Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Chumkaew, Parinuch; Kato, Shigeru; Chantrapromma, Kan

doi:10.1248/cpb.54.1344

Cited by 39 publications

(27 citation statements)

References 11 publications

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“…The ethyl acetate fraction was then subjected to repeated column chromatography on Sephadex LH20, silica gel 60N, octadecylsilyl (ODS) gel, and preparative thin layer chromatography (PTLC) to obtain dasyclamide (2), 9) ent-2b-hydroxymanool (3), 10) chrysin (4), 11) apigenin (5), 12) and kaempferol-3-O-b-D-glucopyranoside (6). 13) All of the known compounds were identified by spectroscopic data including 1D and 2D NMR and by comparison with those published in the literature.…”

Section: Resultsmentioning

confidence: 99%

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

et al. 2010

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Amoora cucullata (Meliaceae) is a tall tree, grown in the coastal areas of Southeast Asia and the Indian Ocean. This plant has been used as a folk medicine for treatment of inflammation, marrow and diarrhea.1) Additionally, juice of the leaves has antibacterial activity and extensively used for the treatment of dysentery, skin and cardiac diseases.2) The crude methanolic extracts of leaves were reported to show antiinflammatory, antinociceptive, diuretic, and central nervous system (CNS) depressant activities.3,4) Phytochemical analysis of the stem bark of Amoora cucullata led to the isolation of fridelin, stigmasterol, b-sitosterol, betulinic acid and caffeic acid.5) Furthermore, analysis of the leaves showed the presence of several polyphenols and tannins, whether from its fruits, several rocagloic acid derivatives were isolated.6) In continuation of our phytochemical screening of A. cucullata leaves, we report the isolation and structure elucidation of one new putrescine bisamide, cucullamide (1), along with five known natural compounds (2-6) ( Fig. 1). The new putrescine bisamide derivative (1) and dasyclamide (2) were evaluated for their Wnt signal inhibitory activities, since we are recently interested in screening studies targeting signaling molecules related to cancer diseases. 7) Results and DiscussionThe fresh leaves of Amoora cucullata were collected from the Sundarbans Mangrove Forests, Bangladesh.8) The methanolic extract of A. cucullata was partitioned successively with ethyl acetate, nBuOH, and water. The ethyl acetate fraction was then subjected to repeated column chromatography on Sephadex LH20, silica gel 60N, octadecylsilyl (ODS) gel, and preparative thin layer chromatography (PTLC) to obtain dasyclamide (2), 9) ent-2b-hydroxymanool (3), 10) chrysin (4), 11) apigenin (5), 12) and kaempferol-3-O-b-D-glucopyranoside (6). 13) All of the known compounds were identified by spectroscopic data including 1D and 2D NMR and by comparison with those published in the literature. All these five known compounds are isolated and reported for the first time from this plant.Compound 1 was isolated as a white solid. On the TLC plate after developing compound 1, it gave a positive color reaction after spraying with Dragendorff reagent and dark fluorescence under UV light at 254 nm. The electrospray ion- Sciences, Chiba University; 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan: b Pharmacy Discipline, Life Science School, Khulna University; Khulua-9208, Bangladesh: and c Chemistry Department, Faculty of Science, Helwan University; Cairo 11795, Egypt. Received April 30, 2010; accepted May 21, 2010; published online May 21, 2010 A new putrescine bisamide derivative named cucullamide (1) was isolated from the leaves of Amoora cucullata, together with five known natural products, dasyclamide (2), ent-2b-hydroxymanool (3), chrysin (4), apigenin (5), and kaempferol-3-O-b-D-glucopyranoside (6). The structure of the new isolated compound was elucidated on the basis of 1D and 2D NMR as well as high resolution-ele...

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Section: Resultsmentioning

confidence: 99%

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

et al. 2010

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“…31 When compared with the 1 H NMR spectrum of rocagloic acid, besides a singlet ascribed to the formyl group that appeared at δ H 7.95, a downfield shift of approximately 1.3 ppm for H-1 was observed due to the hydroxy group at C-1 of rocagloic acid being substituted by an aldehyde group in compound 3 . The CD curve of 3 was found to be quite comparable with that of rocaglamide, with a characteristic absorption at 274 nm.…”

Section: Newly Isolated Rocaglamide Derivatives Since 2006mentioning

confidence: 95%

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species

et al. 2014

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Investigations on the chemistry and biology of rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species during the period 2006–2013 are reviewed. Included are new phytochemical studies of naturally occurring rocaglamide derivatives, an update on synthetic methods for cyclopenta[b]benzofurans, and a description of the recent biological evaluation and mechanism-of-action studies on compounds of this type.

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“…Bioassay-guided separation of E. succirubrum bark led to four new compounds, erythrophlesins A-D (19)(20)(21)(22) 35) (Fig. 8), were isolated.…”

Section: Cassaine Diterpenoid Dimers From the Bark Ofmentioning

confidence: 99%

Bio-active Natural Products with TRAIL-Resistance Overcoming Activity

Ahmed

Ishibashi

2016

Chem. Pharm. Bull.

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Tumor necrosis factor related apoptosis-inducing ligand (TRAIL) has emerged as a promising anticancer agent as it selectively kills cancer cells. However, TRAIL resistance limits its use as a therapeutic agent. An understanding the mechanisms responsible for TRAIL resistance and strategies to overcome it are important for its effective use as an anticancer agent. During our studies to screen natural products from medicinal plants, we identified a number of compounds with synergistic effects on TRAIL-induced apoptosis in tumor cells. This review describes our recent studies on the isolation of bioactive compounds with TRAILresistance overcoming activity.

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Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Cited by 39 publications

References 11 publications

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

Cucullamide, a New Putrescine Bisamide from Amoora cucullata

Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species

Bio-active Natural Products with TRAIL-Resistance Overcoming Activity

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