Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon

Matsuda, Hisashi; Asao, Yasunobu; Nakamura, Seikou; Hamao, Makoto; Sugimoto, Sachiko; Hongo, Masako; Pongpiriyadacha, Yutana; Yoshikawa, Masayuki

doi:10.1248/cpb.57.487

Cited by 46 publications

(32 citation statements)

References 34 publications

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“…28,48) Resveratrol derivatives in the leaves of V. indica display planar structural diversity due to the following: (1) degree of oligomerization ranging to tetramer (monomers: 6-9; dimers: 2, 3, 10-17; trimer: 18; tetramers: 1-3 and 19-30), (2) variation in the skeleton comprising dihydrobenzofuran(s) (1-5, 10-15, and 18-30), tetrahydrofuran (1 and 19), phenanthrene (2, 3, and 10) 18, 21, 22, and 27-30), 2,3-dihydrobenzofuran-5,6-dione (25), 4-methylenecyclohexa-2,5-dienone (26), 3,3a-dihydrobenzofuran-6(2H)-one (30), and (3) C-or O-glucosylation (2, 4, 7-9, 11, 13, 28, and 29). This is the first time that occurrence of the groups flavonolrhamnoside (32) and diterpenoids (34,35) has been reported in the family Dipterocarpaceae. Compounds (6, 8, 9, 11-13, 15-19, 21-23, and 30) have been isolated for the first time from V. indica.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 77%

“…30) 2-b-glucopyranosyloxyphenanthrene-4,6-diol (9), 31) paucifloroside A (11), 23) cis-(Ϫ)-eviniferin (12), 32) upunoside D (13), 33) balanocarpol (14), 34) melanoxylin A (15), 35) malibatol (16), 36) (Ϫ)-ampelopsin F (17), 37) pauciflorol B (18), 23) vaticanol C (20), 38) hemsleyanols C (21) and D (22), 39) pauciflorol C (23), 23) vateriaphenol B (24), 4) nepalensinol G (25), 40) stenophyllol A (26), 41) vaticanol B (27), 38) vaticasides B (28) and C (29), 42) and upunaphenol F (30). 43) The other known compounds were identified to be flavonols [kaempferol 3-O-rhamnoside (31), 44) kaempferol 3-O-rhamnopyranosyl-(1→2)-rhamnopyranoside (32), and quercitrin (33) 45) ], diterpenes [columbin (34) 46) and palmarin (35) 47) ], bergenin (36), 11) and syringin (37).…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

“…The various structures are dependent upon the skeletal variation and the stereoisomers. Comprehensive investigation of the chemical constituents in the leaves of V. indica resulted in the isolation and characterization of a new resveratrol tetramer [vateriaphenol F (1)] and two new O-glucosides of resveratrol oligomers [vateriosides A (2) and B (4)], along with a new natural compound (3), and 33 known compounds [resveratrol derivatives , flavonols (31)(32)(33), diterpenes (34,35), an isocoumarin (36), and a phenylpropanoid (37)]. The structures of the new compounds (1, 2, 4) were elucidated by 2D NMR techniques such as 1 H-1 H correlation spectroscopy (COSY), 13 C-1 H COSY, and heteronuclear multiple bond connectivity (HMBC).…”

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Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleDipterocarpaceaeous plants have been known to have an abundance of stilbene oligomers that have a blocking unit of resveratrol. The woody plant Vateria indica LINN. (Dipterocarpaceae) is distributed in India and Sri Lanka, and the resin has been used as a traditional medicine for sore throat, chronic bronchitis, rheumatism, and diarrhea.1) The stem of the genus Vateria is known to produce biologically active compounds such as oligostilbenoids and monoterpenes. [2][3][4][5][6] Our previous study demonstrated that the leaves also contain stilbene derivatives in high quantity. 6) Recently, the bioactivities of stilbenoids isolated from Dipterocarpaceaeous plants have been reported to have antimicrobial activites, 7,8) antitumor activities, [9][10][11] and regulation of endoplasmic reticulum stress. H COSY, and heteronuclear multiple bond connectivity (HMBC). Stereostructures were proposed by analysis of nuclear Overhauser effect spectroscopy (NOESY), differential rotating frame Overhauser enhancement (ROE), and ROESY spectra, as well as high-resolution (HR) FAB-MS and electrospray ionization (ESI)-MS analysis and circular dichroism (CD) spectroscopic properties. Vateriaphenol F (1) has a unique C 2 -symmetric structure. Results and DiscussionVateriaphenol F (1) and vaterioside A (2) were purified from an acetone extract of V. indica by open column chromatography on DMS, octadecyl silica (ODS), Silica gel, and Sephadex LH-20, as well as HPLC. Vaterioside B (4) was purified from MeOH extract by repeated chromatography.Vateriaphenol F (1) ([a] D 25 Ϫ136°), obtained as a pale-yellow solid, showed positive reaction to Gibbs reagent. The structure is composed of four resveratrol units (A-D; resveratrol A unit: i.e., between rings A 1 and A 2 via carbons C-7a and C-8a). A detailed elucidation was carried out as follows. The molecular formula was assigned to C 56 H 44 O 13 by HR-ESI-MS that showed a pseudomolecular ion [MϩNa] ϩ at m/z 947.2670, indicating 35 degrees of unsaturation. In the 1 H-and 13 C-NMR spectra at rt, some signals due to ring A 2 were broadened in various solvents. In the 1 H-NMR spectrum in acetone-d 6 at Ϫ30°C, the signals due to Pharmacognosy, Gifu Pharmaceutical University; 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan: b Institute of Microbial Chemistry, Tokyo; 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan: and c Survey of Medicinal Plant Unit, Central Council for Research in Ayurveda and Siddha; Tirunelveli-627002, Tamil Nadu, India. Received June 23, 2010; accepted July 15, 2010; published online July 16, 2010 Comprehensive re-investigation of the chemical constituents in the leaves of Vateria indica (Dipterocarpaceae) resulted in the isolation of a novel resveratrol dimeric dimer having a C 2 -symmetric structure, vateriaphenol F (1), and two new O-glucosides of resveratrol oligomers, vateriosides A (2) (resveratrol dimer) and B (4) (resveratrol tetramer), along with a new natural compound (3) and 33 known compounds including 26 resveratrol derivatives. The absolu...

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Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 77%

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

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Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…42) The supernatant fluid of rat lens homogenate was used as a crude enzyme. The enzyme suspension was diluted to produce ca.…”

Section: Effects On Rat Lens Aldose Reductasementioning

confidence: 99%

Medicinal Flowers. XXXX.1) Structures of Dihydroisocoumarin Glycosides and Inhibitory Effects on Aldose Reducatase from the Flowers of Hydrangea macrophylla var. thunbergii

Liu

Nakamura

Zhen

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Key words florahydroside; Hydrangea macrophylla var. thunbergii; medicinal flower; dihydroisocoumarin glycoside; aldose reductase; acylated quinic acid analogThe Saxifragaceae plant, Hydrangea (H.) macrophylla Seringe var. thunbergii Makino, is native to Japan. The processed leaves of this plant (Hydrangea Dulcis Folium) are currently used as a natural medicine for an oral refrigerant and as a sweetener for diabetic patients. In addition, these preparations are listed in the Japanese Pharmacopoeia. Previously, we reported the isolation and structure determination of many chemical constituents with anti-diabetic, anti-allergic, and anti-bacterial activities from the processed leaves and the dried leaves of this plant.2-6) However, a full chemical analysis of the flowers from this plant has not yet been performed. In the course of our chemical and pharmacological studies on Hydrangea plants [2][3][4][5][6][7][8] and medicinal flowers, [9][10][11][12][13][14] we recently reported the isolation and structure elucidation of secoiridoid glycosides named hydrangeamines A and B with a pyridine ring from the flowers of H. macrophylla var. thunbergii cultivated in Nagano prefecture, Japan.15) As a continuing study, six dihydroisocoumarin glycosides, florahydrosides I (1) and II (2), thunberginol (5), and thunberginol D 3′-O-β-dglucopyranoside (6), were isolated from the flowers of H. macrophylla var. thunbergii together with 20 known compounds including five acylated quinic acid analogs. Furthermore, the inhibitory effects of the isolated compounds and its related compounds on aldose reductase were investigated. This paper deals with the structure elucidation of the new dihydroisocoumarin glycosides (1-6) and the inhibitory effects of the constituents and their related compounds, acylated quinic acid analogs, on aldose reductase.A methanol (MeOH) extract (32.2% from the flowers of H. macrophylla var. thunbergii cultivated in Nagano province) was partitioned between EtOAc-H 2 O (1 : 1) to furnish an EtOAc-soluble fraction (8.8%) and an aqueous layer. The aqueous layer was further extracted with 1-butanol

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“…Local communities in North Sumatra have been utilizing the bark of raru to treat diarrheal diseases and diabetes (Soerianegara & Lemmens, 1993). The bark of raru contains ampelopsin F., isoampelopsin F., ε-viniferin, vaticanol A, E, G, lyoniresinol (Matsuda et al, 2009), and flavonoids as antidiabetic, tannins and saponins compounds (Pasaribu, 2010) which are useful as an antimicrobial (bacteria and viruses). fungi and test bacteria were maintained in a petri dish with NA medium.…”

Section: Introductionmentioning

confidence: 99%

Molecular Identification of Endophytic Fungi from Bark of Raru (Cotylelobium melanoxylon) that Produce the Antibacterial Compounds

et al. 2017

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The Dipterocarpaceae plant, raru (Cotylelobium melanoxylon) is widespread in Southeast Asia. The bark of raru has been used by local communities in North Sumatera as antidiarrheal drugs due to its antibacterial compounds. The antibacterial activity of the raru's bark is induced by endophytic fungi that live in the region of the bark. This study aimed to identify the endophytic fungi-producer of antibacterial compounds in the bark of raru (C. melanoxylon) by means of molecular analysis. In general, endophytic fungi have the ability to inhibit the growth of pathogenic bacteria. Thirty-eight isolates of endophytic fungi were isolated from the bark of raru. Selection of isolates for antibacterial activity against Escherichia coli ATCC 35218 and Staphylococcus aureus ATCC 25923 used the dual culture assay. Selection using the dual culture assay yielded 6 endophytic fungal isolates that have the ability to inhibit the growth of test bacteria. EF10A sample was the most powerful isolate inhibiting the growth of both bacteria test. Those six bacteria molecularly identified used a sequence generated from ITS rDNA region. Based on rDNA ITS region sequences, isolate, the producers of the antibacterial compound were identified as Talaromyces cellulolyticus, Penicillium purpurogenum, Aspergillus sp., Trichoderma harzianum, and Aspergillus orizae. The results of this study can be used by researchers to explore more potential endophytic fungi in raru plants (C. melanoxylon) as a source of medicine. The data obtained need to be supported by further research to isolate the bioactive compounds that can inhibit the growth of microbial pathogens.

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Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon

Cited by 46 publications

References 34 publications

Chemical Constituents in the Leaves of Vateria indica

Chemical Constituents in the Leaves of Vateria indica

Medicinal Flowers. XXXX.<sup>1)</sup> Structures of Dihydroisocoumarin Glycosides and Inhibitory Effects on Aldose Reducatase from the Flowers of <i>Hydrangea macrophylla</i> var. <i>thunbergii</i>

Molecular Identification of Endophytic Fungi from Bark of Raru (Cotylelobium melanoxylon) that Produce the Antibacterial Compounds

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