Grayanoid diterpene insect antifeedants and insecticides from Rhododendron molle

Klocke, James A.; Hu, Meiying; Chiu, Shao-I; Kubo, Isao

doi:10.1016/0031-9422(91)85015-r

Cited by 99 publications

(111 citation statements)

References 14 publications

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“…Todos estes fatores têm levado à busca contínua por novos agentes inseticidas eficientes, que representem maior segurança ao homem e ao meio ambiente [1][2][3][4][5] . Inseticidas são substâncias químicas utilizadas para matar, atrair e repelir insetos, sendo sua descoberta, isolamento, síntese, avaliação toxicológica e de impacto ambiental um vasto tópico de pesquisas no mundo inteiro e que tem se desenvolvido bastante nas últimas décadas [1][2][3][4][5][6][7][8][9] .…”

Section: Introductionunclassified

Terpenos com atividade inseticida: uma alternativa para o controle químico de insetos

Júnior¹

2003

Quím. Nova

153

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Section: Introductionunclassified

Terpenos com atividade inseticida: uma alternativa para o controle químico de insetos

Júnior¹

2003

Quím. Nova

153

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“…Os inseticidas botânicos são uma fonte promissora desses compostos. Muitos autores têm estudado a atividade de diversas plantas como Calceolaria andina Beth (Klocke et al 1991), Persea americana Mill (Wrba et al 1992), Aglaia odorata Lour (Ahn et al 1998), Piper nigrum L. (Khambay et al 1999 (Miyakado et al 1989).…”

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Toxicidade de amidas análogas à piperina a larvas de Ascia monuste orseis Godart (Lepidoptera: Pieridae) e Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae)

Estrela¹,

Guedes²,

Maltha³

et al. 2003

Neotrop. Entomol.

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Toxicity of Piperine Amide Analogs to Larvae of Ascia monuste orseis Godart (Lepidoptera: Pieridae) and Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae)ABSTRACT -The objective of this study was to evaluate the toxicity piperine amide analogs to 3 rd -instar larvae of Ascia monuste orseis Godart and Spodoptera frugiperda (J.E. Smith). The bioassays were based on the topical application of 0.5 µl of the following amides: N-isopenthyl-(3,4-metilenodioxiphenyl)-amide, N-isopropyl-(3,4-metilenodioxiphenyl)-amide, N-hexyl-3-(3,4-etilenodioxiphenyl)-amide and piperonyl butoxide. The DL 50 (mg a.i./ mg larva) values of the amides N-isopropyl e N-hexyl to A. monuste orseis were 0,278 and 0,004, respectively, and to S. frugiperda were 1.359 and 0.613, respectively. The steeper slopes of the dose-response curves for both species were obtained with N-isopropyl, indicating the higher homogeneity of response of the pest species studied to this compound. N-isopropyl was also the most promising piperine synthetic analog as insecticide agent among the compounds studied because it was the most toxic amide to both insect-pest species.

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“…[20][21][22][23][24][25][26][27] Our previous research on the flowers of P. formosa led to the discovery of a new grayanane diterpenoid, grayanotoxin XXII.…”

Section: )mentioning

confidence: 99%

“…[20][21][22][23][24][25][26][27] Our previous research on the flowers of P. formosa led to the discovery of a new grayanane diterpenoid, grayanotoxin XXII. 28) Since the secondary metabolites of the different parts of the medicinal plants often differ even growing in the same ecological environments, we further explored the fruits of this plant, in order to look for structural unique and bioactive diterpenoids.…”

mentioning

confidence: 99%

Three New Highly Acylated 3,4-seco-Grayanane Diterpenoids from the Fruits of Pieris formosa

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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The genus Pieris, which includes only 7 species in the world, is a small genus of the big family Ericaceae.1) In previous investigations, more than 40 new grayanane diterpenoids have been isolated from this genus, including asebotoxins I-X, pieristoxins A-K, and pierosides A-C from P. japonica [2][3][4][5][6][7][8][9][10][11][12][13] ; pierisformosins A-D and pierisformosides A-I from P. formosa. [14][15][16][17][18] Recently, two new highly acylated 3,4-seco-grayanane diterpenoids, pierisoids A and B, were isolated from the flowers of P. formosa. 19)Some of these diterpenoids have shown significant physiological properties, including blood pressure and heart rate lowering, cardiotoxic, neurotoxic, growth inhibitory, and insecticidal activities. [20][21][22][23][24][25][26][27] Our previous research on the flowers of P. formosa led to the discovery of a new grayanane diterpenoid, grayanotoxin XXII.28) Since the secondary metabolites of the different parts of the medicinal plants often differ even growing in the same ecological environments, we further explored the fruits of this plant, in order to look for structural unique and bioactive diterpenoids. As a result, three new highly acylated 3,4-seco-grayanane diterpenoids, pierisformotoxins E-G (1-3, Fig. 1), were isolated. In addition, compounds 1-3 were tested for their acetylcholinesterase (AChE) inhibitory and nerve growth factor (NGF)-potentiating activities. Herein, we report the isolation, structure determination and biological activities of compounds 1-3, and this is the first report of the chemical constituents of the fruits of P. formosa. Results and DiscussionThe 75% aqueous acetone extract of the fruits of P. formosa was concentrated under vacuum and then partitioned between EtOAc and H 2 O (1 : 1). The EtOAc layer was subjected repeatedly to column chromatography over silica gel and Sephadex LH-20, and purified by semipreparative HPLC to yield compounds 1-3.Pierisformotoxin E (1), [a] D 27 Ϫ40.1 (cϭ0.14, CHCl 3 ), showed a pseudomolecular ion peak at m/z 655 [MϩCl] Ϫ in the negative electrospray ionization-mass spectra (ESI-MS), and the molecular formula, C 31 (Table 1) showed twenty carbon signals, including three methyls, two methylenes (one olefinic), nine methines (four oxygen-bearing, and two olefinic), and six quaternary carbons (one carboxyl, one olefinic and three oxygen-bearing). Signal at d H 7.59, showing no correlation with any carbons in the heteronuclear single quantum coherence (HSQC) spectrum, was assigned to the exchangeable proton of a hydroxyl group. The aforementioned facts suggested that compound 1 was probably a highly acylated grayanane diterpenoid.By comparing the 1 H-and 13 C-NMR data of compound 1 with those of the polysterified grayanane diterpenoids previously reported, the planar structure of 1 was similar to that of Phytochemical investigation on the fruits of Pieris formosa resulted in the isolation of three new highly acylated 3,4-seco-grayanane diterpenoids, pierisformotoxins E-G (1-3). Their structures were eluc...

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Grayanoid diterpene insect antifeedants and insecticides from Rhododendron molle

Cited by 99 publications

References 14 publications

Terpenos com atividade inseticida: uma alternativa para o controle químico de insetos

Terpenos com atividade inseticida: uma alternativa para o controle químico de insetos

Toxicidade de amidas análogas à piperina a larvas de Ascia monuste orseis Godart (Lepidoptera: Pieridae) e Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae)

Three New Highly Acylated 3,4-seco-Grayanane Diterpenoids from the Fruits of Pieris formosa

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