Antineoplastic agents.  160.  Isolation and structure of combretastatin D-1:  a cell growth inhibitory macrocyclic lactone from Combretum caffrum

Pettit, George R.; Singh, Sheo B.; Niven, Margaret L.

doi:10.1021/ja00233a037

Cited by 45 publications

(57 citation statements)

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“…The 1 H NMR spectrum of 2 resembles that of 1, except for the presence of an O-methyl group at δ H 3.95 (s, 3H) ( Table 1). The 13 C NMR values of all the carbons of 2 agreed closely with those of 1 except for the differences in the chemical shifts of C-10, C-11, and C-12, which were consistent with the presence of an O-methyl group. 15 2D-NMR analysis (Table S2 and Figure S1) showed that 2 was the 11-Omethyl derivative of 1.…”

supporting

confidence: 61%

“…Preliminary 1 H NMR analyses of compounds 1−5 revealed structural similarity and indicated the presence of a rare caffrane 13 4 , suggesting 10 degrees of unsaturation. Its molecular formula suggested the compound to be isomeric to corniculatolide A (5).…”

mentioning

confidence: 99%

“…Isocorniculatolide A (1): C 18 H 18 O 4 ; colorless needles from a mixture of n-hexane and acetone (7:3); R f 0.5 (n-hexane−acetone, 7.5:2.5); mp 202−203°C; UV (CH 3 OH) λ max 279 nm (ε 2739); IR (KBr) ν max 3390, 2963, 1714, 1594, 1518, 1427, 1271, 1218 cm −1 ; 1 H, 13 C, and 2D-NMR data (see Tables 1−3 Experimental Section: collection, extraction, and isolation; spectral data of compounds 1−5; 1 H/ 13 C NMR, DEPT, and all 2D-NMR spectra for 1 to 4; 1 H/ 13 C NMR and DEPT spectra of 5; 1 H NMR of unidentified minor constituent and acetylated compounds of 1 and 5; 1 H NMR spectra of a mixture of subfractions; X-ray data of 1. This material is available free of charge via the Internet at http://pubs.acs.org.…”

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confidence: 99%

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Unusual Isomeric Corniculatolides from Mangrove, Aegiceras corniculatum

et al. 2012

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Four new isomeric macrolides of combretastatin D-2 congeners named isocorniculatolide A (1), 11-O-methylisocorniculatolide A (2), 11-O-methylcorniculatolide A (3), and 12-hydroxy-11-O-methylcorniculatolide A (4), and the known corniculatolide A (5), arjunolic acid, and maslinic acid were isolated from the CHCl(3) extract of the bark of Aegiceras corniculatum. The structures of the new compounds (1-4) were elucidated by a combination of spectroscopic analysis (1-5), chemical modifications, and single-crystal X-ray analysis (1).

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confidence: 61%

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confidence: 99%

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Unusual Isomeric Corniculatolides from Mangrove, Aegiceras corniculatum

et al. 2012

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“…[15][16][17][18][19][20][21][22][23] The A series of combretastatins includes combretastatins A-1 to A-6 2-7, and these have been found to be tubulin polymerization inhibitors. Their structures were established by NMR spectra and further confirmed by total syntheses.…”

Section: Combretastatins Of the A Series And Their Analoguesmentioning

confidence: 99%

Natural stilbenes: an overview

2009

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Natural stilbenes have been a hot research topic due to their intricate structures and diverse biological activities. Although their molecular backbone consists only of 1,2-diphenylethylene units, stilbenes show an enormous diversity with regard to the different units present, the degree of polymerisation, and the pattern of oligomer construction. From January 1995 to the end of 2008, more than 400 new naturally occurring stilbenes were isolated and identified, and this review focuses on their structural diversity, distribution, and bioactivity.

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“…A series of cell growth inhibitory stilbenes [9,[22][23][24], dibenzyls [10], phenanthrenes [25], dihydrophenanthrenes [25], phenanthraquinones [26] and two macrocyclic lactones [27,28] have been isolated from the Combretum caffrum Kuntz, and related species. CA-4 was the most potent of all the isolated compounds as antitumour agent, while combretastatin A-1 (CA-1) and combretastatin A-2 (CA-2) were one-fifth and one-tenth as potent as CA-4, respectively.…”

Section: Combretastatinsmentioning

confidence: 99%

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

Hsieh

Liou²,

Mahindroo

2005

CPD

148

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The design of novel anticancer agents based on the combretastatins, a group of antimitotic agents isolated from the bark of the South African willow tree Combretum caffrum Kuntz, is of considerable contemporary interest. Combretastatin A-4, the most active compound in the group, due to its unique dual features of antitubulin and antivascular properties, has drawn significant attention of medicinal chemists for the design of analogues as novel antitumor agents. To date, 252 references have been published since 1982 and 187 references have been published since 1998 related to combretastatins research. The 102 references related to chemistry efforts can be classified into three different categories including one-atom, two-atom, and three-atom bridgeheads as linker between two aryl rings of combretastatins. This review will particularly elucidate the rationale and strategic tactics towards the development of novel classes of antimitotic agents, based upon combretastatin A-4 as a promising lead.

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Antineoplastic agents. 160. Isolation and structure of combretastatin D-1: a cell growth inhibitory macrocyclic lactone from Combretum caffrum

Cited by 45 publications

References 0 publications

Unusual Isomeric Corniculatolides from Mangrove, Aegiceras corniculatum

Unusual Isomeric Corniculatolides from Mangrove, Aegiceras corniculatum

Natural stilbenes: an overview

Pharmaceutical Design of Antimitotic Agents Based on Combretastatins

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