Petuniolides. Unusual ergostanoid lactones from Petunia species that inhibit insect development

Elliger, Carl A.; Wong, Rosalind Y.; Waiss, Anthony C.; Benson, Mabry

doi:10.1039/p19900000525

Cited by 13 publications

(13 citation statements)

References 6 publications

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“…Metabolites of interest for Petunia sp. were finally identified with SciFinder® database (www.cas.org, American Chemical Society) and literature data (Elliger et al 1988a(Elliger et al ,1988bElliger et al 1989a;Elliger et al 1990aElliger et al ,1990bElliger & Waiss 1991;Elliger et al 1992;Elliger et al 1993;Tarling et al 2013).…”

Section: Uhplc-hr-esi-ms and Ms/ms Analysesmentioning

confidence: 99%

Petunia hybrida PDR2 is involved in herbivore defense by controlling steroidal contents in trichomes

Sasse

Schlegel

Borghi

et al. 2016

Plant Cell & Environment

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As a first line of defense against insect herbivores many plants store high concentrations of toxic and deterrent secondary metabolites in glandular trichomes. Plant Pleiotropic Drug Resistance (PDR)-type ABC transporters are known secondary metabolite transporters, and several have been implicated in pathogen or herbivore defense. Here, we report on Petunia hybrida PhPDR2 as a major contributor to trichome-related chemical defense. PhPDR2 was found to localize to the plasma membrane and be predominantly expressed in multicellular glandular trichomes of leaves and stems. Down-regulation of PhPDR2 via RNA interference (pdr2) resulted in a markedly higher susceptibility of the transgenic plants to the generalist foliage feeder Spodoptera littoralis. Untargeted screening of pdr2 trichome metabolite contents showed a significant decrease in petuniasterone and petuniolide content, compounds, which had previously been shown to act as potent toxins against various insects. Our findings suggest that PhPDR2 plays a leading role in controlling petuniasterone levels in leaves and trichomes of petunia, thus contributing to herbivory resistance.

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Section: Uhplc-hr-esi-ms and Ms/ms Analysesmentioning

confidence: 99%

Petunia hybrida PDR2 is involved in herbivore defense by controlling steroidal contents in trichomes

Sasse

Schlegel

Borghi

et al. 2016

Plant Cell & Environment

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“…14a., 16-Oxido-ent-isopimar-7-ene-6a, 15a-diol [20].-From fraction I, followed by Dynamax C-18 (21.4 X 250 mm) 40% H20 in MeCN, elution volume 200-240 ml, and RSil C-18, 40% H2OinMeCN, elution volume 4M6 ml, yield 200 ppm. Mp 207-210°( MeCN/H20); [ ] (X nm) -16°(589), -17°( 578), -19°(546), -29°(436), -38°(365) (95% EtOH, r= 1.0); ir v max (CHC13) cm-1 3580, 3350 br; 'H nmr (CD}OD) 0.88, 0.96, 1.08, 1.14 (s's, H3-17,-18,-19,-20), 3.60 (ddj = 2, 10 Hz, 1/2 H2-16), 3.79 (dd, 5, 2 Hz, H-15), 3.85 (brs, H-14), 4.15 (d, brt, 10, ca. 2 Hz, H-6), 4.25 (dd, 10, 5 Hz, 1/2 H2-16), 5.65 (brt, ca.…”

Section: Interconversions Of Compoundsmentioning

confidence: 99%

“…Mp 207-210°( MeCN/H20); [ ] (X nm) -16°(589), -17°( 578), -19°(546), -29°(436), -38°(365) (95% EtOH, r= 1.0); ir v max (CHC13) cm-1 3580, 3350 br; 'H nmr (CD}OD) 0.88, 0.96, 1.08, 1.14 (s's, H3-17,-18,-19,-20), 3.60 (ddj = 2, 10 Hz, 1/2 H2-16), 3.79 (dd, 5, 2 Hz, H-15), 3.85 (brs, H-14), 4.15 (d, brt, 10, ca. 2 Hz, H-6), 4.25 (dd, 10, 5 Hz, 1/2 H2-16), 5.65 (brt, ca. 2 Hz, H-7); BC nmr see Table 3; eims m/z [M]+ 320.2335 (C20H32O3 requires 320.2353).…”

Section: Interconversions Of Compoundsmentioning

confidence: 99%

“…2 Hz, H-6), 4.25 (dd, 10, 5 Hz, 1/2 H2-16), 5.65 (brt, ca. 2 Hz, H-7); BC nmr see Table 3; eims m/z [M]+ 320.2335 (C20H32O3 requires 320.2353).…”

Section: Interconversions Of Compoundsmentioning

confidence: 99%

“…6 , 15 a, Diacetoxy-14a., 16-oxido-eat-isoptmar-7 -ene [21].-Compound 20 was acetylated with Ac20 in pyridine and chromatographed on RSil C-18, 100% MeCN, to give 21, elution volume 24-27 ml. 'H nmr (CDC13) 0.91, 0.97 (2), 1.00 (s's, H3-17, -18, -19, -20), 2.05 and 2.08 (s's, OAc's), 3.63 (dd, 7 = 7, 10 Hz, 1/2 H2-16), 3.71 (brs, H-14), 4.18 (dd J = 8, 10 Hz, 1/2 H2-16), 4.95 (ddj = 7, 8 Hz, H-15), 5.42 (ddd,_/= 11, 3, 2 Hz, H-6), 5.84 (br tj = ca. 3 Hz, H-7).…”

Section: Interconversions Of Compoundsmentioning

confidence: 99%

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Diterpenes of Calibrachoa parviflora

Elliger¹,

Wong²,

Benson³

et al. 1992

J. Nat. Prod.

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Califi.n& 94710 hSTRACT.-hVeS of Calibraha pawrflwa gave the huranoids corymbl 6-monuacetate [4} and corymbl 17-monoacetate [5], corymbl 17-(2-methylbutyrate) [6], and corymbl 6-acetate-17-(2-methylbutyrate) 181. Other new kauranoids were ent-hurane-7a, 16@,17-triol 191, its 7-acetate [lo], and its 7-acetate-17-(2-methylburyrate) [ll], the corresponding 7-ketcdiol [12]and its 17-acetate 1133. New pimaranes were 15R, 16dihydroxy-cnt-isopimar-8( 14)-en-7-one 1141 and the ring-closed analogues, 14a, 16-oxido-mt-isopimar-7-en-15a-ol [17j and 14a, 16-oxidoart-isopimar-7-ene-6a, 15a-diol [ZO]. The known diterpenes, entkaurane-l6~,17diol, its 17-acetate, ent-hurane-&, 16p,l?-triol (corymbl), and its 6,17-diacetate were also obtained. C . p a w i f i a did not yield any of the ergostanoids that are characteristic of Petunia species, rhus supporting its recent reassignment into a separate genus.In a continuing investigation of plant resistance toward insect herbivores, we have shown that foliage of various Petunia (Solanaceae) species is toxic to certain insects, and that this effect can be related to the presence in the leaves of a large number of steroidal substances which we have termed petuniasterones and petuniolides (1,2). More recently (3), we reported the occurrence in Petunia infita of a set of novel pyridine ringcontaining analogues of these steroids (petunianines) which are also agents that inhibit insect growth and development. While evaluating plants that are closely related to Petunia it was of interest to examine the allied species Calibrachoa pawtfia (=Petunia pawifia) Jess. (Solanaceae), which has the same range in South America as Petunia and is found in Mexico, Cuba, and the United States as far north as New Jersey. The plants of C. pawifia have 2n = 2x = 18 chromosomes, in contrast to all species of Petunia with 2n= 2x= 14 (4), and this genus has recently been distinguished from that of Petunia ( 5 ) . RESULTS AND DISCUSSIONIn the present study, larvae of the lepidopteran Helic-a zeu (=Hehothis zeu Boddie) survived well on fresh stems and leaves of C. pawifia, and it was, therefore, of interest to determine if any steroids similar to those responsible for toxicity in Petunia occurred in Calibraha, and if so, whether differing structure lessened toxicity. No steroidal substances of the Petunia type were isolated from C. pawifia; however, numerous diterpenes were present including several previously undescribed kauranoids and pimaranes. These findings support the conclusion that C. pawifia is correctly assigned in a genus distinct from Petunia.KAuRANES.-Compounds 1-13 belong to the ent-kaurane series. Diol 1 has been isolated previously from Croton and other genera, and its acetate 2 has been prepared (7,8). The 13C-nmr spectra of 1 and 2 (Table 1) were in agreement with shifts reported for kauranoid systems (9,lO) in general, and with values observed for the relevant carbons of abbeokutone acetate (1 1).Compound 3 has the structure ascribed to corymbol isolated from Turbina cwymbosa (12), but the observ...

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Innovative Strategies in the Search for Bioactive Plant Constituents

Queiroz

Wolfender

2014

Encyclopedia of Analytical Chemistry

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Higher plants represent a rich source of new molecules with interesting pharmacological properties that could be used as lead compounds for the development of new drugs. During the past decade, the investigation of the secondary metabolites from plants has led to the introduction of several important new drugs, such as apomorphine (Apokyn ® ) for the treatment of Parkinson's disease, nitisinone (Orphadin ® ) for the treatment of hereditary tyrosinaemia type 1, and miglustat (Zavesca ® ) for the treatment of the Gaucher disease. Success in drug discovery research using plants is dependent on various issues, but plant selection remains key for all types of these studies. The choice of the appropriate plant material is usually based on information from traditional medicine, chemotaxonomic data, field observation, or random collection. Recently, other approaches have been used, such as reverse pharmacognosy induction of new compounds by stress induction or biotransformation. Extraction and enrichment procedures are also key to avoid chemical degradation and detect the active constituents among hundreds of nonactive constituents before submitting the sample for a first biological screening. New high throughput screening (HTS) strategies have been used to rapidly and efficiently evaluate the biological and chemical potentials of complex matrices, such as plant extracts. In this field, the creation of enriched extracts of natural product (NP) fraction libraries, notably using automatic procedures, opens new possibilities for the research of new lead compounds from higher plants. On the other hand, tremendous advances have been made in molecular biology, affording the development of more predictable in vitro and in vivo bioassays. The combination of metabolite profiling and bioassays that can directly be performed on the fractions that are resolved by analytical high performance liquid chromatography (HPLC) provides the possibility of distinguishing between already‐known bioactive compounds and new molecules directly isolated from crude plant extracts (dereplication). Thus, the tedious isolation of compounds of low interest can be avoided and a targeted isolation of new bioactive products or constituents presenting novel or unusual spectroscopic features can be undertaken. The applications, possibilities, and limitations of the latest technologies applied to the study of plant metabolites, as well as future developments expected in this field, are discussed.

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Petuniolides. Unusual ergostanoid lactones from Petunia species that inhibit insect development

Cited by 13 publications

References 6 publications

Petunia hybrida PDR2 is involved in herbivore defense by controlling steroidal contents in trichomes

Petunia hybrida PDR2 is involved in herbivore defense by controlling steroidal contents in trichomes

Diterpenes of Calibrachoa parviflora

Innovative Strategies in the Search for Bioactive Plant Constituents

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