The Alkaloids of Cephalotaxus drupacea and Cephalotaxus fortunei

Paudler, William W.; Kerley, Gerald I.; McKay, Jerry

doi:10.1021/jo01044a010

Cited by 155 publications

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“…Alcoholic extracts of the powdered leaves and stems of Cephalotaxus genera yield cephalotaxine (1, Figure 1) as the most abundant alkaloid constituent, [1,2] whose structure was unambiguously verified by X-ray crystallographic analysis. [3][4][5][6] While cephalotaxine (1) accounts for approximately 50 % of the mass of the crude alkaloid extract mixture, many minor constituents have also been identified.…”

Section: Introductionmentioning

confidence: 92%

“…[90] Since the most pressing late-stage challenge in the synthesis of the Cephalotaxus esters is the efficient attachment of hindered acyl chain derivatives, an approach was explored whereby novel bond angle strain elements were imparted to these substrates to enable their use in high yielding acylations of cephalotaxine (1). This strategy initially led to the facile synthesis deoxyharringtonine (2), and subsequently to other members of this alkaloid class, namely anyhydroharringtonine (5), homoharringtonine (3), and homodeoxyharringtonine (4) (i.e., see Figure 1). …”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…[3][4][5][6] While cephalotaxine (1) accounts for approximately 50 % of the mass of the crude alkaloid extract mixture, many minor constituents have also been identified. Among these are several rare C3-ester derivatives, including complex variants such as deoxyharringtonine (2), [7] homoharringtonine (3), [8] homodeoxyharringtonine (4), [9] and anhydroharringtonine (5). [10] Early biological evaluations of these alkaloids revealed that several Cephalotaxus esters demonstrate acute toxicity toward various murine leukemia, murine lymphoma, and human epidermoid carcinoma cells.…”

Section: Introductionmentioning

confidence: 99%

“…Keywords: alkaloids · antitumor agents · multidrug resistance · total synthesis of deoxyharringtonine (2). [12] By contrast, cephalotaxine (1) itself was found to be biologically inactive.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Antiproliferative Cephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

Eckelbarger

Wilmot

Epperson

et al. 2008

Chemistry A European J

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Deoxyharringtonine (2), homoharringtonine (3), homodeoxyharringtonine (4), and anhydroharringtonine (5) are reported to be among the most potent members of the antileukemia alkaloids isolated from the Cephalotaxus genus. Convergent syntheses of these four natural products are described, each involving novel synthetic methods and strategies. These syntheses enabled evaluation of several advanced natural and non-natural compounds against an array of human hematopoietic and solid tumor cells. Potent cytotoxicity was observed in several cell lines previously not challenged with these alkaloids. Variations in the structure of the ester chain within this family of alkaloids confer differing activity profiles against vincristine-resistant HL-60/RV+, signalling new avenues for molecular design of these natural products to combat multi-drug resistance.

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Section: Introductionmentioning

confidence: 92%

Section: Wwwchemeurjorgmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Antiproliferative Cephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

Eckelbarger

Wilmot

Epperson

et al. 2008

Chemistry A European J

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“…Consequently, E1 was obtained from the Chinese evergreen tree C. harringtonia K. Koch var. harringtonia (63), and other active alkaloids were isolated from various Cephalotaxus species (64,65). Interestingly, the parent compound, cephalotaxine (E3), is devoid of antitumor activity.…”

Section: Cephalotaxus Speciesmentioning

confidence: 99%

Plant‐Derived Natural Products Research in Drug Discovery

Lee

Itokawa

Akiyama

et al. 2012

Natural Products in Chemical Biology

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Natural Products as Cytotoxic Agents

Pullman,

León,

Cutler

2021

Burger's Medicinal Chemistry and Drug Discovery

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Nature has proved to be a wellspring of important antineoplastic agents. In recent years, there has been a resurgence in the study of natural products with an emphasis on the discovery of novel therapeutic agents. New technologies and approaches such as high‐throughput screening, parallel synthesis, and other programs has facilitated this increased interest in natural products research. The scientific literature indicates that natural sources not previously considered as bioactive have in fact, become potential valuable treasure troves of novel chemical structures. For example, marine products from diverse sources such as thermal vents, sponges, terrestrial thermal vents, glacial cryogenic organisms, and xerophytic and endophytic organisms now give rise to a vast assortment of microorganisms. Additionally, the study of the biosynthetic machineries and biochemical process in microorganism has enhanced the research of cryptic natural products, fueling the search for natural products in the treatment of cancer. It comes as no surprise that nature biosynthesizes chemical compounds that chemists have not considered even in their imaginations. Although this article provides a few of these examples, it is certain that more will be present in the literature as the intellectual property in these discoveries are protected.

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The Alkaloids of Cephalotaxus drupacea and Cephalotaxus fortunei

Cited by 155 publications

References 0 publications

Synthesis of Antiproliferative Cephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

Synthesis of Antiproliferative Cephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

Plant‐Derived Natural Products Research in Drug Discovery

Natural Products as Cytotoxic Agents

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