1914030

The polar fraction of the MeOH extract of the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq. (Caryophyllaceae) was investigated for its constituents and two previously unreported monodesmosides triterpene saponins, telephiifoliosides A and B (1 and 2), along with the known bonushenricoside A (3) were isolated. Their structures were elucidated by combined spectroscopic and spectrometric techniques (¹H NMR, ¹³C NMR, HSQC, ¹H-¹H COSY, HMBC, TOCSY, NOESY, HRESIMS) and chemical methods. The structures of the new saponins were established as; 3-O-α-L-arabinopyranosyljaligonic acid (1), and 3-O-α-L-arabinopyranosylphytolaccagenin ester (2). Upon evaluation of the antiproliferative activity on human malignant epithelial (HeLa) cells, none of the isolated compounds was efficient at the concentration of 33 μM. Highlights This is the first phytochemical study on Corrigiola litoralis subsp. telephiifolia. Two new saponins were isolated from the roots of Corrigiola litoralis subsp. telephiifolia. The isolated compounds were tested for their antiproliferative activity.

Full text of DOI:10.1080/14786419.2021.1914030

Natural Product Research
Formerly Natural Product Letters
ISSN: (Print) (Online) Journal homepage: https://www.tandfonline.com/loi/gnpl20
Two new triterpenoid saponins: telephiifoliosides
A and B from the roots of Corrigiola litoralis subsp.
telephiifolia (Pourr.) Briq
Romuald Tématio Fouedjou, Beaudelaire Kemvoufo Ponou, Rémy Bertrand
Teponno, Matthias Melzig, Chiaki Tanaka, Tomofumi Miyamoto & Léon
Azefack Tapondjou
To cite this article: Romuald Tématio Fouedjou, Beaudelaire Kemvoufo Ponou, Rémy Bertrand
Teponno, Matthias Melzig, Chiaki Tanaka, Tomofumi Miyamoto & Léon Azefack Tapondjou (2021):
Two new triterpenoid saponins: telephiifoliosides A and B from the roots of Corrigiolaꢀlitoralis subsp.
telephiifolia (Pourr.) Briq, Natural Product Research, DOI: 10.1080/14786419.2021.1914030
To link to this article: https://doi.org/10.1080/14786419.2021.1914030
Published online: 03 May 2021.
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NATURAL PRODUCT RESEARCH
https://doi.org/10.1080/14786419.2021.1914030
Two new triterpenoid saponins: telephiifoliosides A and B
from the roots of Corrigiola litoralis subsp. telephiifolia
(Pourr.) Briq
a,b
a,c
ꢀ
ꢀ
Romuald Tematio Fouedjou , Beaudelaire Kemvoufo Ponou , Remy Bertrand
Teponnoa, Matthias Melzigb, Chiaki Tanakac, Tomofumi Miyamotoc and
a
ꢀ
Leon Azefack Tapondjou
aResearch Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of
b
€
Science, University of Dschang, Dschang, Cameroon; Institut fur Pharmazie (Pharmazeutische
c
€
Biologie), Freie Universitat Berlin, Berlin, Germany; Department of Natural Products Chemistry,
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
ABSTRACT
ARTICLE HISTORY
Received 3 January 2021
Accepted 1 April 2021
The polar fraction of the MeOH extract of the roots of Corrigiola
litoralis subsp. telephiifolia (Pourr.) Briq. (Caryophyllaceae) was
investigated for its constituents and two previously unreported
monodesmosides triterpene saponins, telephiifoliosides A and B
(1 and 2), along with the known bonushenricoside A (3) were iso-
lated. Their structures were elucidated by combined spectroscopic
and spectrometric techniques (1H NMR, 13C NMR, HSQC, 1H-1H
COSY, HMBC, TOCSY, NOESY, HRESIMS) and chemical methods.
The structures of the new saponins were established as; 3-O-a-L-
arabinopyranosyljaligonic acid (1), and 3-O-a-L-arabinopyranosyl-
phytolaccagenin ester (2). Upon evaluation of the antiproliferative
activity on human malignant epithelial (HeLa) cells, none of the
isolated compounds was efficient at the concentration of 33 mM.
KEYWORDS
Caryophyllaceae; Corrigiola
litoralis; triterpenoid
saponins; antiprolifera-
tive activity
HIGHLIGHTS
ꢀ This is the first phytochemical study on Corrigiola litoralis
subsp. telephiifolia.
ꢀ Two new saponins were isolated from the roots of Corrigiola
litoralis subsp. telephiifolia.
ꢀ The isolated compounds were tested for their antiprolifera-
tive activity.
ꢀ
beaudelaireponou@yahoo.fr; Leon Azefack Tapondjou
CONTACT Beaudelaire Kemvoufo Ponou
tapondjou2001@yahoo.fr
Supplemental data for this article can be accessed online at https://doi.org/10.1080/14786419.2021.1914030.
ß 2021 Informa UK Limited, trading as Taylor & Francis Group

2
R. T. FOUEDJOU ET AL.
1. Introduction
The Caryophyllaceae family (Kingdom: Plantae, Subkingdom: Tracheobionta,
Superdivision: Spermatophyta, Division: Magnoliophyta, Class: Magnoliopsida, Subclass:
Caryophyllidae, Order: Caryophyllales) includes 86 genera and about 2200 species; dis-
tributed mainly in temperate regions of the Northern hemisphere (Bittrich 1993).
Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq. (Synonym: Corrigiolla telephiifolia
Pourr.) (Pourret 1788) is an herbaceous Caryophyllaceae specie which has been recog-
00
nised by Moroccan legislation as a medicinal plant and is locally called Sarghina00. In
Morocco, it grows in cultivated beds on rocky and sandy soils. It is an herb, widely
branched, with slender prostrate branches and tiny compact inflorescences. When
burned, its roots release an aromatic fume (Lakmichi et al. 2011). They are also used
to treat flu, dermatological diseases, inflammation, cough and jaundice (Faïz et al.
2006-2007). C. litoralis root’s consumed with honey, or simply sprinkled on food is part
of a traditional remedy given to pregnant women (Bellakhdar 1997; Lakmichi et al.
2011). Although C. litoralis is used for the treatment of several diseases, very few
imformation is reported concerning its chemical composition (Rimbau et al. 1999;
Lakmichi et al. 2011).
Triterpene saponins are naturally occurring sugar conjugates of triterpenes. They
are surface-active compounds which gave stable foams in water (Arslan 2014) and
have been shown to possess a broad spectrum of biological and pharmacological
activities (Dinda et al., 2010). In a continuation of our collaborative program of valor-
isation of African medicinal plants potentially containing saponins (Fouedjou et al.
2014; Tapondjou et al. 2013, 2015), we have examined the saponins containing frac-
tion of the MeOH extract from Corrigiola litoralis. The present work describes the isola-
tion and the structural elucidation of two new triterpene saponins: telephiifoliosides A
(1) and B (2), possessing jaligonenic and phytolaccagenic acids as aglycones, respect-
ively together with one known compound (3) (Figure 1). Furthermore, the isolated
compounds were tested for their antiproliferative activity on human malignant epithe-
lial cells (HeLa).
2. Results and discussion
2.1. Isolation and structure elucidation
The air dried and pulverised roots of C. litoralis was extracted at room temperature
with MeOH. Repeated column chromatography of the MeOH extract over silica gel
and Sephadex LH-20 afforded three natural compounds (1-3) including two new sapo-
nins (1 and 2).
Compound 1 was obtained as a white amorphous powder. Its molecular formula
C35H54O11, was obtained from the positive-mode HR-ESI-MS which showed the
pseudo-molecular ion peak at m/z 673.3391 [M þ Na]þ (calcd for C35H54O11Na,
1
673.3564) and, 1323.6861 [2M þ Na]þ. On the basis of the H and 13C NMR spectral
data, compound 1 was identified as an olean-12-ene type pentacyclic triterpene sap-
onin, and this was further confirmed by comparison of its NMR data with those of
known olean-12-ene derivatives (Mahato and Kundu 1994). The aglycone part of 1

NATURAL PRODUCT RESEARCH
3
Figure 1. Structures of compounds 1-3.
1
was identified as jaligonic acid and all the H and 13C NMR spectral data were in good
agreement with literature values of closely related compounds (Wang et al. 2008). The
signal of one anomeric proton at dH 5.05 (d, J ¼ 7.3, H-10), giving HSQC correlation
with the anomeric carbon at dC 106.2 (C-10) was also observed. The identification of
protons belonging to the sugar unit was achieved via TOCSY experiment and their
1
assignment to the respective carbon atoms was deduced from H-1H COSY and HSQC
experiments starting from anomeric protons. The analysis of the chemical shifts of the
sugar part allowed the identification of one arabinopyranosyl unit. The a anomeric
configuration of the arabinopyranosyl units was deduced from the coupling constant
(J ¼ 7.3 Hz). Extensive survey of pentacyclic triterpenoid saponins from Caryophyllaceae
species showed that, the sugar chains are preferably attached at C-3 and C-28
€
(Bottger and Melzig 2011; Arslan 2014). In the case of triterpenoid saponins having
jaligonic acid or its C-30 O-methylester (Phytolaccagenin) as aglycone, C-3 of the agly-
cone resonates at about 82 ppm (Wang et al. 2008). The downfield shift observed for
C-3 (d 82.6) suggested the linkage site of the sugar at C-3. Furthermore, the HMBC cor-
relations observed between the anomeric protons at dH 5.05 (H-10) and the carbon at
dC 82.6 (C-3) the linkage positions of the sugar. The L configuration of the sugar unit
was determined by acid hydrolysis followed by GC analysis of its cysteine and thiazoli-
dine derivatives (see experimental). On the basis of these data, the structure of 1 was
determined as jaligonic acid 3-O-a-L-rabinopyranoside, a new secondary metabolite to
which we gave the trivial name telephiifolioside A.
Compound 2 was also isolated as a white amorphous powder. Its positive ion
mode HR-ESI-MS showed the pseudo-molecular ion peak at m/z 687.3564 [M þ Na]þ
(calcd for C36H56O11Na, 687.3754), corresponding to the molecular formula
C36H56O11Na. This indicated an increment of 14 amu as compared to compound 1,
suggesting the presence of one additional methyl group. An ion fragment was also
1
observed at m/z 515.3222 [M þ H-132-18]þ. Both H and 13C NMR of 2 were very simi-
lar to those of 1. However, a signal of an O-methyl group was observed at dH 3.70
(OCH3), as the only difference detected between 1 and 2. The presence of the O-
methyl group was further supported on the 13C NMR spectrum where an additional
signal was observed at dC 51.0 (OCH3). Compound 2 was then a methyl ester deriva-
tive of 1. The additional O-methyl group was attached to C-30 of the aglycone due to
the HMBC cross peak depicted between protons of at dH 3.70 and C-30 of aglycone at
dC 177.2. Based on the above findings, the structure of compound 2 was elucidated as
3-O-a-L-arabinopyranosyl phytolaccagenin, a new triterpene saponin to which we gave
the trivial name telephiifolioside B.

4
R. T. FOUEDJOU ET AL.
In order to verify if compounds 2 and 3 are natural products and not artifacts
formed during extraction, comparative TLC was performed and revealed their presence
in an aliquot of the EtOH extract of this plant. C-30 O-methyl ester triterpenoid deriva-
tives were previously reported from Chenopodiaceae (Kokanova-Nedialkova et al.
2019), Phytolaccaceae (Wang et al. 2008; Ma et al. 2019) and Molluginaceae (Zhang
et al. 2019) plant species as naturally occurring compounds.
The known metabolite 3 was identified by comparison of its NMR data with those
reported in the literature as 3-O-a-L-arabinopyranosylphytolaccagenin-28-O-b-D-gluco-
pyranosyl ester (bonushenricoside A) previously isolated from the roots of
Chenopodium bonushenricus L. (Kokanova-Nedialkova et al. 2019).
2.2. Antiproliferative activity
Due to the fact that, cancer is one of the most prominent human diseases and
because several triterpene saponins were reported to be cytotoxic against a large
panel of cancer cells (Lacaille-Dubois 2005), the three isolated saponins were tested
for their antiproliferative activity against Human malignant epithelial cells (HeLa). All
the compounds were not efficient at the concentration of 33 mM.
3. Experimental
3.1. General experimental procedures and instrumentation
Optical rotations were measured on a JASCO DIP-370 Digital Polarimeter. High-
Resolution ESI-TOF-MS were measured on a Bruker Micro TOF II LC/MS Spectrometer
(Column oven: 50 ꢁC, Flow rate: 0.4 mL/min, Run time: 0.8 min for 1 and 0.1 min for 2).
1
The 1 D and 2 D NMR spectra (1H NMR, 13C NMR, HSQC, H-1H COSY, HMBC, TOCSY,
NOESY) were performed in C5D5N-D2O (20:1) using a Varian INOVA-600 NMR spectrom-
eter (600 MHz for 1H and 150 MHz for 13C spectra). All chemical shift (d) values are
given in ppm units with reference to tetramethylsilane (TMS) as the internal standard,
and the coupling constants (J) are in Hz. Silica gel (63-200 mm Merck 64271) and
Sephadex LH-20 (Sigma 9041-37-6) were used for column chromatography. TLC was
carried out on precoated Kieselgel 60 F254 (0.25 mm, Merck) plates developed with
EtOAc-MeOH and EtOAc-MeOH-H2O mixtures and/or on Kieselgel 60 RP-18 F254
S
(0.25 mm, Merck KGaA 64271 Darmstadt, Germany) developed with MeOH-H2O mix-
tures. Spots on TLC plates were visualised by spraying with 20% H2SO4 and heating
for 5 min at 70 ꢁC. GC-MS was performed with GC-MS QP2010SE (Shimadzu, Japan)
with Inert Cap 5MS/Sil i.d. 0.25 ꢂ 30 m (GL Sciences Inc., Japan) [Column temperature:
100-280 ꢁC, rate of temperature increase: 10 ꢁC/min]. The following sugar samples
were commercially obtained and used for GC-MS analysis; D-glucose, L-glucose
(Aldrich Chem. Co., Japan), D-arabinose, L-arabinose (Kishida Chemical Co., Ltd., Japan),
L-cysteine methyl ester hydrochloride (Kanto Chemical Co., Inc., Japan), N-trimethylsily-
limidazole (TMS-imidazole) (Tokyo Kasei Kogyo Co., Ltd., Japan). Fetal bovine serum
(FBS) was purchased from Nichirei Bioscience Inc. (Tokyo, Japan) and heat-inactivated
at 56 ꢁC for 30 min for cell culture.

NATURAL PRODUCT RESEARCH
5
3.2. Plant material
The dried roots of Corrigiola litoralis were provided from the local market in the west
of Morroco in June 2016. Professor A. Ouyahya, a taxonomist from the Scientific
ꢁ
National Institute (Rabat) where a voucher specimen (N RAB65892) was deposited in
the Botany Department, identified the plant.
3.3. Extraction and isolation
The dried and ground roots of C. litoralis (2 Kg) were extracted three times (each time
for 24 h) with MeOH (4 L) at room temperature. The filtrate obtained was concentrated
until dryness under reduced pressure to yield a dark crude extract (290 g) using a
rotary evaporator (yield 14.5%). Part of this extract (270 g) was subjected to column
chromatography on silica gel, using a gradient of EtOAc in hexane then, MeOH in
EtOAc to give seven fractions (CT1-CT7).
Fraction CT3 was subjected to Sephadex LH-20 column chromatography eluted
with MeOH to give four main subfractions (CT31-4). One of the above subfractions
(CT34; 157 mg) was submitted to silica gel column chromatography eluted with EtOAc-
MeOH (98:2) to afford 1 (2.16 mg). Sephadex LH-20 filtration of fraction CT5 using
MeOH as elution solvent afforded five subfractions (CT51-5). Further silica gel column
chromatography with isocratic elution (EtOAc-MeOH-H2O; 97:2:1) of subfraction CT53
(57 mg) gave two subfractions CT531 and CT532. CT531 (23 mg) was further purified
over silica gel column chromatography with isocratic elution (EtOAc-MeOH-H2O;
97:2:1) to give 2 (1.73 mg). Subfraction CT6 was purified over silica gel column chro-
matography eluted with EtOAc-MeOH-H2O (95:5:2) to afford 3 (4.33 mg).
3.3.1. Telephiifolioside A (1)
ꢁ
22
1
White amorphous powder (MeOH); ½aꢃD ¼ þ 40.00 (C ¼ 0.0009 g/mL, MeOH); H-NMR
(600 MHz, C5D5N:D2O, 20:1): dH (ppm) Aglycone: 5.71 (brs, H-12), 4.76 (d, J ¼ 3.7 Hz, H-
2), 4.30 (o, H1-23), 4.29 (o, H-3), 3.65 (d, J ¼ 11.2 Hz, H2-23), 3.59 (brd, J ¼ 9.7 Hz, H-18),
2.48 (brd, J ¼ 11.2 Hz, H1-19), 2.39 (o, H1-7), 2.39 (H1-21), 2.32 (dd, J ¼ 14.2 and 3.2 Hz,
H1-1), 2.18 (o, H-16), 2.17 (o, H-15), 2.05 (o, H-11),2.02 (o, H2-7), 1.90 (H2-19), 1.84 (H-5),
1.80 (H-9), 1.78 (H-6), 1.75 (H1-22), 1.54 (H2-21), 1.52 (s, H-25), 1.39 (s, H-29), 1.34 (s, H-
27), 1.33 (H2-22), 1.28 (o, H1-1), 1.28 (s, H-24), 1.06 (s, H-26); Arabinose: 5.05 (d,
J ¼ 7.3 Hz, H-10), 4.51 (dd, J ¼ 7.3 and 9.1, H-20), 4.30 (o, H-40), 4.28 (o, H1-50), 4.15 (dd,
J ¼ 3.3 and 9.1, H-30), 3.75 (H2-50); and 13C-NMR (150 MHz, C5D5N:D2O; 20:1): dC (ppm)
Aglycone: 180.0 (C-28), 179.6 (C-30), 144.6 (C-13), 123.1 (C-12), 82.6 (C-3), 70.4 (C-2),
64.7 (C-23), 48.3 (C-9), 47.3 (C-5), 46.2 (C-17), 43.8 (C-1), 43.2 (C-18 and C-20), 42.9 (C-
19), 42.6 (C-4), 42.0 (C-14), 39.6 (C-8), 36.7 (C-10), 34.2 (C-7), 32.7 (C-22), 30.9 (C-21),
28.9 (C-29), 28.1 (C-15), 26.0 (C-27), 23.7 (C-11 and C-16), 17.7 (C-6), 17.3 (C-26), 17.0
(C-25), 14.8 (C-24); Arabinose: 106.2þ(C-10), 74.2 (C-30), 72.5 (C-20), 69.2 (C-40), 66.8 (C-
50); HR-ESI-MS m/z 673.3391 [M þ Na] (calcd for 673.3564, C35H54O11Na).
3.3.2. Telephiifolioside B (2)
White amorphous powder (MeOH); ½aꢃD ¼ þ 60.00ꢁ (C ¼ 0.0010 g/mL, MeOH); dH
22
(ppm) Aglycone: 5.62 (brs, H-12), 4.76 (d, J ¼ 3.2 Hz, H-2), 4.30 (o, H1-23), 4.28 (o, H-3),

6
R. T. FOUEDJOU ET AL.
3.65 (d, J ¼ 11.2 Hz, H2-23), 3.28 (brd, J ¼ 9.7 Hz, H-18), 2.33 (dd, J ¼ 14.2 and 3.6 Hz, H1-
1), 2.25 (H-19), 2.16 (H1-21), 2.09 (o, H-16), 2.16 (o, H-15), 2.07 (H1-22), 2.02 (o, H-11),
1.96 (H2-22), 1.82 (H-5), 1.81 (H2-19), 1.79 (H-9), 1.78 (H-6), 1.66 (o, H-7), 1.53 (s, H-25),
1.45 (H2-21), 1.29 (s, H-27), 1.28 (o, H2-1), 1.28 (s, H-24), 1.22 (s, H-29), 1.05 (s, H-26),
3.70 (s, OCH3); Arabinose: 5.06 (d, J ¼ 7.4 Hz, H-10), 4.52 (dd, J ¼ 7.4 and 9.0, H-20), 4.29
(o, H-40), 4.27 (o, H1-50), 4.15 (dd, J ¼ 3.4 and 9.1, H-30), 3.76 (H2-50); and 13C-NMR
(150 MHz, C5D5N:D2O; 20:1): dC (ppm) Aglycone: 181.8 (C-28), 177.2 (C-30), 144.4 (C-
13), 123.3 (C-12), 82.5 (C-3), 70.4 (C-2), 64.6 (C-23), 48.3 (C-9), 47.3 (C-5), 43.9 (C-17),
43.8 (C-1), 43.2 (C-18), 42.6 (C-4), 42.5 (C-14, C-19 and C-20), 39.6 (C-8), 36.6 (C-10),
34.3 (C-22), 32.6 (C-7), 30.5 (C-21), 28.2 (C-15), 28.0 (C-29), 26.0 (C-27), 23.7 (C-11), 23.6
(C-16), 17.7 (C-6), 17.3 (C-26), 17.0 (C-25), 14.7 (C-24), 51.0 (OCH3); Arabinose: 106.2 (C-
10), 74.1 (C-30), 72.5 (C-20), 69.2 (C-40), 66.8 (C-50); HR-ESI-MS m/z 687.3564 [M þ Na]þ
(calcd for 687.3754, C36H56O11Na).
3.4. Acid hydrolysis of saponins and GC-MS analysis
Each saponin (0.3 mg) was heated in 1 M HCl (0.1 mL) at 90 ꢁC for 3 h. The reaction
mixture was dried in vacuo and dissolved in pyridine (0.2 mL). TMS-imidazole (50 mL)
was added to the part of solution (0.1 mL) then heated at 50 ꢁC for 30 min. The reac-
tion mixture was diluted with H2O (0.2 mL) and extracted with hexane (0.1 mL) then
analysed by GC-MS by comparison with standard samples derivatised in the same con-
ditions. L-Cysteine methyl ester hydrochloride (ca. 1.0 mg) was added to the remaining
pyridine solution (0.1 mL) and heated at 60 ꢁC for 1 h then the TMS derivative was also
prepared as described for each isolated compound and analysed by GC-MS. Only the
derivatives of monosaccharide L-arabinose (Rt 17.75) was characterised for compounds
1 and 2 while D-glucose (Rt 19.51 min) and L-arabinose (Rt 17.75) were characterised
for compound 3 by comparison of their retention times with those of authentic sam-
ples treated in the same way as described above.
Standard TMS-Cys-Sugars (Rt, min)
TMS-Cys-D-glucose, Rt ¼19.51; TMS-Cys-L-glucose, Rt ¼ 19.64;
TMS-Cys-L-arabinose, Rt ¼ 17.67; TMS-Cys-D-arabinose, Rt ¼ 17.90
3.5. Antiproliferative assay
Human malignant epithelial cells (HeLa) were cultured in Eagle’s minimum essential
medium (EMEM) supplemented with 10% fetal bovine serum (FBS) kept in an incuba-
tor at 37 ꢁC in a humidified air containing 5% CO2. FBS was purchased from Nichirei
Bioscience Inc. (Tokyo, Japan). Cell viability was determined by a Cell-Titer 96 Aqueous
Non-Radioactive Cell Proliferation (MTS) Assay (Promega, WI, USA) according to the
manufacturer’s protocol. HeLa cells (1 ꢂ 104 cells/well) were seeded in 96 well plates
and incubated for 24 h, subsequently grown with compounds for additional 48 h, and
then cell proliferation assay was performed (Teponno et al. 2016). Cells were counted
after 24 h then, after 48 h. Cisplatin was used as a reference drug.

NATURAL PRODUCT RESEARCH
7
4. Conclusion
Two new triterpene saponins namely telephiifoliosides A and B were isolated from the
commercial roots of C. litoralis, a Moroccan medicinal plant. Their structures were elu-
cidated on the basis of extensive NMR, mass spectroscopic data, chemical reactions,
and in comparison of their NMR data with those reported in the literature. The iso-
lated compounds showed no antiproliferative activity against the human cancer cell
lines HeLa at the concentration of 33 mM. The isolation of saponins from C. litoralis is
in perfect agreement with the result reported by Daoudi et al. (2017), which revealed
the presence of saponins in the aqueous extract of a sample of this plant collected in
the Atlas Region-Morocco. The Caryophyllaceae family is well known to be a rich
€
source of triterpene saponins having an oleanane-type skeleton as aglycone (Bottger
and Melzig 2011). This work corroborated the previously reported results and let us to
suggest that the oleanane-type skeleton might represent a chemiotaxonomic marker
of the Caryophyllaceae family.
Acknowledgements
The authors are grateful to Professor Benoit Loura Benguellah, Dean of the Faculty of Mines and
Petroleum Industries of the University of Maroua (Cameroon) for his assistance in the gathering
of the plant material from Morocco. Compounds were isolated when the first author was on a
research visit at the Institute of Pharmacy of the Free University of Berlin (Germany) in the con-
€
text of Freie Universitat Research Alumni Program. We would like to thank Dr Alexander Weng
€
and Ms Cornelia Gorick for their technical assistance.
Disclosure statement
The authors confirm that this article content has no conflict of interests.
References
Arslan I. 2014. Simenoside A, a new triterpenoid saponin from Gypsophila simonii Hub.-Mor.
Chem Biodivers. 11(3):445–449.
ꢀ
ꢀ
Bellakhdar J. 1997. La Pharmacopee Marocaine Traditionnelle: Medecine Arabe Ancienne et
Savoir Populaire. Paris, France: Ibis Press.
Bittrich V. 1993. Caryophyllaceae. In: Kubitzki K, Rohwer JG, Bittrich V, editors. The families and
genera of vascular plants, Vol. 2. Flowering plants, dicotyledons. Heidelberg: Springer; p. 653.
€
Bottger S, Melzig MF. 2011. Triterpenoid saponins of the Caryophyllaceae and Illecebraceae fam-
ily. Phytochem Lett. 4(2):59–68.
Daoudi A, Bammou M, Ibijbijen J, Nassiri L. 2017. Antibacterial activity of aqueous extracts of
Anacyclus pyrethrum (L) Link and Corrigiola telephiifolia Pourr. from the middle Atlas Region-
Moroco. Eur Sci J. 13:116–128.
Dinda B, Debnath S, Mohanta BC, Harigaya Y. 2010. Naturally occurring triterpenoid saponins.
Chem Biodivers. 7(10):2327–2580.
Faïz CA, Alami IT, Saidi N. 2006-2007. Domestication of some MAP species “in Biological
Diversity, Cultural and Economic value of medicina, herbal and aromatic plants in Morocco.
Annu Rep. :15–22.
Fouedjou TR, Teponno RB, Quassinti L, Bramucci M, Petrelli D, Vitali AL, Fiorini D, Tapondjou AL,
Barboni L. 2014. Steroidal saponins from the leaves of Cordyline fruticosa (L.) A. Chev. and
their cytotoxic and antimicrobial activity. Phytochem Lett. 7:62–68.

8
R. T. FOUEDJOU ET AL.
Kokanova-Nedialkova Z, Nedialkov P, Momekov G. 2019. Saponins from the roots of
Chenopodium bonus-henricus L. Nat Prod Res. 33(14):2024–2031.
Lacaille-Dubois M-A. 2005. Bioactive saponins with cancer related and immunomodulatory activ-
ity: recent developments. Atta-ur-Rahman (Ed.), Stud Nat Prod Chem. 32:209–246.
Lakmichi H, Bakhtaoui FZ, Gadhi CA, Ezoubeiri A, El Jahiri Y, El Mansouri A, Zrara I, Loutfi K.
2011. Toxicity profile of the aqueous ethanol root extract of Corrigiola telephiifolia Pourr.
(Caryophyllaceae) in rodents, evidence-based. Complem Altern Med. 2011:1–10.
Ma X-P, Lou H-Y, Zhang W-F, Song J-R, Li Y, Pan W-D. 2019. Triterpenoids from Phytolacca aci-
nosa. Chem Nat Compd. 55(2):292–295.
Mahato S, Kundu PA. 1994. 13C NMR spectra of pentacyclic triterpenoids, A compilation and
some salient features. Phytochemistry. 37(6):1517–1575.
ꢀ
Pourret PA. 1788. Extrait de la Chloris narbonensis, Renfermee dans la Relation d’un Voyage fait
ꢀ ꢀ
ꢀ
depuis Narbonne jusqu’ au Montserrat, par les Pyrenees. Mem Acad Sci. 3:297–334.
Rimbau V, Cerdan C, Vila R, Iglesias J. 1999. Antiinflammatory activity of some extracts from
plants used in the traditional medicine of North-African countries (II). Phytother Res. 13(2):
128–132.
€
Tapondjou AL, Siems JK, Bottger S, Melzig FM. 2013. New steroidal saponins from the flowers of
Dioscorea bulbifera var. sativa. Phytochemistry. 95:341–350.
€
Tapondjou AL, Siems JK, Bottger S, Melzig FM. 2015. Steroidal saponins from the mesocarp of
the fruits of Raphia farinifera (Gaertn.) Hyl. (Arecaceae) and their cytotoxic activity. Nat Prod
Commun. 10:1941–1944.
Teponno RB, Tanaka C, Jie B, Tapondjou AL, Miyamoto T. 2016. Trifasciatosides A-J, steroidal sap-
onins from Sansevieria trifasciata. Chem Pharm Bull (Tokyo). 64(9):1347–1355.
Wang LY, Bai LM, Nagasawa T, Hasegawa T, Yang XY, Sakai J, Bai YH, Kataoka T, Oka S, Hirose K,
et al. 2008. Bioactve triterpene saponins from the roots of Phytolacca americana. J Nat Prod.
71(1):35–40.
Zhang D, Fu Y, Yang J, Li X-N, San MM, Naing T, Wang Y, Yang X. 2019. Triterpenoids and Their
Glycosides from Glinus oppositifolius with Antifungal Activities against Microsporum gypseum
and Trichophyton rubrum. Molecules. 24(12):2206.