Hexahydrofarnesyl Acetone-Rich Extractives from Hildegardia barteri

The variation in habitat has a direct effect on the plants and as a consequence, changes their content of the bioactive constituents and biological activities. The present study aimed to explore the variation in the essential oils (EOs) and phenolics of Heliotropium curassavicum collected from the coastal and inland habitats. Additionally, we determined their antioxidant and allelopathic activity against the weed, Chenopodium murale. Fifty-six compounds were identified as overall from EOs, from which 25 components were identified from the coastal sample, and 52 from the inland one. Sesquiterpenes were the main class in both samples (81.67% and 79.28%), while mono (3.99% and 7.21%) and diterpenes (2.9% and 1.77%) represented minors, respectively. Hexahydrofarnesyl acetone, (-)-caryophyllene oxide, farnesyl acetone, humulene oxide, farnesyl acetone C, and nerolidol epoxy acetate were identified as major compounds. The HPLC analysis of MeOH extracts of the two samples showed that chlorogenic acid, rutin, and propyl gallate are major compounds in the coastal sample, while vanilin, quercetin, and 4′,7-dihydroxyisoflavone are majors in the inland one. The EOs showed considerable phytotoxicity against C. murale with IC50 value of 2.66, 0.59, and 0.70 mg mL−1 for germination, root, and shoot growth, respectively from the inland sample. While the coastal sample attained the IC50 values of 1.58, 0.45, and 0.66 mg mL−1. MeOH extracts revealed stronger antioxidant activity compared to the EOs. Based on IC50 values, the ascorbic acid revealed 3-fold of the antioxidant compared to the EO of the coastal sample and 4-fold regarding the inland sample. However, the ascorbic acid showed 3-fold of the antioxidant activity of the MeOH extracts of coastal and inland samples. Although H. curassavicum is considered as a noxious, invasive plant, the present study revealed that EO and MeOH extracts of the H. curassavicum could be considered as promising, eco-friendly, natural resources for antioxidants as well as weed control, particularly against the weed, C. murale.

Section: Resultsmentioning

confidence: 99%

Habitat Affects the Chemical Profile, Allelopathy, and Antioxidant Properties of Essential Oils and Phenolic Enriched Extracts of the Invasive Plant Heliotropium Curassavicum

Abd‐ElGawad

Elshamy

Al‐Rowaily

et al. 2019

“…Hexahydrofarnesyl acetone (phytone) and hexadecenoic acid (palmitic acid) are important components in both samples of the EOs analyzed in this study. According to the literature, phytone shows strong antimicrobial activity and broad-spectrum inhibition against various fungal strains [15]. Palmitic acid has antioxidant, nematidical, pesticide, antiandrogenic, hemolytic and 5-alpha reductase activities [16].…”

Section: Gas Chromatography and Mass Spectrometry (Gc-ms) Analysis Ofmentioning

confidence: 99%

Endemic Veronica saturejoides Vis. ssp. saturejoides–Chemical Composition and Antioxidant Activity of Free Volatile Compounds

Nazlić

Kremer

Grubešić

et al. 2020

Chemical profile and antioxidant activity of the species Veronica saturejoides Vis. ssp. saturejoides (Plantaginaceae)—which is endemic to Croatia, Bosnia and Herzegovina and Montenegro —were investigated. Volatile compounds produced by glandular trichomes (composed of one stalk cell and two elliptically formed head cells according to scanning electron microscope investigation) were isolated from the plants collected in two locations. Additionally, as a part of specialized metabolites, total polyphenols, total tannins, total flavonoids and total phenolic acids were determined spectrophotometrically. In the lipophilic volatile fractions-essential oils, the most abundant compounds identified were hexahydrofarnesyl acetone, caryophyllene oxide and hexadecanoic acid. In total, the class of oxygenated sesquiterpenes and the group of fatty aldehydes, acids and alcoholic compounds dominated in the essential oils. In the hydrophilic volatile fractions-hydrosols, the most abundant compounds identified were trans-p-mentha-1(7),8-dien-2-ol, allo-aromadendrene and (E)-caryophyllene. A group of oxygenated monoterpenes and the sesquiterpene hydrocarbons dominated in the hydrosols. Antioxidant activity of essential oils and hydrosols was tested with two methods: 2,2′-diphenyl-1-picrylhydrazyl (DPPH) and oxygen radical absorbance capacity (ORAC). Essential oils showed higher antioxidant activity than hydrosols and showed similar antioxidant activity to Rosmarinus officinalis essential oil. Obtained results demonstrate that this genus is a potential source of volatiles with antioxidant activity.

“…Only one apocarotenoid-derived compound, hexahydrofarnesyl acetone, was identified with a high relative concentration (7.92%), whereas it was completely absent from the other reported ecospecies of C. amblyocarpa [ 26 , 27 , 28 , 37 ]. Hexahydrofarnesyl acetone is a widely distributed major compound in the EOs of several plants such as Bassia muricata [ 10 ], Heliotropium curassavicum [ 33 ], Hildegardia barteri [ 39 ], Trianthema portulacastrum [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

Chemical Composition, Allelopathic, Antioxidant, and Anti-Inflammatory Activities of Sesquiterpenes Rich Essential Oil of Cleome amblyocarpa Barratte & Murb.

Abd‐ElGawad

Elgamal

El‐Amier

et al. 2021

The integration of green natural chemical resources in agricultural, industrial, and pharmaceutical applications allures researchers and scientistic worldwide. Cleome amblyocarpa has been reported as an important medicinal plant. However, its essential oil (EO) has not been well studied; therefore, the present study aimed to characterize the chemical composition of the C. amblyocarpa, collected from Egypt, and assess the allelopathic, antioxidant, and anti-inflammatory activities of its EO. The EO of C. amblyocarpa was extracted by hydrodistillation and characterized via gas chromatography–mass spectrometry (GC-MS). The chemometric analysis of the EO composition of the present studied ecospecies and the other reported ecospecies was studied. The allelopathic activity of the EO was evaluated against the weed Dactyloctenium aegyptium. Additionally, antioxidant and anti-inflammatory activities were determined. Forty-eight compounds, with a prespondence of sesquiterpenes, were recorded. The major compounds were caryophyllene oxide (36.01%), hexahydrofarnesyl acetone (7.92%), alloaromadendrene epoxide (6.17%), myrtenyl acetate (5.73%), isoshyobunone (4.52%), shyobunol (4.19%), and trans-caryophyllene (3.45%). The chemometric analysis revealed inconsistency in the EO composition among various studied ecospecies, where it could be ascribed to the environmental and climatic conditions. The EO showed substantial allelopathic inhibitory activity against the germination, seedling root, and shoot growth of D. aegyptium, with IC50 values of 54.78, 57.10, and 74.07 mg L−1. Additionally, the EO showed strong antioxidant potentiality based on the IC50 values of 4.52 mg mL−1 compared to 2.11 mg mL−1 of the ascorbic acid as standard. Moreover, this oil showed significant anti-inflammation via the suppression of lipoxygenase (LOX) and cyclooxygenases (COX1, and COX2), along with membrane stabilization. Further study is recommended for analysis of the activity of pure authentic materials of the major compounds either singularly or in combination, as well as for evaluation of their mechanism(s) and modes of action as antioxidants or allelochemicals.