New pregnane saponins from Ecdysanthera rosea and their cytotoxicity
Graphical Abstract
Two new pregnane saponins, ecdysantheroside A (1) and ecdysantheroside B (2) were isolated from Ecdysanthera rosea. Ecdysantheroside B showed cytotoxicity against cells A549, MDA435, HepG2, and HUVEC.
Introduction
Ecdysanthera rosea Hook. et Arn., mainly distributed in tropical Asia, is an Apocynaceous liana, whose roots and stems have been used as analgesic, antiphlogistic, and spasmolytic agents in Chinese folk medicine [1]. Researchers have isolated some compounds such as ecdysantherin [2], 20-Epi-Kibataline, 3β, 14β, 20-trihydroxy-18oic (18 → 20) lactone pregnen-5 [3], 5-O-caffeoylquinic derivers, scopoletin [4], D-friedours-14-en-11α, 12α-epoxy-3β-yl palmitate [5] and some triterpenoids [6] from this plant. In previous studies, we have isolated six compounds such as hydroquinone diglycoside acyl esters, ecdysanrosin A, sesquiterpene, 5β-hydroperoxycostic acid and apocarotenoid, 2, 4, 7-trimethyl-2, 4, 6, 8-tetraene-dialdehyde [7]. However, the potential medicinal importance of the plant and our interest in new active compounds prompted us to investigate E. rosea further and two new steroidal glucosides were obtained further from E. rosea. The cytotoxicity of the two new steroidal glucosides, together with five other compounds isolated from E. rosea was tested against human acute lymphoblastic T-cell leukemia cells CEM, human umbilical vein endothelial cells HUVEC, human erythroleukemia cells K562, hepatocellular carcinoma cells HepG2, human carcinomic alveolar basal epithelial cells A549, and human mammary carcinoma cells MDA435 by MTT cytotoxicity assay [8].
Section snippets
General
Optical rotations were measured with a Horiba SEPA-300 polarimeter. UV Spectra were obtained with a Shimadzu 210A double-beam spectrophotometer. IR spectra were recorded with a Bio-Rad FTS-135 infrared spectrophotometer using the potassium bromide pellet technique. 1D and 2D-NMR Spectra were recorded with Bruker AM-400 and DRX-500 instruments with TMS as internal standard. EI–MS was measured with VG AutoSpec 3000 spectrometers. ESI–MS and HR–ESI–MS were measured with API QSTAR Pulsarimass
Results and discussion
Ecdysantheroside A (1) was found to possess a molecular formula of C28H41O7 based on the negative FAB-MS (m/z 489 [M–H]−), negative HR-FAB-MS (m/z = 489.2863 [M–H]−, calcd.: 489.2852) and the NMR spectroscopic data (Table 1). IR spectrum showed the absorption bands due to hydroxyl (3441 cm− 1), carbonyl (1744 cm− 1) and olefinic-bond (1640 cm− 1) groups. The 13C NMR spectrum of compound 1 displayed 28 carbon signals including one methoxy, 21 carbons of which were assigned to the aglycon part and 6 to
Acknowledgement
This work was supported by the National Natural Science Foundation (30860037 and 20872148) and the Department of Science and Technology in Yunnan Province (20080A007). The authors are grateful to the analytical group of the Laboratory of Phytochemistry, Kunming Institute of Botany, Chinese Academy of Sciences for measuring NMR, MS and IR data.
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Review on Pregnane Glycosides and Their Biological Activities
2022, Phytochemistry LettersCitation Excerpt :These plants mainly grow in arid areas such as India, Arabia, and southwest China. Various pregnane glycosides have been isolated from following plants: the whole plant of Caralluma tuberculate (Abdel-Sattar et al., 2008), the roots of Cynanchum paniculatum (Zhao et al., 2016), the leaves and pericarps of Solenostemma argel (Plaza et al., 2005), the stems of Gymnema sylvestre (Xu et al., 2015), the twigs of Pergularia pallida (Khare et al., 1984), the leaves of Oxystelma esculentum (Hamed et al., 2004), the aerial parts of Ecdysanthera rosea (Zhu et al., 2011), and the seeds of Adonis aestivalis Linné (Minpei et al., 2018). Monodesmoside-type pregnane glycosides possess an oligosaccharide chain at C-3 of the aglycon consisting of one to six sugar units.
Diverse lignans with anti-inflammatory activity from Urceola rosea
2019, FitoterapiaCitation Excerpt :All part of U. rosea has been used as Dai nationality (in China) herbal medicine for the treatment of rheumatism pain, furuncle, sore throat [1], while the leaves were used for anti-inflammatory and anti-infectious remedy or against kidney stones in Vietnam [2]. A few phytochemical studies on U. rosea were carried out and described the isolation of steroids, triterpenoids, sesquiterpenes, lignans, flavonoids, and phenol glycosides [2–7]. As a continuing search for bioactive and diverse ingredients from medicinal plants [8–10], the anti-inflammatory ingredients of the caulis of the title plant were investigated and led to the isolation of 17 lignans with diverse types, including diarylpropanes (1–4), aryltetralins (5–7), dibenzylbutane (8), furanoids (9–11), furofuranoid (12), and sesquineolignans (13–17) (Fig. 1).
Phytochemical and analytical characterization of constituents in Urceola rosea (Hook. & Arn.) D.J. Middleton leaves
2018, Journal of Pharmaceutical and Biomedical AnalysisCytotoxic triterpenes with diverse skeletons from Amoora tsangii
2016, Phytochemistry LettersNew antimicrobial pregnane glycosides from the stem of Ecdysanthera rosea
2014, FitoterapiaCitation Excerpt :for 801.4401). The similar IR and NMR spectra data indicated that compound 6 possessed the same aglycone but different sugar moiety to ecdysantheroside A [12]. The anomeric protons at δH 5.25 (br d, J = 9.2 Hz, H-1′), δH 5.10 (br d, J = 9.3 Hz, H-1″) and δH 4.68 (br d, J = 9.2 Hz, H-1‴) suggested that there were three sugar units, and the assumption was further confirmed by analyzing the derivatives of its acid hydrolyzate.