Silvestrol and Episilvestrol, Potential Anticancer Rocaglate Derivatives from <i>Aglaia silvestris.</i>

Hwang, Bang Yeon; Su, Bao Ning; Chai, Heebyung; Mi, Qiuwen; Kardono, Leonardus B.S.; Afriastini, Johar J.; Riswan, Soedarsono; Santarsiero, Bernard D.; Mesecar, Andrew D.; Wild, Robert B.; Fairchild, Craig R.; Vite, Gregory D.; Rose, William C.; Farnsworth, Norman R.; Cordell, Geoffrey A.; Pezzuto, John M.; Swanson, Steven M.; Kinghorn, A. Douglas

doi:10.1021/jo040008h

Cited by 34 publications

(96 citation statements)

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“…Silvestrol (11) was first isolated from the fruits of Aglaia sylvestris (M. Roemer) Merrill (Meliaceae) (later re-identified as Aglaia foveolata Pannell) collected in Indonesia (Hwang et al, 2004). The chloroform-soluble extract was found to be cytotoxic to several human cancer cell lines and, more importantly, the extract was active in the P-388 in vivo test system.…”

Section: Anti-cancer Drug Discoverymentioning

confidence: 99%

Drug discovery from medicinal plants

2005

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Section: Anti-cancer Drug Discoverymentioning

confidence: 99%

Drug discovery from medicinal plants

2005

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“…Pervilleine A is currently in preclinical development (Mi et al, 2003). Silvestrol (17) was first isolated from the fruits of Aglaila sylvestre (M. Roemer) Merrill (Meliaceae) (Hwang et al, 2004). Silvestrol exhibited cytotoxicity against lung and breast cancer cell lines (Cragg and Newman, 2005).…”

Section: Plant-derived Anti-cancer Agents For Future Developmentmentioning

confidence: 99%

Anticancer agents from medicinal plants

Shoeb

2008

Bangladesh J Pharmacol

140

113

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“…In the 1 H NMR spectrum, the 11 protons in the low-field region could be attributed to three aromatic rings, including a monosubstituted benzene ring at δ H 7.29-7.40 (5H, m, H-2″-6″), a 1,4-disubstituted benzene ring at δ H 7.06 (2H, d, J = 8.9 Hz, H-3′, 5′) and 7.70 (2H, d, J = 8. 9 Hz, H-2′, 6′), as well as a 1,2,3,5 tetrasubstituted benzene ring at δ H 6.16 (1H, d, J = 2.2 Hz, H-7) and 6.19 (1H, d, J = 2.3 Hz, H-9). Also observed were an oxygenated methine singlet at δ H 4.67 (1H, s, H-10), two methine protons at δ H 3.50 (1H, d, J = 5.2 Hz, H-3) and 4.30 (1H, d, J = 5.4 Hz, H-4), which coupled to each other in the 1 H-1 H COSY spectrum as well as three methoxy groups at δ H 3.88 (3H, s, OCH 3 -6), 3.87 (3H, s, OCH 3 -4′), and 3.76 (3H, s, OCH 3 -8) (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…which revealed the presence of four rocaglaol derivatives (9)(10)(11)(12). In addition, the occurrence of unknown cytotoxic compounds was suggested with possible molecular formulas of C 29 H 28 O 9 and C 27 H 26 O 7 .…”

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confidence: 95%

“…Cyclopenta [b]benzopyran derivatives, with most of them being rocaglaol and related analogues, and triterpenoids, mainly of the glabretal-, baccharane-, and dammarane-types, were isolated as the major constituents from the above-mentioned taxa. [6][7][8][9][10][11][12][13] Among the flavaglines from Aglaia species, two cyclopenta [b]benzofurans have been reported to exhibit inhibitory activity in vivo in tumor-bearing experimental animals, 2-5 namely, rocaglamide 14 and silvestrol. 9,[15][16][17][18] Silvestrol was isolated and fully structurally characterized from A. foveolata Pannell 9 , obtained from Kalimantan, Indonesia, and also obtained from A.…”

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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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Silvestrol and Episilvestrol, Potential Anticancer Rocaglate Derivatives from Aglaia silvestris.

Cited by 34 publications

References 0 publications

Drug discovery from medicinal plants

Drug discovery from medicinal plants

Anticancer agents from medicinal plants

Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis

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