Genus Garcinia Research Articles

Polyprenylated Benzoylphloroglucinols Isolated from Garcinia Species and Their Cytotoxic Effects on Cancer Cell Lines.

Polyprenylated benzoylphloroglucinols (PPBPs) make up a group of complex natural products with anticancer potentials that are mainly distributed in Garcinia plants. As part of our intensive exploration on new bioactive substances from this genus, we report two undescribed PPBPs, picrorhizones I (1) and J (2), along with four known analogues (3-6) from the stem bark of Garcinia picrorhiza and Garcinia gracilis. The new structures were elucidated on the basis of spectroscopic analysis, particularly 1D and 2D NMR and HRESIMS, whereas the absolute configurations were determined by a combination of ECD and NMR calculations coupled with a DP4+ probability analysis. Being the least class in genus Garcinia, picrorhizone I possesses a type-A structure with the position of a benzoyl moiety attaching to one of the bridgehead carbons of a bicyclo[3.3.1]nonane skeleton, which differs from its major type-B counterparts. This work also represents the first report on the occurrence of PPBPs in G. gracilis. The cytotoxic evaluation of the isolated compounds revealed that isogarcinol (4) and garciyunnanin L (5) significantly inhibited the growth of KB and Hela S3 cancer cells with IC50 values lower than 10 μM, while 5 was also strongly active against the Hep G2 cancer cell line with an IC50 value of 8.02 μM. Among the B-class derivatives bearing a lavandulyl side chain, cyclization of the moiety in the bicyclic phloroglucinol skeleton enhanced the cytotoxic properties on cancer cells.

Caudiquinol: A Meroterpenoid with an Intact C20 Geranylgeranyl Chain Isolated from Garcinia caudiculata.

The tropical Garcinia genus of flowering plants is a prolific producer of aromatic natural products including polyphenols, flavonoids, and xanthones. In this study, we report the first phytochemical investigation of Garcinia caudiculata Ridl. from the island of Borneo. Fractionation, purification, and structure elucidation by MS and NMR resulted in the discovery of two meroterpenoids. One was a benzofuranone lactone previously isolated from Iryanthera grandis and Rhus chinensis, and the second was a new hydroquinone methyl ester that we named caudiquinol. Both natural products are rare examples of plant meroterpenoids with an intact geranylgeranyl chain.

Chromones and biflavonoids from Garcinia pedunculata and Garcinia nujiangensis and their anti-inflammatory activity

Plants of the Garcinia genus were rich in structurally diverse and naturally bioactive components, while limited studies have been reported for Garcinia pedunculata Roxb. and G. nujiangensis C. Y. Wu & Y. H. Li. Four previously undescribed compounds including three chromones, garpedunchromones A-C (1–3), and one biflavonoid, nujiangbiflavone A (14), along with fifteen known analogs (4–13, 15–19) were isolated from G. pedunculata and G. nujiangensis. The structures of the isolated compounds were determined based on their HRESIMS data, extensive NMR spectroscopic analyses, and ECD calculations. The chromone derivatives were isolated from Garcinia for the first time. Compound 14 was a rare biflavonoid with C-3─C-6″ linkage. The biological evaluation of these isolates against NO production was conducted in the LPS-induced RAW 264.7 cells, resulting in the identification of a series of potent NO inhibitors, of which garpedunchromone B (2) was the most active with an IC50 value of 18.11 ± 0.96 μM. In the network pharmacology studies, the potential targets of compounds and inflammation were obtained from PharmMapper and GeneCards database. GO and KEGG enrichment analysis revealed that the overlapped targets were closely related to the major pathogenic processes linked to inflammation. Garpedunchromone B and proteins binding sites were being predicted.

Taxonomic Studies on Indian Guttiferae III. the Genus <I>Garcinia</I> Linn. S.l.

The paper deals with the taxonomic treatment of the genus Garcinia Linn, (including Xanthochymus Roxb.) as occurring in India. The study was undertaken with a view to enumerate the wild types of Indian Garcinias that produce the 'gummi-gutt' or gamboge of commerce and which may be utilized in the improvement of the fruit of mangosteen (G. mangostana Linn.). Thirty five species are recognized in the area, of which thirty one species occur wild ; the rest are introduced into cultivation. Ten species are restricted to the Andaman and Nicobar Islands. One Burmese species, G. loniceroides T. Anders., has been discovered in Assam. A new variety of G. echinocarpaThwaites, namely var. monticola Mahesh., is reported from southern India. These are described in detail and their synonymy, distribution, uses, vernacular names, etc. are ascertained. A key to the species is presented.G. eugeniaefolia Wall, ex T. Anders., is incorporated in G. brevirostris Scheff. G. ovalifolia Hook.f. var. macrantha T. Anders, (syn. G. malabarica Talb., non Desr.) is raised to specific rank as G. talbotii Raiz. ex Santapau. G. affinis Wall, ex Pierre, G. pictoria Roxb., and G. acuminata Planch. & Triana, are treated as distinct species. T. Anderson (1874) in the Flora of British India has united G. kydia Roxb. with G. cowa Roxb. It is concluded here that these species should be kept separate. The details are discussed in this paper.

An updated infrageneric classification of the pantropical species-rich genus Garcinia L. (Clusiaceae) and some insights into the systematics of New Caledonian species, based on molecular and morphological evidence.

Garcinia L. is a pantropically distributed genus comprised of at least 250 species of shrubs and trees and has centers of diversity located in Africa/Madagascar, Australasia, and Southeast Asia. The genus is notable due to its extreme diversity of floral form, common presence in lowland tropical rainforests worldwide, and potential pharmacological value. Across its entire geographic range, Garcinia lacks a recent taxonomic revision, with the last genus-level taxonomic treatment of Garcinia conducted over 40 years ago. In order to provide an evolutionary-based framework for a revised infrageneric classification of the genus and to investigate in more detail the systematics of New Caledonian species, we conducted molecular phylogenetic analyses using DNA sequence data for the nuclear ITS region on all samples, and for three chloroplast intergenic spacers (psbM-trnD, trnQ-rps16 and rps16-trnK) on a subset of our overall sampling. Our phylogenetic analyses are the most comprehensive to date for the genus, containing 111 biogeographically and morphologically diverse Garcinia species. The analyses support a broad circumscription of Garcinia, including several previously segregated genera (e.g. Allanblackia, Clusianthemum, Ochrocarpos p.p., Pentaphalangium, Rheedia, and Tripetalum). We recovered nine major clades falling within two major lineages, and we delimit 11 sections. We discuss each of the clades, assign them sectional names, discuss their distinguishing morphological features, compare our taxonomic treatment with the most recent sectional treatment, list representative species, note geographic distribution, and highlight some questions that deserve future investigations. We propose nine new nomenclatural combinations, four new names, and three new lectotypes. In New Caledonia (NC), a total of ten, all endemic, species are recognized and were included in our phylogenetic analyses, with several replicates per species (with the exception of G.virgata and G.urceolata, represented by a single accession each). New Caledonian species were retrieved within three separate clades, respectively including 1) G.balansae; 2) G.comptonii, G.neglecta, G.urceolata, G.virgata; and 3) G.amplexicaulis, G.densiflora, G.pedicellata, G.puat, G.vieillardii. Within NC, the phylogenies did not support the distinction between a putative undescribed species and G.balansae. However, it confirmed the distinction between NC species and both G.vitiensis (found in Fiji and Vanuatu) and G.adinantha (found in Fiji), suggesting that all NC species should be considered as endemics.

Characteristics of Garcinia seed fats and their potential usages as functional ingredients: A review

SummaryFruits of commercial Garcinia genus have been used for centuries in subtropic and tropic areas. However, large amounts of their seeds and included kernels are generally discarded as wastes or treated as low‐value agricultural products due to lack of appropriate processing technologies. The kernels have considerable values as sources of specialty fats and liposoluble bioactive compounds. Typical Garcinia seed fats for commercial purposes are mainly kokum (Garcinia indica) butter, mangosteen (Garcinia mangostana) seed fat and yellow mangosteen (Garcinia xanthochymus). These fats contained special sn‐1,3‐disaturated‐2‐unsaturated triacylglycerols, especially StOSt, POSt, StLSt and PLSt (P, palmitic acid; St, stearic acid; O, oleic acid and L, linolic acid), which are quite different from the triacylglycerol structure in common vegetable oils. Their improved usages in chocolate fats, trans‐free shortenings, dressings, salad and cooking oils, oleogels and antioxidants were concluded in this review. The health benefits contributed by their functional micronutrients (e.g. tocopherols, phytosterols, polyphenols and flavonoids) were further discussed to expand their application in functional foods, pharmaceuticals and cosmetics.

Achachairu—a Potential Fruit Crop for Florida

Garcinia humilis is an emerging tropical fruit crop in South Florida commonly known as achachairu. Achachairu has attracted much interest as a healthy fruit crop because it is rich in many nutrients such as foliate, vitamins, riboflavin, minerals, and antioxidants. The current use is limited and localized. To help Extension faculty, growers, and students better understand the potential of achachairu (Garcinia humilis [Vahl] CD Adam) and Garcinia madruno as profitable crops and their health benefits, this publication is synthesized from literature sources and has been networked with farmers, food processors, chefs, and photographers. This publication provides an overview of achachairu and ocoro (Garcinia madruno [Kunth] Hammel)—two common species in the Garcinia genus—including cultivation methods and use of the two crops grown in Florida.

Bioactivities of β-mangostin and its new glycoside derivatives synthesized by enzymatic reactions.

Beta-mangostin is a xanthone commonly found in the genus Garcinia. Unlike α-mangostin, to date, there have only been a few studies on the biological activity and derivatization of β-mangostin. In this study, two novel glycosylated derivatives of β-mangostin were successfully synthesized via a one-pot enzymatic reaction. These derivatives were characterized as β-mangostin 6-O-β-d-glucopyranoside and β-mangostin 6-O-β-d-2-deoxyglucopyranoside by TOF ESI/MS and 1H and 13C NMR analyses. Beta-mangostin showed cytotoxicity against KB, MCF7, A549 and HepG2 cancer cell lines, with IC50 values ranging from 15.42 to 21.13 µM. The acetylcholinesterase and α-glucosidase inhibitory activities of β-mangostin were determined with IC50 values of 2.17 and 27.61 µM, respectively. A strong anti-microbial activity of β-mangostin against Gram-positive strains (Bacillus subtilis, Lactobacillus fermentum and Staphylococcus aureus) was observed, with IC50 values of 0.16, 0.18 and 1.24 µg ml-1, respectively. Beta-mangostin showed weaker activity against Gram-negative strains (Salmonella enterica, Escherichia coli and Pseudomonas aeruginosa) as well as Candida albicans fungus, with IC50 and MIC values greater than the tested concentration (greater than 32 µg ml-1). The new derivatives of β-mangostin showed weaker activities than those of β-mangostin, demonstrating the important role of the hydroxyl group at C-6 of β-mangostin in its bioactivity.

Schomburginones A‒J, geranylated benzophenones from the leaves of Garcinia schomburgkiana and their cytotoxic and anti-inflammatory activities

Ten undescribed benzophenones, schomburginones A−J, together with 14 known analogs were isolated from the leaves of Garcinia schomburgkiana, an edible plant native to the Indochina region. The structures of the undescribed compounds were elucidated by NMR combined with HRMS spectroscopy, while their absolute configurations were determined using ECD and single-crystal X-ray diffraction analysis. The isolated metabolites represent benzophenone derivatives containing a modified monoterpene unit, including tri- and tetracyclic skeletons, which are rarely found in genus Garcinia. The cytotoxic evaluation on three cancerous cell lines demonstrated that schomburginone G, schomburginone H, and 3-geranyl-2,4,6-trihydroxybenzophenone were active against HeLa cells with IC50 values in the range of 12.2–15.7 μM, respectively, and selective compared to the non-cancerous L929 cells (SI > 3.5). In addition, the three cytotoxic compounds together with clusiacyclol A showed significant NO inhibitory activity in RAW 264.7 macrophage cells over 85% inhibition without obvious cytotoxicity at a final concentration of 100 μM. The promising activities of these compounds in cytotoxic and anti-inflammatory assays make them attractive for further study in the development of anticancer drugs.

Morelloflavone as Phytomedicine-An Ethnopharmacological Review on the Therapeutical Properties, Biological Efficacy and Pharmacological Activity

Background:Flavonoids are low molecular weight class secondary metabolites found to be present throughout the plant kingdom. Structurally, flavonoid class phytochemicals consist of C6-C3-C6 chemical structures with different substitution patterns and have drug-like nature. Morelloflavone is a biflavonoid class phytochemical found to be present abundantly in the Garcinia genus. Morelloflavone has been investigated in the scientific field for its numerous pharmacological activities. The present work aims to discuss the scientific progress of health beneficial aspects and pharmacological potential of morelloflavone in medicine.Methods:The purpose of this work is to provide scientific information about the biological potential and health beneficial effects of flavonoids in medicine with special reference to the morelloflavone. In this work, we have collected the scientific data of morelloflavone for the biological potential and pharmacological activities against different types of human illnesses with their mechanism of action from Google, Google Scholar, Science Direct and PubMed and analyzed. Further, the preventive role of morelloflavone against various types of human illnesses and the mechanism of action have also been discussed in the present work. This work will provide upto- date information on the health beneficial aspects of morelloflavone in medicine for the prevention and treatment of human complications.Results:Morelloflavone exhibited a wide-range of pharmacologic activity in regulating numerous kinds of human disorders. Present work revealed the health beneficial aspects and pharmacological activities of morelloflavone for the prevention and treatment of human disorders due to its anti-microbial, anti-plasmodial, anti-oxidant, anti-atherosclerosis, anti-inflammatory, anti-tumor anti-restenosis, anti-HIV, aphrodisiac, anti-Alzheimer's and apoptotic potential in the medicine. Further, its biological potential on phospholipase A2, melanin, kallikreins, monoamine oxidase, aromatase, Eg5 Inhibition and proprotein convertases have been also analyzed in the present work. Analytical data signified the importance of modern analytical tools for the separation and isolation of morelloflavone in medicine.Conclusion:Present work revealed the detailed pharmacological activities of morelloflavone that can be utilized in the future for the development of new pharmacologic agents.

Deciphering the Analysis of the Genetic Diversity of Mangosteen (Garcinia mangostana L.) from Various Regions of Origin in Java, Indonesia

ABSTRACT: The genetic improvement of a plant to produce high-yielding varieties depends on genetic variability. It is widely known that the mangosteen plant (Garcinia mangostana L.) does not have genetic variability because it has an apomictic reproductive mechanism. Analysis of genetic diversity can be carried out by analysis of similarities and clusters between accessions of plants or with their close relatives of the Garcinia genus. This research was carried out to analyze the genetic diversity of 50 mangosteen accessions at mangosteen production centers in four provinces in Java, Indonesia (Banten, West Java, Central Java, and East Java provinces) using RAPD-based primers. RAPD-based amplification revealed a total of 30 amplicons, 28 as polymorphic and two as monomorphic, with an average percentage of polymorphism of 72.22%. The results of PCR-RAPD visualization produce bands measuring 300 bp - 1500 bp. The dendrogram shows the grouping of all types of G. mangostana L. in general. The primer used can amplify the samples properly. Genetic variation occurs with coefficient values ranging from 25% to 100%. This study also explains the pattern of the spread of G. mangostana L. in Java for the first time. These results can be used as a reference for conserving G. mangostana L. and future breeding.

Effects of Ethanolic and Aqueous Extracts of Garcinia gardneriana Leaves in an In Vivo Experimental Model Induced by a Hyperlipidic Diet

The study of medicinal plants, such as the genus Garcinia (Clusiaceae), in the treatment of non-communicable chronic diseases has aroused the interest of researchers. However, there are no studies in the literature that have investigated the effects of Garcinia gardneriana in experimental models of obesity for possible metabolic alterations. Swiss mice receiving a high-fat diet were supplemented with aqueous or ethanolic extract of G. gardneriana at doses of 200 or 400 mg/kg/day. It was found that there was a reduction in food consumption in experimental groups compared with the control groups, and the group supplemented with aqueous extract at a dose of 200 mg/kg/daydisplayed a reduction in weight. The results showed an increase in the values of high density lipoprotein (HDL-c), total cholesterol, triglycerides and fasting blood glucose. G. gardneriana did not protect against insulin resistance, and caused in an increase in monocyte chemoattractant protein-1 (MCP-1) concentrations and a reduction in interleukin 10 (IL-10). In addition, hepatic steatosis and microvesicular steatosis were indicated. It was revealed that, under the experimental conditions in the study, G. gardneriana did not prevent weight gain or comorbidities; that is, a different behavior was obtained from that described in the literature with regard to the medicinal potential of the Garcinia species, which is probably related to the phytochemical properties.

Anti-Inflammatory Activity of Stem Barks Ethanol Extracts of Asam Kandis On Male White Rats

Inflammation is a complex series of changes in tissue due to tissue injury caused by bacteria, trauma, chemicals, heat, and pain. Gamboge (Garcinia xanthochymus) is a fruit-bearing tree native to Southeast Asia. Plants of the genus garcinia are rich in secondary metabolites such as flavonoids, steroids, and triterpenes which have potential pharmacological activity. This study aimed to determine the anti-inflammatory activity based on the reduction in edema volume of Gamboge (Garcinia xanthochymus) stem bark. The inquiry was experimental. Through maceration, an ethanol extract of the gamboge stem was created. The animals were divided into five groups, each containing five white male rats. The test given was a suspension of gamboge ethanol extract at doses of 200, 400, and 600 mg/kgBW, a negative control of 1% Na CMC suspension, and a positive control of 2.25 mg/kgBW sodium diclofenac. Observations were made for 6 hours, and then data were analyzed using a two-way analysis of variance (ANOVA) test. The results showed that gamboge ethanolic extract was proven to have an anti-inflammatory effect in white male rats induced by carrageenan starting at doses of 200, 400, and 600 mg/kgBW, marked by a significant difference to the negative control (p<0.05). The 600mg/kgBW dose group showed no significantly different results from the positive control group (p>.05). These results concluded that the dose group 600mg/kgBW was the best dose of gamboge stem ethanol extract had an anti-inflammatory activity based on reducing the volume of leg edema of white male rats.
 Keywords: Asam Kandis Stem Bark; Anti-Inflammation; Male White Rats

Plastomes of Garcinia mangostana L. and Comparative Analysis with Other Garcinia Species.

The two varieties of mangosteen (Garcinia mangostana L.) cultivated in Malaysia are known as Manggis and Mesta. The latter is preferred for its flavor, texture, and seedlessness. Here, we report a complete plastome (156,580 bp) of the Mesta variety that was obtained through a hybrid assembly approach using PacBio and Illumina sequencing reads. It encompasses a large single-copy (LSC) region (85,383 bp) and a small single-copy (SSC) region (17,137 bp) that are separated by 27,230 bp of inverted repeat (IR) regions at both ends. The plastome comprises 128 genes, namely, 83 protein-coding genes, 37 tRNA genes, and 8 rRNA genes. The plastome of the Manggis variety (156,582 bp) obtained from reference-guided assembly of Illumina reads was found to be nearly identical to Mesta except for two indels and the presence of a single-nucleotide polymorphism (SNP). Comparative analyses with other publicly available Garcinia plastomes, including G. anomala, G. gummi-gutta, G. mangostana var. Thailand, G. oblongifolia, G. paucinervis, and G. pedunculata, found that the gene content, gene order, and gene orientation were highly conserved among the Garcinia species. Phylogenomic analysis divided the six Garcinia plastomes into three groups, with the Mesta and Manggis varieties clustered closer to G. anomala, G. gummi-gutta, and G. oblongifolia, while the Thailand variety clustered with G. pedunculata in another group. These findings serve as future references for the identification of species or varieties and facilitate phylogenomic analysis of lineages from the Garcinia genus to better understand their evolutionary history.

Dulxanthone A from Ethyl Acetate Extract of Garcinia nigrolineata Stem Bark

The genus Garcinia is the largest genus of the Guttiferae family which is widely distributed in tropical and subtropical regions. There are 64 species of Garcinia in Indonesia, one of which is Garcinia nigrolineata known as “Kandis keling". This plant is reported as a source of secondary metabolites like xanthones. Xanthones are known to have interesting activities, such as anti-oxidant, anti-inflammatory, cytotoxic and antibacterial. This study aims to isolate xanthone compounds from stem bark of G. nigrolineata and determine their structures by using various spectroscopic methods. Samples were macerated with ethyl acetate. The ethyl acetate extract was then separated and purified by chromatographic method to obtain pure C6e isolates. The C6e isolates were characterized using UV, IR, 1HNMR, 13C-NMR, HMQC, 1H-1H COSY, HMBC and mass spectroscopy methods. The C6e isolates obtained were in the form of yellow oil as much as 5.6 mg. Based on the results of structural elucidation, the C6e isolates were xanthone compounds with the molecular formula of C19H18O6, namely dulxanthone A.

GC-TOF-MS-based metabolomics correlated with bioactivity assays unveiled seasonal variations in leaf essential oils of two species in Garcinia L.

The genus Garcinia L. is known for its many practical uses, particularly as medicines and food. However, few studies have reported the seasonal influence on Garcinia metabolites. The objective of this study was to evaluate the seasonal effects on the chemical composition and bioactivity of Garcinia essential oils (EOs), using the native G. xanthochymus Hook.f. and endemic G. yunnanensis Hu in southwest China. Gas chromatography time-of-flight mass spectrometry-based metabolomics uncovered qualitative and quantitative variations of 118 EO compounds, mainly comprising sesquiterpene hydrocarbons, oxygenated sesquiterpenes and esters. Chemometric approaches, including principal component analysis and partial least-squares-discriminant analysis (PLS-DA), further indicated that EO profiles varied distinctly according to seasons. From PLS-DA models built on seasonal samples, a total of 15 differential compounds, such as ethyl palmitate and β-bisabolene, were characterized from G. xanthochymus and 19 compounds, including pentadecane and hexadecanoic acid, from G. yunnanensis. Biological assays demonstrated that the bioactivities of leaf EOs from both species were also notably affected by seasonality. The most promising season to harvest Garcinia leaves for their cytotoxic and anti-inflammatory EOs is winter, with IC50 values lower than 20 μg/mL; for antibacterial, it is spring with MIC50 values lower than 135 μg/mL against Listeria monocytogenes. Correlation analysis further indicated that some EOs, such as β-copaene, β-bisabolene and hexadecanoic acid, were positively associated with the observed bioactivity results. These findings, taken together, suggest that EOs from Garcinia leaves have strong biological activities, but their seasonal variation needs to be carefully considered for future product development.

Antioxidant property of secondary metabolites from Garcinia genus: A short review

Species from the Garcinia genus (Clusiaceae family) are used in the treatment of many diseases and metabolic disorders frequently associated with the oxidative stress. The characteristic metabolites found in this genus are xanthones and benzophenones, which have antioxidant properties, among relevant biological potentials. This review provides a specific vision about antioxidant activity of Garcinia species, reporting in vitro and in vivo assays, described from the last five years. The research about antioxidant properties of Garcinia species and their constituents can be directed in the development of new medicines and drugs.

CHEMICAL CONSTITUENTS OF DICHLOROMETHANE EXTRACT FROM THE STEM BARK OF GARCINIA FAGRAEOIDES

The Garcinia genus belonging to the Clusiaceae family (Guttiferae) has been reported to be a rich source of polyisoprenylated benzophenones, xanthones and biflavonoids with various biological activities. Garcinia fagraeoides A.Chev is an evergreen hardwood tree found only in the north provinces of Viet Nam and Guangxi province of China. Its stem bark and leaves have been used in Vietnamese traditional medicine for treatment of malaria and dermatitis diseases. In our continuing studies on chemical constituents and biological activities from the genus Garcinia, the phytochemical of Garcinia fagraeoides’s stem bark collected from Thua Thien Hue province was investigated. Repeated chromatography steps over silica gel and Sephadex LH-20 of the dichloromethane partition from the methanol extract of Garcinia fagraeoides’s stem bark led to the isolation of five compounds including one polyisoprenylated benzophenone (isogarcinol (1)), two tetraoxygenated xanthones (rubraxanthone (2), a-mangostin (3)), ferulic acid (4), and pyromeconic acid (5). Their structures were elucidated mainly by analysis of their 1D, 2D NMR spectroscopy and ESI-MS data, and by comparison with reported data. The absolute configuration of isogarcinol (1) was determined by comparison of its experimental optical rotation and NMR data with the values of its stereoisomer. This is the first reported isolation of compounds 1-5 from the stem bark of Garcinia fagraeoides.

Garcinia spp: Products and by-products with potential pharmacological application in cancer

The Garcinia genus belongs to the Clusiaceae family and is composed of approximately 240 species, distributed throughout the tropical regions, with a significant representation in Brazil. Their edible fruits have a high dietary value and have been recognized for their economic value as food and health. By-products of Garcinia fruits, such as the peel and seed of Garcinia brasiliensis, are a rich source of fibers, proteins, and bioactive metabolites, producing flour with an energetic value near wheat flour and antioxidant properties. Peel waste of G. mangostana (mangosteen) has been used as a green absorbent to recover valuable metals such as gold and silver from electronic waste. Many Garcinia species have obtained great prominence for extracts and isolated compounds, such as polyphenols, bioflavonoids, anthocyanins, benzophenones, and xanthones in the treatment of various illnesses. Thus, natural products isolated from Garcinia species have been described as having a chemical diversity and potential for medicinal uses with emphasizing adipogenesis, diabetes, cardiovascular illness, and cancer. This review comprises works published from January 2017 to March 2022 and highlights the promising anticancer activity and potential use of natural compounds from Garcinia species and fruit wastes.

Theoretical study of keto-enol tautomerism in 7-epi-clusianone by quantum chemical calculations of NMR chemical shifts.

Plants from the Garcinia genus have been used worldwide due to their therapeutic properties. Among the various metabolites isolated from this genus, 7-epi-clusianone, a tetraprenylated benzophenone, stands out for its wide range of identified biological activities. This benzophenone can exist in five tautomeric forms, although the benzene-d6 and chloroform-d3 solution nuclear magnetic resonance (NMR) spectra revealed only two tautomeric forms (B and C) in equilibrium, with concentration ratio depending on the solvent in which the spectrum was obtained. Calculated energy values suggested that tautomeric forms B and E would be prevalent in benzene-d6 solution, in contrast to the experimental data. Considering this conflicting result, we employed the statistical DP4 + method based on 13C and 1H NMR chemical shift calculations, in the gas phase and in benzene-d6 solution, to confirm that the B and C tautomeric forms of 7-epi-clusianone are the most prevalent in the experimental conditions.