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

doi:10.1016/S0040-4020(01)00664-0

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 › peer-review

25 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 language	English
Pages (from-to)	7107-7112
Number of pages	6
Journal	Tetrahedron
Volume	57
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4020(01)00664-0
Publication status	Published - 2001 Aug 13
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by program project P01 CA48112 funded by the National Cancer Institute, NIH, Bethesda, MD. We thank Dr K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, for the mass spectral data. We are grateful to the Research Resources Center, University of Illinois at Chicago, for the provision of certain spectroscopic equipment used in this investigation.

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)00664-0

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@article{4d9d337ea33a4c40ac779d0ce8c6a83e,

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

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.",

keywords = "29-nor-3,4-seco-cycloartane, Antirhea acutata, Cyclooxygenase-1 and -2, Rubiaceae",

author = "Dongho Lee and Muriel Cuendet and Franklin Axelrod and Chavez, {Pedro I.} and Fong, {Harry H.S.} and Pezzuto, {John M.} and {Douglas Kinghorn}, A.",

note = "Funding Information: This work was supported by program project P01 CA48112 funded by the National Cancer Institute, NIH, Bethesda, MD. We thank Dr K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, for the mass spectral data. We are grateful to the Research Resources Center, University of Illinois at Chicago, for the provision of certain spectroscopic equipment used in this investigation. ",

year = "2001",

month = aug,

day = "13",

doi = "10.1016/S0040-4020(01)00664-0",

language = "English",

volume = "57",

pages = "7107--7112",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "33",

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T1 - Novel 29-nor-3,4-seco-cycloartane triterpene methyl esters from the aerial parts of Antirhea acutata

AU - Lee, Dongho

AU - Cuendet, Muriel

AU - Axelrod, Franklin

AU - Chavez, Pedro I.

AU - Fong, Harry H.S.

AU - Pezzuto, John M.

AU - Douglas Kinghorn, A.

N1 - Funding Information: This work was supported by program project P01 CA48112 funded by the National Cancer Institute, NIH, Bethesda, MD. We thank Dr K. Fagerquist, Mass Spectrometry Facility, Department of Chemistry, University of Minnesota, Minneapolis, MN, for the mass spectral data. We are grateful to the Research Resources Center, University of Illinois at Chicago, for the provision of certain spectroscopic equipment used in this investigation.

PY - 2001/8/13

Y1 - 2001/8/13

N2 - 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.

AB - 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.

KW - 29-nor-3,4-seco-cycloartane

KW - Antirhea acutata

KW - Cyclooxygenase-1 and -2

KW - Rubiaceae

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U2 - 10.1016/S0040-4020(01)00664-0

DO - 10.1016/S0040-4020(01)00664-0

M3 - Article

AN - SCOPUS:0035855279

SN - 0040-4020

VL - 57

SP - 7107

EP - 7112

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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