Cytotoxic 13,28 Epoxy Bridged Oleanane-Type Triterpenoid Saponins from the Roots of Ardisia crispa

Abstract

Ardisiacrispin D–F (1–3), three new 13,28 epoxy bridged oleanane-type triterpenoid saponins, together with four known analogues (4–7) were isolated from the roots of Ardisia crispa. The structures of 1–7 were elucidated based on 1D and 2D-NMR experiments and by comparing their spectroscopic data with values from the published literatures. Ardisiacrispin D–F (1–3) are first examples that the monosaccharide directly linked to aglycone C-3 of triterpenoid saponins in genus Ardisia are non-arabinopyranose. In the present paper, all compounds are evaluated for the cytotoxicity against three cancer cell lines (HeLa, HepG2 and U87 MG) in vitro. The results show that compounds 1, 4 and 6 exhibited significant cytotoxicity against Hela and U87 MG cells with IC50 values in the range of 2.2 ± 0.6 to 9.5 ± 1.8 µM. The present investigation suggests that roots of A. crispa could be a potential source of natural anti-tumor agents and their triterpenoid saponins might be responsible for cytotoxicity.

Anti‐inflammatory activity of a new lactone isolated from the leaves of Ardisia crenata Sims

“…The roots are commonly used for the treatment of sore throat, dysmenorrhea and rheumatism, [3][4][5] and research on chemical constituents showed that triterpenoid saponins, isocoumarins, phenols and benzoquinones were the main chemical constituents in A. crenata Sims, [6][7][8] and studies on these chemical constituents found that triterpenoid saponins had better anti-tumour activity. [9] Moreover, lactones are rarely isolated in A. crenata Sims, and this kind of active ingredients often have better antiinflammatory activities. [10][11][12] Interleukins (ILs), as key mediator in the systemic anti-inflammatory response, play a crucial role in the process of inflammation.…”

Terpenoids with Cytotoxic Activity from Roots of Ardisia crispa

“…[3 -8] In previous phytochemical investigations, terpenoids are considered to be the characteristic phytochemicals of A. crispa with significant cytotoxic activity. [9] In order to further search potentially cytotoxic terpenoids from A. crispa, an extract of the roots of this species was chemically investigated. Herein, the isolation and structural elucidation of three new terpenoids ardisiacrispins G-I (1, 4, 8) and eight known derivatives (Figure 1) and cytotoxic activity were reported.…”

“…In modern pharmacology research, the roots of A. crispa exhibited abundant biological activities, such as anti‐tumor, anti‐inflammatory and suppressed angiogenesis effects [3–8] . In previous phytochemical investigations, terpenoids are considered to be the characteristic phytochemicals of A. crispa with significant cytotoxic activity [9] . In order to further search potentially cytotoxic terpenoids from A. crispa , an extract of the roots of this species was chemically investigated.…”

The complete chloroplast genome sequence of Ardisia crispa Thunb.

“…The root of A. crispa has primarily been used as traditional medicines for a long time by Asians (Yin et al. 2022 ). For instance, it is widely used in Malaysia to treat diseases such as ever, pain, swelling, rheumatism, and blood circulation (Blin et al.…”

“…The triterpenoid saponins inside of the A. crispa root may be the main components that exert cytotoxicity in the biological activities of anti-tumor (Yin et al. 2022 ). In Guangxi province of China, A. crispa is also called ‘Zhu Ye Feng’, which is a kind of classical Yao Medicine (Hou et al.…”