Mammea Coumarins from the Flowers of Mammea siamensis

Mahidol, Chulabhorn; Kaweetripob, Wirongrong; Prawat, Hunsa; Ruchirawat, Somsak

doi:10.1021/np010579u

Cited by 37 publications

(30 citation statements)

References 13 publications

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“…[1][2][3][4] They show diverse biological and pharmacological activities ranging from antimicrobial, anti-arrhythmic, antitumor, antifungal, anti-HIV, anti-osteoporosis to anti-inflammatory. [5][6][7][8][9][10][11][12] Apart from their pharmaceutical applications, [13][14] coumarins have been used as additives in foods, perfumes and cosmetics as well as in the preparation of optical brighteners, laser dyes, fluorescent labels and nonlinear optical chromophores.…”

Section: Introductionmentioning

confidence: 99%

Facile iron(III) chloride hexahydrate catalyzed synthesis of coumarins

Prateeptongkum¹,

Duangdee²,

Thongyoo³

2015

Arkivoc

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Section: Introductionmentioning

confidence: 99%

Facile iron(III) chloride hexahydrate catalyzed synthesis of coumarins

Prateeptongkum¹,

Duangdee²,

Thongyoo³

2015

Arkivoc

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“…The flowers of this plant have been used for preparing a heart tonic in Thai traditional medicine ("Sarapi" in Thai). [1][2][3][4][5][6][7][8][9][10] Several coumarins, [1][2][3][4][5][6][7] xanthones, 8,9) triterpenoids, 10) and steroids 10) have been isolated from the flowers, 1,2,6,7,10) seeds, 3,9) twigs, 4,8) and bark 5) of this plant. In the course of our characterization studies on bioactive constituents in Thai natural medicine, 1,[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] we reported that the methanol extract of the flowers of M. siamensis and its coumarin constituents showed inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 cells.…”

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confidence: 99%

Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of Mammea siamensis

et al. 2016

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Key words Mammea siamensis; mammeasin; aromatase inhibitor; geranylated coumarin; Calophyllaceae Mammea siamensis (MIQ.) T. ANDERS. is a species of flowering plant in the Calophyllaceae family and is widely distributed in Thailand, Laos, Cambodia, Vietnam, and Myanmar. The flowers of this plant have been used for preparing a heart tonic in Thai traditional medicine ("Sarapi" in Thai). [1][2][3][4][5][6][7][8][9][10] Several coumarins, [1][2][3][4][5][6][7] xanthones, 8,9) triterpenoids, 10) and steroids 10) have been isolated from the flowers, 1,2,6,7,10) seeds, 3,9) twigs, 4,8) and bark 5) of this plant. In the course of our characterization studies on bioactive constituents in Thai natural medicine, 1,[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] we reported that the methanol extract of the flowers of M. siamensis and its coumarin constituents showed inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 cells.1) Further studies revealed that the methanol extract inhibited enzymatic activity against aromatase. Separation of the active constituents in the extract allowed us to isolate two new geranylated coumarins, mammeasins C (1) and D (2). This paper describes the isolation and structure elucidation of these new coumarins (1, 2) and the inhibitory effects of the coumarin constituents (1-26) on aromatase. 26) Results and Discussion Effects of the Methanol Extract from the Flowers of M. siamensis against Human Recombinant AromataseBreast cancer is one of the most common reasons for mortality in women. 26,27) Estrogens and estrogen receptors are well known to play an important role in the development and progression of hormone-dependent breast cancer; for this reason, estrogens and estrogen receptors are widely studied molecular targets. [28][29][30] The presence of high concentrations of estrogen in breast tissue increases the risk of developing breast cancer and the ability of immature breast tissue cells to strongly bind to carcinogens, decreasing their DNA repair capacity. 31,32) Aromatase, a CYP19 enzyme, is the rate-limiting enzyme in the conversion of testosterone and androstenedione to the estrogens, estrone and estradiol. [26][27][28][29][30][32][33][34] It is involved in the final step of the estrogen biosynthetic pathway and its selective inhibition will not affect the production of other steroids in the pathway. 32,[35][36][37] The source of estrogen production in breast cancer tissues is intratumoral aromatase, and thus, inhibition of aromatase may inhibit the growth stimulation effect of estrogens in breast cancer tissues. Therefore, aromatase is considered a useful therapeutic target in the treatment and prevention of estrogen-dependent breast cancer. 32)The dried flowers of M. siamensis (collected from Nakhonsithammarat Province, Thailand) were extracted with methanol under reflux (25.66% from the dried flowers). The methanol extract was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish an EtOAc-soluble fraction (6.84%) and an aqueous ...

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“…Fr. OSE3 (460 mg) was separated using CC (silica gel, 0-25% EtOAc-petroleum ether) and then RP 18 (MeOH-H 2 O) and finally GPC to yield 1,6,7-trihydroxyxanthone (7, 12.0 mg), 1,3,7-trihydroxyxanthone (8,6.0 mg) and 1,7-dihydroxy-3-methoxyxanthone (9, 5.0 mg).…”

Section: Methodsmentioning

confidence: 99%

“…3) Earlier studies have shown that the genus is a rich source of coumarins and xanthones, some of which have potential pharmacological and therapeutic properties. [4][5][6][7][8][9] We here report the chemical constituents of the bark of Mammea siamensis collected in south Vietnam with the isolation of a new and four known coumarins as well as seven xanthones. In addition, new data on the anti-proliferative activity of the coumarins surangins C-D and theraphins B-C and their methylated derivatives were generated using sulforhodamine B (SRB) assay on four human cancer cell lines, MCF-7 (breast adenocarcinoma), HeLa, DLD-1 (colon cancer) and NCI-H460 (human lung cancer).…”

Section: Regular Articlementioning

confidence: 95%

Cytotoxic Coumarins from the Bark of Mammea siamensis

Ngo

Nguyen

et al. 2010

Chem. Pharm. Bull.

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A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D-and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC 50 in the range of 1.6-5.7 mM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.

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Mammea Coumarins from the Flowers of Mammea siamensis

Cited by 37 publications

References 13 publications

Facile iron(III) chloride hexahydrate catalyzed synthesis of coumarins

Facile iron(III) chloride hexahydrate catalyzed synthesis of coumarins

Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of <i>Mammea siamensis</i>

Cytotoxic Coumarins from the Bark of Mammea siamensis

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