A new triterpenoid saponin from the roots of Ardisia crenata

doi:10.1016/j.cclet.2011.01.027

Chinese Chemical Letters

Volume 22, Issue 8, August 2011, Pages 957-960

https://doi.org/10.1016/j.cclet.2011.01.027 Get rights and content

Abstract

A new triterpenoid saponin, 3β-O-{β-d-glucopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl}-16α, 28-dihydroxyolean-12-en-30-oic acid 30-O-β-d-glucopyranosyl ester (ardisicrenoside N, 1), together with two known saponins, ardisicrenoside C (2) and D (3), were isolated from the roots of Ardisia crenata Sim. Their structures were elucidated by extensive spectral analysis and chemical evidences. Saponins 1 showed cytotoxicity against MCI-7 and NCI-H460 cancer cell lines at 11.0 μmol/L and 22.1 μmol/L in vitro.

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Cited by (13)

Triterpenoid saponins and phenylpropanoid glycoside from the roots of Ardisia crenata and their cytotoxic activities
2021, Chinese Journal of Natural Medicines
Two new triterpenoid saponins, ardisicrenoside R and S (1 and 2), and one new phenylpropanoid glycoside, ardicrephenin (3), along with five known compounds (4−8), were isolated from roots of Ardisia crenata. Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods. Compounds 2−7 were evaluated for their cytotoxic activities against A549, MCF-7, HepG2 and MDA-MB-231 cell lines by MTT assay. Ardicrenin (6) showed significant cytotoxicity, with IC₅₀ values of 1.17 ± 0.01, 1.19 ± 0.06, 3.52 ± 0.23, and 16.61 ± 1.02 μmol·L⁻¹, respectively.
Novel method for improving ardicrenin content in hairy roots of Ardisia crenata Sims plants
2020, Journal of Biotechnology
Citation Excerpt :
In China, this species is usually used as an traditional medicinal plants (Yin and Zhao, 2004). Recent studies have shown that its main medicinal active ingredients are triterpenoid saponins, which is new anti-HIV and anti-tumor candidates similar to camptothecin and taxol (Chen et al., 2007; Jin, 2008; Zhang et al., 2010; Liu et al., 2007, 2011; Zhang et al., 2011). In the past decades, acquired immunodeficiency syndrome (AIDS) and cancer have been two leading causes of human death.
To develop an alternative medicine related with taxol/camptothecin, a hairy roots induction system for measuring triterpenoid saponin ardicrenin was established. In the current study, mature and healthy seeds of Ardisia crenata plants were selected for obtaining aseptic seedlings. Two Agrobacterium rhizogenes strains ATCC 15834 and A4 were used to infect aseptic euphylla for inducing hairy roots of A. crenata plants. For the best combination of seeds germination, a Murashige-Skoog medium containing 1.0 mg L⁻¹ 6-benzylaminopurine and 1.0 mg L⁻¹ naphthalene acetic acid was made, which reached a rate of 92.4 %. Results showed that ATCC 15834 and A4 both induced hairy roots of A. crenata for improving ardicrenin production. The PCR analysis demonstrated that ATCC 15834 and A4 Ri plasmid T-DNA had been successfully transferred and integrated into the genome of leaf cell nuclei, however the Vir region was not. Further, ardicrenin content in hairy roots ACHR 15834 8.2 %) induced by ATCC 15834 was quantified by the RP-HPLC, which was also 1.8-, 2.7-, 9.4- and 2.6-fold greater than those of ACHR 4 induced by A4 (4.5 %), ACR C formed by tissue culture (3.1 %), euphylla (0.8 %) and NR C formed nature (3.2 %), respectively. Taken together, hairy root lines of A. crenata obtained were able to express naturally more ardicrenin than natural plants.
Three new triterpenoid saponins from the roots of Ardisia crenata and their cytotoxic activities
2016, Natural Product Research
Three new triterpenoid saponins, ardisicrenoside O (1), ardisicrenoside P (2) and ardisicrenoside Q (3) together with three known compounds, 3β,16α-dihydroxy-30-methoxy-28, 30-epoxy-olean-12-en, cyclamiretin A 3-O-β-d-glucopyranosyl-(1→2) -α-l-arabinopyranoside and cyclamiretin A 3-O-β-d-glucopyranosyl-(1→4) -α-l-arabinopyranoside were isolated from the roots of Ardisia crenata Sims. Their structures were determined by one- and two-dimensional NMR techniques, including HSQC, HMBC and TOCSY experiments, as well as acid hydrolysis and GC analysis. All isolates were evaluated for the cytotoxic activities on two human cancer cell lines and compounds 3, 5 and 6 showed significant cytotoxicity.
Ethnobotanical study of Zhuang medicinal herbs of Ardisia: variety systematization, traditional uses, phytochemistry, pharmacology, clinical application, and toxicity
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A new triterpenoid saponin from the roots of Ardisia crenata

Abstract

Phytochemistry

The Dictionary of Chinese Traditional Medicine

J. Asian Nat. Prod. Res.