Discovery and Chemistry of Naturally-Occurring Anticancer Agents

Cassady, John M.; Chang, Ching‐Jer; Cooks, R. Graham

doi:10.1007/978-3-642-74017-6_16

Cited by 3 publications

(3 citation statements)

References 53 publications

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“…IR absorption at 1757.0 and 1716.2 cm-', 'H-NMR (500 MHz, C6DJ signals at 6 1.552 ppm (s, 3H), for the terminal lactone methyl, and at 6 2.61 ppm (H2), 1.983 (ddd, H3a), 1.88 (H3b), 1.88 (H35a), and 2.628 (dd, H35b) suggested the presence of fragment B. This terminal methylketo-lactone was described in bullatacinone (Hui et al, 1989b) and was also recently reported trans O H threo threo erythro in isoannonacin and isoannonacin-10-one (Cassady et al, 1988 andXu et al, 1989) and in squamone (Li et al, 1990). I3C-NMR signals at 177.012 (Cl), 43.800 (C2), 78.456 (C4), 203.991 (C36), and 36.943 (C37) confirmed the above fragment B.…”

Section: Resultssupporting

confidence: 63%

Bullatalicinone, a new potent bioactive acetogenin, and squamocin from annona bullata (Annonaceae)

Hui

Rupprecht

Anderson

et al. 1991

Phytotherapy Research

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Further fractionation of the EtOH extract of the bark of Annona bullata Rich. (Annonaceae) has led to the isolation of a new nonadjacent bis-tetrahydrofuran acetogenin, bullatalicinone, and the known adjacent bistetrahydrofuran acetogenin, squamocin. These two compounds showed potent and selective cytotoxicities for certain human tumor cell lines. Their structures have been elucidated by chemical and spectral methods. Bullatalicinone is the methylketo-lactone derivative of bullatalicin which we found previously in this plant.

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Section: Resultssupporting

confidence: 63%

Bullatalicinone, a new potent bioactive acetogenin, and squamocin from annona bullata (Annonaceae)

Hui

Rupprecht

Anderson

et al. 1991

Phytotherapy Research

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“…Initial screening in the BST of the defatted seeds of A. muricata showed the ethanolic extracts to be highly active. Our bioactivity-directed fractionation of this plant material previously led to the isolation of seven known mono-tetrahydrofuran (THF) ring acetogenins, including the annonacin series, − the muricatetrocins and gigantetrocins, and muricatacin, a possible oxidation product derived from the annonacin series which provided insights into the absolute stereochemistry of these compounds. Cavé and co-workers previously reported the isolation, structure determination, and biological activities of four new mono-THF ring acetogenins, murisolin, corossolin, corossolone, and solamin, from the seeds.…”

mentioning

confidence: 99%

Five Novel Mono-tetrahydrofuran Ring Acetogenins from the Seeds of Annona muricata

Rieser¹,

Fang

et al. 1996

J. Nat. Prod.

120

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Bioactivity-directed fractionation of the seeds of Annona muricata L. (Annonaceae) resulted in the isolation of five new compounds: cis-annonacin (1), cis-annonacin-10-one (2), cis-goniothalamicin (3), arianacin (4), and javoricin (5). Three of these (1-3) are among the first cis mono-tetrahydrofuran ring acetogenins to be reported. NMR analyses of published model synthetic compounds, prepared cyclized formal acetals, and prepared Mosher ester derivatives permitted the determinations of absolute stereochemistries. Bioassays of the pure compounds, in the brine shrimp test, for the inhibition of crown gall tumors, and in a panel of human solid tumor cell lines for cytotoxicity, evaluated relative potencies. Compound 1 was selectively cytotoxic to colon adenocarcinoma cells (HT-29) in which it was 10,000 times the potency of adriamycin.

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“…The search for plant-derived anticancer drugs began in 1950 with the discovery and development of bisindole alkaloids [vincristine (VCR) and vinblastine (VLB)] from Catharanthus roseus (Apocynaceae) and the isolation of cytotoxic podophyllotoxins. The National Cancer Institute (NCI, USA) initiated its extensive plant collection program from the temperate regions in 1960 that led to the discovery of many novel chemical entities having varied cytotoxic activities (Cassady and Douros, 1980), including taxanes and camptothecins. Later on, the plant collection program was also focused on tropical and subtropical regions of the world.…”

Section: Introductionmentioning

confidence: 99%

Medicinal plant-derived therapeutics for treatment of neoplasms in modern and traditional systems of medicine

MANI,

SHUKLA,

SHUKLA

2020

JMAPS

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Cancer poses an important challenge for mankind. Plants have provided major remedies and clues for its treatment. Plant-derived compounds (phytomolecules) are an important source of several clinically-useful anticancer drugs. Here we summarize the current status of plant-based therapies for cancer treatment. Examples of clinically-useful anticancer phytomolecules are taxol, vincristine, vinblastine, camptothecin derivatives -topotecan and irinotecan, and etoposide derived from epipodophyllotoxin. Several promising compounds like, combretastatin A-4 phosphate and flavopiridol are in various stages of clinical development. IPI-926, a semi-synthetic analog of steroid alkaloid cyclopamine, has shown promise against several cancers including pancreatic cancer and leukemia and has been under clinical trials. Besides, there are several other promising molecules that are receiving attention. Most of the drugs are directly used after isolation and purification from renewable resources or they can be produced after efficient chemical modification of the same. Simultaneously, it must be appreciated that traditional systems of medicine like Ayurveda have also described cancerlike diseases (with alternative names like Arbuda, Granthi and Gulma) and prescribed plant-based therapies for curing them. Logically, if modern science takes cues from Ayurveda and targets such plants, a higher probability of hit rates in anticancer drug discovery is expected.

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Discovery and Chemistry of Naturally-Occurring Anticancer Agents

Cited by 3 publications

References 53 publications

Bullatalicinone, a new potent bioactive acetogenin, and squamocin from annona bullata (Annonaceae)

Bullatalicinone, a new potent bioactive acetogenin, and squamocin from annona bullata (Annonaceae)

Five Novel Mono-tetrahydrofuran Ring Acetogenins from the Seeds of Annona muricata

Medicinal plant-derived therapeutics for treatment of neoplasms in modern and traditional systems of medicine

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