Terpenoids and Bibenzyls from Three Argentine Liverworts

Abstract

A new rosane diterpenoid, 3α-hydroxy-5,15-rosadien-11-one (3), was isolated, together with a known rosane diterpenoid, 5,15-rosadiene-3,11-dione (4), and an aromadendrane sesquiterpenoid, ent-cyclocolorenone (5), from the Et2O extract of an unidentified Argentine liverwort Anastrophyllum species. Moreover, four known sesquiterpene lactones 6–9 and two known bibenzyls 10, 11 were isolated from the Et2O extracts of Argentine Frullania brasiliensis and Radula voluta, respectively. The structures of compounds 3–11 were determined by the use of NMR techniques.

Natural sesquiterpenoids

“…The bioproduction of patchoulol and 7-epi-a-selinene by recombinant microorganism expressing Valeriana jatamansi sesquiterpene synthase has been patented. 405 and Porella chilensis. 404 The carabrane sesquiterpene 513 has been obtained from Carpesium faberi.…”

Transcriptome analysis of polycyclic sesquiterpene biosynthesis in Leonurus sibiricus L.

“…In recent years, a number of novel components have been isolated and purified from plants and have a variety of biological activities [15,16], many of which can be used as lead compounds for drug development [17,18]. Sesquiterpene is a kind of the most abundant substance existing in the plant essential oils which often have a strong odor and may protect themselves from animals, insects and parasites [19,20].…”

Diterpenoids From the Argentine and Malaysian Liverworts Anastrophyllum and Jungermannia Species

“…Here we wish to report the newly isolated lipophilic terpenoids and their structural elucidation and biological activity. ent-5,15-Rosadien-3-one (1) and (3S)-ent-5,15rosadien-3-ol (2) were isolated from the ether extract of the unknown Argentine Anastrophyllum species by chromatographic separation, together with two known rosanes, (3S)-ent-3hydroxy-5,15-rosadien-11-one (3) 5 and ent-5,15rosadiene-3,11-dione (4), 6 and a known aromadendrane sesquiterpene ketone, entcyclocolorenone (5), 7,8 as shown in Figure 1. Physical and spectral data were determined by spectral analyses and chemical derivatives.…”

“…The stereostructure of compound 3 has already been reported as 3α-hydroxy-5,15-rosadien-11-one by our group from circular dichroism (CD) spectroscopy measurements, which showed a positive Cotton effect (λ max = 297); however, the absolute configuration remains to be clarified. 5 Therefore, compound 3 was derived to both (R)- (6) and (S)-2-methoxy-2trifluoromethylphenylacetic acid (MTPA) (7) esters, and the 1 H nuclear magnetic resonance (NMR) spectrum of each derivative was measured. 9 The Δδ values in the 1 H NMR spectra are shown in Figure 2.…”