Antineoplastic Agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives)

George Pettit, Yanhui Meng, R. Patrick Gearing, Delbert L. Herald, Robin Pettit, Dennis L. Doubek, Jean Chapuis, Larry P. Tackett

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Bioassay (P388 lymphocytic leukemia cell line and human tumor cell lines)-guided separation of the extracts prepared from the tropical and coastal trees Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives) led to the isolation of a new lignan designated as hernanol (1) and 12 previously known lignans: (-)-deoxypodophyllotoxin (2), deoxypicropodophyllin (3), (+)-epiaschantin (4), (+)-epieudesmin (5), praderin (6), 5′-methoxyyatein (7), podorhizol (8), deoxypodorhizone (9), bursehernin (10), kusunokinol (11), clusin (12), and (-)-maculatin (13). The oxidative cyclization (with VOF3) of lignans 8, 9, and 10 resulted in a new and unusual benzopyran (14), isostegane (15), and a new dibenzocyclooctadiene lactone (16), respectively. The structure and relative stereochemistry of hernanol (1) and lignans 3, 7, 8, 9, 10, 11, and 12 were determined by 1D and 2DNMR and HRMS analyses. The structures and absolute stereochemistry of structures 2, 4, 5, 6, 13, 14, 15, and 16 were unequivocally determined by single-crystal X-ray diffraction analyses. Evaluation against the murine P388 lymphocytic leukemia cell line and human tumor cell lines showed podophyllotoxin derivatives 2 and 3 to be strong cancer cell line growth inhibitors and substances 4, 5, 8, and 15 to have marginal cancer cell line inhibitory activities. Seven of the lignans and one of the synthetic modifications (14) inhibited growth of the pathogenic bacterium Neisseria gonorrhoeae.

Original languageEnglish (US)
Pages (from-to)214-220
Number of pages7
JournalJournal of Natural Products
Volume67
Issue number2
DOIs
StatePublished - Feb 2004

Fingerprint

Hernandiaceae
Hernandia
Indian Ocean Islands
Maldives
Lignans
antineoplastic agents
Malaysia
Antineoplastic Agents
lignans
Cells
cell lines
Lymphoid Leukemia
Cell Line
lymphocytic leukemia
Stereochemistry
Tumor Cell Line
stereochemistry
Growth Substances
Tumors
Podophyllotoxin

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Antineoplastic Agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives). / Pettit, George; Meng, Yanhui; Gearing, R. Patrick; Herald, Delbert L.; Pettit, Robin; Doubek, Dennis L.; Chapuis, Jean; Tackett, Larry P.

In: Journal of Natural Products, Vol. 67, No. 2, 02.2004, p. 214-220.

Research output: Contribution to journalArticle

Pettit, George ; Meng, Yanhui ; Gearing, R. Patrick ; Herald, Delbert L. ; Pettit, Robin ; Doubek, Dennis L. ; Chapuis, Jean ; Tackett, Larry P. / Antineoplastic Agents. 522. Hernandia peltata (Malaysia) and Hernandia nymphaeifolia (Republic of Maldives). In: Journal of Natural Products. 2004 ; Vol. 67, No. 2. pp. 214-220.
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