Abstract
Three new polyhydroxylated oleanane triterpenoids, cissatriterpenoid A−C (1−3), along with one known analogue (4), were isolated from the whole plant of Cissampelos pareira var. hirsuta. Their chemical structures were elucidated by extensive spectroscopic data (IR, HR-ESI-MS, 1H-NMR, 13C-NMR, DEPT, 1H-1H COSY, HSQC, HMBC, NOESY) and the microhydrolysis method. The isolation of compounds 1–4 represents the first report of polyhydroxylated oleanane triterpenoids from the family Menispermaceae. All isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines, and the inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Compound 3 showed the most potent cytotoxic activities against the A549, SMMC-7721, MCF-7, and SW480 cell lines, with IC50 values of 17.55, 34.74, 19.77, and 30.39 μM, respectively, whereas three remaining ones were found to be inactive. The preliminary structure–activity relationship analysis indicated that the γ-lactone ring at C-22 and C-29, and the olefinic bond at C-12 and C-13 were structurally required for the cytotoxicity of polyhydroxylated oleanane triterpenoids against these four cell lines. Based on lipid-water partition coefficients, compound 3 is less lipophilic than 1 and 4, which agrees with their cytotoxic activities. This confirms the potential of C. pareira var. hirsuta in the tumor treatment.
Highlights
Publisher’s Note: MDPI stays neutralSo far, cancer has become the most common disease threatening human health and life worldwide
Phytochemical investigation of C. pareira var. hirsuta resulted in the isolation of three new polyhydroxylated oleanane triterpenoids, cissatriterpenoid A−C (1−3), and one known analogue (4)
More than 500 polyhydroxylated oleanane triterpenoids have been found in the families Cyrillaceae, Hippocastanceae, Loganiaceae, Myrsinaceae, Pittosporaceae, Sapindaceae, Symplocaeae, Styracaceae, Theaceae, Lecythidaceae, and Umbelliferae since 1934 [17]
Summary
Cancer has become the most common disease threatening human health and life worldwide. Oleanane triterpenoids are phyrophosphate oligomers of six isopentenyl structure units They possess extensive and important biological activities, such as cardio-, hepato-, and gastro-protective, anti-inflammatory, antiviral, antidiabetic, antimicrobial, antiparasitic, analgesic and wound-healing effects, as well as inducing apoptosis in cancer cells [2]. Oleanane triterpenoids exhibit cytotoxic effects in many cancer cell lines, such as oral, esophageal, liver, brain, colorectal, ovary, breast, lung, skin cancers, and leukemia [4] They regulate multiple cellular signaling pathways, including nuclear factor-KB, AKT, signal transducer and activator of transcription 3, mammalian target of with regard to jurisdictional claims in published maps and institutional affiliations. Our previous chemical and pharmacological investigations on C. pareira pareira hirsuta revealed presence of polyhydroxylated pregnane glycosides, var. As our ongoing research for potential cytotoxic natural products products from traditional medicines, new polyhydroxylated oleanane from traditional. Are reported and cytotoxicity, and NO inhibitory of those isolates are reported
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