Euphane triterpenoids of Cassipourea lanceolata from the Madagascar rainforest

Abstract

Fractionation of an ethanol extract of a Madagascar collection of the leaves and fruit of Cassipourea lanceolata Tul. led to the isolation of three euphane triterpenoids 1-3. The 1 H and 13 C NMR spectra of all compounds were fully assigned using a combination of 2D NMR experiments, including COSY, TOCSY, HSQC (HMQC), HMBC and ROESY sequences. The three compounds showed weak antiproliferative activities against the A2780 human ovarian cancer cell line, with IC 50 values of 25, 25 and 32 μM, respectively.

Melanin Production Inhibitors from the West African Cassipourea congoensis

“…C. malosana is also reported to be closely related to, and often confused with, Cassipourea flanaganii Schinz (Alston) (Rhizophoraceae) and C. flanaganii is, used traditionally in South Africa as a skin-lightening agent [12]. The Cassipourea genus is reported to yield sulfur-containing compounds that include gerrardine [13], guinesine B, and guinesine C [14], sulfur-containing amides that include cassipoureamide A and B [15], euphane and lupane type triterpenoids [16,17], flavonols, flavonol glycoside and biflavonoids [18][19][20] and bioactive monocyclic diterpenoids [16] . Extractives from the stem bark of C. malosana, including 2 novel flavan dimers, were tested against human ovarian cancer cells and showed very little activity [21].…”

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

“…Both of the compounds were tested for antiplasmodial activity against chloroquine-resistant strain FcB1 of P. falciparum, and compound 18 displayed moderate activity, with an IC 50 value of 2.8 µM, while compound 17 was inactive. 6) The same authors isolated three related new bisindole alka-loids from the same plant: goniomedinone (19); goniomedine A-methylene chloride (20); and goniomedine A-N-oxide (21). As stated in their report, those three novel compounds may have been artifacts formed through spontaneous oxidation and tertiary amine quaternization during plant extraction.…”

“…The two most active compounds (51 and 52) displayed very similar antiproliferative activities when tested against other cancer cell lines, including H522-T1 non-small cell lung cancer and A2058 human melanoma lines. 19) 3.4. Triterpenoids Bioassay-guided fractionation of an ethanol extract of a Madagascar collection of the leaves and fruit of Cassipourea lanceolata TUL.…”

The chemistry and bioactivity of Southern African flora I: a bioactivity versus ethnobotanical survey of alkaloid and terpenoid classes

“…169 The isolated compounds were tested using the A2780 ovarian cancer cell line assay as described. Hou et al isolated the three new euphane triterpenoids; 1b,3b,11a,26-tetrahydroxy-7,24E-euphadiene (89), 3b,26-dihydroxy-8,24E-euphadien-11-one (90) and (24S)-1b,3b,24,25-tetrahydroxy-7,9(11)-euphadiene (91) from the ethanol extract of the leaves and fruit of this plant collected from Madagascar.…”