Cytotoxic constituents of the bark of Plumeria rubra collected in Indonesia.
By bioactivity-directed fractionation, six cytotoxic constituents have been characterized from the bark of Plumeria rubra collected in Indonesia. Three iridoids, fulvoplumierin [1], allamcin [2], and allamandin [3], as well as 2,5-dimethoxy-p-benzoquinone [4], were found to be active constituents of the P. rubra petroleum-ether- and CHCl3-soluble extracts. Cytotoxic compounds isolated from the H2O-soluble extract of the bark were the iridoid plumericin [5], and the lignan liriodendrin [6]. Each of these substances was found to demonstrate general cytotoxic activity when evaluated with a panel of cell lines composed of murine lymphocytic leukemia (P-388) and a number of human cancer cell-types (breast, colon, fibrosarcoma, lung, melanoma, KB). Five additional iridoids, 15-demethylplumieride [7], plumieride [8], alpha-allamcidin [9], beta-allamcidin [10], and 13-O-trans-p-coumaroylplumieride [11], were obtained as inactive constituents. Compound 7 was found to be a novel natural product, and its structure was determined by spectroscopic methods and by conversion to plumieride [8]. The configuration of the C-4 stereocenter was unambiguously assigned for compounds 9 and 10, and certain nmr reassignments have been provided for compound 1.
Kardono
L B
LB
Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois, Chicago 60612.
Tsauri
S
S
Padmawinata
K
K
Pezzuto
J M
JM
Kinghorn
A D
AD
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification*; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007192:Indenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D039823:Iridoids; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007941:Leukemia P388 / Q000188:drug therapy; D017705:Lignans; D008031:Lignin / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000032:analysis*; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D016227:Benzoquinones; D005663:Furans; D005960:Glucosides; D007192:Indenes; D039823:Iridoids; D007783:Lactones; D017705:Lignans; D011714:Pyrans; D011809:Quinones; C006451:allamandin; C017333:fulvoplumierin; D008031:Lignin; C068510:allamcin; C068512:liriodendrin; C068511:plumericin; C068509:2,5-dimethoxy-4-benzoquinone