Non-volatile floral oils of Diascia spp. (Scrophulariaceae)

Dumri, Kanchana; Seipold, Lars; Schmidt, Jürgen; Gerlach, Günter; Dötterl, Stefan; Ellis, Allan G.; Wessjohann, Ludger A.

doi:10.1016/j.phytochem.2007.12.012

Cited by 26 publications

(32 citation statements)

References 33 publications

(47 reference statements)

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“…The first solvent system was selected as it was found beneficial to also extract more lipophilic compounds well, for e.g. steroids (Seipold et al 2004;Dumri et al 2008).…”

Section: Extraction and Fractionationmentioning

confidence: 99%

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Multiple readout assay for hormonal (androgenic and antiandrogenic) and cytotoxic activity of plant and fungal extracts based on differential prostate cancer cell line behavior

Bobach

Schurwanz

Franke

et al. 2014

Journal of Ethnopharmacology

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“…The first solvent system was selected as it was found beneficial to also extract more lipophilic compounds well, for e.g. steroids (Seipold et al 2004;Dumri et al 2008).…”

Section: Extraction and Fractionationmentioning

confidence: 99%

“…The flowers are known to secrete an acylglycerol containing oil (cf. Seipold et al 2004;Dumri et al 2008). The extract of Heteropterys chrysophylla was shown to exhibit antifungal activity against several Cladosporium species (Agripino et al, 2004).…”

Section: Heteropterys Chrysophyllamentioning

confidence: 99%

Multiple readout assay for hormonal (androgenic and antiandrogenic) and cytotoxic activity of plant and fungal extracts based on differential prostate cancer cell line behavior

Bobach

Schurwanz

Franke

et al. 2014

Journal of Ethnopharmacology

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“…-The glandular trichome exudates on the leaves of P. tomentosa were found to contain O-(fatty acyl)glycerols exclusively, and the twenty-five new O-(fatty acyl)glycerols 1, 4, 5, 6, 7, 8, 10 -14, and 16 -30 were characterized along with the five known ones 2, 3, 6, 9, and 15 [12] [20]. Among these, compounds 12 (20%), 17 (14%), 18 (12%), and 10 (12%) were relatively abundant.…”

Section: -O-[(3r6s)-3-(acetyloxy)-6-hydroxyoctadecanoyl]glycerol) (1mentioning

confidence: 98%

“…Putative precursors, 3-hydroxy-and 3,n-dihydroxy-substituted fatty acids could be detected in neither the glandular trichome exudate nor the leaf extract of P. tomentosa. Recently, closely related glycerides have been characterized in the floral oils of Orchidaceae and Scrophulariaceae plants [12] [19] [21]. In addition, 3-(acetyloxy)-, 5-(acetyloxy)-, 7-(acetyloxy)-3-hydroxy-, 9-(acetyloxy)-3-hydroxy-, and 9-(acetyloxy)-5-hydroxy-substituted fatty acids were characterized as constituents of these plants floral oils [13] [22].…”

Section: -O-[(3r6s)-3-(acetyloxy)-6-hydroxyoctadecanoyl]glycerol) (1mentioning

confidence: 99%

“…The acylglycerol mixture (the Et 2 O extract) was saponified with LiOH in aqueous 1,2-dimethoxyethane ((MeOCH 2 ) 2 ), and the liberated fatty acid mixture was treated with ethereal CH 2 N 2 to give fatty acid methyl esters, which showed two spots by TLC analysis, the polar broad spot being subsequently separated into four spots. The while the minor peak exhibited the respective fragmentation ions at m/z 313 ([CH(OSiMe 3 )C 15 H 31 ] þ ) and 175 [12]. The less polar fraction was, therefore, determined to be a 10 : 1 mixture of methyl 3-hydroxyeicosanoate (31a) and methyl 3-hydroxyoctadecanoate (32a) (Fig.…”

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confidence: 99%

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Acylglycerols (=Glycerides) from the Glandular Trichome Exudate on the Leaves of Paulownia tomentosa

Asai

Hara

Kobayashi

et al. 2009

Helvetica Chimica Acta

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Chemical investigations of the glandular trichome exudates on the leaves of Paulownia tomentosa (Scrophulariaceae) led to the identification of the thirty acylglycerols (=glycerides) 1–30, including five known ones (2, 3, 6, 9, and 15) (Fig. 1). Spectroscopic analysis combined with GC/MS studies of the glycerides and the liberated fatty acids, in the form of trimethylsilyl ether derivatives and trimethylsilylated methyl esters, respectively, established that the constituents belonged to 1,3‐di‐O‐acetyl‐2‐O‐(fatty acyl)glycerols, 1‐O‐acetyl‐2‐O‐(fatty acyl)‐sn‐glycerols, and 2‐O‐(fatty acyl)glycerols, wherein the fatty acyl moiety was either an eicosanoyl or an octadecanoyl group bearing OH and/or AcO groups at the 3‐, 3,6‐, 3,7‐, 3,8‐, or 3,9‐positions. The 1‐O‐acetyl‐2‐O‐[(3R,6S)‐3‐(acetyloxy)‐6‐hydroxyeicosanoyl]‐sn‐glycerol (12; 20% of the total glycerides), 2‐O‐[(3R,8R)‐3,8‐bis(acetyloxy)eicosanoyl]glycerol (17; 14%), 2‐O‐[(3R,9R)‐3,9‐bis(acetyloxy)eicosanoyl]glycerol (18; 12%), and 2‐O‐[(3R)‐3‐(acetyloxy)eicosanoyl]glycerol (10; 12%) were relatively abundant constituents. The configurations of the stereogenic centers of the fatty acyl moieties were determined by 1H‐NMR analysis of the monoesters obtained from (R)‐ and (S)‐2‐(naphthalen‐2‐yl)‐2‐methoxyacetic acid ((R)‐ and (S)‐2NMAOH and the hydroxy‐substituted fatty acid methyl esters (Fig. 2). The configuration at C(2) of the glycerol moiety of the 1‐O‐acetyl‐2‐O‐(fatty acyl)glycerols was determined to be (2S) by chemical conversion of, e.g., G‐2 (=2/3 1 : 10) to (+)‐3‐O‐[tert‐butyl)diphenylsilyl]‐sn glycerol of known absolute configuration.

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1‐Acetyl‐3‐[(3R)‐hydroxyfatty acyl]glycerols: Lipid Compounds from Euphrasia rostkoviana Hayne and E. tetraquetra (Bréb.) Arrond.

Lorenz¹,

Knittel²,

Conrad³

et al. 2016

Chemistry & Biodiversity

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Five homologous acetylated acylglycerols of 3-hydroxyfatty acids (chain lengths C(14) - C(18)), named euphrasianins A - E, were characterized for the first time in Euphrasia rostkoviana Hayne (Orobanchaceae) by gas chromatography/mass spectrometry (GC/MS) and high-performance liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry (HPLC/APCI-MS(n) ). In addition to mass spectrometric data, structures of euphrasianins were verified via a three-step total synthesis of one representative homologue (euphrasianin A). The structure of the latter was confirmed by 1D- and 2D-NMR experiments as well as high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS). The absolute configuration of the 3-hydroxyfatty acid moiety at C(3) was found to be R in the natural euphrasianins, which was determined by alkaline hydrolysis and methylation of a purified fraction, followed by chiral GC analysis. Furthermore, in extracts of Euphrasia tetraquetra (Bréb.) Arrond. euphrasianins C and E were detected exclusively, indicating that this subclass of lipid constituents is possibly valuable for fingerprinting methods.

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Non-volatile floral oils of Diascia spp. (Scrophulariaceae)

Cited by 26 publications

References 33 publications

Multiple readout assay for hormonal (androgenic and antiandrogenic) and cytotoxic activity of plant and fungal extracts based on differential prostate cancer cell line behavior

Multiple readout assay for hormonal (androgenic and antiandrogenic) and cytotoxic activity of plant and fungal extracts based on differential prostate cancer cell line behavior

Acylglycerols (=Glycerides) from the Glandular Trichome Exudate on the Leaves of Paulownia tomentosa

1‐Acetyl‐3‐[(3R)‐hydroxyfatty acyl]glycerols: Lipid Compounds from Euphrasia rostkoviana Hayne and E. tetraquetra (Bréb.) Arrond.

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