Rocaglamides, Glycosides, and Putrescine Bisamides from Aglaia dasyclada

Chaidir,; Lin, Wenhan; Ebel, Rainer; Ra, Edrada; Wray,; Nimtz, Manfred; Sumaryono, Wahono; Proksch, Peter

doi:10.1021/np0102354

Cited by 33 publications

(25 citation statements)

References 15 publications

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“…Two methoxyl groups, three aromatic rings, one phenyl group, one parasubstituted phenyl, and one aromatic ring with meta positions unsubstituted were deduced from the 1 H NMR spectrum ( Table 1). Analysis of the 1 H and 13 C NMR spectra of 2 indicated a similar skeleton to those of aglains [6]. However, the down-field carbon signal (d C 76.0, s) indicated that 2 had a new 2-hydroxy-2-methylbutyryl group, similar to aglaxiflorins A -D [10].…”

Section: Resultsmentioning

confidence: 93%

“…Its UV spectrum indicated absorptions at 208 and 278 nm, consistent with the characteristic of lignans. In addition, the 1 H NMR spectrum of 1 showed four methoxyl groups, one phenyl group, one trisubstituted phenyl group, and one oxygenated benzene group with two meta protons, indicating typical signals of rocaglamides or aglains [6]. Its characteristic quaternary signals of d C 101.5 (s, C-3a) and 93.0 (s, C-8b) in the 13 C NMR spectrum (Table 1) further suggested it was a rocaglamide analog rather than aglains [7].…”

Section: Resultsmentioning

confidence: 99%

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Two new lignans from twigs of Aglaia odorata

Peng

Zeng

et al. 2015

Journal of Asian Natural Products Research

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Two new lignans from twigs of Aglaia odorata

Peng

Zeng

et al. 2015

Journal of Asian Natural Products Research

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“…1) As part of our continuing search for bioactive constituents from Thai medicinal plants, [2][3][4] separate hexane and dichloromethane soluble extracts of the fruits of A. cucullata were found to exhibit significant cytotoxic activity when evaluated against a panel of human cell lines. Fractionation of the hexane and dichloromethane extracts led to the isolation of two new naturally occurring cyclopenta [b]benzofuran, 1-O-formylrocagloic acid (1) and 3Ј-hydroxyrocagloic acid (2), along with five known compounds, rocaglaol (3), 5) rocagloic acid (4), 6) 3Ј-hydroxymethylrocaglate (5), 7) 1-Oformylmethyl rocaglate (6), 5) and methylrocaglate (7), 5) from the fruits of A. cucullata. The structures of the known compounds were elucidated by comparison of their physical and spectral data with literature values.…”

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confidence: 99%

Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Chumkaew

Kato

Chantrapromma

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new rocaglamide derivatives, 1-O-formylrocagloic acid (1) and 3-hydroxy rocagloic acid (2), together with five known compounds, rocaglaol (3), rocagloic acid (4), 3-hydroxymethylrocaglate (5), 1-O-formylmethyl rocaglate (6), and methylrocaglate (7), were isolated from the fruits of Amoora cucullata. Their structures were elucidated by spectroscopic methods. Compounds 1-3, 6, and 7 exhibited potent cytotoxicity against KB, BC, and NCI-H187 cell lines, whereas 4 and 5 showed selective cytotoxicity against NCI-H187 cell line.

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“…10,44 In addition, if there were a C-4 α-oriented phenyl ring, the 6-OCH 3 protons would be shielded from around δ H 3.88 to approximately 3.11. 10,43 In the 1 H NMR spectrum of compound 1, the 6-OCH 3 protons appeared at δ H 3.88, which implied the absence of any shielding effect from the benzene ring, and confirmed the β orientation of the C-4 phenyl group. The observed NOESY cross peaks of H-10/H-3, H-2′(6′) and H-2″(6″), as well as H-3/H-2′(6′) and H-2″(6″), further supported the 3-βH and 4-αH orientation and established the endo relationship between H-10 and H-3 ( Figure 1).…”

Section: Resultsmentioning

confidence: 77%

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

Li¹,

Acuña²,

Li³

et al. 2013

Planta Med

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Eight new compounds, including two cyclopenta [b]benzopyran derivatives (1, 2), two cyclopenta [b]benzofuran derivatives (3, 4), three cycloartane triterpenoids (5-7), and an apocarotenoid (8), together with 16 known compounds, were isolated from the chloroform-soluble partitions of separate methanol extracts of a combination of the fruits leaves and twigs, and of the roots of Aglaia perviridis collected in Vietnam. Isolation work was monitored using human colon cancer cells and facilitated with an LC/MS dereplication procedure. The structures of the new compounds (1-8) were determined on the basis of spectroscopic data interpretation. The Mosher ester method was employed to determine the absolute configurations of 5-7, and the absolute configurations of the 9,10-diol unit of compound 8 was established by a dimolybdenum tetraacetate [Mo 2 (AcO) 4 ] induced circular dichroism (ICD) procedure. Seven known rocaglate derivatives (9-15) exhibited significant cytotoxicity against the HT-29 cell line, with rocaglaol (9) being the most potent (ED 50 0.0007 µM). The new compounds 2-4 were also active against this cell line, with ED 50 values ranging from 0.46 to 4.7 µM. The cytotoxic compounds were evaluated against a normal colon cell line, CCD-112CoN. In addition, the new compound perviridicin B (2), three known rocaglate derivatives (9, 11, 12), as well as a known sesquiterpene, 2-oxaisodauc-5-en-12-al (17), showed significant NF-κB (p65) inhibitory activity in an ELISA assay.* Corresponding Author. Tel: +1-614-247-8094. Fax: +1-614-247-8119. kinghorn@pharmacy.ohio-state.edu. # Dedicated to Dr. Lester A. Mitscher, of the University of Kansas, for his pioneering work on the discovery of bioactive natural products and their derivatives ASSOCIATED CONTENT Supporting Information. 1 H, 13 C and 2D NMR spectra of compounds 1-8, 1 H NMR of (R)-and (S)-MTPA esters of 5-7. This material is available free-of-charge via the Internet at http://pubs.acs.org. NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2014 March 22. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptAglaia Lour., containing more than 120 species, is the largest genus of the plant family Meliaceae. 1 Aglaia species have attracted considerable interest in the area of natural products research, since they are a rich source of the "flavagline" class of bioactive agents. Flavagline derivatives have been proposed to be biogenetically derived from the coupling of a flavonoid unit and a cinnamic acid amide moiety, and can be divided into three subtypes, namely, the cyclopenta [b]benzofurans, the cyclopenta [b]benzopyrans, and the benzo [b]oxepines. [2][3][4][5] More than 100 flavaglines have been isolated from over 30 Aglaia species to date. [2][3][4][5] In a search for new anticancer agents from tropical plants, several Aglaia species, including Aglaia crassinervia, 6 A. edulis, 7 A. elliptica, 8 A. foveolata, 9-11 A. ponapensis, 12 and A. rubiginosa, 13 mainly collected from Indonesia, have been in...

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Rocaglamides, Glycosides, and Putrescine Bisamides from Aglaia dasyclada

Cited by 33 publications

References 15 publications

Two new lignans from twigs of Aglaia odorata

Two new lignans from twigs of Aglaia odorata

Potent Cytotoxic Rocaglamide Derivatives from the Fruits of Amoora cucullata

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

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