NMR Study Of Seven Coumarins From Mammea Siamensis

Abstract

Seven known mammea coumarins, mammea A/AA cyclo D ( 1 ), mammea A/AD cyclo D ( 2 ), mammea A/AB cyclo D ( 3 ), mammea A/AC cyclo F ( 4 ), mam-mea A/AB cyclo F ( 5 ), mammea A/AA cyclo F ( 6 ), mammea B/AC cyclo F ( 7 ), were isolated for the first time from the hexane extract of Mammea siamensis . A detailed analysis of both 1D and 2D NMR spectral data of these compounds was made.

Geranylated Coumarins From Thai Medicinal Plant Mammea siamensis With Testosterone 5α-Reductase Inhibitory Activity

“…Fraction 5-2 (517.0 mg) was purified by HPLC [Cosmosil 5C 18 -MS-II, MeOH−1% aqueous AcOH (85:15, v/v)] to give mammea A/AC cyclo F (35, 4.6 mg, 0.0019%) (Morel et al, 1999;Prachyawarakorn et al, 2000;Guilet et al, 2001) together with mammeas A/AA (17, 101.2 mg, 0.0418%), A/AC (19, 112.9 mg, 0.0466%), A/AA cyclo D (24, 2.7 mg, 0.0011%), E/BC cyclo D (29, 14.0 mg, 0.0058%), and E/BD cyclo D (30, 1.8 mg, 0.0015%) (Mahidol et al, 2002). Fraction 5-3 (515.4 mg) was purified by HPLC [Cosmosil 5C 18 -MS-II, MeOH−1% aqueous AcOH (85:15, v/v)] to give mammea A/AA cyclo F (34, 13.2 mg, 0.0010%) (Prachyawarakorn et al, 2000;Guilet et al, 2001) together with 19 (45.6 mg, 0.0035%), 24 (14.9 mg, 0.0011%), mammeas A/AB cyclo D (25, 46.4 mg, 0.0035%) and A/AC cyclo D (26, 30.1 mg, 0.0023%). Fraction 6 (6.29 g) was subjected to reversed-phase silica gel CC [200 g, MeOH-H 2 O (80:20 → 90:10 → 95:5, v/v) → MeOH → acetone] to afford 10 fractions [Fr.…”

“…The flowers of this plant have traditionally been used as a heart tonic, fever-lowering, and enhancement of appetite in Thailand (Morikawa et al, 2012;Tung et al, 2013;Ninomiya et al, 2016;Sangkaruk et al, 2017). Previous chemical studies on the flowers (Kaweetripob et al, 2000;Prachyawarakorn et al, 2000Prachyawarakorn et al, , 2006aMahidol et al, 2002;Morikawa et al, 2012;Ninomiya et al, 2016), seeds (Laphookhieo et al, 2006(Laphookhieo et al, , 2007, twigs (Poobrasert et al, 1998;Prachyawarakorn et al, 2006a,b), and bark (Ngo et al, 2010) of M. siamensis reported on the isolation of several coumarins and xanthones, etc. With regard to the biological studies on M. siamensis and its constituents, cytotoxicity, antiproliferative, and apoptotic effects against several tumor and cancer cell lines (Ngo et al, 2010;Tung et al, 2013;Noysang et al, 2014;Uto et al, 2016;Sangkaruk et al, 2017), suppressive effects on inducible nitric oxide synthase expression in RAW264.7 cells (Morikawa et al, 2012), and aromatase inhibitory activity (Ninomiya et al, 2016;Tanabe et al, 2017) have been reported.…”

Dereplication of Mammea neurophylla metabolites to isolate original 4-phenylcoumarins

“…This indicated 295 the presence of a hydroxyisopropyl group as found in mammea 296 cycloF (Prachyawarakorn et al, 2000). Moreover, two doublets 297 of one proton [d H 4.67 and 5.71 (J = 3.0 Hz)] attributable to an 298 oxymethine and a benzylic oxymethine respectively.…”

Regioisomers of Acylcoumarins from the Flowers of Mammea siamensis

“…However, only 6 genera, Calophyllum, Garcinia, Hypericum, Mesua, Cratoxylum, and Mammea are found in Thailand [2]. Several Mammea species have been shown to contain xanthones [3][4][5] and coumarins [6][7][8][9][10][11][12][13], which showed cytotoxic activity [14], antileukaemic [15], and antimicrobial activities [16]. Previously, we have reported the isolation and structural characterization of ten coumarins, mammea E/BA cyclo D, mammea E/BC cyclo D, mammea E/BD cyclo D, mammea A/BC, mammea E/AC cyclo D, mammea B/AC cyclo D, mammea A/AC cyclo D, mammea B/AC cyclo F, mammea A/AA cyclo F, and mammea A/AC cyclo F from the flowers of Mammea siamensis [13].…”