Phenylethylpyranone and Aristolochic Acid Derivatives from Aristolochia urupaensis

Abstract

A new pyranone, (S)-2-(4-hydroxyphenylethyl)-6-methyl-2,3-dihydro-4H-pyran-4-one, with unusual carbon skeleton, and three new aristolochic acid derivatives (7-O-methylaristolochic acid F, sodium 7-O-methylaristolochate F and sodium aristolochate F) were isolated from Aristolochia urupaensis (Aristolochiaceae) stems together with 31 known compounds. The structures of the compounds were determined by spectroscopic analyses, including Fourier transform infrared (FTIR) and 1D and 2D nuclear magnetic resonance (NMR) techniques, and high-resolution mass spectrometry (HRMS).

The isolation-biological activities (2014–2022), bio, semi, total synthesis (1978–2022) and SAR studies of a potential naturally engineered scaffold aristolactam

“…The isolated aristolactams from the ethanolic and ethanolic Soxhlet extracts of stems of Aristolochia urupaensis (Holzbach et al (2017)) were identified as aristolactam IIIa N -β-glucoside 76 , aristolactam II 43 , cepharanone A N -β-glucoside 77 , and aristolactam IIIa 57 . 45 A systematic bioassay guided fractionation of the ethanolic extract from the stem bark of Goniothalamus marcanii Craib by Thanuphol et al (2018) resulted in the isolation of three known aristolactam alkaloids namely, piperolactam C 53 , cepharanone B 44 and taliscanine 78 . 46 The cytotoxic activities of the isolated compounds against human tumor cell lines have been evaluated through the SRB assay by using doxorubicin.…”

Recent developments in detoxication techniques for aristolochic acid-containing traditional Chinese medicines

“…Nowadays, AAs are considered to be one of the most potent carcinogens, especially AA-I and AA-II. [3][4][5] Although the true carcinogenic mechanism has not been fully identied, it is generally acknowledged that AA-I and AA-II are both important carcinogens and have a relatively high content compared to other AA analogues in most AA-containing herbs. Meanwhile, the cytotoxic data suggests that the nitro and methoxy groups are determinants of the nephrotoxicological potency.…”

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

“…Phenanthrene is a polycyclic aromatic hydrocarbon which contains three benzene rings. The phenanthrenes can be used as fundamental building blocks or intermediates in the synthesis of complex natural products such as tuberosinone [1], aristolactam Ia [2] and (−)- R -tylophorine [3] (Fig. 1).…”