Phragmalin limonoids from Chukrasia tabularis

Nakatani, Munehiro; Abdelgaleil, Samir A. M.; Saad, Mona M. G.; Huang, Ruo Chun; Doe, Matsumi; Iwagawa, Tetsuo

doi:10.1016/j.phytochem.2004.08.010

Cited by 78 publications

(58 citation statements)

References 19 publications

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“…Tabulalide K (6) was isolated as white amorphous powder, and its molecular formula was established to be C 39 H 46 O 19 by its HR-ESI-MS ion at m/z 841.2509 [MϩNa] ϩ (Calcd: 6) which was confirmed by the presences of an orthoacetate group, a b-substituted furanyl ring, oxygenated C-19 methylene signals, the characteristic proton signals of 4,29,1-ring bridge. Four acetyls was attached to C-3, C-12, C-19, and C-30 based on the HMBC correlations (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…C-NMR spectroscopic data indicated that 9 was also a phragmalin limonoid orthothester as tabulalide D, 6) with the additional signals corresponding to a propionyl group [d H 2.34 (q, Jϭ7.6 Hz, 2H), 1.12 (t, Jϭ7.6 Hz, 3H); d C 173. 3, 27.7, 8.7].…”

Section: Resultsmentioning

confidence: 99%

“…6,9) Compounds 2-12 were tested for cytotoxic activity against five human cancer cell lines, MCF-7 (human breast cancer), Hela (human cervical cancer), SGC-7901 and BGC-823 (human gastric cancer), HepG2 (human liver cancer), by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The preliminary result showed that compound 2 exhibited moderate cytotoxic activity against MCF-7 with IC 50 value of 20.4 mmol/l and weak cytotoxic activity against SGC-7901 with IC 50 value of 63.4 mmol/l.…”

Section: Resultsmentioning

confidence: 99%

“…1,2) The genus chukrasia (Meliaceae) 3) was revealed to be a rich resource of structure diversified phragmalin-type limonoids as well as orthoesters. [4][5][6][7][8][9] Our previous study on phragmalin-type limonoids from Chukrasia tabularis var. velutina afforded a series of 16-norphragmalin limonoids 10,11) and a new class of C-15-acyl phragmalin-type limonoids orthoesters.…”

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Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

Luo

Wang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleThe orthoester group contains a carbon atom bearing three alkoxy or aryloxy groups, and, combined with additional attachments and/or rings, constructs often various structural skeletons of stereochemical complexity, such as daphnane diterpenoids, phragmalin-type limonoids, and bufadienolide and ergostanoid steroids, some of which showed anticancer, antifeedant, and insecticidal activities. 1)Phragmalin-type limonoid orthoester is an important branch of orthoesters with phragmalin limonoid as the basic skeleton, discovered exclusively from the genera of Meliaceae.1,2) The genus chukrasia (Meliaceae) 3) was revealed to be a rich resource of structure diversified phragmalin-type limonoids as well as orthoesters. [4][5][6][7][8][9] Our previous study on phragmalin-type limonoids from Chukrasia tabularis var. velutina afforded a series of 16-norphragmalin limonoids 10,11) and a new class of C-15-acyl phragmalin-type limonoids orthoesters.12) In our present research, nine new phragmalintype limonoid orthoesters, tabulalides F-N (1-9), together with three known compounds, tabulalides C and D and tabularisin N (10-12), were isolated from the ethanol extract of this plant. The structures of these new compounds ( Fig. 1) were elucidated using extensive 2D spectroscopic technologies, and the absolute configurations of 1 and 2 were determined by circular dichroism (CD) exciton chirality method.1,13) Tabulalide F (1) possesses a rare orthoisobutylate moiety in phragmalin limonoid orthoesters.Anticancer activity is the important aspect of limonoids from Meliaceae, and a precursor of phragmalin limonoid was found to be a novel Hsp90 inhibitor.14,15) So, we evaluated cytotoxic activity of compounds 2-12 against five human cancer cell lines, MCF-7 (human breast cancer), Hela (human cervical cancer), SGC-7901 and BGC-823 (human gastric cancer), HepG2 (human liver cancer). The preliminary results indicated that compund 2 exhibts moderate cytotoxic activity against MCF-7 with IC 50 value of 20.4 mmol/l and weak cytotoxic activity against SGC-7901 with IC 50 value of 63.4 mmol/l. The other isolates show weak cytotoxic activity or noncytotoxic (IC 50 Ͼ100 mmol/l) anainst other cancer cell lines. Herein, the isolation, structural elucidation, and cytotoxic activity of these isolates were reported. Results and DiscussionTabulalide F (1) was isolated as white amorphous powder. Its molecular formula was established to be C 38 H 44 O 17 by the high resolution-electrospray ionization (HR-ESI)-MS ion at m/z 783.2470 [MϩNa] ϩ (Calcd: C 36 H 44 O 16 Na, 783.2471). The IR absorption bands at 3499, 1737 and 1641 cm Ϫ1 suggested the presence of hydroxyl, ester, and a,b-unsaturated ester carbonyl groups. The data from decoupling and subsequent 1D-and 2D-NMR studies ( 1 H, 13 C, heteronuclear multiple bond connectivity (HMBC), heteronuclear single quantum coherence (HSQC), and rotating frame Overhauser enhancement spectroscopy (ROESY)) (Fig. 2) Nine new phragmalin-type limonoid orthoesters, tabulalides F-N (1-9), together with th...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

Luo

Wang

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Possui, ainda, um grande potencial como fonte de compostos biologicamente ativos provenientes de plantas medicinais. Plantas da família Meliaceae são conhecidas por conter uma variedade de compostos descritos como inseticidas, antialimentares e reguladores do crescimento (NAKATANI et al, 2004). Dentro dessa família, destaca-se a Azadirachta indica, conhecida por nim, que é considerada uma das mais importantes, graças à sua atividade sistêmica, eficiência em baixas concentrações e baixa toxicidade aos mamíferos (GALLO et al, 2002).…”

Section: Introductionunclassified

Atividade inseticida in vitro do óleo de sementes de nim sobre Lutzomyia longipalpis (Diptera: Psychodidae)

Maciel¹,

Morais²,

Beviláqua³

et al. 2010

Rev. Bras. Parasitol. Vet. (Online)

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ResumoLutzomyia longipalpis é o principal vetor da Leishmaniose visceral no Brasil. O objetivo deste trabalho foi avaliar o efeito do óleo de sementes de nim (Azadirachta indica) sobre ovos, larvas e adultos do vetor. Os insetos foram capturados no campo e mantidos no laboratório a ± 27 °C e 80% de umidade relativa. Cinco tratamentos com diferentes concentrações foram realizados, usando-se dois controles negativos, um com água destilada e outro com Tween 80 (3%) e um controle positivo com cipermetrina. Os ovos foram borrifados com o óleo em diferentes concentrações e avaliou-se o número de larvas eclodidas por 10 dias consecutivos. A mortalidade das larvas foi observada até a pupação, e a mortalidade dos adultos foi observada após 24, 48, e 72 horas. A análise estatística foi feita pelo teste de Tukey a 5% de probabilidade. No teste com ovos, a maior concentração obteve 65,16 ± 3,24% de eficácia. O teste com larvas apresentou 67,75 ± 2,21% de eficácia na concentração de 100 mg.mL -1. Com adultos, a eficácia na concentração de 100 mg.mL -1 foi de 96,64 ± 4,11%, após 24 horas. A análise fitoquímica revelou a presença de triterpenos. Esses resultados demonstram o potencial uso desse óleo no controle deste vetor.Palavras-chave: nim, flebotomíneos, óleo, leishmaniose, inseticidas botânicos. AbstractLutzomyia longipalpis is the main vector of visceral leishmaniasis in Brazil. The objective was to evaluate the effect of oil from (Azadirachta indica) neem seeds on eggs, larvae and adults of the vector. The insects were captured in the field and kept in the laboratory at ± 27 °C and 80% relative humidity. Five treatments with different concentrations were performed using two negative controls (distilled water and Tween 80) and a positive control. The eggs were sprayed with the oil at different concentrations and the number of hatched larvae evaluated for 10 days. Mortality of larvae was observed to pupation and adult mortality was observed after 24, 48, and 72 hours. Statistical analysis was performed by Tukey test at 5% probability. The highest oil concentration of eggs obtained 65.16 ± 3.24% efficacy for reducing egg hatching. The test with larvae showed 67.75 ± 2.21% efficacy at a concentration of 100 mg.mL -1 . In adults, the efficacy of the 100 mg.mL -1 concentration was 96.64 ± 4.11% after 24 hours. The phytochemical analysis revealed the presence of triterpenes. These results demonstrate the potential use of this oil in the control of this vector.

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D‐Ring‐Opened Phragmalin‐Type Limonoids from Chukrasia tabularis var. velutina

Luo

Wang

et al. 2011

Chemistry & Biodiversity

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Five new D-ring-opened phragmalin-type limonoids, tabulalins A-E (1-5, resp.), were isolated from the stem bark of Chukrasia tabularis var. velutina. In the structures of these new isolates, the D-ring (C(16)/C(17) δ-lactone ring) of phragmalins was cleaved, and rare C(16)/C(30) δ-lactone ring in 1-3 or C(16)/C(8) γ-lactone ring in 4 and 5 were formed. The structures of these new compounds were elucidated based on extensive 1D- and 2D-spectroscopic analyses (HSQC, HMBC, and ROESY) and HR-ESI-MS. The major compounds, 2, 3, and 5, were evaluated for their inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in a macrophage (RAW264.7) cell line with IC(50) values of 15.3±0.6, 13.0±0.5, and 17.1±0.7 μM, respectively.

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Phragmalin limonoids from Chukrasia tabularis

Cited by 78 publications

References 19 publications

Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

Atividade inseticida in vitro do óleo de sementes de nim sobre Lutzomyia longipalpis (Diptera: Psychodidae)

D‐Ring‐Opened Phragmalin‐Type Limonoids from Chukrasia tabularis var. velutina

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