Search

Patrinia scabiosaefolia is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the discovery of nine unique iridoids and iridoid glycosides, including three new iridoids (1-3) and six previously unknown irioid glycosides (5-10), and one known compound (4). Among them, compound 1 was a deformed iridoid, while compounds 3, 5-7, and 10 formed a new ring in their skeletons which was uncommon in this genus. For compound 3, the new ring existed between C-3 and C-10, while a 1,3-dioxane appeared between C-7 and C-10 in compounds 5-7 and 10. Moreover, compound 10 was a bis-iridoid glycoside, which was the first reported in P. scabiosaefolia. And the sugar of irioid glycosides (5-10) was glucose at C-11, except in 9 which had a 5-deoxyglucose moiety. All their structures were confirmed based on the extensive spectroscopic analysis, including IR, UV, HR-ESI-MS, ECD, and 1D- and 2D-NMR experiments. Their cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, SW480 were also tested.

Four undescribed bis-iridoid glycosides, named phukettosides A–D, and one iridoid glycoside, referred to as phukettoside E, were isolated and fully characterized from the leaves of Morinda umbellata L. Phytochemical analysis also revealed the presence of eight known compounds. The structures were determined through extensive analysis of 1D and 2D-NMR spectroscopic and HRMS spectral data, and the absolute configurations of the isolates were deduced through ECD calculations. Biogenetic pathways for the bis-iridoid glycosides, phukettosides A–C, through intermolecular Diels-Alder type reactions, were proposed. The isolated compounds, with the exception of phukettosides B and D, were evaluated against a panel of cancer cell lines (MOLT-3, HuCCA-1, A549, HeLa, HepG2, and MDA-MB-231) and a non-cancerous cell line (MRC-5) for their cytotoxicity. None of the isolates had significant cytotoxic effects on the tested cell lines. [Display omitted] • Bis- and mono-iridoid glycosides were isolated from Morinda umbellata leaves. • The bis-iridoid glycosides probably arise from intermolecular Diels-Alder reactions. • The absolute configurations were confirmed by ECD calculation. • Cancer chemoprevention and the cytotoxicity of the isolates were evaluated. [ABSTRACT FROM AUTHOR]

Six new compounds, including four new lignans, dipsalignan A (1), B–D (3–5), and two new bis-iridoid glycoside dimmers, dipsanosides M (7) and N (8), together with two known compounds (2) and (6), have been isolated from the roots of Dipsacus asper Wall. Their structures were established on the basis of spectroscopic data (MS, 1D, 2D NMR, and CD) and chemical methods. All the isolated compounds were tested against human immunodeficiency virus-1 (HIV-1) integrase inhibition activities, and only compounds 1, 2, 7, and 8 displayed weak activities.

Abstract Four new iridoids (1 – 4), together with three known iridoids (5 – 7), one known flavonoid glycoside, three phenolic acids and one phytosterol were isolated from the roots of Valeriana dioscoridis. Their structures were elucidated by means of NMR spectroscopy and mass spectrometry. This is the first report on the phytochemical composition of the non-volatile constituents of V. dioscoridis and the occurrence of a bis-iridoid glycoside in the genus Valeriana. The antiproliferative effects of the iridoids (1 – 7) were evaluated against three human cancer cell lines of gynacological origin (HeLa, A2780 and T47D) at 10, 30 and 60 μM concentrations, using the MTT assay and they elicited modest antiproliferative activity when compared to the reference agent, cisplatin. Graphical abstract Unlabelled Image [ABSTRACT FROM AUTHOR]

Patrinia scabiosaefolia is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the discovery of nine unique iridoids and iridoid glycosides, including three new iridoids ( 1 - 3 ) and six previously unknown irioid glycosides ( 5 - 10 ), and one known compound ( 4 ). Among them, compound 1 was a deformed iridoid, while compounds 3 , 5 - 7 , and 10 formed a new ring in their skeletons which was uncommon in this genus. For compound 3 , the new ring existed between C-3 and C-10, while a 1,3-dioxane appeared between C-7 and C-10 in compounds 5 - 7 and 10 . Moreover, compound 10 was a bis-iridoid glycoside, which was the first reported in P . scabiosaefolia . And the sugar of irioid glycosides ( 5 - 10 ) was glucose at C-11, except in 9 which had a 5-deoxyglucose moiety. All their structures were confirmed based on the extensive spectroscopic analysis, including IR, UV, HR-ESI-MS, ECD, and 1D- and 2D-NMR experiments. Their cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, SW480 were also tested., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2021 Liu, Niu, Zhou, Meng, Chen, Wang, Hu and Kang.)