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Fitoterapia
journal homepage: www.elsevier.com/locate/ fitote
Steroidal saponins from the aerial parts of Cordyline fruticosa L. var.
strawberries
Beaudelaire K. Ponou
a,b
, Rémy B. Teponno
a
, Azefack L. Tapondjou
a
,
Marie-Aleth Lacaille-Dubois
c
, Luana Quassinti
d
, Massimo Bramucci
d
, Luciano Barboni
b,
⁎
a
Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Box 183, Dschang, Cameroon
b
School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, I-62032 Camerino, Italy
c
Laboratoire de Pharmacognosie, UFR des Sciences de Santé, PEPITE EA 4267, Université de Bourgogne Franche-Comté, 7, Boulevard Jeanne d'Arc, BP 87900, 21079
Dijon Cedex, France
d
School of Pharmacy, Physiology Division, University of Camerino, Via Gentile III da Varano, I-62032 Camerino, Italy
ARTICLE INFO
Keywords:
Cordyline fruticosa
Agavaceae
Steroidal saponins
Fruticoside
Fruticogenin
ABSTRACT
A new sulfated steroidal derivative (fruticogenin A: 1-sulfo-australigenin-3-sodium sulphate, 1) and three new
steroidal saponins named fruticoside K (3-sulfo-spirostan-25(27)-ene-1β,3β-diol-1-O-[α-L-rhamnopyranosyl-
(1 → 4)-β-D-fucopyranoside], 2), fruticoside L (3-sulfo-spirostan-25(27)-ene-1β,3β,6α-triol-1-O-[α-L-rhamno-
pyranosyl-(1 → 4)-β-D-fucopyranoside], 3) and fruticoside M (spirostan-25(27)-ene-1β,3α-diol-1-O-[α-L-rham-
nopyranosyl-(1 → 2)-α-L-rhamnopyranoside], 4) were isolated from the aerial parts of Cordyline fruticosa L. var.
strawberries. Their structures were established on the basis of 1D and 2D NMR data, mass spectrometry and
chemical methods. Compounds 2 and 4 exhibited weak cytotoxicity against melanoma (A375), breast adeno-
carcinoma (MDA-MB-231), and colon carcinoma (HCT116) human tumor cell lines.
1. Intoduction
Agavaceae is a large family of about 480 species distributed in
tropical, subtropical and arid regions [1]. They are particularly known
as rich sources of steroids and their glycoside derivatives, mainly with
spirostane, cholestane and furostane type skeletons [1–4]. The leaves of
numerous Cordyline species have been used for the treatment of various
diseases including dysentery, rheumatism, inflammations [5–8]. In our
continuous search of potentially interesting new and bioactive saponins
from Cameroonian medicinal plants [9–11], some of us have initially
reported three new steroidal saponins from Cordyline fruticosa L. var.
florica [12]. In the present paper we report the isolation and structural
characterization of one new sulfated steroidal derivative 1 together
with three new steroidal saponins (2–3) from the aerial parts of Cor-
dyline fruticosa L. var. strawberries. The new compounds were in-
vestigated for their cytotoxic activity against MDA-MB 231, A375, and
HCT116 human tumor cell lines and the results are also reported.
2. Experimental
2.1. General
Optical rotations were measured on PerkinElmer 241 MC polari-
meter. API-ES mass spectra were carried out on an Agilent Technologies
LC/MSD Trap SL (G2445D SL). HRESIMS was recorded on an Agilent
Technologies 6540 UHD Accurate Mass Q-ToF LC/MS. Nuclear mag-
netic resonance (NMR) spectra, including correlation spectroscopy
(COSY), rotating-frame Overhauser effect spectroscopy (ROESY), het-
eronuclear multiple-bond correlation (HMBC), heteronuclear single-
quantum coherence (HSQC) experiments were performed in deuterated
(CD
3
)
2
SO on a varian Mercury plus Spectrometer operating at 400 MHz
(
1
H) and 100 MHz (
13
C), respectively. All chemical shifts (δ) are given
in ppm units with reference to the residual solvent signal, and the
coupling constants (J) are in Hz. Isolation was carried out using va-
cuum-liquid chromatography (VLC) on reversed-phase RP-18 silica gel
(Silicycle, 75–200 μm), medium-pressure liquid chromatography
(MPLC) on silica gel 60 (Merck, 15–40 μm) (Gilson apparatus) [13],
Büchi column (460 × 25 mm and 250 × 15 mm).
https://doi.org/10.1016/j.fitote.2019.03.019
Received 19 February 2019; Received in revised form 18 March 2019; Accepted 22 March 2019
⁎
Corresponding author.
E-mail address: luciano.barboni@unicam.it (L. Barboni).
Fitoterapia 134 (2019) 454–458
Available online 23 March 2019
0367-326X/ © 2019 Elsevier B.V. All rights reserved.
T