Nitrogen-Containing Volatiles from Marine Salinispora pacifica and Roseobacter-Group Bacteria

Abstract

Bacteria can produce a wide variety of volatile compounds. Many of these volatiles carry oxygen, while nitrogen-containing volatiles are less frequently observed. We report here on the identification and synthesis of new nitrogen-containing volatiles from Salinispora pacifica CNS863 and explore the occurrence in another bacterial lineage, exemplified by Roseobacter-group bacteria. Several compound classes not reported before from bacteria were identified, such as dialkyl ureas and oxalamides. Sulfinamides have not been reported before as natural products. The actinomycete S. pacifica CNS863 produces, for example, sulfinamides N-isobutyl- and N-isopentylmethanesulfinamide (5, 6), urea N,N'-diisobutylurea (16), and oxalamide N,N'-diisobutyloxalamide (17). In addition, new imines such as (E)-1-(furan-2-yl)-N-(2-methylbutyl)methanimine (8) and (E)-2-((isobutylimino)methyl)phenol (13) were identified together with several other imines, acetamides, and formamides. Some of these compounds including the sulfinamides were also released by the Roseobacter-group bacteria Roseovarius pelophilus G5II, Pseudoruegeria sp. SK021, and Phaeobacter gallaeciensis BS107, although generally fewer compounds were detected. These nitrogen-containing volatiles seem to originate from biogenic amines derived from the amino acids valine, leucine, and isoleucine.

Flowers of European pear release common and uncommon volatiles that can be detected by honey bee pollinators

“…The mass spectra resembled those of (E)-N-(3-methylbutyl)-1-phenylmethanimine ( Fig. 1C; Table 1), but with a shift of the intense ions m/z 91 and 118 in the latter to m/z 92 and 119 in the newly identified pear compounds (Harig et al 2017). This shift suggested the target compounds to be imines, derived from 3-pyridinecarboxaldehyde present in the pear volatiles.…”

“…Most pear cultivars (Pyrus communis L.) rely on insect pollination, as flowers are self-incompatible (Schanderl 1937;Schumacher 1989;Free 1993;Delaplane et al 2000;Jackson 2003). The Western honey bee (Apis mellifera L.) occurs in most of the (commercial) orchards and is overall the most important pollinator of pear (Stephen 1958;McGregor 1976;Free 1993;Delaplane et al 2000;Jackson 2003;Monzón et al 2004). Only in some orchards is the solitary bee Osmia cornuta used as managed pollinator, and in these cases as effective as the honey bee (Monzón et al 2004).…”

“…Pollination by animals is one of the most important ecosystem services (Ollerton et al 2011), as not only wild plants but also agricultural crops benefit from animal pollination (McGregor 1976;Free 1993;Williams 1994 in Klein et al 2007;Delaplane et al 2000;Khan and Khan 2004;Klein et al 2007). Klein et al (2007) described an increase in yield for 39 crops due to animal pollination, which overall is responsible for an estimated 35% of global food production.…”

“…Klein et al (2007) described an increase in yield for 39 crops due to animal pollination, which overall is responsible for an estimated 35% of global food production. The most important pollinators of fruit crops are social honey bees (McGregor 1976;Free 1993;Delaplane et al 2000). Nonetheless, the contribution of bumble bees (Shipp et al 1994;Dogterom et al 1998;Dag et al 2006) and other wild bees to the pollination of crops is substantial as well (Free 1993;Maccagnani et al 2003;Monzón et al 2004;Holzschuh et al 2012;Rader et al 2016).…”

Microbe-driven chemical ecology: past, present and future

“…Recently, Schulz-Bohm et al have shown that volatile compounds can diffuse within 20 minutes over distance of >12cm, which is a veritable distance for most soil microorganisms [11]. Despite their mostly hydrophobic nature, volatiles are widely produced in both terrestrial and aquatic environments by marine plankton, algae, animals and marine bacteria [12][13][14][15].…”