Bouvardin and Deoxybouvardin, Antitumor Cyclic Hexapeptides from Bouvardia ternifolia (Rubiaceae)

D. Jolad Shivanand; Joseph J. Hoffmann; Sterling J. Torrance; Richard M. Wiedhopf; Jack R. Cole; Satish K. Arora; Robert B. Bates; Robin L. Gargiulo; George R. Kriek

doi:10.1021/ja00466a043

Bouvardin and Deoxybouvardin, Antitumor Cyclic Hexapeptides from Bouvardia ternifolia (Rubiaceae)

D. Jolad Shivanand, Joseph J. Hoffmann, Sterling J. Torrance, Richard M. Wiedhopf, Jack R. Cole, Satish K. Arora, Robert B. Bates, Robin L. Gargiulo, George R. Kriek

Research output: Contribution to journal › Article › peer-review

233 Scopus citations

Abstract

Bouvardin (C40H48N6O10) and deoxybouvardin (C40H48N6O9), both of which show high antitumor activity in the 3PS, B1, and KB systems, were isolated from the methanol extract of Bouvardia ternifolia (Rubiaceae). An x-ray study on bouvardin containing a methanol of crystallization (P212121, a=9.009 (3), b=12.623 (4), c=42.970 (19) Å, Z=4) and hydrolytic studies showed it to be Ia, a cyclic hexapeptide composed of two L-alanines, a D-alanine, and three modified N-methyl-L-tyrosines. The most unusual feature is a 14-membered ring formed by oxidative coupling of the phenolic oxygen of one tyrosine with a carbon ortho to the phenolic hydroxyl group of an adjacent tyrosine. Spectral comparison with bouvardin indicated deoxybouvardin to be Ib, identical with bouvardin except for the lack of a β-hydroxyl group on one of the tyrosines.

Original language	English (US)
Pages (from-to)	8040-8044
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	99
Issue number	24
DOIs	https://doi.org/10.1021/ja00466a043
State	Published - 1977
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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@article{181ecd60ef3745539a56f3ef724b3d31,

title = "Bouvardin and Deoxybouvardin, Antitumor Cyclic Hexapeptides from Bouvardia ternifolia (Rubiaceae)",

abstract = "Bouvardin (C40H48N6O10) and deoxybouvardin (C40H48N6O9), both of which show high antitumor activity in the 3PS, B1, and KB systems, were isolated from the methanol extract of Bouvardia ternifolia (Rubiaceae). An x-ray study on bouvardin containing a methanol of crystallization (P212121, a=9.009 (3), b=12.623 (4), c=42.970 (19) {\AA}, Z=4) and hydrolytic studies showed it to be Ia, a cyclic hexapeptide composed of two L-alanines, a D-alanine, and three modified N-methyl-L-tyrosines. The most unusual feature is a 14-membered ring formed by oxidative coupling of the phenolic oxygen of one tyrosine with a carbon ortho to the phenolic hydroxyl group of an adjacent tyrosine. Spectral comparison with bouvardin indicated deoxybouvardin to be Ib, identical with bouvardin except for the lack of a β-hydroxyl group on one of the tyrosines.",

author = "Shivanand, {D. Jolad} and Hoffmann, {Joseph J.} and Torrance, {Sterling J.} and Wiedhopf, {Richard M.} and Cole, {Jack R.} and Arora, {Satish K.} and Bates, {Robert B.} and Gargiulo, {Robin L.} and Kriek, {George R.}",

year = "1977",

doi = "10.1021/ja00466a043",

language = "English (US)",

volume = "99",

pages = "8040--8044",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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}

TY - JOUR

T1 - Bouvardin and Deoxybouvardin, Antitumor Cyclic Hexapeptides from Bouvardia ternifolia (Rubiaceae)

AU - Shivanand, D. Jolad

AU - Hoffmann, Joseph J.

AU - Torrance, Sterling J.

AU - Wiedhopf, Richard M.

AU - Cole, Jack R.

AU - Arora, Satish K.

AU - Bates, Robert B.

AU - Gargiulo, Robin L.

AU - Kriek, George R.

PY - 1977

Y1 - 1977

N2 - Bouvardin (C40H48N6O10) and deoxybouvardin (C40H48N6O9), both of which show high antitumor activity in the 3PS, B1, and KB systems, were isolated from the methanol extract of Bouvardia ternifolia (Rubiaceae). An x-ray study on bouvardin containing a methanol of crystallization (P212121, a=9.009 (3), b=12.623 (4), c=42.970 (19) Å, Z=4) and hydrolytic studies showed it to be Ia, a cyclic hexapeptide composed of two L-alanines, a D-alanine, and three modified N-methyl-L-tyrosines. The most unusual feature is a 14-membered ring formed by oxidative coupling of the phenolic oxygen of one tyrosine with a carbon ortho to the phenolic hydroxyl group of an adjacent tyrosine. Spectral comparison with bouvardin indicated deoxybouvardin to be Ib, identical with bouvardin except for the lack of a β-hydroxyl group on one of the tyrosines.

AB - Bouvardin (C40H48N6O10) and deoxybouvardin (C40H48N6O9), both of which show high antitumor activity in the 3PS, B1, and KB systems, were isolated from the methanol extract of Bouvardia ternifolia (Rubiaceae). An x-ray study on bouvardin containing a methanol of crystallization (P212121, a=9.009 (3), b=12.623 (4), c=42.970 (19) Å, Z=4) and hydrolytic studies showed it to be Ia, a cyclic hexapeptide composed of two L-alanines, a D-alanine, and three modified N-methyl-L-tyrosines. The most unusual feature is a 14-membered ring formed by oxidative coupling of the phenolic oxygen of one tyrosine with a carbon ortho to the phenolic hydroxyl group of an adjacent tyrosine. Spectral comparison with bouvardin indicated deoxybouvardin to be Ib, identical with bouvardin except for the lack of a β-hydroxyl group on one of the tyrosines.

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Bouvardin and Deoxybouvardin, Antitumor Cyclic Hexapeptides from Bouvardia ternifolia (Rubiaceae)

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