Sesquiterpene Lactones from Pyrethrum Flowers

Doskotch, Raymond W.; El‐Feraly, Farouk S.; Hufford, Charles D.

doi:10.1139/v71-341

Cited by 40 publications

(12 citation statements)

References 6 publications

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“…In the Asteraceae family, glandular trichomes are particularly rich in sesquiterpenoids (Seaman et al, 1980;Heinrich et al, 2002;Göpfert et al, 2005;Bertea et al, 2006). Indeed, apart from pyrethrins, pyrethrum extracts also contain a variety of sesquiterpene lactones (STLs), such as pyrethrosin (chrysanthin) (Barton and Demayo, 1957;Barton et al, 1960), chrysanin, dihydro-b-cyclopyrethrosin, chrysanolide, and b-cyclopyrethrosin (Doskotch and Elferaly, 1969;Doskotch et al, 1971). STLs are generally characterized by a five-membered a-methyleneg-lactone ring.…”

Section: Introductionmentioning

confidence: 99%

Bidirectional Secretions from Glandular Trichomes of Pyrethrum Enable Immunization of Seedlings

et al. 2012

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Glandular trichomes are currently known only to store mono-and sesquiterpene compounds in the subcuticular cavity just above the apical cells of trichomes or emit them into the headspace. We demonstrate that basipetal secretions can also occur, by addressing the organization of the biosynthesis and storage of pyrethrins in pyrethrum (Tanacetum cinerariifolium) flowers. Pyrethrum produces a diverse array of pyrethrins and sesquiterpene lactones for plant defense. The highest concentrations accumulate in the flower achenes, which are densely covered by glandular trichomes. The trichomes of mature achenes contain sesquiterpene lactones and other secondary metabolites, but no pyrethrins. However, during achene maturation, the key pyrethrin biosynthetic pathway enzyme chrysanthemyl diphosphate synthase is expressed only in glandular trichomes. We show evidence that chrysanthemic acid is translocated from trichomes to pericarp, where it is esterified into pyrethrins that accumulate in intercellular spaces. During seed maturation, pyrethrins are then absorbed by the embryo, and during seed germination, the embryo-stored pyrethrins are recruited by seedling tissues, which, for lack of trichomes, cannot produce pyrethrins themselves. The findings demonstrate that plant glandular trichomes can selectively secrete in a basipetal direction monoterpenoids, which can reach distant tissues, participate in chemical conversions, and immunize seedlings against insects and fungi.

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Section: Introductionmentioning

confidence: 99%

Bidirectional Secretions from Glandular Trichomes of Pyrethrum Enable Immunization of Seedlings

et al. 2012

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“…The 'H-nmr spectrum (table 1) contained a pair of one-proton split doublets at 5.83 and 6.14 ppm, characteristic of methylene protons of ,ß'-unsaturated 7-lactones. The extra splitting <J=0.9 Hz) of the typical doublets, which is caused by geminal coupling, is observed with tram lactones bearing an oxygen function with -stereochemistry at the carbon adjacent to the lactonic carbon C-7 for either C-7 to C-6 or C-7 to C-8 lactones (2,6,8,9). 'H-nmr peaks for an acetate, an olefinic methyl, and another exocyclic methylene were also present.…”

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confidence: 99%

Six Additional Sesquiterpene Lactones From Liriodendron tulipifera

Doskotch¹,

Wilton²,

Harraz³

et al. 1983

J. Nat. Prod.

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The leaves of Liriodendron tulip~era yielded four sesquiterpene lactones: dihydrochrysanolide (l), p-cyclolipiferolide (S), l l , 13-dehydrolanuginolide 0, and laurenobiolide (3), of which the first two are new compounds. P-Cyclolipiferolide (5), was prepared by acid cyclization of lipiferolide (6), and the stereochemistry at C-1, C-4, and C-5 was determined by nuclear Overhauser effect studies. Dihydrochrysanolide (1) was converted to chrysanolide (2) by MnO, oxidation, and the stereochemistry of the hydroxyl-bearing carbon, C-1, was established as S by the Horeau procedure. 11,13-Dehydrolanuginolide (7) was identified from physical data and by conversion to tulipinolide diepoxide (8), a derivative of tulipinolide (9) and a well-characterized lactone. Tulipinolide 1, 10-epoxide, a product of partial oxidation of tulipinolide with m-chloroperoxybenzoic acid, was characterized by spectral data. The root bark afforded a-(11) and P-liriodenolide (12), which were identified by direct comparison with products from the cyclization of epitulipinolide 1, IO-epoxide, and are new natural products.The leaves and root bark of Liriodendron tulipifera L. (Fam. Magnoliaceae), commonly called yellow or tulip poplar, have reported for them nine sesquiterpene lactones (1-6), some of which possess cytotoxic and insect antifeeding activity (7). Further studies have yielded six additional members, four of which are new natural products, and are the subject of this report.Dihydrochrysanolide (1) was isolated from a partition fraction of the ethanolic extract residue of the leaves by repeated chromatography and crystallization. High resolution ms supported the formula C,,H2,05, and the ir spectrum suggested hydroxyl, ester, lactonic, and olefinic functions. The 'H-nmr spectrum (table 1) contained a pair of one-proton split doublets at 5.83 and 6.14 ppm, characteristic of methylene protons of a,P'-unsaturated y-lactones. The extra splitting y=0.9 Hz) of the typical doublets, which is caused by geminal coupling, is observed with trans lactones bearing an oxygen function with a-stereochemistry at the carbon adjacent to the lactonic carbon C-7 for either C-7 to C-6 or C-7 to C-8 lactones (2,6,8,9). 'H-nmr peaks for an acetate, an olefinic methyl, and another exocyclic methylene were also present. Double irradiation experiments beginning at H-13 identified H-7, from which the protons on C-5 through C-9 were located, and from the multiplicities and chemical shifts the substituents were likewise assigned.The stereochemistry of H-7 was assigned as a, as in the case for the lactones of established structure from this source. The cd spectrum with a negative Cotton effect peak at 252 nm for the n H + transition of the lactone carbonyl was in conflict, according to Geissman and co-workers (lo), with the 'H-nmr data for the 7,8-trans lactone.However, it was of the same sign as observed for laurenobiolide (3) (1 l), pyrethrosin (1,lO-epoxide of 3), and chrysanolide ( 2 ) (8), three other 7,8-trans lactones that disobey the generality. The remaining ...

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“…Pyrethrum cinerariifolium Trevir. produces sesquiterpene lactones (SLs) as well as pyrethroids [ 1 , 2 ]. It is well known that most of the Asteroideae produce SLs [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

Chemical Defense of Yacón (Smallanthus sonchifolius) Leaves against Phytophagous Insects: Insect Antifeedants from Yacón Leaf Trichomes

Tsunaki

Morimoto

2020

Plants

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Yacón is a perennial crop with high insect resistance. Its leaves have many glandular trichomes, which may be related to pest resistance. In order to collect the constituents of glandular trichomes, leaves were rinsed using dichloromethane (DCM) to obtain the rinsate, and the plant residues were subsequently extracted by DCM to obtain a DCM extract containing the internal constituents of yacón leaves. Biologic evaluations revealed that insect antifeedant activity was stronger for the rinsate than for the DCM extract against the common cutworm. The major constituents of rinsate were isolated by silica gel flash chromatography and were identified as sesquiterpene lactones (SLs), uvedalin (1) and enhydrin (2) and uvedalin aldehyde (3), collectively known as melampolides. Although SLs 1 and 2 exhibited remarkably strong insect antifeedant activity, SL 3 and reduced corresponding derivatives (4 and 5) of 1 and 2 exhibited moderate insect antifeedant activity. Additionally, the two analogs, parthenolide (6) and erioflorin (7) showed moderate insect antifeedant activity. The results indicate that the substituent patterns of SLs may be related to the insect antifeedant activities. The insect antifeedant activities of SLs 1 and 2 were similar to that of the positive control azadirachtin A (8), and thus these natural products may function in chemical defense against herbivores.

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Sesquiterpene Lactones from Pyrethrum Flowers

Cited by 40 publications

References 6 publications

Bidirectional Secretions from Glandular Trichomes of Pyrethrum Enable Immunization of Seedlings

Bidirectional Secretions from Glandular Trichomes of Pyrethrum Enable Immunization of Seedlings

Six Additional Sesquiterpene Lactones From Liriodendron tulipifera

Chemical Defense of Yacón (Smallanthus sonchifolius) Leaves against Phytophagous Insects: Insect Antifeedants from Yacón Leaf Trichomes

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