Triterpenoic acids of Prunella vulgaris var. lilacina and their cytotoxic activities in vitro.
The column chromatographic separation of the MeOH extract from the aerial parts of Prunella vulgaris var. lilacina Nakai led to the isolation of fifteen triterpenoic acids (2-6, 9-13, 16-20), four flavonoids (14, 21-23), four phenolics (7, 8, 15, 24), and a diterpene (1). Their structures were determined by spectroscopic methods to be trans-phytol (1), oleanic acid (2) ursolic acid (3), 2alpha,3alpha,19alpha-trihydroxyurs-12en-28oic acid (4), 2alpha,3alpha-dihydroxyurs-12en-28oic acid (5), maslinic acid (6), caffeic acid (7), phydroxy cinnamic acid (8), 2alpha,3alpha,19alpha,23-tetrahydroxyurs-12en-28oic acid (9), 2alpha,3alpha,23-trihydroxyurs-12en-28oic acid (10), 2alpha,3beta-dihydroxyurs-12en-28oic acid (11), 2alpha,3beta,24-trihydroxyolea-12en-28oic acid (12), (12R, 13S)-2alpha,3alpha,24,trihydroxy-12,13-cyclo-taraxer-14-en-28oic acid (13), quercertin 3-O-beta-D-glucopyranoside (14), rosmarinic acid (15), 2alpha,3alpha,24-trihydroxyurs-12,20(30)-dien-28oic acid (16), 2alpha,3alpha,24-trihydroxyolea-12en-28oic acid (17), 2alpha,3beta,19alpha,24-tetrahydroxyurs-12en-28oic acid 28-O-Dglucopyranoside (18), 2alpha,3alpha,19alpha,24-tetrahydroxyurs-12en-28oic acid 28-O-D-glucopyranoside (19), prunvuloside A (20), kaempferol 3-O-alpha-L-rhamnopyranosyl(1-->6)-beta-D-glucopranoside (21), kaempferol 3-O-beta-D-glucopyranoside (22), quercertin 3-O-alpha-L-rhamnopyranosyl(1-->6)-beta-D-glucopyranoside (23), and 2-hydroxy-3-(3',4'-dihydroxyphenly)propanoic acid (24). Compounds 1, 8-12, 17, 21, 23, and 24 were isolated from this plant source for the first time. The isolated compounds were evaluated for their cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT15 cells in vitro using the sulforhodamin B bioassay (SRB) method. Compound 3 exhibited moderate cytotoxic activity against A549, SK-OV-3, SK-MEL-2, and HCT15 cells, with ED(50) values of 3.71, 3.65, 13.62, and 5.44 microM, respectively.
Lee
Il Kyun
IK
Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University, Suwon, 440-746, Korea. krlee@skku.ac.kr
Kim
Do Hoon
DH
Lee
Seung Young
SY
Kim
Kyung Ran
KR
Choi
Sang Un
SU
Hong
Jong Ki
JK
Lee
Jei Hyun
JH
Park
Young Hyun
YH
Lee
Kang Ro
KR
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D004396:Coloring Agents; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D031347:Prunella / Q000737:chemistry*; D012235:Rhodamines; D013056:Spectrophotometry, Ultraviolet; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D004396:Coloring Agents; D007202:Indicators and Reagents; D012235:Rhodamines; D014315:Triterpenes; C022027:lissamine rhodamine B