Unusual chromenes from Peperomia blanda

(S)-2-Methyl-2-(4-methylpent-3-enyl)-6-(propan-2-ylidene)-3,4,6,7-tetrahydropyrano[4,3-g]chromen-9(2H)-one

“…The relative stereochemistry of C-2 was determined by NOESY experiments, pairs of NOESY correlations, H-1'/H-2' and Me-6'/H-3, suggested that the Me-6' was in β-oriented. The relative stereochemistry of C-2 is also confirmed according the structural similarity and optical rotation, [α] 20 D +25.1° to blandachromene I [19] and lhotzchromene [20], therefore the S-configuration at C-2 was suggested. Based on physicochemical properties and spectral data along with biogenetic point of view occurance of chromone constituents in Piperomia genus, consequently, the structure of the new chromene was determined to be (S)-2-methyl-2-(4-methylpent-3-enyl)-6-(propan-2-ylidene)-3,4,6,7-tetrahydropyrano[4,3-g]chromen-9(2H)-one, and was named peperochromen A.…”

Meroterpenes from Peperomia oreophila Hensch. and Peperomia arifolia Miq.

“…The occurrence of the new phenol 1 (the chromene 2 in P. oreophila), as well of 1 in P. arifolia together with previous chemical studies made on Peperomia species, 5,9,[11][12][13][14][15] suggests that these meroterpenes derived from orsellinic acid could be used as taxonomic markers for Peperomia species. The occurrence of 1 and 2 in these species indicates a specific biosynthetic pathway with regioselectivity at the prenylation and geranylation steps.…”

“…4 Indeed, the chemical variability of Peperomia species became evident with the isolation of amides, benzoic acid/chromenes, flavonoids, lignoids and phenylpropanoids. [5][6][7][8] Additionally, the meroterpenes appear to be a noteworthy class of compounds among Peperomia species with the aromatic moiety resulting from orsellinic acid with a variable degree of prenylations such as those described from P. obtusifolia, 9,10 P. galioides, 11 P. blanda, 12 benzopyrans from P. clusiifolia, 13 P. amplexicaulis, 14 prenylated quinones from P. galioides, 15 and chromenes from P. serpens 16 and P. villipetiola. 6 As a part of our continuing investigation aiming at the chemotaxonomic study of Peperomia species, Peperomia oreophila was selected due to the richness of signals in the 1 H nuclear magnetic resonance (NMR) spectrum.…”

Secondary Metabolites From Peperomia Sui

“…1) experiments. Compound 2 was identical with peperovulcanone A, which was reported as a new compound with a E-geometry from P. vulcanica by Tane Many bioactive compounds, including ployketides, lignans and chromenes, isolated from Peperomia species have been reported in recent studies [2][3][4][5][6][7] . Most compounds possessed cytotoxicity activity.…”

“…Less than 11 species of Peperomia has been undergone phytochemical studies in previously researches. Its common constituents are phenylpropanoid, benzopyran, chromone, prenylated quinone, secolignan, and acylcyclohexane-1,3-dione [2][3][4][5][6][7] . The methanolic extracts of the whole plant of this species showed significant cytotoxicity on high-throughput screening against HONE-1 and NUGC-3 cancer cell lines in vitro.…”