Constituents of the Argentine Liverwort Plagiochila diversifolia and Their Insecticidal Activities

Abstract

Three new compounds, a bicyclogermacrene (1) and two 2,3-secoaromadendrane esters (2 and 3), together with (13S)-13-hydroxylabda-8,14-diene (4), fusicogigantone B (5), 3α,14-diacetoxy-2-hydoxybicyclogermacrene (6), fusicogigantone A (7), neofuranoplagiochilal (8), plagiochiline B (9), furanoplagiochilal (10), trans-nerolidol, spathulenol, α-tocopherol, and (+)-globulol were isolated from an Argentine collection of Plagiochila diversifolia. Their structures were elucidated by extensive mono and bidimensional NMR studies. Compounds 4, 5, and 6, incorporated to the larval diet at 100 μg per g of diet, reduced the larval growth of Spodoptera frugiperda (Lepidoptera: Noctuidae) by 70 ± 25, 57 ± 23, and 33 ± 16%, respectively. Compounds 4 and 5 produced 70% and 60% larval mortality at early instars. The latter also showed antifeedant properties in the Choice Test, with a feeding ratio of 0.54 ± 0.16.

Transcriptome Analysis and Identification of Sesquiterpene Synthases in Liverwort Jungermannia exsertifolia

“…At present, the mining of STSs has attracted extensive attention, and the new STSs have greatly improved the application field of natural products [32]. J. exsertifolia accumulates specific sesquiterpenes, such as aromadendrene and viridiflorol in its essential oils (Table 1) which have biological activities [33]. Therefore, this study attempted to conduct an analysis of the transcriptome of J. exsertifolia in order to find more STSs responsible for the biosynthesis of bioactive sesquiterpenes.…”

Modern Use of Bryophytes as a Source of Secondary Metabolites

“…Metabolites such as marchantin A, plagochilin E, and riccardin C exhibit cytotoxic activities against chemoresistant prostate cancer [3,100]. In addition to the aforementioned active compounds, those with antioxidant [135][136][137], anti-inflammatory [138][139][140], psychoactive [111], antiviral [141], muscle-relaxing [142], neuroprotective [142,143], anti-HIV [144], and insecticidal activities can be distinguished [145,146]. Compounds with nematicidal activity have potential in agricultural industry as natural plant-protection products.…”

Discovery and Anticancer Activity of the Plagiochilins from the Liverwort Genus Plagiochila

“…They also identified plagiochilins D, E and F from P. asplenioides , together with a few related compounds such as furanoplagiochilal, plagiochilal A-B and plaigiochilide [ 28 ] ( Figure 3 ). Similarly, plagiochilins A and B have been identified from P. semidecurrens [ 30 ] and P. diversifolia [ 31 ]. Plagiochilin A was found also in P. elegans , together with isoplagiochilide [ 32 ].…”

“…Another study has investigated the insecticidal activity of natural products isolated from P. diversifolia , but in that case the only plagiochilin tested was plagiochilin B and no activity was reported. In this case, a marked insecticidal action was observed with another epoxide-containing compound called fusicogigantone B, a fusicoccane-type diterpenoid [ 31 ]. Both fusicogigantones A and B, isolated from P. bursata and P. diversifolia , respectively, have been shown to inhibit the growth of another species of Lepidoptera ( Spodoptera frugiperda ) [ 17 , 31 ].…”

“…In this case, a marked insecticidal action was observed with another epoxide-containing compound called fusicogigantone B, a fusicoccane-type diterpenoid [ 31 ]. Both fusicogigantones A and B, isolated from P. bursata and P. diversifolia , respectively, have been shown to inhibit the growth of another species of Lepidoptera ( Spodoptera frugiperda ) [ 17 , 31 ]. Plagiochilin A was shown to display a noticeable antiprotozoal activity, reducing the growth of the amastigote form of Leishmania amazonensis , with an IC 50 value of 7.1 µM.…”