A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest [1a]

Abstract

Antiproliferative bioassay-guided fractionation of the ethanolic extract of the endemic Madagascan plant Metaporana sericosepala led to the first natural product isolation of a butenolide diterpene which was synthesized during an anti-inflammatory study in 1988. The structure of the compound was elucidated as 3-homofarnesyl-4-hydroxybutenolide (1) by analysis of its spectroscopic data, including 1D- and 2D-NMR data and chemical evidence. The once synthetic compound can now also be considered as a natural product. Compound 1 had modest antiproliferative activity towards the A2780 ovarian cancer cell line with an IC50 value of 8 μM.

Therapeutic Perspective of Vitamin C and Its Derivatives

“…Presley et al isolated a butenolide diterpene from the plant Metaporana sericosepala (Figure S7) [133]. The compound exhibited inhibitory activity on ovarian cancer cells (A2780).…”

Phototriggered Butenolide Formation from a Cyclobutenedione and an Acidic Nucleophile

“…In the reactions involving the bisketene, various products including butenolide derivatives can be produced. Because butenolides are seen in many bioactive natural product 10,11,12 and synthetic compounds 13,14 , the butanolide synthesis from cyclobutenedione could be useful for the synthesis of bioactive butenolide libraries. Since the ring opening of cyclobutenedione does not proceed at room temperature without light, the location and timing of the bisketene generation is completely controllable by ON/OFF state of light irradiation.…”