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Chemistry of Essential Oils
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Figure 6.29 shows some of the plant-derived feedstocks used in the synthesis of lipids and polyketides (Sell, 2006). Rapeseed oil provides erucic acid (173) that can be ozonolyzed to give brassylic acid (174) and heptanal (175), both useful building blocks. The latter can also be obtained, together with undecylenic acid (176), by pyrolysis of ricinoleic acid (177) that is available from castor oil. Treatment of undecylenic acid (176) with acid leads to movement of the double bond along the chain and eventual cyclization to give γ-undecalactone (178), which has been found in narcissus oils. Aldol condensation of heptanal (175) with cyclopentanone, followed by Baeyer–Villiger oxidation, gives δ-dodecalactone (179), identified in the headspace of tuberose. Such aldol reactions, followed by appropriate further conversions, are important in the commercial production of analogues of methyl jasmonate (26) and jasmone (27).
Environmental Factors Impacting Bioactive Metabolite Accumulation in Brazilian Medicinal Plants
Published in Luzia Valentina Modolo, Mary Ann Foglio, Brazilian Medicinal Plants, 2019
Camila Fernanda de Oliveira Junkes, Franciele Antonia Neis, Fernanda de Costa, Anna Carolina Alves Yendo, Arthur Germano Fett-Neto
Biotic responses are normally mediated by signaling compounds, such as jasmonic acid (JA), jasmonoyl isoleucine (Ile-JA) and methyl jasmonate (MeJA), synthesized from linolenic or hexadecatrienoic acids starting with lipoxygenase (LOX) activity. JA and related compounds have a key role in regulation of herbivory and wounding responses by modulating global changes in gene expression. Another example of a major biotic signaling compound is salicylic acid (SA) and its methyl analog, methyl salicylate (MeSA), which have been shown to take part in defense signaling against pathogens, leading to systemic acquired resistance (SAR) and providing long-term defense (Heil and Ton, 2008). Both JA and SA may co-participate and cross talk in herbivory and pathogen responses. Ethylene (ET) also has an important role in plant protection, acting as virulence factor of pathogens and signaling compound in disease resistance, depending on the situation (van Loon et al., 2006). The simulation of herbivory by applying mechanical damage can induce the formation of JA and ET (Bailey et al., 2005). Besides, SA or JA exposure triggers events such as production of ROS and increased cytoplasmic Ca2+, which can stimulate certain biochemical reactions and production of secondary metabolites (Lin et al., 2001) (see Table 6.3).
Preclinical Antidepressant-Like Effects of Terpenes, Polyphenolics, and Other Non-Flavonoid Phytochemicals
Published in Scott Mendelson, Herbal Treatment of Major Depression, 2019
Methyl jasmonate is a single-ringed, cyclopentane-containing organic acid released by certain plants, including Jasminum sambac, in response to external stress, injury, or pathogenic invasions. Interestingly, this is also a role played by resveratrol in plants. Both acute128 and sub-chronic129 intraperitoneal administration of methyl jasmonate decreased immobility of mice in the forced swim and tail suspension tests. Sub-chronic intraperitoneal administration of methyl jasmonate also produced antidepressant-like effects in mice injected with lipopolysaccharide. It lowered serum corticosterone levels, and reduced concentrations of malondialdehyde and TNF-α in brain homogenate. Brain levels of glutathione were increased.130 In mice subjected to chronic unpredictable stress, methyl jasmine exhibited a so-called “adaptogenic” effect. It reduced serum corticosterone levels, attenuated oxidative stress and malondialdehyde levels in brain tissue, maintained glutathione levels, and decreased neuronal cell loss.131
Targeting glucose metabolism to develop anticancer treatments and therapeutic patents
Published in Expert Opinion on Therapeutic Patents, 2022
Yan Zhou, Yizhen Guo, Kin Yip Tam
Jasmonates (a plant stress hormones family) and some of their synthetic derivatives exhibited anticancer effects both in vitro and in vivo [43,44]. O Fingrut and E Flescher found in 2002 that jasmonic acid (JA) and methyl jasmonate (MJ) induced apoptosis in lymphoblastic leukemia cells and suppressed cell proliferation, as well as tumor growth in various human cancer cell lines [45]. In 2018, Vered Behar’s team reported methods of using HK2/mitochondria-detaching compounds, including jasmonate derivatives and piperazine derivatives, as well as pharmaceutical compositions for treating, inhibiting, or suppressing a HK2-expressing cancer [14]. Among these compounds, it was found that one of the Jasmonate derivatives (1–9) inhibited colony formation and decreased cell viability of CTCL tumor cells in a dose-dependent manner (0.50–3.00 µM). In addition to that, 1–9 was reported to be a selective HK2 inhibitor with minimal effect on HK1.
Edible Tuber Amorphophallus paeoniifolius (Dennst.) Extract Induces Apoptosis and Suppresses Migration of Breast Cancer Cells
Published in Nutrition and Cancer, 2021
Munmi Majumder, Manoj Sharma, Siddhartha Maiti, Rupak Mukhopadhyay
Identifying constituent compounds of an active extract is important to correlate association with anticancer effect. HR-LCMS analysis of the active ethyl acetate fraction of the extract showed the presence of five active compounds with reported anticancer activities. Among these compounds, Pyridoxine (Vitamin B6), in combination with other vitamins and zinc, showed anticancer activity against bladder cancer (13). The active form, pyridoxine 5′-phosphate, targeted pyridoxine 5′-phosphate oxidase and down regulated its expression in ovarian cancer cells leading to reduced proliferation (38). The flavonoid Cosmosiin induced apoptosis in stomach cancer cells and reduced risk of breast cancer (14). Fisetin, a well-known flavonoid, showed anticancer, and antimetastatic activity on various cancer cell lines like HL-60 (39), AsPC‐1 (40), SiHa and CaSki (41), HT-29 (42), MCF-7 (15). Plant stress hormone methyl jasmonate, also demonstrated antioxidant activity and inhibited metastasis and angiogenesis of cancer cells (16). Finally, dihydrogambogic acid showed potent anticancer activity against cell lines like MCF-7, HT-29, T47D (17).
Exposure of calcium carbide induces apoptosis in mammalian fibroblast L929 cells
Published in Toxicology Mechanisms and Methods, 2021
Indranil De, Rajesh S, Avneet Kour, Henna Wani, Prashant Sharma, Jiban Jyoti Panda, Manish Singh
When fruits are harvested at fully ripened state, they become softer and get prone to damages and rotting during transportation to far off marketplaces. Such damages impose financial losses on the farmers. To avoid such financial losses, and to retain the texture of fruits during transportation to the final consumer destination, the fruits are often picked unripened and transported to far off places. Upon reaching to the destined markets, the fruits are not ready to be sold at high prices due to being unripe, hence the farmers and vendors confront to the issues of reaching immediate profits. These complications coupled with commercial interests give rise to the practice of artificially ripening the fruits with the use of various chemicals called artificial fruit ripeners (AFRs). AFRs are also used in the pursuit of supplying fruits in off-season as well. Ethylene, methyl jasmonate, ethephon, ethereal, formalin, ethylene glycol, and calcium carbide are some of the chemicals which are generally used for artificial fruit ripening (Islam et al. 2016). AFRs like ethylene and methyl jasmonate are relatively safer to use but they are quite costly (FDA-EPA 2013). Calcium carbide (CaC2) on the other hand is relatively cheaper and produces acetylene which is a structural analogue of ethylene (Figure 1(A,B)).