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Both the enantiomers of racemic 4- O -tosyl-6- O -benzyl- myo -inositol-1,3,5-orthoformate (2) were isolated by preferential crystallization and used to synthesize several enantiomeric myo -inositol derivatives - natural ononitol, natural laminitol, precursors for myo -inositol phosphates and an oxabicyclo [2.2.1] heptane derivative. This work demonstrates the potential of the enantiomeric tosylates D2 and L2 to serve as versatile starting materials for the absolute asymmetric synthesis of inositol derivatives and other natural products from symmetric myo -inositol since no optically active molecular entity was required for the resolution of 2. [Display omitted] • First absolute asymmetric synthesis of inositol derivatives. • Enantiomeric myo -inositol derivatives as potential chiral pool molecules. • Access to the same enantiomeric inositol derivative from both D- and L-synthons. [ABSTRACT FROM AUTHOR]

Investigation of interactions between the target protein molecule and ligand allows for an understanding of the nature of the molecular recognition, functions, and biological activity of protein–ligand complexation. In the present work, non-specific interactions between a model protein (Bovine Serum Albumin) and four cyclitols were investigated. D-sorbitol and adonitol represent the group of linear-structure cyclitols, while shikimic acid and D-(–)-quinic acid have cyclic-structure molecules. Various analytical methods, including chromatographic analysis (HPLC-MS/MS), electrophoretic analysis (SDS-PAGE), spectroscopic analysis (spectrofluorimetry, Fourier transform infrared spectroscopy, and Raman spectroscopy), and isothermal titration calorimetry (ITC), were applied for the description of protein–cyclitol interactions. Additionally, computational calculations were performed to predict the possible binding places. Kinetic studies allowed us to clarify interaction mechanisms that may take place during BSA and cyclitol interaction. The results allow us, among other things, to evaluate the impact of the cyclitol's structure on the character of its interactions with the protein. [ABSTRACT FROM AUTHOR]

Novel stereodivergent total syntheses of all the seven stereoisomers of (−)‐shikimic acid [(−)‐SA 1] have been systematically performed. (+)‐ent‐SA ent‐1 was synthesized from (−)‐SA 1 via 9 steps in 31 % overall yield; (−)‐3‐epi‐SA 2 was synthesized from (−)‐SA 1 via 5 steps in 66 % overall yield; (+)‐3‐epi‐ent‐SA ent‐2 was synthesized from (−)‐SA 1 via 7 steps in 43 % overall yield; (−)‐4‐epi‐SA 3 was synthesized from (−)‐SA 1 via 11 steps in 32 % overall yield; (+)‐4‐epi‐ent‐SA ent‐3 was synthesized from (−)‐SA 1 via 7 steps in 42 % overall yield; (−)‐5‐epi‐SA 4 was synthesized from (−)‐SA 1 via 6 steps in 56 % overall yield; and (+)‐5‐epi‐ent‐SA ent‐4 was synthesized from (−)‐SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (−)‐SA 1 were further studied by two dimensional (2D) 1H NMR technique. [ABSTRACT FROM AUTHOR]

Two unnatural regioisomeric glycosylated Gilvocarcin analogues were proposed as model compounds to study the origin behind the biosynthetic development of the Gilvocarcins, a class of bioactive C‐aryl glycoside natural products. More specifically, the origins behind the proposed O‐ to C‐glycoside migration in the evolution of the biosynthesis for these classes of Angucycline antibiotic natural products. For stability reasons a 5a‐carbasugar motif was used to mimic the sugar portion of the molecule and of synthetic ease the proposed abiotic rearrangement move the sugar analogue along with its O‐glycoside linkage. The two proposed regioisomeric analogues were synthesized by a regio‐divergent synthetic pathway and featured a Mitsunobu‐like invertive cyclictolization reaction to install the carbasugar motif. The two regioisomeric Gilvocarcin analogues were evaluated as antibiotic with Gilvocarcin M as a control. Only one of the two isomers showing weak antibiotic activity as compared to Gilvocarcin M. [ABSTRACT FROM AUTHOR]

The stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate, methyl-substituted dihaloconduritol-A is reported. Bromination of 2-methylbenzo-1,4-quinone followed by the reduction in the carbonyl groups with NaBH4 to give a dioldibromo compound. The diol was converted to diacetates by acetylation with Ac2O-pyridine. Reaction of methyl-dioldibromodiacetate with LiOH gave stereoselectively the monoepoxide compound. Controlled reaction of the epoxide with AcCl in methylene chloride furnished the desired new dihaloconduritol-A derivative which was characterized by spectroscopic methods. All the synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, COSY (2D-NMR), and HRMS analyses. [ABSTRACT FROM AUTHOR]

Myo-inositol has been established as an important growth-promoting factor of mammalian cells and animals. The role of myo-inositol as a lipotropic factor has been proven, in addition to its involvement as co-factors of enzymes and as messenger molecules in signal transduction. Myo-inositol deficiency leads to intestinal lipodystrophy in animals and “inositol-less death” in some fungi. Of late, diverse uses of myo-inositol and its derivatives have been discovered in medicinal research. These compounds are used in the treatment of a variety of ailments from diabetes to cancer, and continued research in this direction promises a new future in therapeutics. In different diseases, inositols implement different strategies for therapeutic actions such as tissue specific increase or decrease in inositol products, production of inositol phosphoglycans (IPGs), conversion of myo-inositol (MI) to D-chiro-inositol (DCI), modulation of signal transduction, regulation of reactive oxygen species (ROS) production, etc. Though inositol pharmacology is a relatively lesser-known field, recent years of research has generated a critical mass of information on the subject. This review aims to summarize our current understanding on the role of inositol derivatives in ameliorating the symptoms of different diseases.

Myo -inositol has been established as an important growth-promoting factor of mammalian cells and animals. The role of myo -inositol as a lipotropic factor has been proven, in addition to its involvement as co-factors of enzymes and as messenger molecules in signal transduction. Myo -inositol deficiency leads to intestinal lipodystrophy in animals and "inositol-less death" in some fungi. Of late, diverse uses of myo -inositol and its derivatives have been discovered in medicinal research. These compounds are used in the treatment of a variety of ailments from diabetes to cancer, and continued research in this direction promises a new future in therapeutics. In different diseases, inositols implement different strategies for therapeutic actions such as tissue specific increase or decrease in inositol products, production of inositol phosphoglycans (IPGs), conversion of myo -inositol (MI) to D- chiro -inositol (DCI), modulation of signal transduction, regulation of reactive oxygen species (ROS) production, etc. Though inositol pharmacology is a relatively lesser-known field, recent years of research has generated a critical mass of information on the subject. This review aims to summarize our current understanding on the role of inositol derivatives in ameliorating the symptoms of different diseases. [ABSTRACT FROM AUTHOR]

This study was conducted to determine the effect of exogenous cyclitol (dl-cyclopentane-1,2,3-triol) on barley (Hordeum vulgare L.) during the alleviation of drought stress by using proteomics and physiological approaches. With the relative water content, water potential declined in barley depending on time under drought stress. This decline was lower in cyclitol-treated plants than in untreated plants. The stomatal pore width and open stoma number were higher in cyclitol-treated barley than in untreated plants under drought stress. The abscisic acid (ABA) and proline levels increased with the severity of drought in most treatments. The ABA level was lower in cyclitol-treated plants than in untreated plants under drought stress. Cyclitol treatments reduced O 2. − fluorescence in leaf cells under drought stress. Total differentially expressed proteins were identified in cyclitol treatment under stressful and unstressful conditions. Photosynthesis (approx. 49%) and energy metabolism (approx. 27%) were upregulated by cyclitol treatment under drought. Moreover, CML42, acting as a negative ABA regulator, also increased by cyclitol treatment. This increase may be important in controlling stomata movements under drought stress. Our results suggest that exogenous cyclitol enhances the drought tolerance of barley seedlings by modulating the photosynthesis, energy pathway, biosynthesis, and signal transduction. [ABSTRACT FROM AUTHOR]

In the present study, (3a R ,7a S )-1,3,3a,4,7,7a-hexahydroisobenzofuran was submitted to photooxygenation and two isomeric hydroperoxides were successfully obtained. Without any further purification, reduction of the hydroperoxides with titanium tetraisopropoxide catalyzed by dimethyl sulfide gave two alcohol isomers in high yields. After acetylation of alcohol with Ac 2 O in pyridine, epoxidation reaction of formed monoacetates with m -CPBA, then chromatographed and followed by hydrolysis of the acetate groups with NH 3 in CH 3 OH resulted in the formation of epoxy alcohol isomers respectively. These epoxy alcohol isomers were subjected to trans -dihydroxylation reaction with acid (H 2 SO 4 ) in the presence of water to afford triols. Acetylation of the free hydroxyl groups produced benzofuran triacetates in high yields. Ring-opening reaction of furan triacetates with sulfamic acid catalyzed in the presence of acetic acid/acetic anhydrate and subsequently hydrolysis of the acetate groups with ammonia gave the targeted cyclohexane carbasugar-based pentols. All products were separated and purified by chromatographic and crystallographic methods. Structural analyses of all compounds were conducted by spectral techniques including NMR and X-ray analyses. The biological inhibition activity of the target compounds was tested against glycosidase enzymes, α - and β -glucosidase. [ABSTRACT FROM AUTHOR]

scyllo-Inositol derived 1,2- trans -diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. This provides a potential route for the preparation of ring modified inositol derivatives. DFT calculations suggest that this epoxide formation could be proceeding through the intermediacy of the cyclohexane ring-inverted axial-rich conformer (1,2- trans -diaxial halohydrin). This is supported by the results of DFT calculations on the formation of inositol orthoformate, where the product is locked in the axial-rich conformation, while the starting inositol has the equatorial-rich conformation. [ABSTRACT FROM AUTHOR]

A method for the preparation of benzene derivatives from myo -inositol, an abundantly available phyto chemical is described. 1,3-Bridged acetals of inososes undergo step-wise elimination leading to the formation of polyoxygenated benzene derivatives. This aromatization reaction proceeds through the intermediacy of a β-alkoxyenone, which could be isolated. This sequence of reactions starting from myo -inositol, provides a novel route for the preparation of polyoxygenated benzene derivatives including polyoxygenated biphenyl. This scheme of synthesis demonstrates the potential of myo -inositol as a sustainable non-petrochemical resource for aromatic compounds. [ABSTRACT FROM AUTHOR]

Bauhinia rufescens is a medicinal plant used in the treatment of mycosis, diarrhea and malaria. Leaves of B. rufescens were extracted with organic solvent in a gradient of petroleum ether, ethyl acetate and methanol. Silica gel column purification of methanol extract afforded the isolation of a cyclitol, identified as 3-O-methyl-D-inositol. The crude extracts and the isolated compound were evaluated for their anticholinesterase inhibitory activity using bioautographic and microplate techniques. The cyclitol demonstrated higher activity in the microplate assay relative to the crude extract with IC50 value of 463.77 fiM. The Inhibitory activity exhibited by the cyclitol against acetylcholinesterase enzyme indicates its potential as a drug agent for the treatment of Alzheimer's disease. [ABSTRACT FROM AUTHOR]

The first syntheses of four stereoisomeric diaminocyclooctane diols, as well as a chlorocyclooctane aminodiol, are reported. In the first part, photooxygenation of cis,cis -1,3-cyclooctadiene gave a bicyclic endoperoxide, which was reduced with zinc followed by mesylation of the hydroxyl groups. Treatment with sodium azide afforded 1,4- and 1,2-cyclooctene diazides. Oxidation of the double bonds in the isomeric diazides with OsO 4 , followed by hydrogenation of the azide groups, led to 3,8-diaminocyclooctane-1,2-diol and 3,4-diaminocyclooctane-1,2-diols. In the second part, cis -3,8-diazidocyclooctene was converted into the corresponding epoxide. Stereospecific hydrolysis of the epoxide ring with HCl (g) in methanol, and hydrogenation of the azide groups gave 3,8-diamino-2-chloro-cyclooctan-1-ol. Bromination of the double bond in cyclooctene diacetate, followed by acetate deprotection, azidolysis of the bromides, and hydrogenation of the azide groups resulted in the formation of 2,3-diaminocyclooctane-1,4-diol. [ABSTRACT FROM AUTHOR]

Changes in the accumulation of two types of α-D-galactosides: raffinose family oligosaccharides and galactosyl pinitols were compared with changes in the activities of galactosyltransferases during winter vetch (Vicia villosa Roth.) seed development and maturation. Occurrence of galactinol and raffinose in young seeds and changes in activities of galactinol synthase and raffinose synthase during seed development indicated that formation of raffinose oligosaccharides (RFOs) preceded synthesis of galactopinitols. Although transfer of galactose residues into raffinose oligosaccharides increased as seeds were maturing, at late stages of seed maturation the accumulation of galactopinitols was preferred to that of RFOs. In the present study, activities of enzymes transferring galactose moieties from galactinol to D-pinitol forming galactopinitol A, and further transfer of galactose moieties from galactinol to mono- and di-galactopinitol A were detected throughout seed development and maturation. This is a new observation, indicating biological potential of winter vetch seeds to synthesize mono-, di- and tri-galactosides of D-pinitol in a pathway similar to RFOs. The pattern of changes in activities of stachyose synthase and enzymes synthesizing galactopinitols (named galactopinitol A synthase and ciceritol synthase) suggests that formation of stachyose, mono- and di-galactopinitol A (ciceritol) is catalyzed by one enzyme. High correlation between activities of verbascose synthase and enzyme catalyzing synthesis of tri-galactopinitol A from galactinol and ciceritol (named tri-galactopinitol A synthase) also suggests that biosynthesis of both types of tri-galactosides was catalyzed by one enzyme, but distinct from stachyose synthase. Changes in concentrations of galactosyl acceptors (sucrose and D-pinitol) can be a factor which regulates splitting of galactose moieties between both types of galactosides in winter vetch seeds.

Minor variations in the molecular structure of constituent molecules of reactive crystals often yield crystals with significantly different properties due to altered modes of molecular association in the solid state. Hence, these studies could provide a better understanding of the complex chemical processes occurring in the crystalline state. However, reactions that proceed efficiently in molecular crystals are only a small fraction of the reactions that are known to proceed (with comparable efficiency) in the solution state. Hence, for consistent progress in this area of research, investigation of newer reactive molecular crystals which support different kinds of reactions and their related systems is essential. The crystal structures and acyl-transfer reactivity of a myo-inositol-1,3,5-orthoformate-derived dibenzoate and its carbonate (4- O-benzoyl-2- O-phenoxycarbonyl- myo-inositol 1,3,5-orthoformate, C21H18O9) and thiocarbonate (4- O-benzoyl-2- O-phenoxythiocarbonyl- myo-inositol 1,3,5-orthoformate, C21H18O8S) analogs are compared with the aim of understanding the relationship between crystal structure and acyl-transfer reactivity. Insertion of an O atom in the acyl (or thioacyl) group of an ester gives the corresponding carbonate (or thiocarbonate). This seemingly minor change in molecular structure results in a considerable change in the packing of the molecules in the crystals of myo-inositol-1,3,5-orthoformate-derived benzoates and the corresponding carbonates. These differences result in a lack of intermolecular acyl-transfer reactivity in crystals of myo-inositol-1,3,5-orthoformate-derived carbonates. Hence, this study illustrates the sensitivity of the relative orientation of molecules, their packing and ensuing changes in the reactivity of resulting crystals to minor changes in molecular structure. [ABSTRACT FROM AUTHOR]

A sequence of vinylalumination of α-substituted aldehydes, ring-closing metathesis (RCM), and palladium-catalyzed allylic substitution was utilized to prepare the biologically active natural products, pericosines, from d-ribose. The anti-adduct of vinylalumination was transformed into pericosine A after RCM, removal of the 4-methoxybenzyl protecting group, and chlorination. The diacetate of the anti-adduct was converted to pericosine C after the palladium-catalyzed, SN2′-type, allylic substitution. However, an unexpected dimeric product was generated in utilizing this approach to prepare pericosine E. [ABSTRACT FROM AUTHOR]

Voglibose, an N -1,3-dihydroxypropylaminocyclitol, has widely been used as an effective α-glucosidase inhibitor for diabetes therapy. Several attempts have been made to synthesize closely related analogues through the coupling of various aminocyclitols and propane-1,3-diol; however, most of them showed weaker or no inhibition. In this communication, we synthesized a pair of new N -1,3-dihydroxypropylaminocyclitols ( 10 and 11 ) using (+)- proto -quercitol ( 1 ) as a cyclitol core structure. The newly synthesized compounds revealed potent rat intestinal α-glucosidases, particularly against maltase, with IC 50 values at submicromolar. Subsequent study on mechanisms underlying the inhibition of 11 indicated the competitive manner towards maltase and sucrase. The potent inhibition of these compounds was elaborated by docking study, in which their binding profiles towards key amino acid residues in the active site were similar to that of voglibose. Therefore, introduction of propane-1,3-diol moiety to suitable cyclohexane core structure such as aminoquercitol would be a potential approach to discover a new series of effective α-glucosidase inhibitors. [ABSTRACT FROM AUTHOR]

Conversion of a myo-inositol derivative into a scyllo-inositol-derived scaffold with C3v symmetry bearing three axial pyridyl appendages is presented. This pre-organized hexadentate ligand allows complexation of silver(I). The crystal structure of the complex was established.

The biological activity of alcohol and epoxide groups containing bicyclic skeletal structures was investigated in terms of antibiotic and toxic effects at cellular level. The present protocol, which utilizes readily available starting materials and mild reaction conditions, provides an attractive approach to a series of functionalized bicyclic alcohol and epoxide derivatives with promising biological applications. In this protocol, while some of the bicyclic compounds were synthesized as in the literature, the other bicyclic compounds were synthesized by new synthetic methods. The antibiotic and toxic properties of the synthesized bicyclic compounds were investigated, and some of their biological activities were tested in prokaryotic and eukaryotic systems. (rac)-Dimethyl 3,8-dioxatricyclo[3.2.1.0]oct-6-ene-6,7-dicarboxylate, one of the synthesized molecules that showed antibiotic activity, was tested in two different living systems (prokaryotic and eukaryotic) in terms of biological and toxic effects at cellular level using a peripheral lymphocyte culture assay. Mitotic index for this compound was calculated in lymphocyte cultures. [ABSTRACT FROM AUTHOR]

The cyclohexane-1,2,3,4,5-pentol,CHO is a natural product extracted from Adiscanthus fusciflorus ( Rutaceae). It crystallizes in the non-centrosymmetric space group P2 with one molecule in the asymmetric unit and it has been postulated to have at least ten strong O-H...O intermolecular interactions, two per each OH group of one molecule, producing a three-dimensional network. The crystal packing is defined by O-H...O hydrogen bonds. Due to the crucial role of the hydrogen bonds in defining the crystal structure, theoretical investigations in the gas phase have been carried out in order to explore the hydrogenbonding mechanism through a quantitative Kohn-Sham molecular orbital and corresponding energy decomposition analyses. The existence of a covalent component in hydrogen bonds has been proved which originates from donor-acceptor orbital interactions in the σ-electron system. Our analyses show that the stability of the crystal structure is enhanced by the formation of two hydrogen bonds with two vicinal molecules for each OH group in CHO molecule with respect to the formation of one or two hydrogen bonds with only one vicinal molecule, thus confirming the proposed existence of ten strong O-H...O intermolecular interactions for each molecule in the asymmetric unit. The presence of a cooperativity effect is observed which originates from a charge separation induced by the two vicinal molecules hydrogenbonded to an OH group in CHO molecule. [ABSTRACT FROM AUTHOR]

Synthetic sequences starting from commercially available myo -inositol necessarily involve protection–deprotection strategies of its six hydroxyl groups. Several strategies have been developed/attempted over the last several decades leading to the synthesis of naturally occurring phosphoinositols, their analogs, and cyclitol derivatives. Of late, myo -inositol 1 , 3 -acetals, which can be obtained by the reductive cleavage of myo -inositol orthoesters have emerged as early intermediates for the synthesis of phosphorylated and other inositol derivatives. This mini-review is an attempt to illustrate the economy and convenience of using myo -inositol 1 , 3 -acetals as early intermediates during syntheses from myo -inositol. [ABSTRACT FROM AUTHOR]

Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis , cis -1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis , cis -1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. [ABSTRACT FROM AUTHOR]

Abstract: Decahydronaphthalene-1,2,3,4,5,6,7-heptol, a new polycyclitol, was synthesized starting from p-benzoquinone. An endo selective Diels–Alder cycloaddition between p-benzoquinone and 1-acetoxybutadiene followed by stereoselective reduction with NaBH4/CeCl3·7H2O led to the formation of an allylic cis-diol. The formed diol was converted into its acetate with Ac2O/pyridine, in a transformation that required inert atmosphere conditions to suppress a competing aromatization. Controlled oxidation by OsO4 of two olefinic bonds followed by acetylation yielded the heptaacetate whose structure was established unequivocally via application of X-ray crystallographic methods. Removal of the acetate groups by NH3 provided the target heptol. In addition, the carbonic anhydrase inhibitory potency of the title compound was investigated and it was shown to be a potent inhibitor compared to the standard CA inhibitors. [Copyright &y& Elsevier]

Abstract: Transformation of cyclohexa-1,3- and 1,4-dienes to carbasugars is described. Photooxygenation of dienes gave bicyclic endoperoxides, which were reduced with thiourea to the corresponding 1,4-diols with cis-configuration. Lactonization of the remaining double bond by oxidative addition of acetic acid to the double bond in the presence of Mn(OAc)3 followed by lactone ring-opening reaction gave the target branched carbasugars. [Copyright &y& Elsevier]

Abstract: Cyclitols were prepared from corresponding allylic hydroperoxides, synthesized by photooxygenation of the appropriate cyclic alkenes. These hydroperoxides were then separately treated with a catalytic amount of OsO4. Synthesized dl-cyclopentane-1,2,3-triol 9 (A), dl-cyclohexane-1,2,3-triol 12 (B), and dl-cycloheptane-1,2,3-triol 15 (C) were used in the investigation of plant stress. Antioxidants, lipid peroxidation, and water status of chickpea species exposed to synthetic cyclitols under water deficit were examined. Cyclitol derivatives significantly decreased leaf water potential, lipid peroxidation and H2O2 levels of wild and cultivated species under water deficit. Cyclitol treatments affected antioxidant enzyme activities differently in both species under water deficit. The highest SOD activity was found in A10-treated Cicer arietinum (cultivar) and C10-treated Cicer reticulatum (wild type) under water deficit. CAT activity increased in C. arietinum exposed to A cyclitols, while it increased slightly and then decreased in cyclitol-treated C. reticulatum under stress conditions. AP and GR activities were significantly increased in C. arietinum under water deficit. AP activity increased in C derivatives-treated C. arietinum, while it remained unchanged in C. reticulatum on day 1 of water deficit. GR activity was increased in A derivaties-treated C. arietinum and C derivatives-treated C. reticulatum on day 1 of water deficit and decreased with severity of stress (except for B10-treated C. arietinum). The level of AsA in C treatments and GSH in A treatments increased in C. arietinum on day 1 of water deficit, while in C. reticulatum, AsA and GSH levels decreased under stress conditions. We conclude that exogenous synthetic cyclitol derivatives are biologically active and noncytotoxic, resulting in higher antioxidant activities and lower water potential, thus increasing the water deficit tolerance of chickpea under water deficit, especially of cultivated chickpea. We also propose that synthetic cyclitol derivatives can reduce reactive oxygen species and membrane damage and are beneficial for stress adaptation. [Copyright &y& Elsevier]

Rhynchosia minima, commonly known as jumby bean, is used as a remedy for respiratory ailments in various parts of the world. It is also used by South African traditional healers to treat heart or chest pain. This study aimed to investigate the bioactive constituents of the leaf extracts of R. minima against selected fungal isolates that have been identified as risk factors in respiratory illness. Rhynchosia minima leaves were extracted sequentially using hexane, dichloromethane, ethyl acetate and methanol in increasing order of polarity. The extracts were subjected to repeated chromatographic techniques, for phytochemical isolation. The extracts and isolated compounds were screened against Candida albicans and Cryptococcus neoformans by determining the minimum concentration that inhibited fungal growth. Six flavonoids, one norisoprenoid and one cyclitol were isolated and characterized by 1D and 2D NMR and HR-ESI-MS. The extracts obtained in the study had moderate to weak antifungal activities, with MICs ranging from 312.5 to 1250.0 μg/mL against both fungi. Four isolated compounds were also screened, with two of them exhibiting activity against C. albicans (MIC=6.25 μg/mL) that was comparable to amphotericin B, the positive control. These two compounds also had better antifungal potential against C. neoformans with an MIC=6.25 μg/mL, compared to the MIC of 12.5 μg/mL of amphotericin B. Seven of the eight isolated compounds were obtained from the extracts of Rhynchosia minima for the first time. Two of the isolated compounds demonstrated activity comparable or superior to amphotericin B activity. The notable potency displayed by these compounds warrants further investigation on their development as antifungal agents., (© 2022 The Authors. Chemistry & Biodiversity published by Wiley-VHCA AG, Zurich, Switzerland.)