Thunwadee Limtharakul

• Doctor of Philosophy
• Chiang Mai University

Two new cassane diterpenoids, 14β-hydroxycassa-11(12),13(15)-dien-12,16-olide ( 1 ) and 6′-acetoxypterolobirin B ( 3 ), together with a known analogue, identified as 12α,14β-dihydroxycassa-13(15)-en-12,16-olide ( 2 ), were isolated from the fruits of Pterolobium macropterum . Compound 1 is a cassane diterpenoid with a Δ ¹¹⁽¹²⁾ double bond conjugate...

Three new isoflavonoids, millexatins N-P (1-3), along with seven known compounds (6-10), were isolated from the acetone extract of the young twigs of Millettia extensa. The structures were characterized by NMR spectroscopic and mass spectrometric analyses. Millexatin N (1) is an unusual geminal diisoprenylated isoflavone with a modified ring A. Mil...

A highly diastereoselective method for the synthesis of syn--amino alcohols and enantioenriched anti--amino alcohols has been developed involving -hydroxyl aldehydes and chiral -phenylaminoxyaldehydes or -benzoyloxyaldehydes, respectively in Petasis borono-Mannich allylation...

The phytochemical investigation of the fruit and leaf extracts of Maclura cochinchinensis (Lour.) Corner (Moraceae) resulted in the isolation and identification of four undescribed isoflavones (macluracochinones A-D) and one undescribed flavone (macluracochinone E), together with 24 known compounds. The structures of the undescribed compounds were...

Daldiniaeschsone A (1), a rare tricyclic polyketide having a chromone unit fused to a δ-lactone and its symmetrical 6,6′-biphenyl dimer, daldiniaeschsone B (2), together with three known compounds (3−5), were isolated from a plant-derived endophytic fungus, Daldinia eschscholtzii SDBR-CMUNKC745. Their structures were elucidated by extensive 1D and...

A new clerodane diterpene, 2β-methoxyhardwickiic acid (1), and four known compounds (2–5) were isolated from the twigs of Monoon membranifolium. The structure of the new compound was determined by extensive spectroscopic methods and ESITOFMS data. The absolute configuration of 1 was established by a comparison of its ECD spectrum and specific rotat...

The phytochemical investigation of the twig and root extracts of Erythrina subumbrans (Hassk.) Merr. (Fabaceae) resulted in the isolation and identification of a new pterocarpan, erythrinocarpan (1), along with 27 known compounds (2–28). All isolated compounds were evaluated for their antidiabetic, antimicrobial, and anti-inflammatory properties. C...

The phytochemical investigation of the methanol extracts of the leaves and twigs of Mitrephora tomentosa Hook. f. & Thomson resulted in the isolation and identification of undescribed polyacetylenic ester-neolignan derivatives, along with six known compounds. These six undescribed natural products were named as mitrephentosins A-F. The structures o...

Two rare flavones having a hybrid benzyl benzoate ester-flavone structural framework, desmoschinensisflavones A and B (1 and 2), together with 12 known compounds (3–14) were isolated from the fruit, leaf, and twig extracts of Desmos chinensis (red flower). The new structures were characterized by UV, IR, NMR, and HRESITOFMS data. Desmoschinensisfla...

The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereoch...

The phytochemical investigation of the flower and twig extracts of Garcinia mckeaniana yielded a new xanthone, mckeanianone F (1) and a new biphenyl, mckeaniabiphenyl (2) together with 15 known compounds. The isolated compounds were characterized using spectroscopic techniques and mass spectrometry. Some of the isolated compounds from the twigs exh...

A new farnesylindole, (R)-3-(8'-hydroxyfarnesyl)-indole (1), as a scalemic mixture (33% ee) along with nine known compounds (2-10), including one farnesylindole, three flavanones, three flavone derivatives and two chalcone derivatives were isolated from the methanolic crude extract of the flowers from Anomianthus dulcis. All compounds were purified...

The phytochemical investigation of the leaf extract of Uvaria cherrevensis (Annonaceae) yielded three new cyclohexene (9Z)-octadec-9-enyl ethers, cherrevenols M-O (1–3), and a known fatty ester derivative (4). The structures of the isolated compounds were elucidated by spectroscopic and computer-aided molecular modelling methods. Ozone Induced Diss...

The chemical study of leaf extracts from Uvaria cherrevensis resulted in the identification of 11 new polyoxygenated cyclohexenes, cherrevenols A-K (1-11), and a new seco-cyclohexene derivative, cherrevenol L (12). Nine known compounds (13-21) were also isolated. Three of the isolated compounds are chlorinated polyoxygenated cyclohexenes. The struc...

A new 2-arylbenzofuran, spathobenzofuran (1), together with ten known compounds including a 2-arylbenzofuran, three pterocarpans and six isoflavones were isolated from the acetone crude extract of the stems of Spatholobus parviflorus. All compounds were characterised by spectroscopic methods. Compound 4 was active (MIC 8 µg/mL) against Gram-negativ...

A new macrocyclic lactone, 12-hydroxycorniculatolide A (1), along with three known compounds, corniculatolide A (2), 12-hydroxy-11-O-methylcorniculatolide A (3) and 6,7-dimethoxycoumarin (4) were isolated from the methanolic extract of the twigs of Lumnitzera littorea. All compounds were characterized using spectroscopic methods. All compounds were...

The phytochemical investigation of the fruit extracts of Uvaria cherrevensis led to the isolation and characterization of four new C-benzyl flavonoids; cherrevenones A-D (1-4) together with 11 known compounds. The isolated compounds were characterized using spectroscopic techniques. Compounds 1, 3, 5 and 11 showed moderate inhibitory activities aga...

Two new dihydrooxoprotoberberine alkaloids; miliusathorines A (1) and B (2), a new natural flavone, miliusathorone (3), together with twenty-two known compounds (4–25) were isolated from the combined stem and root extract and the leaf extract of Miliusa thorelii. The structures of all isolated compounds were elucidated by spectroscopic methods and...

The phytochemical investigation of an alkaloidal extract of Holarrhena pubescens roots led to the isolation and identification of a new pregnene-type alkaloid, mokluangin D (1), together with nine known steroidal alkaloids (2–10). The structure of the new metabolite was determined on the basis of spectroscopic analyses including 1D- and 2D-NMR spec...

The first phytochemical investigation of the twig extracts of Maclura fruticosa led to the isolation and identification of a new xanthone, maclurafruticosone (1), together with 14 known compounds (2-15). All compounds were elucidated using spectroscopic methods as well as through comparisons made with data reported in the literature. Some isolated...

Three new 2-phenylnaphthalene derivatives, cherrevenaphthalenes A-C (1-3), and a new polyoxygenated cyclohexene derivative, (-)-uvaribonol F (4) together with six known compounds, 5-10, were isolated from the stem and root extracts of Uvaria cherrevensis (Annonaceae). The structures of all isolated compounds were elucidated by spectroscopic analysi...

Two new benzophenones (1 and 2) and four new xanthones (4–6 and 17) together with 24 known compounds (3, 7–16 and 18–30) were isolated from the roots and twigs of Cratoxylum sumatranum ssp. neriifolium. Their structures were elucidated by spectroscopic methods. Compounds 5 and 26 showed antibacterial activity against Micrococcus luteus, Bacillus ce...

The first phytochemical investigation of the leaf and branch extracts of Garcinia mckeaniana has led to the isolation and characterization of five new polyoxygenated and prenylated xanthones, mckeanianones A-E (1–5), and one new biflavone, mckeaniabiflavone (6), together with thirteen known compounds (7–19). The diprenylated pyrano-xanthones (1–3)...

Five new oxoprotoberberine alkaloids, miliusacunines A-E (1-5), along with nine known compounds, 6-14, were isolated from an acetone extract of the leaves and twigs of Miliusa cuneata. Their structures were elucidated by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicities against the KB and Vero cell lines and for...

An alkaloidal extract of the bark of Holarrhena pubescens showed several inhibition zones of acetylcholinesterase (AChE) inhibitor, using a bioautographic assay. Activity-guided fractionation afforded three new steroidal alkaloids, mokluangins A-C (1-3), together with three known compounds, antidysentericine (4), holaphyllamine (5), methylholaphyll...

The first phytochemical investigation of Casearia graveolens twigs led to the isolation and identification of a new clerodane diterpene, caseariagraveolin (1), together with six known compounds (2-7). Their structures were elucidated by intensive analysis of their spectroscopic data. Compound 1 showed strong cytotoxicity against oral cavity and bre...

Phytochemical investigation of Garcinia propinqua roots led to the isolation and identification of a new xanthone, doitunggarcinone D (1), together with 15 known compounds (2-16). Their structures were elucidated by intensive analysis of spectroscopic data. Compounds 3, 6, 7, 14, 15 and 16 exhibited strong antibacterial activity against Bacillus su...

The phytochemical investigations of Cratoxylum spp. including C. cochinchinense, C. formosum ssp. prunifrolum and C. sumatranum led to the isolation and identification of thirty eight compounds. Twelve, fourteen, and twelve compounds were isolated from C. cochinchinense stem barks, C. formosum ssp. prunifrolum roots and C. sumatranum twigs, respect...

One new p-quinonoid aporphine alkaloid, obtusipetadione (1), and eleven known compounds (2-12) were isolated from the acetone extract of the twigs of Dasymaschalon obtusipetalum. Their structures were elucidated by spectroscopic methods. The cytotoxic and antimalarial activities of the isolated compounds were evaluated. Compound 1 showed significan...

Five new xanthones, garciniacowones A-E (1-5), together with 14 known xanthones, 6-19, were isolated from the young fruits and fresh flowers of Garcinia cowa. The structures of 1-5 were elucidated by analysis of their 1D and 2D NMR spectra and mass spectrometric data. The compounds 1-19 were tested in vitro for their antimicrobial activity and for...

The first phytochemical investigation of Glycosmis puberula twigs led to the isolation and identification of a new quinolone alkaloid, glycosmispuberulone (1), along with ten known compounds (2-11). The structures were elucidated by spectroscopic analyses and comparison with previously reported data. Their antibacterial activities against Gram-posi...

Two new dammaranes, dysomollisol (1) and dysomollisone (2), along with seven known compounds (3-9) were isolated and identified from the fruits of Dysoxylum mollissimum. The structures of these compounds were determined on the basis of spectroscopic analyses, including 1D and 2D NMR, UV, IR and mass spectrometry. The antibacterial activity and cyto...

The phytochemistry of Kopsia arborea Blume has received considerable attention, which has resulted in the isolation of a number of new unusual indole alkaloids with intriguing structures. In this study, a new eburnane-type alkaloid, phutdonginin (1), together with eight known alkaloids: 19-OH-(-)- eburnamonine (2), melodinine E (3), kopsinine (4),...

Phytochemical investigation of the roots of Cratoxylum formosum spp. pruniflolnnm led to the isolation and identification of a new xanthone, namely cratopruniforone (1), together with 13 known compounds (2-14). Some of these more abundant compounds were evaluated for their antibacterial activities.

Two novel carbazole alkaloids, guillauminines A and B (1 and 2), and sixteen known compounds were isolated and identified from the acetone extract of Clausena guillauminii roots. Their structures were elucidated by spectroscopic methods. The cytotoxic, antimalarial and antimycobacterial activities of the isolated compounds were evaluated.

A phytochemical investigation of the acetone extract from the immature fruits of Garcinia cowa led to the isolation of two novel tetraoxygenated xanthones, garcicowanones A (1) and B (2), together with eight known tetraoxygeanted xanthones. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their a...

Ceriops tagal is a mangrove plant in RHIZOPHORACEAE family which plays an importance role in coastal ecological balance and exhibit versatile pharmacological area. In this study, leaves and barks were collected from Rajamangala beach, Rajamangala University of Technology Srivijaya, Trang province and were dried to successively extract with hexane,...

The genus Garcinia is a well known rich source of bioactive xanthones and benzophenones. Some species of this genus also produce flavonoids and biphenyls as minor constituents. In this study, two new biphenyls, doitungbiphenyls A (1) and B (2), along with two biphenyls, schomburgbiphenyl (3) and nigrolineabiphenyl B (4); and four xanthones, 1,3,6-t...

Murraya koenigii is a tropical to subtropical small tree belonging to the Rutaceae family. The plant is native to India and is distributed in most of Southern Asia. The leaves of this plant are highly aromatic, and young leaves are used as a vegetable herb in the Southern part of Thailand. Various parts of the plant have been reported as a folk med...

Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.

A phytochemical investigation of the twigs of Glycosmis cochinchinensis led to the isolation of two new alkaloids, glycosmisacridone (1) and glycosmisindole (2), together with eight known compounds (3-10). Their structures were elucidated by intensive analysis of their spectroscopic data. Compound 9 exhibited moderate antibacterial activity against...

AgNO3-catalyzed cyclization of propargyl amines of type (I) and (VI) followed by 1,3-allylic rearrangement allows a new access to 2-benzofuranmethamines.

Garcinia cowa is an abundant source of bioactive phytochemicals. Phytochemical investigations of the plant parts indicated that the fruit, twig and stem are the best source of secondary metabolites, providing flavonoids, phloroglucinols and xanthones respectively. Seventy-eight of these compounds have been identified from the plant and several have...

Chemical investigation of an alkaloidal extract of Alstonia macrophylla bark led to the isolation and identification of two new nitrogenous derivatives, alstoniaphyllines A (1) and B (2), a new indole alkaloid, alstoniaphylline C (4), and eight known alkaloids (3, 5-11). Alstonisine (9) exhibited antiplasmodial activity against Plasmodium falciparu...

Five carbazole alkaloids, clausenawallines G-K (1-5), along with 12 known alkaloids (6-17) were isolated from the twigs of Clausena wallichii. Their structures were established using spectroscopic methods and the antibacterial activity of compounds 1-5 was evaluated.

Propargyl amines 4, where R3 is aryl, undergo 5-exo-dig cyclization reactions under relatively mild conditions (AgNO3, DMF, 60 deg C, 1 h) to give 3-amino-2,3-dihydro-2-arylmethylidenebenzofurans 5 (R3 = aryl). In contrast, substrates where R3 is alkyl, undergo competing 6-endo-dig and 5-exo-dig cyclization processes. The hydroxymethyl substrate 4...

The first phytochemical investigation of Caesalpinia furfuracea twigs led to the isolation and identification of four new compounds including two isopimarane diterpenes, caesalfurfuric acids A (1) and B (2), and two flavans, (2R)-caesalflavans A (5) and B (6), together with four known compounds, 4-epi-isopimaric acid (3), methyl (E)-3-(3,4-dihydrox...

This chapter describes the isolation, structure elucidation, glycosidase inhibitory activities, and the synthesis of the four naturally occurring casuarines. These are casuarine, casuarine-6-O-α-d-glucoside, 6-epi-casuarine (uniflorine A), and 3-epi-casuarine.

Two new compounds, garciniacowol (1) and garciniacowone (2) along with 15 knowncompounds were isolated from the stem barks of Garcinia cowa. Their structures weredetermined by intensive spectroscopic methods. The structure of 1 was a symmetrical dimericdihydrobenzopyran derivative, whereas the framework of 2 was a triprenyl caged-xanthoneprecursor....

Five new phenolic compounds, designated candenatenins G–K (1–5), along with four known compounds, were isolated from the heartwood of Dalbergia candenatensis. The structures of these compounds were elucidated by HR-EI-MS, 1H and 13C NMR, COSY, HMQC, HMBC, and NOESY spectra. Compound 5 exhibited potent activity against DPPH radical scavenging with I...

A new phenylpropanoid derivative, harmandianone (1), along with four known compounds: verimol B (2), (E)-3-(2-hydroxy-4-methoxy-phenyl)propanoate (3), (E)-methyl p-coumarate (4), and (E)-5- methoxy-2-(prop-1-enyl)phenol (5) was isolated from the acetone extract of Clausena harmandiana fruits. All structures were characterized by spectroscopic metho...

The purification of the acetone extract from the inflorescences of Garcinia cowa led to the isolation of a new benzophenone derivative, cowanone (1), together with seven known xanthones, α-mangostin (2), β-mangostin (3), cowanin (4), fuscaxanthone A (5), 9-hydroxycalabaxanthone (6), garcinianone A (7) and cowanol (8). The structures of the isolated...

The first phytochemical investigation of Garcinia propinqua has led to the isolation and identification of three new compounds, including two rearranged benzophenones, doitunggarcinones A (1) and B (2), and a xanthone, doitunggarcinone C (3), together with seven known compounds (4-10). The structures of 1-3 were elucidated on the basis of spectrosc...

This review reports on recent developments on the structure, biological activities and synthesis of hyacinthacine alkaloids and related compounds.

Six coumarins (1-6) and twelve alkaloids (7-18) were isolated from the roots of Clausena excavata. Their structures were elucidated on the basis of spectroscopic methods. This is the first report on the isolation of compounds 1, 7 and 17 from C. excavata. Compound 1 is also the first example of an unsymmetrical dimer coumarin isolated from Clausena...

A new amide, zanthorhetsamide (1), along with nine known compounds (2-10) was isolated from the roots and stem barks of Zanthoxylum rhetsa. The structure was characterized by spectroscopic methods. In addition, the antibacterial activity of the isolates was evaluated. Dihydrochelerythrine (4) exhibited strong activity against methicillin-resistant...

Two new furanocoumarins, lucidafuranocoumarins B (1) and C (2), were isolated from the twigs of Feroniella lucida, together with five known compounds (3–7). The structures of these compounds were identified on the basis of extensive spectroscopic methods. The absolute configurations of lucidafuranocoumarin C at C-2″ and C-5″ were established as R-...

A new hydroperoxyquinolone alkaloid, glycopentaphyllone (1), along with nine compounds (2–10), was isolated from the fruits of Glycosmis pentaphylla. Their structures were elucidated on the basis of spectroscopic methods. The absolute configuration of glycopentaphyllone at C-2′ was established as S-configuration by applying Mosher's method. In addi...

Three new carbazole alkaloids, harmandianamines A-C (1-3), together with fifteen known compounds (4-18) were isolated from the twigs of Clausena harmandiana. The structures were elucidated by spectroscopic methods, including UV, IR, NMR, and MS. The antibacterial activity against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphyl...

Four new carbazole alkaloids, clausenawallines C-F (1-4), along with 18 known compounds (5-22) were isolated from the roots of Clausena wallichii. Compounds 3, 9, and 22 exhibited significant antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 (MRSA SK1) and Staph. aureus TISTR 1466 with MIC values in the range 4-16 μg/mL...

Figure optionsView in workspace Highlights ► Phytochemical investigation of the roots of Micromelum graduliferlum. ► The isolation of eight coumarins (1–8) and two carbazole alkaloids (9 and 10). ► The first report of carbazole alkaloids from the genus Micromelum. ► Carbazole alkaloids 9 and 10 might be a useful chemotaxonomic marker of the specie...

Two new dimeric carbazole alkaloids, clausenawallines A and B, were isolated from the roots of Clausena wallichii. Their structures were elucidated by spectroscopic methods. Clausenawalline A was evaluated for its biological activities [anti-malaria (IC50 2.46μg/mL), anti-TB (MIC 12.50μg/mL)] and cytotoxicity against three human cancer cell lines [...

Two new carbazole alkaloids, mafaicheenamines D (1) and E (2), together with twelve known compounds (3–14) were isolated from the roots of Clausena lansium. Spectroscopic methods, including NMR, UV, IR, and MS spectral data were used for structural characterization. Some of isolates were evaluated for their cytotoxicity against three human cancer c...

The new depsidone cowadepsidone (I) is isolated together with six known xanthones from the twigs of Garcinia cowa.

A new depsidone, cowadepsidone (7), along with six known xanthones (1-6) were isolated from the twigs of Garcinia cowa. Their structures were determined on the basis of spectroscopic methods. The cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines of compounds 2-7 were also reported.

The synthesis of the natural product 3-epi-casuarine and two tricyclic ether bridged analogues, plus 7-deoxy-3,6-diepi-casuarine, 7-epi-australine, 1-epi-castanospermine and 1,6-diepi-castanospermine is described. The glycosidase inhibitory activities of these compounds, along with that of uniflorine A and other polyhydroxylated pyrrolizidines and...

A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

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The total synthesis of (+)-uniflorine A has allowed for the structural reassignment and the configurational assignment of the alkaloid (-)-uniflorine A from a 1,2,6,7,8-pentahydroxyindolizidine structure to (-)-(1 R,2 R,3 R,6 R,7 S,7a R)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine (6- epi-casuarine).

The diastereoselective synthesis of the C-2 epimer and the C-1, C-2 di-epimers of the putative structure of the alkaloid uniflorine A has been achieved. The synthesis of the latter di-epimers employed a novel pyrrolo[1,2-c]oxazin-1-one precursor to allow for the reversal of π-facial diastereoselectivity in an osmium(VIII)-catalyzed syn-dihydroxylat...

We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, dire...

Nine xanthones, nigrolineaxanthones A-I, together with nine known xanthones, were isolated from the crude methanol extract of the stem bark of Garcinia nigrolineata; two of which have previously been reported as synthetic xanthones. The structures were elucidated by analysis of spectroscopic data, especially using 1D and 2D NMR spectroscopic data.

The polyhydroxylated alkaloids uniflorines A and B were isolated in 2000 from the leaves of the tree Eugenia uniflora L. The common name for this tree is Surinam Cherry and the water soluble extracts of its leaves have been used as an antidiabetic agent in Paraguayan traditional medicine. Uniflorines A and B showed moderate activity in inhibiting t...