Triterpenoids from the fruit galls of Actinidia polygama

Sashida, Yutaka; Ogawa, Kazunori; Mori, Noriaki; Yamanouchi, Tsuyoshi

doi:10.1016/0031-9422(92)83634-b

Cited by 81 publications

(40 citation statements)

References 8 publications

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“…Conclusive evidence was provided by HMBC showing 3 J correlations of H-3 and H-1 with C-1 and C-3, respectively. The signal of C-4 in 13 C NMR spectrum showed a significant downfield shift confirming oxidation at both C-23 and C-24 [13] which could further be confirmed by HMBC correlations (Fig. 2).…”

Section: Resultssupporting

confidence: 72%

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Ahmad

Mehmood

Fatima

et al. 2007

Magnetic Reson in Chemistry

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Salsolins A (1) and B (2), the new triterpenes, have been isolated from the chloroform soluble fraction of Salsola baryosma along with 2alpha,3beta,23,24-tetrahydroxyurs-12-en-28-oic acid (3) reported for the first time from this species. Their structures have been assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC and HMBC experiments. The compounds 1-3 showed significant antioxidant activity.

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Section: Resultssupporting

confidence: 72%

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Ahmad

Mehmood

Fatima

et al. 2007

Magnetic Reson in Chemistry

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“…2). The 2D, 3E-configurations of the two secondary hydroxyl groups of compound 1 were in agreement with the similarity of the observed coupling constant (J = 9.5 Hz) between the H-2D and H-3E protons and those of the related compounds, 3-O-trans-p-coumaroyl asiatic acid (J = 9.8 Hz) (Sashida et al, 1992) and actinidic acid (J = 9.6 Hz) (Lahlou et al, 2001), as confirmed by the NOESY spectrum of compound 1 (Fig. 3), where NOE was observed between H-2 and H-25, indicating that the H-2 and H-3 protons were in the D and E positions,…”

Section: Figsupporting

confidence: 79%

“…The IR spectrum of compound 1 showed hydroxyl (3490-3380 cm -1 ), conjugated ester (1712 cm -1 ) and carbonyl (1667 cm -1 ) absorptions. The 1 H-and 13 C-chemical shifts of compound 1 (Table I) were very similar to those of a known coumaroyl urs-12-ene, 3-O-trans-p-coumaroyl asiatic acid isolated from Actinidia polygama (Sashida et al, 1992), with the exception of ring E, which appeared at the resonance for the exocyclic methylene rather than the methyl group. The presence of a trans-p-coumaroyl moiety was suggested from the 1 H-NMR resonances at G H 6.65 (1H, d, J = 16.0 Hz), 7.17 (2H, d, J = 8.5 Hz), 7.56 (2H, d, J = 9.0 Hz) and 7.97 (1H, d, J = 16.0 Hz) and the dominant fragment ion peak at m/ z 147 in the EIMS.…”

Section: Resultsmentioning

confidence: 56%

A new pancreatic lipase inhibitor isolated from the roots of Actinidia arguta

et al. 2008

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A new coumaroyl triterpene, 3-O-trans-p-coumaroyl actinidic acid (1), as well as five known triterpenes, ursolic acid (2), 23-hydroxyursolic acid (3), corosolic acid (4), asiatic acid (5) and betulinic acid (6) were isolated from an EtOAc-soluble extract of the roots of Actinidia arguta. The structure of compound 1 was elucidated from interpretation of the spectroscopic data, particularly by extensive 1D and 2D NMR studies. All the isolates (1-6) were evaluated in vitro for their inhibitory activities on pancreatic lipase (PL). Of the isolates, the new compound 1 possessed the highest inhibitory activity on PL, with an IC(50) of 14.95 microM, followed by ursolic acid (2, IC(50) = 15.83 microM). The other four triterpenes (3-6) also showed significant PL inhibitory activity, with IC(50) values ranging from 20.42 to 76.45 microM.

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“…Separation by a combination of silica gel, octadecyl silica (ODS) column chromatography, and preparative HPLC afforded three new compounds, 1-3, and five known compounds, rotundic acid, 4) tormentic acid, 5) 2a,3a,23-trihydroxy-12,20(30)-ursadien-28-oic acid, 6) 1a,2a,3a,24-tetrahydroxy-12-oleanen-28-oic acid, 7) and 1-O-feruloylglucose. 8) The structures of the known compounds were determined by interpretation of their spectroscopic data as well as by comparison with reported data.…”

Section: Resultsmentioning

confidence: 99%

The First Cyclic Phenolic Acid Glycoside Dimer and New .ALPHA.-Tetralone and Triterpenoid Glucosides from Gentiana loureirii

Xie

et al. 2010

Chem. Pharm. Bull.

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NotesGentiana loureirii GRISEB. (Gentianaceae), a perennial herb widely distributed in South China, 1) is a Chinese folk medicine used for the treatment of various disorders related to inflammation and infections.2) We previously reported the isolation of iridoids, flavonoids, and oleanolic acid as its predominant constituents.3) In further investigation on the minor constituents of this plant, a novel phenolic acid glycoside, cyclic 4-O-b-D-glucopyranosylcaffeic acid dimer (1), a new a-tetralone, 4-hydroxy-6-methyl-a-tetralone 4-O-b-D-glucopyranoside (2), and a new triterpenoid saponin, 3b,30-dihydroxy-12-ursen-28-oic acid 28-O-b-D-glucopyranosyl ester (3), were isolated along with five known compounds, rotundic acid, tormentic acid, 2a,3a,23-trihydroxy-12,20(30)-ursadien-28-oic acid, 1a,2a,3a,24-tetrahydroxy-12-oleanen-28-oic acid, and 1-O-feruloylglucose. Herein, we report the isolation and structure elucidation of these new compounds. Results and DiscussionThe EtOH extract of the whole plants of Gentiana loureirii was fractionated with petroleum ether, CHCl 3 , EtOAc, and nBuOH. Separation by a combination of silica gel, octadecyl silica (ODS) column chromatography, and preparative HPLC afforded three new compounds, 1-3, and five known compounds, rotundic acid, 4) tormentic acid, 5) 2a,3a,23-trihydroxy-12,20(30)-ursadien-28-oic acid, 6) 1a,2a,3a,24-tetrahydroxy-12-oleanen-28-oic acid, 7) and 1-O-feruloylglucose.8) The structures of the known compounds were determined by interpretation of their spectroscopic data as well as by comparison with reported data. and the carbonyl carbon at d C 166.7 (C-9) were observed, indicating attachments of the glucose moiety to C-4 of the caffeic acid residue via a glycosidic linkage and the caffeoyl group to C-6Ј of the glucose moiety via an ester linkage. These findings in the NMR spectra in combination with the molecular formula suggested a symmetrical structure composed of two 4-O-b-D-glucopyranosylcaffeic acid units which were connected with each other by ester linkages between each C-6Ј in one unit and the carbonyl carbon (C-9) in the other unit to form a 26-membered macrolide ring. The large coupling constant (Jϭ10.3 Hz) observed between H-5Ј and H-6Јb in the 1 H-NMR spectrum was in accord with the energy-minimized structure (Fig. 1) obtained by MOPAC in CS Chem3D, which showed a dihedral angle of near 180°between H-5Ј and H-6Јb bonds. Therefore compound 1, tentatively named cyclic 4-O-b-Dglucopyranosylcaffeic acid dimer, was established to have the

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Triterpenoids from the fruit galls of Actinidia polygama

Cited by 81 publications

References 8 publications

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

Structural determination of salsolins A and B, new antioxidant polyoxygenated triterpenes from Salsola baryosma, by 1D and 2D NMR spectroscopy

A new pancreatic lipase inhibitor isolated from the roots of Actinidia arguta

The First Cyclic Phenolic Acid Glycoside Dimer and New .ALPHA.-Tetralone and Triterpenoid Glucosides from Gentiana loureirii

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