{"title":"Secondary metabolites from the barks of Garcinia griffithii T. Anderson (Clusiaceae) and their chemophenetic significance","authors":"Noor Aimi Othman , Sook Yee Liew , Kooi Yeong Khaw , Abdulwali Ablat , Saiful Anuar Karsani , Kok Hoong Leong , Patricia Blanchard , Severine Derbré , Khalijah Awang","doi":"10.1016/j.bse.2024.104869","DOIUrl":null,"url":null,"abstract":"<div><p>A total of thirteen compounds consisting of nine xanthones; cowagarcinone C (<strong>1</strong>), doitunggarcinone C (<strong>2</strong>), nigrolineaxanthone E (<strong>3</strong>), nigrolineaxanthone Q (<strong>4</strong>), β-mangostin (<strong>5</strong>), 7-<em>O</em>-methylgarcinone E (<strong>6</strong>), dulcisxanthone F (<strong>7</strong>), ananixanthone (<strong>8</strong>) and nigrolineaxanthone N (<strong>9</strong>), two polycyclic polyprenylated acylphloroglucinols (PPAPs); garcinielliptone J (<strong>13</strong>) and garcinialone (<strong>14</strong>) as well as two terpenoids; 30-hydroxycycloartenol (<strong>15</strong>) and garcinane (<strong>16</strong>), were putatively identified with a good confidence level from dichloromethane extract of <em>Garcinia griffithii</em> T. Anderson using the <sup>13</sup>C NMR-based dereplication and MixONat software. In addition, three xanthones; euxanthone (1,7-dihydroxyxanthone) (<strong>10</strong>), forbexanthone (<strong>11</strong>) and 1,5-hydroxy-3,6-dimethoxy-2,7-diprenylxanthone (<strong>12</strong>) were successfully isolated. The structure of the isolated compounds was confirmed through the analysis of spectroscopic data and comparison with reported data. The <sup>13</sup>C NMR data of forbexanthone (<strong>11</strong>) was reported for the first time. Interestingly, the dichloromethane extract and 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone (<strong>12</strong>) which were evaluated for their exhibited α-glucosidase inhibitory activity exhibited potent inhibition toward the enzyme with IC<sub>50</sub> values of 0.66 μg/mL and 3.02 μM, respectively as compared to the standard, acarbose (IC<sub>50</sub> = 392 μg/mL or 608 μM). Notably, ananixanthone (<strong>8</strong>) has not been reported from the genus <em>Garcinia</em> while compounds <strong>1</strong>–<strong>7</strong>, <strong>9</strong>, <strong>11</strong> and <strong>13</strong>–<strong>16</strong> being reported from <em>Garcinia griffithii</em> for the first time. In addition, the chemophenetic significance of all the compounds has also been discussed.</p></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":"116 ","pages":"Article 104869"},"PeriodicalIF":1.4000,"publicationDate":"2024-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biochemical Systematics and Ecology","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0305197824000875","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
A total of thirteen compounds consisting of nine xanthones; cowagarcinone C (1), doitunggarcinone C (2), nigrolineaxanthone E (3), nigrolineaxanthone Q (4), β-mangostin (5), 7-O-methylgarcinone E (6), dulcisxanthone F (7), ananixanthone (8) and nigrolineaxanthone N (9), two polycyclic polyprenylated acylphloroglucinols (PPAPs); garcinielliptone J (13) and garcinialone (14) as well as two terpenoids; 30-hydroxycycloartenol (15) and garcinane (16), were putatively identified with a good confidence level from dichloromethane extract of Garcinia griffithii T. Anderson using the 13C NMR-based dereplication and MixONat software. In addition, three xanthones; euxanthone (1,7-dihydroxyxanthone) (10), forbexanthone (11) and 1,5-hydroxy-3,6-dimethoxy-2,7-diprenylxanthone (12) were successfully isolated. The structure of the isolated compounds was confirmed through the analysis of spectroscopic data and comparison with reported data. The 13C NMR data of forbexanthone (11) was reported for the first time. Interestingly, the dichloromethane extract and 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone (12) which were evaluated for their exhibited α-glucosidase inhibitory activity exhibited potent inhibition toward the enzyme with IC50 values of 0.66 μg/mL and 3.02 μM, respectively as compared to the standard, acarbose (IC50 = 392 μg/mL or 608 μM). Notably, ananixanthone (8) has not been reported from the genus Garcinia while compounds 1–7, 9, 11 and 13–16 being reported from Garcinia griffithii for the first time. In addition, the chemophenetic significance of all the compounds has also been discussed.
期刊介绍：
Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology).
In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.
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