Chemical characterization of lysyl oxidase inhibitor from avocado seed oil

Rosenblat, Gennady; Kagan, Herbert M.; Shah, Manzoor Ahmad; Spiteller, Gerchard; Néeman, I.

doi:10.1007/bf02638904

Cited by 9 publications

(6 citation statements)

References 24 publications

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“…Currently, the potential of the avocadofurans as new class of insecticides is under investigation. Recent in vitro studies showed that furan-containing compounds extracted from avocado seed oils may cause lysyl oxidase (protein-L-lysine: oxidoreductase) inhibition, and may serve as an antifibrotic drug in diseases involving excess collagen and elastin deposition (Rosenblat et al, 1995). Thus, more research on mammalian toxicity and phytotoxicity will be required before these compounds are considered for insect control.…”

Section: Discussionmentioning

confidence: 99%

Effect of avocadofurans on larval survival, growth, and food preference of the generalist herbivore, Spodoptera exigua

Rodriguez‐Saona¹,

Trumble²

1999

Entomologia Exp Applicata

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We examined the effect of two avocadofurans, 2‐(pentadecyl)furan and 2‐(heptadecyl)furan, from avocado idioblast oil cells on maturation and larval feeding behavior of a generalist insect herbivore, Spodoptera exigua (Hübner) (Lepidoptera: Noctuidae). Experiments were conducted using two larval sizes: early‐stadium larvae refer to those larvae from experiments initiated with neonates while late‐stadium larvae refer to those larvae from experiments initiated with third instars. In order to use selected sublethal doses for developmental and behavioral studies on early‐ and late‐stadium larvae, log‐dose probit lines were determined using diet incorporation bioassays. Both avocadofurans had similar toxicities to early‐stadium larvae [LC50= 2.2 and 1.9 μmoles/g of diet for 2‐(pentadecyl)furan and 2‐(heptadecyl)furan, respectively] and late‐stadium larvae (LC50= 3.0 and 3.4 μmoles/g of diet, respectively). In diet bioassays extending from egg hatch to adult emergence, the avocadofurans significantly prolonged larval developmental times and reduced S. exigua pupal weights. In 7 d no‐choice bioassays initiated with cohorts of newly‐molted third instars, the avocadofurans significantly reduced larval weights at various sublethal concentrations (below LC50 values). To test larval feeding deterrence effects of these avocadofurans, choice tests were conducted using early and older instar larvae. A significantly higher proportion of early‐stadium larvae preferred control diet over diet treated with either avocadofuran at several sublethal concentrations. Similarly, choice tests with late‐stadium larvae showed greater proportions of larvae on control diet than treated diet even at concentrations below the LC50. Moreover, late‐stadium larvae consumed significantly more of the control diet than the treated diet. Thus, the avocadofurans may act as feeding deterrents as well as toxicants in plant protection against non‐adapted insect herbivores.

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Section: Discussionmentioning

confidence: 99%

Effect of avocadofurans on larval survival, growth, and food preference of the generalist herbivore, Spodoptera exigua

Rodriguez‐Saona¹,

Trumble²

1999

Entomologia Exp Applicata

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“…Moreover, sugar alcohol and ketoses with variable carbon chain length were isolated from avocado (Figure 4). Notable insecticidal, cytotoxic, and antifungal activities were also reported for the furan and furanone derivatives isolated from Persea species [18,31,32,33,34,35,36,37] (Figure 5), where the saturation of the furan ring was detrimental for the insecticidal activity [38]. The insecticidal activity of the furan derivatives was augmented by the diterpenoids compounds [39,40,41,42,43], especially in P. indica (Figure 6).…”

Section: Introductionmentioning

confidence: 99%

The Odyssey of Bioactive Compounds in Avocado (Persea americana) and Their Health Benefits

et al. 2019

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Persea americana, commonly known as avocado, has recently gained substantial popularity and is often marketed as a “superfood” because of its unique nutritional composition, antioxidant content, and biochemical profile. However, the term “superfood” can be vague and misleading, as it is often associated with unrealistic health claims. This review draws a comprehensive summary and assessment of research performed in the last few decades to understand the nutritional and therapeutic properties of avocado and its bioactive compounds. In particular, studies reporting the major metabolites of avocado, their antioxidant as well as bioavailability and pharmacokinetic properties, are summarized and assessed. Furthermore, the potential of avocado in novel drug discovery for the prevention and treatment of cancer, microbial, inflammatory, diabetes, and cardiovascular diseases is highlighted. This review also proposes several interesting future directions for avocado research.

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“…Batna and Spitellar (4) suggest that they may act as antioxidants in plants. Furanoid acids inhibit lysyl oxidase and may be useful in the treatment of diseases that entail excess collagen and elastin deposition (5). Their biosynthetic pathway is not clear.…”

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confidence: 99%

Analysis of furanoid esters in soybean oil and the effect of variety and environment on furanoid ester content

Hammond

White

et al. 1997

J Americ Oil Chem Soc

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An improved method was developed to analyze the major furanoid esters in soybean oil. The method is based on urea fractionation of the methyl esters, silver ion chromatography, and gas chromatography of the furanoid concentrate. Activation of the soybean lipoxygenase decreased the amount of furanoid ester recovered from the oil, but the degumming of crude soybean oil and the choice of solvent used to extract soybean lipids caused no change in furanoid ester content. Fifty-six soybean varieties, representing a wide range in maturity group and geographical origin, were grown in Puerto Rico and used to determine the range of furanoid ester contents. Furanoid ester II ranged from 0.033-0.29 mg/g, and ester III ranged from 0.058-0.27 mg/g. The two major furanoid esters were positively correlated with each other and with maturity group. Growth environment as well as variety caused significant differences in furanoid content. JAOCS 74, 1099-1103 (1997). KEY WORDS:Analysis, effect of growth environment, effect of variety, furanoid fatty acids.Fatty acids containing a furan ring, or furanoid fatty acids, were first discovered by Morris et al. (1) in the seed oil of Exocarpus cupressiformis. More than 30 furanoid acids have been reported in a variety of animal and plant sources.The physiological role of these acids remains a matter of speculation. They may be involved in animal reproductive rhythms (2) and embryo development (3). Batna and Spitellar (4) suggest that they may act as antioxidants in plants. Furanoid acids inhibit lysyl oxidase and may be useful in the treatment of diseases that entail excess collagen and elastin deposition (5). Their biosynthetic pathway is not clear.Besides the seed oil of E. cupressiformis, furanoid esters have been found in algae (Chlorophyta sp.), mushroom (Agaricus bisporus), and yeast (Saccharomyces cerevisiae); they are also found in the roots and shoots of grasses (Poaceae sp.), clover (Trifolium pratense), dandelion (Taraxacum officinale), chive (Allium sativum), wheat (Triticum aestivum), rice (Oryza sativa), potato (Solanum tuberosum), cabbage (Brassica oleracea), orange (Citrus sinensis osbeck), lemon (Citrus limon), strawberries (Fragaria sp.), and birch leaves (Betula pendula) (6) as well as the latex of Hevea brasiliensis (7). Furanoid esters occur in greater amounts in the green parts of plants than in the stems, roots, and seeds.Three furanoid acids were identified in soybean oil by Guth and Grosch (8) and are shown in Figure 1. Guth and Grosch (8) reported that the three furanoid esters totaled 250-390 mg/kg in soybean oil, 70-120 mg/kg in wheat germ oil, 13-36 mg/kg in rapeseed oil, and 17-24 mg/kg in corn oil. Furanoid esters were absent in olive and sunflower oils. Analyses of the soybean cultivar Century and five soybean genotypes that lacked one or two of the three lipoxygenase isoenzymes revealed that their seed oils contained 190-225 mg/kg of furanoid ester II and 91-132 of ester III (9). The concentrations of furanoid esters were not correlated with lipoxygenase ...

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Chemical characterization of lysyl oxidase inhibitor from avocado seed oil

Cited by 9 publications

References 24 publications

Effect of avocadofurans on larval survival, growth, and food preference of the generalist herbivore, Spodoptera exigua

Effect of avocadofurans on larval survival, growth, and food preference of the generalist herbivore, Spodoptera exigua

The Odyssey of Bioactive Compounds in Avocado (Persea americana) and Their Health Benefits

Analysis of furanoid esters in soybean oil and the effect of variety and environment on furanoid ester content

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