Phenylpropanoid glycosides of Gnidia polycephala

Munkombwe, Namboole Moses; Galebotswe, Pelotshweu; Modibesane, Kabelo; Morebodi, Nametso

doi:10.1016/s0031-9422(03)00211-5

Cited by 27 publications

(9 citation statements)

References 4 publications

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“…The absolute configuration of compound 15 was established by comparison of experimental and calculated ECD spectra and corroborated by X-ray crystallography. Known compounds were identified as daphnane ester 1, 16 excoecariatoxin (2), 17,18 yuanhuacine (5), 19 2′-hydroxy-3′-methoxyflavone (6), 20 2′,3′- dimethoxyflavone (7), 21 6-hydroxy-2′,3′-dimethoxyflavone (8), 22 7,7′-dimethoxy-6,6′-biscoumarin (9), 23 lasiocephalin (10), 23 daphnauranol A (13), 24 and chamaejasmone D (14). 25 (Table 1) were virtually identical to those of yuanhuacine (5).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…13 Previous phytochemical studies of stems and roots of G. polycephala revealed the presence of phenolic acids and their derivatives. 14 We here report daphnane-type diterpenoid orthoesters (DDOs) as a new scaffold for hERG channel inhibitors, identified via HPLC-based activity profiling of the root extract. In addition, we performed a detailed phytochemical profiling of the extract, which led to the characterization of 2-phenylpyranones with an unprecedented tetrahydro-4H-5,8-epoxypyrano [2,3-d]oxepin-4-one skeleton (15 and 16), two new DDOs (3 and 4), two new guaiane sesquiterpenoids (11 and 12), and 10 known compounds (1, 2, 5−10, 13, and 14).…”

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confidence: 99%

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hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

Mieri¹,

Du²,

Neuburger³

et al. 2015

J. Nat. Prod.

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The hERG channel is an important antitarget in safety pharmacology. Several drugs have been withdrawn from the market or received severe usage restrictions because of hERG-related cardiotoxicity. In a screening of medicinal plants for hERG channel inhibition using a two-microelectrode voltage clamp assay with Xenopus laevis oocytes, a dichloromethane extract of the roots of Gnidia polycephala reduced the peak tail hERG current by 58.8 ± 13.4% (n = 3) at a concentration of 100 μg/mL. By means of HPLC-based activity profiling daphnane-type diterpenoid orthoesters (DDOs) 1, 4, and 5 were identified as the active compounds [55.4 ± 7.0% (n = 4), 42.5 ± 16.0% (n = 3), and 51.3 ± 9.4% (n = 4), respectively, at 100 μM]. In a detailed phytochemical profiling of the active extract, 16 compounds were isolated and characterized, including two 2-phenylpyranones (15 and 16) with an unprecedented tetrahydro-4H-5,8-epoxypyrano[2,3-d]oxepin-4-one skeleton, two new DDOs (3 and 4), two new guaiane sesquiterpenoids (11 and 12), and 10 known compounds (1, 2, 5-10, 13, and 14). Structure elucidation was achieved by extensive spectroscopic analysis (1D and 2D NMR, HRMS, and electronic circular dichroism), computational methods, and X-ray crystallography.

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Section: ■ Results and Discussionmentioning

confidence: 99%

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confidence: 99%

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

Mieri¹,

Du²,

Neuburger³

et al. 2015

J. Nat. Prod.

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“…2) were assigned based on comparison of the mass spectra (low and high resolution ESI-QIT-MS recorded on a Bruker-Hewlett Packard 1100 Esquire-LC system mass spectrometer), and NMR spectra (recorded on a Bruker AV-600 spectrometer with a 5 mm CPTCI cryoprobe) with the literature (Graziano et al, 1971;Fukuda et al, 1983Fukuda et al, , 1985Fukuda et al, , 1986Fukuda et al, , 1993Son et al, 1991;Lee et al, 1996;Martin et al, 1996;Munkombwe et al, 2003;Ahmad et al, 2011;Nagasawa et al, 2011) and standards.…”

Section: Preparation Of the Tinospora Crispa Extract And Isolation Ofmentioning

confidence: 99%

Hypotensive and cardio-chronotropic constituents of Tinospora crispa and mechanisms of action on the cardiovascular system in anesthetized rats

Praman

Mulvany

Williams

et al. 2012

Journal of Ethnopharmacology

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“…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). 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.…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

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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Phenylpropanoid glycosides of Gnidia polycephala

Cited by 27 publications

References 4 publications

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala

Hypotensive and cardio-chronotropic constituents of Tinospora crispa and mechanisms of action on the cardiovascular system in anesthetized rats

Chemical Constituents in the Leaves of Vateria indica

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