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

Phytochemicals with Chemopreventive Activity Obtained from the Thai Medicinal Plant Mammea siamensis (Miq.) T. Anders.: Isolation and Structure Determination of New Prenylcoumarins with Inhibitory Activity against Aromatase

“…5-6 (1110.0 mg)), as previously reported [ 21 ]. 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 mammeasins M ( 3 , 5.0 mg, 0.0021%) and O ( 5 , 3.7 mg, 0.0015%) together with mammeas A/AA ( 24 , 101.2 mg, 0.0418%), A/AC ( 26 , 112.9 mg, 0.0466%), A/AA cyclo D ( 28 , 3.7 mg, 0.0015%), E/BC cyclo D ( 33 , 14.0 mg, 0.0058%), E/BD cyclo D ( 34 , 1.8 mg, 0.0007%), and A/AC cyclo F ( 40 , 4.6 mg, 0.0019%) [ 18 , 19 , 21 ]. 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) and 10 fractions were obtained (Fr.…”

“…The latter was subjected to Diaion HP-20 column chromatography (H 2 O → MeOH) according to previously reported protocols, which yielded H 2 O- and MeOH-eluted fractions (13.50% and 4.22%, respectively). From the EtOAc-soluble fraction, we previously isolated 37 coumarin constituents ( 6 – 42 ) using normal-phase silica gel and reversed-phase ODS column chromatographic purification, and finally HPLC [ 18 , 19 , 20 , 21 , 22 ]. In this study, mammeasins K ( 1 , 0.0008%), L ( 2 , 0.0006%), M ( 3 , 0.0021%), N ( 4 , 0.0007%), and O ( 5 , 0.0015%) were isolated ( Figure 1 ).…”

“…M. siamensis flowers were collected from Nakhonsithammarat Province, Thailand, in September 2006, as described previously [ 18 , 19 , 21 , 22 ]. Plant material was identified by one of the authors (Y.P.).…”

“…T. Anders. [ 18 , 19 , 20 , 21 , 22 ], have been indicated in several bio-functional properties of coumarins, including anti-inflammatory [ 16 , 17 , 18 ], hepatoprotective [ 17 ], aromatase [ 19 , 20 ] and 5α-reductase inhibitory [ 21 ], and anti-proliferative activities [ 22 ]. We attempted a further separation of the constituents from the flower part of M. siamensis (Calophyllaceae family), which is traditionally used in Thailand as a heart tonic, antipyretic, and appetite enhancer.…”

Indole Glycosides from <i>Calanthe discolor</i> with Proliferative Activity on Human Hair Follicle Dermal Papilla Cells

“…In traditional Chinese medicine, the dried whole plant of C. discolor has been used for anti-inflammatory, antibacterial, and antitoxic purposes. 2,3) During the course of our studies on the characteristics of bioactive constituents from natural sources that are useful for cosmetics, such as melanogenesis inhibitory, [4][5][6][7][8][9][10][11][12][13] collagen synthesis-promoting, collagenase and hyaluronidase inhibitory, [14][15][16][17][18][19] and 5α-reductase inhibitory 20) activities, we previously found that the methanol extract of the underground part of C. discolor and its constituents showed hair-restoring activity in C3H mice and promoted blood flow in the dorsal skin of rats. 3) Herein, to continue our study of the bioactive constituents from this plant material used for cosmetics, we show that the methanol extract exhibits proliferative activity on human hair follicle dermal papilla cells (HFDPC).…”