Cyperane and eudesmane-type sesquiterpenoids from Chinese liverwort and their anti-diabetic nephropathy potential

Abstract

Six new sesquiterpenoids, including cyperane (1 and 2) and eudesmane (3–6) types, and one known eudesmane derivative (7), were isolated from the Chinese liverwort Chiloscyphus polyanthus var. rivularis (Schrad.) Nees.

Unprecedented 4,9‐Seco‐Oplopanane and Seven Drimane Sesquiterpenoids from the Chinese Liverwort Lejeunea flava (Sw.) Nees

“…Sesquiterpenoids from liverworts exhibit diverse biological functions, [1,2] including anti‐inflammatory, [3] anti‐diabetic nephropathy, [4] cytotoxicity, [5] radical scavenging effects, [6] and antimicrobial activity [7] . Lejeuneaceae are the largest family of liverworts, that have been chemically studied systematically, and separated into nearly 1000 species in 91 genera according to chemotaxonomy [8] .…”

Unified Approach to ent-Eudesmane-Type Terpenoid Synthesis: Total Synthesis of Sinupol and Eutyscoparin A

“…-3.6 (c 0.32, CHCl3). IR (neat): 2930, 2847, 1714, 1633, 1453, 1274 cm −1 .1 H NMR (400 MHz, CDCl3): δ = 7.62 (dd, J = 11.6, 15.1 Hz, 1H),6.05 (d, J = 11.6 Hz, 1H), 5.80 (d, J = 15.1 Hz, 1H), 5.32 (m, 1H), 4.20 (q, J = 7.2 Hz, 2H), 2.18-2.03 (m, 2H), 2.02-1.85 (m, 2H), 1.91 (d, J = 0.9 Hz, 3H), 1.71 (m, 1H), 1.68-1.44 (m, 3H), 1.60 (s, 3H), 1.41-1.17 (m, 4H), 1.29 (t, J = 7.2 Hz, 3H), 0.82 (s, 3H) 13. C NMR (100 MHz, CDCl3): δ = 167.6 (C), 154.4 (C), 141.2 (CH), 134.7 (C), 121.8 (CH), 121.2 (CH), 119.2 (CH), 60.1 (CH2), 49.3 (CH), 46.7 (CH), 40.0 (CH2), 37.9 (CH2), 32.3 (C), 28.5 (CH2), 26.3 (CH2), 22.9 (CH2), 21.1 (CH3), 15.7 (CH3), 15.6 (CH3), 14.3 (CH3).…”

“…1 Among them, identification from Asteraceae is particularly common, and more than 1000 eudesmane sesquiterpenoids have already been reported. 2 This ever-growing class of important secondary metabolites exhibits significant biological activities: plant growth inhibitory, 3 insect antifeedant, 4 antibacterial, 5 anti-diabetic nephropathic, 6 and anti-inflammatory. 7 Most eudesmane-type sesquiterpenoids have a general absolute configuration of 5R, 7R, and 10R, but some eudesmane-type sesquiterpenoids have opposite absolute configurations that correspond to the enantiomers.…”

Cyperane-Type and Related (Nor)Sesquiterpenoids from the Root Bark of Acanthopanax gracilistylus and Their Inhibitory Effects on Nitric Oxide Production

“…C yperane-type sesquiterpenoids are relatively rare in nature, and only 14 representatives of this class have so far been reported from the families Cyperaceae, 1,2 Asteraceae, 3−8 Lauraceae, 9,10 Lamiaceae, 11 and Geocalycaceae 12 (Table S1, Supporting Information). Among those identified, cyperolone is a plant growth inhibitor isolated from the tubers of Cyperus rotundus.…”

“…10 In addition, (3S,5S,7R,10S)-and (3R,5R,7R,10S)-3,7-dihydroxycyperan-4-one, obtained from the Chinese liverwort, exhibited antidiabetic nephropathy activities. 12 In recent years, cyperane-type natural products have attracted the attention of synthetic chemists due to their potential bioactivities. 14 The root bark of Acanthopanax gracilistylus (Araliaceae), a well-known traditional Chinese medicine (TCM) with the Chinese name "Wu-Jia-Pi" (Acanthopanacis Cortex), is widely used to treat arthritis, rheumatism, lameness, and paralysis.…”