TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=0035855279&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)00664-0
DO - 10.1016/S0040-4020(01)00664-0
M3 - Article
AN - SCOPUS:0035855279
VL - 57
SP - 7107
EP - 7112
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 33
ER -