The phloroglucinol mallotojaponin
C (1) from Mallotus oppositifolius,
which was previously shown by us
to have both antiplasmodial and cytocidal activities against the malaria
parasite Plasmodium falciparum, was synthesized in
three steps from 2′,4′,6′-trihydroxyacetophenone,
and various derivatives were synthesized in an attempt to improve
the bioactivity of this class of compounds. Two derivatives, the simple
prenylated phloroglucinols 12 and 13, were
found to have comparable antiplasmodial activities to that of mallotojaponin
C.
Investigation of a DCM extract of
the bark of Pleiogynium
timoriense from the former Merck collection of natural product
extracts for antiproliferative activity indicated that it was active
with an IC50 value of 1.3 μg/mL against the A2780
ovarian cancer cell line. Bioassay-directed fractionation of this
extract yielded the three new bioactive trihydroxyalkylcyclohexenones 1–3. Their structures were determined
by a combination of spectroscopic and chemical methods. Compounds 1–3 exhibited submicromolar antiproliferative
activity against the A2780 human ovarian cancer cell line, with IC50 values of 0.8, 0.7, and 0.8 μM, respectively.
As part of the International Cooperative Biodiversity Group (ICBG) program, in a search for antiproliferative compounds, an ethanol extract of Polyscias duplicata was investigated due to its antiproliferative activity against the A2780 human ovarian cell cancer line (IC50 6 µg/mL). Seven known oleanane glycosides, 3β-[(α-l-arabinopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oic acid (1, IC50 8 µM), 3β-[(α-l-arabinopyranosyl)oxy]-16α,23-dihydroxyolean-12-en-18-oic acid (2, IC50 13 µM), 3β-[(O-β-d-glucopyranosyl-(1→3)-α-l-arabinopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oic acid (3, IC50 7 µM), 3β-[(O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oic acid (4, IC50 2.8 µM), 3β-[(O-β-d-glucopyranosyl-(1→3)-α-l-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (5, IC50 10 µM), 3β-[(O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (6, IC50 3.4 µM), and 3β-[(α-l-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (7, IC50 3.4 µM) were isolated, and their structures determined using spectroscopic methods.
In a continuing collaboration in a search for new antiproliferative compounds in Madagascar as part of an International Cooperative Biodiversity Group (ICBG), an ethanol extract of Molinaea retusa Radlk. (Sapindaceae) was investigated on the basis of its moderate antiproliferative activity against the A2780 human ovarian cancer cell line (IC50 16 μg/mL). One new compound, 2″,3″,4″,6′-de-O-acetylcupacinoside (1, IC50 15.4 μM) and two known compounds, cupacinoside (2, IC50 9.5 μM) and 6-de-O-acetylcupacinoside (3, IC50 10.9 μM), were isolated by bioassay-directed fractionation using liquid-liquid partitioning, column chromatography, and HPLC. Compounds 2 and 3 also had moderate antiplasmodial activities, with IC50 values of 4.0 and 6.4 μM, respectively, against Plasmodium falciparum, Dd2 strain. The structures were determined using spectroscopic methods.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.