Novel Glycerolipids and Glycolipids from the Surface Lipids of<i>Nicotiana benthamiana</i>

Matsuzaki, Toshiake; Shinozaki, Yasuhiro; Hagimori, Manabu; Tobita, Tetsuya; Shigematsu, Hitoshi; Koiwai, Akira

doi:10.1271/bbb.56.1565

Cited by 27 publications

(19 citation statements)

References 4 publications

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“…Sucrose esters isolated from cuticular extracts of other Nicotiana species have been suggested to possess only two C 3 to C 8 acyl moieties and may have from one to four acetyl groups on the fructose. In summary, about 19 different structural types (Figure 1) of sucrose esters have been reported for Nicotiana species, and for any sugar type, a series of homologs are found due to differing acyl groups (7)(8)(9)(10)(11)(12)(13)(14). Sucrose esters regardless of their structure present real challenges in terms of isolation, sample preparation, and molecular characterization because the materials are partially esterified with linear and branched fatty acids of variable chain length.…”

Section: Introductionmentioning

confidence: 99%

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

Ashraf‐Khorassani

Nazem

Taylor

et al. 2008

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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SUMMARYIsolation, fractionation, and identification of sucrose esters from aged oriental tobacco employing supercritical fluids have been completed. Underivatized sucrose ester-rich extracts were obtained using supercritical CO 2 at densities greater than 0.73 g/mL. Lower density CO 2 provided extracts with notable amounts of tobacco derived material; yet, no detectable sucrose ester content. Preparative supercritical fluid chromatography (SFC) provided for an additional purification of the sucrose ester-enriched fraction after column optimization. Structural assignments of the SFC fractions were facilitated using gas chromatography/mass spectrometry (GC/MS) accompanied by N,Obis(trimethylsilyl)trifluoroacetamide-dimethylformamide (BSTFA-DMF) derivatization of the free hydroxyl groups and high performance-liquid chromatography/mass spectrometry (HPLC/MS). From a relative quantitative perspective regardless of tobacco type, sucrose esters having an acetyl group on C 6 of the glucose function (Group III) were in higher concentration compared to both the concentration observed for sucrose ester of Group I (acetyl group on C 3 of fructose) and sucrose ester of Group II (no acetyl group on either glucose or fructose). Saturated fatty acid constituents were found to range from a maximum total of 18 carbons to a minimum total of 13 carbons. Unsaturated and isomeric fatty acid homologues were detected within the Group II sucrose ester. [Beitr. Tabakforsch. Int. 23 (2008) RESUMELes esters de saccharose de tabac oriental mûr ont été isolés, fractionnés et identifiés par des fluides supercritiques. Des extraits riches en esters de saccharose non dérivatisés ont été obtenus par extraction avec un dioxyde de carbone supercritique d'une densité supérieure à 0,73 g/mL. Des extraits obtenus avec un dioxyde de carbone moins dense sont riches en composants provenant du tabac, avec des teneurs en esters de saccharose non détectables. Une purification supplémentaire de la fraction

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Section: Introductionmentioning

confidence: 99%

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

Ashraf‐Khorassani

Nazem

Taylor

et al. 2008

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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“…To this end, it is interesting to explore glandular trichome exudates of the other major genera of the Geraniaceae family. Sugar esters, in particular esters with shorter-chain acyl groups, glucose esters, 25) sucrose esters 26,27) and inositol esters, 28) have been characterized as glandular trichome exudates from a limited genera of different families. Our present and previous results indicated that secondary metabolites contained in glandular trichome exudates would be much more structurally diverse than ever before expected.…”

Section: Resultsmentioning

confidence: 99%

n-Octyl .ALPHA.-L-Rhamnopyranosyl-(1.RAR.2)-.BETA.-D-glucopyranoside Derivatives from the Glandular Trichome Exudate of Geranium carolinianum

Asai

Sakai

Ohyama

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Chemical investigation of the glandular trichome exudate from Geranium carolinianum L. (Geraniaceae) led to the characterization of unique disaccharide derivatives, n-octyl, named caroliniasides A-C, respectively. These structures were determined by spectral means. n-Alkyl glycoside derivatives have been isolated from the glandular trichome exudates for the first time. This rare type of secondary metabolites could be applicable to chemotaxonomic perspective because they are found in glandular trichome exudates of plants belonging to the genus Geranium, according to our studies.

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“…Antixenotic resistance of various Brassica species to turnip root fl y, Delia fl oralis , has been reportedly linked to the presence of wax esters (Shepherd et al 1999a , b ). Glycerolipids in combination with glycolipids such as glucose and sucrose esters make Nicotiana benthamiana resistant to attack by the hornworm, Manduca sexta (Matsuzaki et al 1992 ). In addition, there are a number of secondary metabolites that provide defense to plants against pests.…”

Section: Leaf Waxes and Exudatesmentioning

confidence: 99%

Phytochemical Pesticides

Walia¹,

Saha²,

Rana³

2014

Advances in Plant Biopesticides

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Many phytochemical pesticides exhibiting broad spectrum of activity against pests and diseases have long been considered as attractive alternative to synthetic chemical pesticides as they are biodegradable, target specifi c, and pose no or less hazard to the environment or to human health. Although a large number of studies suggest that plant-based materials do affect arthropod pests, vectors, and other pathogens, yet only a handful of botanicals are currently used in agriculture, and there are few prospects for commercial development of new botanical products. Several factors appear to limit the success of botanicals, most notably regulatory barriers and the availability of competing products of microbial origin that are cost-effective and relatively safe compared with their predecessors. In the context of agricultural pest management, botanical pesticides are best suited for use in organic food production and can play a much greater role in the production and post-harvest protection of food and food products in developing countries. There is thus a need to organize natural sources, develop quality control, adopt standardization strategies, and modify regulatory mechanisms.

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Novel Glycerolipids and Glycolipids from the Surface Lipids ofNicotiana benthamiana

Cited by 27 publications

References 4 publications

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

Isolation, Fractionation, and Identification of Sucrose Esters from Various Oriental Tobaccos Employing Supercritical Fluids

n-Octyl .ALPHA.-L-Rhamnopyranosyl-(1.RAR.2)-.BETA.-D-glucopyranoside Derivatives from the Glandular Trichome Exudate of Geranium carolinianum

Phytochemical Pesticides

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