Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata

Dongho Lee, Muriel Cuendet, Franklin Axelrod, Pedro I. Chavez, Harry H S Fong, John M. Pezzuto, A. Douglas Kinghorn

Research output: Contribution to journal › Article

18 Citations (Scopus)

Abstract

Four novel 29-nor-3,4-seco-cycloartanes, (6S)-hydroxy-25-methoxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (1), (6S,25)-dihydroxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (2), (6S)-hydroxy-24-oxo-29-nor-3,4-seco-cycloart-4(30),25-dien-3-oic acid methyl ester (3), and (6S)-hydroxy-(24ξ)-hydroperoxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3- oic acid methyl ester (4), along with a semi-synthetic acetylated derivative, (6S,24ξ)-diacetyloxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3-oic acid methyl ester (5), were isolated and characterized from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Their structures and absolute stereochemistry were elucidated by spectroscopic and chemical methods. Compounds 1-5 are based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton. Compound 4 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC50 45.7 and 18.4 μM, respectively), while the other four isolates were inactive.

Original languageEnglish
Pages (from-to)7107-7112
Number of pages6
JournalTetrahedron
Volume57
Issue number33
DOIs
Publication statusPublished - 2001 Aug 13
Externally publishedYes

Fingerprint

Triterpenes
Esters
Antennas
Acids
Cyclooxygenase 1
Rubiaceae
Stereochemistry
Cyclooxygenase 2
Skeleton
Inhibitory Concentration 50
Assays
cycloartane
Derivatives

Keywords

  • 29-nor-3,4-seco-cycloartane
  • Antirhea acutata
  • Cyclooxygenase-1 and -2
  • Rubiaceae

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Lee, D., Cuendet, M., Axelrod, F., Chavez, P. I., Fong, H. H. S., Pezzuto, J. M., & Douglas Kinghorn, A. (2001). Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata. Tetrahedron, 57(33), 7107-7112. https://doi.org/10.1016/S0040-4020(01)00664-0

Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata. / Lee, Dongho; Cuendet, Muriel; Axelrod, Franklin; Chavez, Pedro I.; Fong, Harry H S; Pezzuto, John M.; Douglas Kinghorn, A.

In: Tetrahedron, Vol. 57, No. 33, 13.08.2001, p. 7107-7112.

Research output: Contribution to journal › Article

Lee, D, Cuendet, M, Axelrod, F, Chavez, PI, Fong, HHS, Pezzuto, JM & Douglas Kinghorn, A 2001, 'Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata', Tetrahedron, vol. 57, no. 33, pp. 7107-7112. https://doi.org/10.1016/S0040-4020(01)00664-0
Lee D, Cuendet M, Axelrod F, Chavez PI, Fong HHS, Pezzuto JM et al. Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata. Tetrahedron. 2001 Aug 13;57(33):7107-7112. https://doi.org/10.1016/S0040-4020(01)00664-0
Lee, Dongho ; Cuendet, Muriel ; Axelrod, Franklin ; Chavez, Pedro I. ; Fong, Harry H S ; Pezzuto, John M. ; Douglas Kinghorn, A. / Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata. In: Tetrahedron. 2001 ; Vol. 57, No. 33. pp. 7107-7112.
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abstract = "Four novel 29-nor-3,4-seco-cycloartanes, (6S)-hydroxy-25-methoxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (1), (6S,25)-dihydroxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (2), (6S)-hydroxy-24-oxo-29-nor-3,4-seco-cycloart-4(30),25-dien-3-oic acid methyl ester (3), and (6S)-hydroxy-(24ξ)-hydroperoxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3- oic acid methyl ester (4), along with a semi-synthetic acetylated derivative, (6S,24ξ)-diacetyloxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3-oic acid methyl ester (5), were isolated and characterized from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Their structures and absolute stereochemistry were elucidated by spectroscopic and chemical methods. Compounds 1-5 are based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton. Compound 4 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC50 45.7 and 18.4 μM, respectively), while the other four isolates were inactive.",
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AU - Axelrod, Franklin

AU - Chavez, Pedro I.

AU - Fong, Harry H S

AU - Pezzuto, John M.

AU - Douglas Kinghorn, A.

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KW - Cyclooxygenase-1 and -2

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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