Synthesis of Minor Xanthones from Garcinia mangostana

Bennett, Graham J.; Lee, Hiok-Huang; Lee, Liak-Phong

doi:10.1021/np50072a010

Cited by 25 publications

(11 citation statements)

References 24 publications

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“…Table 2 presents natural products whose syntheses have been reported in the last twenty years by the reasons stated above. Nevertheless, in the 80s and 90s, several studies still reported syntheses of xanthones as a methodology to assign unambiguously the structures of isolated compounds [174][175][176]. For previous studies, considering the synthesis of phytoxanthones, see references [8,9].…”

Section: Synthesis Of Natural Productsmentioning

confidence: 99%

“…As xanthone (42) was sluggish in the Corey-Fuchs olefination it was first converted to dibromoalkene (173), which subsequently furnished the corresponding 1,1-bis(trimethylsilylethynyl) alkene (174). Desilylation of compound (174) gave the parent diyne (175). A transition metal-catalyzed double ring closure of the 1,1-diaryl-2,2-diethynylethylene (175) resulted, although in low yields, in a naphthalene ring system (176) embedded in a larger polycyclic network.…”

Section: Synthesis Of Xanthonesmentioning

confidence: 99%

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Synthesis of Xanthones: An Overview

Sousa¹,

Pinto

2005

CMC

125

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Among the known synthetic routes to obtain xanthones, the Grover, Shah, and Shah reaction, the cyclodehydration of 2, 2'-dihydroxybenzophenones and electrophilic cycloacylation of 2-aryloxybenzoic acids are the most popular methods. Due to important biological applications of xanthones, some synthetic strategies leading to more complex derivatives have been widely explored in the past years. Thus, the purpose of this review is to report some recent improvements of the classical synthetic methods as well as of some non-classical methods to obtain simple oxygenated xanthones. The strategies for introduction of substituents into the xanthonic nucleus are also summarized. Furthermore, different approaches used to synthesize complex structures, with an emphasis on the total synthesis of bioactive natural products, accomplished in the last twenty years, are also discussed. Besides the synthesis of xanthones, the reactivity of the xanthonic nucleus and its role as a key intermediate for the synthesis of other important classes of compounds are also highlighted.

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Section: Synthesis Of Natural Productsmentioning

confidence: 99%

Section: Synthesis Of Xanthonesmentioning

confidence: 99%

Synthesis of Xanthones: An Overview

Sousa¹,

Pinto

2005

CMC

125

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“…For the synthesis of gartanin ( 30 ), Bennett and colleagues designed a method (Scheme 2) that was published in 1990 [87]. Reaction of 2,3,6-trimethoxybenzoic acid ( f ) and phloroglucinol ( g ) was conducted in P 2 O 5 and MeSO 3 H and yielded 1,3-dihydroxy-5,8-dimethoxyxanthone ( h ).…”

Section: Synthesis Of Mangosteen Xanthonesmentioning

confidence: 99%

“…Then, 3-methylbut-2-enylation of 1,3-dihydroxy-5,8-dimethoxyxanthone produced 1-hydroxy-3,5,8-trimethoxy-2,4-di-(3-methylbut-2-enyl)-xanthone ( i ), which was demethylated in hot aqueous morpholine to give gartanin ( 30 ). Using a similar synthetic process, the mangosteen xanthone 10 , 1,5,8-trihydroxy-3-methoxy-2-[3-methylbut-2-enyl]xanthone, was also synthesized [87]. No yield of this synthetic work was reported in the literature.…”

Section: Synthesis Of Mangosteen Xanthonesmentioning

confidence: 99%

Structural Characterization, Biological Effects, and Synthetic Studies on Xanthones from Mangosteen (Garcinia mangostana), a Popular Botanical Dietary Supplement

Chin

Kinghorn²

2008

MROC

119

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Mangosteen (Garcinia mangostana L., Clusiaceae) is a popular botanical dietary supplement in the United States, where it is used principally as an antioxidant. It is referred to as the “queen of fruits” in Thailand, a country of origin. The major secondary metabolites of mangosteen, the xanthones, exhibit a variety of biological activities including antibacterial, antifungal, antiinflammatory, antioxidant, antiplasmodial, cytotoxic, and potential cancer chemopreventive activities. Moreover, some of the xanthones from mangosteen have been found to influence specific enzyme activities, such as aromatase, HIV-1 protease, inhibitor κB kinase, quinone reductase, sphingomyelinase, topoisomerase and several protein kinases, and they also modulate histamine H1 and 5-hydroxytryptamine2A receptor binding. Several synthetic procedures for active xanthones and their analogs have been conducted to obtain a better insight into structure-activity relationships for this compound class. This short review deals with progress made in the structural characterization of the chemical constituents of mangosteen, as well as the biological activity of pure constituents of this species and synthetic methods for the mangosteen xanthones.

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“…-The AcOEt-soluble fraction of the EtOH extract from the pericarp of mangosteen was subjected to repeated column chromatography (CC) over silica gel, Sephadex LH-20, and ODS to afford the two new compounds 1 and 2, along with six known xanthones (Fig. 1), i.e., 4',5'-dihydro-1,3,6-trihydroxy-6',6'-dimethyl-2,5-bis(3-methylbut-2-en-1-yl)pyrano [2',3': 7,8]xanthone (3) [9], 1,5,8-trihydroxy-3-methoxy-2-(3-methyl-2-buten-1-yl)xanthone (4) [10], garcinone E (5) [11], mangostenone D (6) [12], mangostanol (7) [13], and smeathxanthone A (8) [14]. Their structures were identified by means of spectroscopic methods, and by comparison with literature data.…”

mentioning

confidence: 99%

Two New Prenylated Xanthones from the Pericarp of Garcinia mangostana (Mangosteen)

Zhou

Huang

Hao

et al. 2011

Helvetica Chimica Acta

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Two new prenylated xanthones (¼ 9H-xanthen-9-ones), garcimangosxanthones D (1) and E (2), together with the six known xanthones 3 -8, were isolated from the pericarp of Garcinia mangostana. Their structures were determined by analysis of their spectroscopic data. All of the isolated compounds were biologically evaluated for their in vitro cytotoxic activity against A549, Hep-G2, and MCF-7 humancancer cell lines and antioxidant activity. Compound 1 exhibited moderate cytotoxicity against Hep-G2 (IC 50 ¼ 19.2 mm) and weak cytotoxicity against MCF-7 (IC 50 ¼ 62.8 mm) cell lines, and compound 2 showed moderate cytotoxicity against A549, Hep-G2, and MCF-7 cell lines with IC 50 values of 12.5 -20.0 mm ( Table 2). Both compounds 1 and 2 demonstrated a weak antioxidant activity with ferric reducing antioxidant power (FRAP) values of 41 AE 7 and 130 AE 4 mmol/g, respectively (Table 3).

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Synthesis of Minor Xanthones from Garcinia mangostana

Cited by 25 publications

References 24 publications

Synthesis of Xanthones: An Overview

Synthesis of Xanthones: An Overview

Structural Characterization, Biological Effects, and Synthetic Studies on Xanthones from Mangosteen (Garcinia mangostana), a Popular Botanical Dietary Supplement

Two New Prenylated Xanthones from the Pericarp of Garcinia mangostana (Mangosteen)

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