Tumor inhibitors. 120. Phyllanthocin, a novel bisabolane aglycone from the antileukemic glycoside, phyllanthoside

Kupchan, S. Morris; LaVoie, Edmond J.; BRANFMAN, A. R.; Fei, B Y; Bright, Willard M.; Bryan, R. F.

doi:10.1021/ja00451a074

Cited by 63 publications

(36 citation statements)

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“…Completion of the X-ray crystal structure determinations of phyllanthocindiol methyl ester (26) and phyllanthose acetate (36) clearly substantiates the assignment of structure 2a to phyllanthostatin 3 and confirms the previous (2a, 6) assignments of phyllanthostatins 1 and 2 ( l a , c) and of phyllanthoside (16). Presently, the results of these structural elucidations are being employed in establishing structures for related glycosides in this potentially important series of biosynthetic products.…”

supporting

confidence: 79%

Structure of the principal antineoplastic glycosides of Phyllanthusacuminatus Vahl

Pettit¹,

Cragg²,

Niven³

et al. 1983

Can. J. Chem.

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A series of degradative and X-ray crystallographic studies has led to unequivocal evidence for the structure (3a) assigned to the unique disaccharide phyllanthose. In turn, the X-ray crystal structure of phyllanthose confirms structures previously assigned to the potentially important antineoplastic plant glycosides phyllanthostatins 1 and 2 (1a, c) and phyllanthoside (1b). The chemical degradation and crystallographic analyses allowed assignment of structure 2a to phyllanthostatin 3.

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supporting

confidence: 79%

Structure of the principal antineoplastic glycosides of Phyllanthusacuminatus Vahl

Pettit¹,

Cragg²,

Niven³

et al. 1983

Can. J. Chem.

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“…Phyllanthoside was first isolated from an ethanolic extract prepared from the Central American tree Phyllanthus acuminatus, based on bioassay guided cytotoxicity fractionation (Kupchan et al 1977). Phyllanthoside is rapidly converted to an inactive metabolite, within ∼2 min of intravenous injection in mice or dogs (Moore and Powls 1986).…”

Section: Novel Protein Synthesis Inhibitorsmentioning

confidence: 99%

Eukaryotic protein synthesis inhibitors identified by comparison of cytotoxicity profiles

Chan¹,

Khan²,

Harvey³

et al. 2004

RNA

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The National Cancer Institute (NCI) Human Tumor Cell Line Anti-Cancer Drug Screen has evaluated the cytotoxicity profiles of a large number of synthetic compounds, natural products, and plant extracts on 60 different cell lines. The data for each compound/extract can be assessed for similarity of cytotoxicity pattern, relative to a given test compound, using an algorithm called COMPARE. In applying a chemical biology approach to better understand the mechanism of eukaryotic protein synthesis, we used these resources to search for novel inhibitors of translation. The cytotoxicity profiles of 31 known protein synthesis inhibitors were used to identify compounds from the NCI database with similar activity profiles. Using this approach, two natural products, phyllanthoside and nagilactone C, were identified and characterized as novel protein synthesis inhibitors. Both compounds are specific for the eukaryotic translation apparatus, function in vivo and in vitro, and interfere with translation elongation. Our results demonstrate the feasibility of utilizing cytotoxicity profiles to identify new inhibitors of translation.

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“…(Euphorbiaceae). Isolation of phyllanthocin from Phyllanthus brasiliensis Muell (Kupchan et al, 1977), phyllaemblicins A-F and G1-G8 from Phyllanthus emblica Linn (Lv et al, 2014a;Zhang et al, 2000aZhang et al, ,b, 2001, and phyllanthacidoids A-U from Phyllanthus acidus Skeels (Lv et al, 2014b;Vongvanich et al, 2000) have been previously reported. These compounds showed potent antileukemic (Kupchan et al, 1977), cytotoxic (Vongvanich et al, 2000) and anti-viral (Liu et al, 2009;Lv et al, 2014a,b) activities, which attracted considerable attention by pharmacologists and organic chemists (Moore and Powis, 1986;Smith et al, 1991).…”

Section: Introductionmentioning

confidence: 87%

Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations

Xin

et al. 2015

Phytochemistry

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Tumor inhibitors. 120. Phyllanthocin, a novel bisabolane aglycone from the antileukemic glycoside, phyllanthoside

Cited by 63 publications

References 0 publications

Structure of the principal antineoplastic glycosides of Phyllanthusacuminatus Vahl

Structure of the principal antineoplastic glycosides of Phyllanthusacuminatus Vahl

Eukaryotic protein synthesis inhibitors identified by comparison of cytotoxicity profiles

Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations

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