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Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Yoshiaki Noma, Yoshinori Asakawa
Fermentation of citronellyl acetate with A. niger resulted in the formation of a major metabolite, 8-hydroxycitronellol, accounting for approximately 60% of the total transformation products, accompanied by 38% citronellol. Fermentation of geranyl acetate with A. niger gave geraniol and 8-hydroxygeraniol (50% and 40%, respectively, of the total transformation products).
Chemistry of Syzygium cumini
Published in K. N. Nair, The Genus Syzygium, 2017
Acyclic monoterpenoids are derivatives of 2,6-dimethyloctane, a head-to-tail combination of two isoprenes. β-Ocimene (1) and its geometrical isomer (E)-β-ocimene (2), (Z)-β-ocimene (3), β-myrcene (4), and alloocemene (5) are the most common nonoxygenated acyclic monoterpenoids that are formed by elimination of the pyrophosphate group from geranyl pyrophosphate. Geranyl acetate (6), geranyl butyrate (7), and geranyl isobutyrate (8) are esters of geraniol reported in EOs. Additional rearrangements and oxidation of geranyl pyrophosphate provide compounds such as citronellal (9), citronellyl acetate (10), linalool (11), geraniol (12), linalyl acetate (13), and linalyl propionate (14), along with neryl acetate (15). A complete list of acyclic monoterpenoids spotted in EOs from different morphological parts is given in Table 6.2 and Figure 6.1.
An Overview of Hepatocellular Carcinoma with Emphasis on Dietary Products and Herbal Remedies
Published in Nutrition and Cancer, 2022
Deepa S. Mandlik, Satish K. Mandlik
Pepper extracts decreased cell viability of rat hepatoma McA-RH7777 cells in an In Vitro study though showing no cytotoxicity. The intracellular accumulation of ROS was blamed for the selective cytotoxicity (89). By immunomodulation and promoting apoptosis, the glycoprotein isolated from Zanthoxylum piperitum may be able to prevent chemical-induced liver carcinogenesis. The glycoprotein (20 mg/kg) increased the expression of granzyme B, perforin and natural killer cell activities, as well as pro-apoptotic factors (caspase-3, bid and cytochrome c) in the liver of DEN-treated Balb/c mice (90). In Vitro experiments with the cancer cell line revealed that administration of Zanthoxylum avicennae extract in rats inhibited cell proliferation by inducing cell cycle arrest and apoptosis, as well as preventing cell metastasis and invasion by downregulating MMP-2/-9 (91). Following that, mechanistic research showed that phosphatase 2 A activation was responsible for the anti-tumor effects. The dried pericarp of Zanthoxylum schinifolium was used to extract the essential oil, which contained geranyl acetate, sabinene and citronella. In HepG2 cells, this volatile extract stimulated ROS production in a dose-dependent manner, resulting in increased apoptotic cell death (92).
Lemongrass essential oil and its components cause effects on survival, locomotion, ingestion, and histological changes of the midgut in Anticarsia gemmatalis caterpillars
Published in Toxin Reviews, 2022
Angelica Plata-Rueda, Muhammad Fiaz, Bruno Pandelo Brügger, Veronica Cañas, Rogerio Pereira Coelho, José Cola Zanuncio, Luis Carlos Martínez, José Eduardo Serrão
The LEO and its most abundant components cause mortality, compromise locomotion and food consumption and histopathological changes in the midgut of the VBM caterpillars under laboratory conditions. The LEO, citral, and geranyl acetate were toxic to VBM and exerted a strong effect through oral exposure. The LEO and its components lead to VBM mortality in a concentration–dependent manner, as demonstrated in other Noctuidae caterpillars such as Mentha pulegium (Lamiaceae) to Anarta trifolii Hufnagel (Darabi and Khajehali 2017), Piper aduncum (Piperaceae) to Chrysodeixis includens Walker (Sanini et al. 2017), and Petroselinum crispum (Apiaceae) to Pseudaletia unipuncta Haworth (Sousa et al. 2015). The VBM caterpillars exposed to different concentrations of LEO or components reduced insect mobility, muscle contraction, unrecoverable paralysis, and consequently, death. In this context, symptoms in VBM were similar as caused by terpenoid neurotoxins found in plant essential oils (Keane and Ryan 1999, Enan 2001). The LD50 of three compounds here tested to VBM are low, ca. 10 µg insect−1, exhibit toxicity against caterpillars and mortality increase at higher concentrations, reinforcing their potential to control this pest.
Phytochemical and biological activities of some Iranian medicinal plants
Published in Pharmaceutical Biology, 2022
Salome Dini, Qihe Chen, Faezeh Fatemi, Younes Asri
D. kotschyi (Figure 1(J)) aerial parts are used in traditional medicine to treat stomach, headache, toothache and liver disorders (Heydari et al. 2019; Fallah et al. 2020). The chemical composition and antioxidant activity of D. kotschyi essential oil were analysed by DPPH and GC/MS methods, respectively. The results showed that the essential oil containing neral geranial, geranyl acetate and α-pinene had good antioxidant potential (Ashrafi et al. 2017; Fallah et al. 2020). The essential oils from cultivated and wild D. kotschyi were tested for their inhibitory effects against 12 microbial strains by MIC and MBC tests. This activity was more marked against Gram-positive bacteria, while, essential oil from the wild was the most effective to halt C. albicans growth, the essential oil from crops was more marked against Gram-positive bacteria (B. subtilis) (Ghavam et al. 2021). Ashrafi et al. (2017) reported that D. kotschyi essential oil showed the greatest bactericidal activities against the highly susceptible strains of most Gram-positive organisms (except E. faecalis) with MIC values of 80–160 μg/mL and a few Gram-negative organisms; Salmonella typhi, S. paratyphi and S. enterica (80–160 μg/mL). In a comparative study, the antimicrobial activities of D. polychaetum Bornm., D. kotschyi and D. multicaule Montbret & Aucher ex Benth. were investigated wherein D. kotschyi essential oil with MIC of 200 μg/mL exhibited the strongest antimicrobial activity against S. epidermidis (Khodaei et al. 2018). D. kotschyi essential oil inhibitory effects against K. pneumonia as the third leading cause of hospital-acquired pneumonia were reported which can be replaced with conventional antibiotics such as amoxicillin (Shakib et al. 2018). In an investigation, the chemical composition and antibacterial efficacy of D. kotschyi essential oil were isolated by three different techniques (HD, solvent-free microwave extraction (SFME) and MAHD). The lowest MICs (2 mg/mL) were of the essential oil extracted by MAHD and SFME against S. aureus. However, the maximal limonene compounds were found in the essential oil obtained by HD (Moridi Farimani et al. 2017).