Diterpenoid fingerprints in pine foliage across an environmental and chemotypic matrix: Isoabienol content is a key trait differentiating chemotypes

Abstract

Diterpenoids constitute an important part of oleoresin in conifer needles, but the environmental and genetic controls on diterpenoid composition are poorly known. We studied the presence of diterpenoids in four pine populations spanning an extensive range of nitrogen (N) availability. In most samples, isoabienol was the main diterpenoid. Additionally, low contents of (Z)-biformene, abietadiene isomers, manoyl oxide isomers, labda-7,13,14-triene and labda-7,14-dien-13-ol were quantified in pine needles. According to the occurrence and content of diterpenoids it was possible to distinguish 'non diterpenoid pines', 'high isoabienol pines', 'manoyl oxide - isoabienol pines' and 'other diterpenoid pines'. 'Non diterpenoid pines', 'high isoabienol pines' and 'other diterpenoid pines' were characteristic to the dry forest, yet the majority of pines (>80%) of the bog Laeva represented 'high isoabienol pines'. 'Manoyl oxide - isoabienol pines' were present only in the wet sites. Additionally, orthogonal partial least-squares analysis showed, that in the bogs foliar nitrogen content per dry mass (N) correlated to diterpenoids. Significant correlations existed between abietadienes, isoabienol and foliar N in 'manoyl oxide - isoabienol pines', and chemotypic variation was also associated by population genetic distance estimated by nuclear microsatellite markers. Previously, the presence of low and high Δ-3-carene pines has been demonstrated, but the results of the current study indicate that also diterpenoids form an independent axis of chemotypic differentiation. Further studies are needed to understand whether the enhanced abundance of diterpenoids in wetter sites reflects a phenotypic or genotypic response.

Ballodiolic Acid A and B: Two New ROS, (•OH), (ONOO−) Scavenging and Potent Antimicrobial Constituents Isolated from Ballota pseudodictamnus (L.) Benth.

“…Diterpenes and diterpenoids are reported for antiviral, antibacterial, antiparasitic, antifungal, and antiprotozoal action. Some terpenoids are toxic to microorganisms and insects and play an important role in plant protection [ 43 , 44 ]. Extract of Stevia and its glycosides (for example, steviol), in addition to their value as sweeteners, has a therapeutic effect against cystic fibrosis.…”

Verification of Chromatographic Profile of Primary Essential Oil of Pinus sylvestris L. Combined with Chemometric Analysis

“…The identified diterpenoids belong to the labdane, abietane or pimarane group. The diterpenoid profile among the primary EOs was similar, although the abundance of the diterpenoids is also influenced by different environmental factors, genetic conditions and chemical reactivity [ 33 ]. The most intense peak of the diterpene area of 1 , 6 , 18 , 21 – 23 , 25 , 26 , 31 and 33 – 36 was identified as isoabienol, which belongs to the abienol group.…”

“…Pinus sylvestris L. (PS) is the most widely distributed pine due to its ability to adapt to various climatic conditions and to grow on different soil types [ 3 , 4 ]. Furthermore, this species shows extensive genetic variability and can mainly be categorized into 3-carene, α-pinene or isoabienol chemotypes [ 33 ]. Closely related pine trees are Pinus cembra L. (PC), Pinus mugo T URRA (PMu) or Pinus nigra J. F. A RNOLD (PN) (phylogenetic tree, Figure S1 ).…”

Terpenoids as Potential Geroprotectors

“…Diterpenes are diterpenoids and have antiviral, antibacterial, antiparasitic, and antifungal, antiprotozoal action. Some terpenoids are toxic to microorganisms and insects and play an important role in plant protection [ 220 , 227 ]. Extract of Stevia and its glycosides (for example, steviol), in addition to their value as sweeteners, have a therapeutic effect against cystic fibrosis.…”