Oleanane-type triterpenes from Viburnum awabuki

Kagawa, Masami; Matsuda, Hiroyuki; Nakahara, Mai; Takahashi, Hironobu; Takaoka, Shigeru

doi:10.1016/s0031-9422(98)80080-0

Cited by 22 publications

(15 citation statements)

References 9 publications

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“…Besides, comparison of the 13 C NMR data (Table) with those found in the literature for 3β,28-dihydroxy-11-oxo-olean-12-ene 6 allowed the identification of the structure of the triterpene moiety as being 3β-hydroxy-11-oxo-olean-12-ene. C NMR data of this compound with the data described for 3β,11α-dihydroxy-olean-12-ene 5,7 ( Table 1) allowed to establish the β relative stereochemistry for the hydroxy group at C-11 in compound 3.…”

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confidence: 90%

Fatty Acid Esters of Triterpenes from Erythroxylum passerinum

Barreiros¹,

David²,

Pereira³

et al. 2002

J. Braz. Chem. Soc.

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confidence: 90%

Fatty Acid Esters of Triterpenes from Erythroxylum passerinum

Barreiros¹,

David²,

Pereira³

et al. 2002

J. Braz. Chem. Soc.

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“…foedidum from Simao County, Yunnan Province, P. R. China, was investigated phytochemically. Four new lignans (1)(2)(3)(4) together with six known ones were found. The isolation and structural elucidation of the four new lignans are reported here.…”

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confidence: 98%

“…Phytochemical studies revealed that Viburnum species mainly contain triterpenoids, 4,5) iridoids, 6) vibsane-type diterpenes, 7,8) lignans, 9) and phenolic glycosides. 10) Vibsane-type diterpenes are an unusual group of natural products, which can be subdivided into three classes consisting of sevenmembered ring, eleven-membered ring, and rearranged types.…”

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confidence: 99%

Four New Lignans from Viburnum foetidum var. foedidum

Chen

et al. 2009

Chem. Pharm. Bull.

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NotesPlants of the Viburnum genus, which belong to the family Caprifliaceae, comprise about 230 species and are mainly distributed in Asia and South America. China has more than 70 species.1) The use of Viburnum species in Chinese popular folk medicine has a long history. For example, the leaves and skins of V. cylindricum, called shuihongmu in China, are used for the treatment of cough, diarrhea, rheumatoid arthritis, and tumefaction.2) V. odoratissimum, commonly known as shanhushu, is used for tumefaction and bone fractures. 3)Phytochemical studies revealed that Viburnum species mainly contain triterpenoids, 4,5) iridoids, 6) vibsane-type diterpenes, 7,8) lignans, 9) and phenolic glycosides. 10) Vibsane-type diterpenes are an unusual group of natural products, which can be subdivided into three classes consisting of sevenmembered ring, eleven-membered ring, and rearranged types.1) These diterpenoids have interesting biological activities such as piscicidal activity, plant growth regulatory activity, and cytotoxic activity. 11,12) As a part of our search for new vibsane-type diterpenoids, the 70% aqueous acetone extract of the aerial part of the V. foetidum var. foedidum from Simao County, Yunnan Province, P. R. China, was investigated phytochemically. Four new lignans (1-4) together with six known ones were found. The isolation and structural elucidation of the four new lignans are reported here. Results and DiscussionThe 70% aqueous acetone extract of the aerial parts of V. foetidum var. foedidum was successively subjected to silica gel and Sephadex LH-20 column chromatography as well as semipreparative HPLC to afford 10 lignans (1-10). Compounds 5-10 were identified as prinoresinol (5), 13) syringaresinol (6), 14) olivil (7), 15) 4,4Ј,7,7Ј-tetrahydroxy-3,3Ј-dimethoxy-9,9Ј-epoxylignan (8), 16) 4,4Ј,8,9-texahydroxy-3,3Ј-dimethoxy-7,9Ј-epoxylignan (9), 17) and padocin (10), 18) respectively, based on comparisons of their spectral data with those already reported. 13) The clearest differences between compound 1 and lariciresinol were less CH, a more oxygenated quaternary carbon (d 71.4), and an obvious upfield shift of C-9 in 1. Considering the characteristic NMR spectrum discussed above and the fact that 1 had an additional more ring system compared with that of lariciresinol, 1 was deduced to be 8,9-epoxy-lariciresinol. The formation of 8,9-epoxy led to the upfield shift of C-9 and the presence of an oxygenated quaternary carbon (d 71.4).In the rotating frame Overhauser enhancement spectroscopy (ROESY) of 1, the correlation of H-7 with H-8Ј indicated that both H-7 and H-8Ј were in the b-orientation. However, the ROESY spectrum could not provide sufficient information to elucidate the stereochemistry of C-8. After many attempts with different solvents, a single crystal of 1 was obtained in MeOH-H 2 O (95 : 5). A single crystal X-ray analysis clarified the relative configuration of C-8 and unambiguously confirmed the structure of 1 (Fig. 1).Compound 2, a white amorphous powder, had the molecu- The 70% aqueous a...

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Phytochemical studies have revealed that Viburnum species mainly contained triterpenoids, 1,2) iridoids, 3) vibsanetype diterpenes, 4,5) lignans, 6) and phenolic glycosides.

7)Viburnum chingii P. S. HSU is mainly distributed in southwest of Yunnan province, China. A literature search revealed that no phytochemical study has been undertaken within this species.

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confidence: 99%

“…Phytochemical studies have revealed that Viburnum species mainly contained triterpenoids, 1,2) iridoids, 3) vibsanetype diterpenes, 4,5) lignans, 6) and phenolic glycosides.…”

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confidence: 99%

Triterpenoids and Diterpenoids from Viburnum chingii

Chen

et al. 2011

Chem. Pharm. Bull.

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Phytochemical studies have revealed that Viburnum species mainly contained triterpenoids, 1,2) iridoids, 3) vibsanetype diterpenes, 4,5) lignans, 6) and phenolic glycosides. 7)Viburnum chingii P. S. HSU is mainly distributed in southwest of Yunnan province, China. A literature search revealed that no phytochemical study has been undertaken within this species. As a part of our work, we chemically examined the acetone extract of V. chingii leaves. Two new oleanane triterpenoids (1-2) and one new vibsane-type diterpenoid (3) were isolated from this plant, along with seven known compounds, vibsaol B (4), 8) 2a,3b-dihydroxy-20(29)-lupene (5), 9) 6a-hydroxy-3-on-20(29)-lupen-28-oic acid (6), 10) 3,6-dion-20(29)-lupen-28-oic acid (7), 10) hederagenin acid (8), 11) castanopsone (9), 12) and 3b,6a-dihydroxy-20(29)-lupene (10). 13) Compounds 1-10 were tested cytotoxicity against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Herein, we describe the isolation, structure elucidation of 1-3, and cytotoxicity of 1-10.The acetone extract of V. chingii leaves was successively subjected to silica gel chromatography, Sephadex LH-20 as well as RP-18 to afford three new compounds (1-3) and 7 known ones (4-10).Compound 1, white amorphous powder, had a molecular formula of C 31 H 52 O 3 according to its positive high resolution-electrospray ionization-mass spectra (HR-ESI-MS) (495.3802, [MϩNa] ϩ ) and 13 C-NMR analysis, demanding 6 degrees of unsaturation. The IR showed the presence of hydroxyl groups (3440 cm Ϫ1) and double bond (1631 cm Ϫ1 ). The 13 C-and distortionless enhancement by polarization transfer (DEPT) spectral data showed seven quaternary carbons (an olefinic one), seven methines (an olefinic one and three oxygen bearing ones), eight methylenes, eight methyls, and one methoxy group (Table 1). The 1 H-NMR and heteronuclear single quantum coherence (HSQC) spectra also confirmed the observations in the 13 C-NMR spectrum. The 13 C-and 1 H-NMR spectroscopic data accounted for all the hydrogens except for two ones, indicating the presence of two free hydroxyls. Apart from one degree of unsaturation from the double bond, the remaining five ones in 1 were assumed to be the presence of five rings. Considering the characteristic of 13 C-and 1 H-NMR data, 1 was ascribed to be derivate of oleanene triterpenoids. The double bond was located between C-12 and C-13 because H-15, H-18, and H-19 showed the heteronuclear multiple bond connectivity (HMBC) correlations with the olefinic quaternary carbon (d C 151.5, C-13). The HMBC correlations from H-9 and H-18 to the olefinic methine (d C 119.2, C-12) further confirmed the location of the double bond. The methoxy group exhibited HMBC correlation with C-11 identified by the hydrogen spin system of H-11/H-12 from Two new oleanane triterpenoids (1-2) and one new vibsane-type diterpenoid (3), together with 7 known compounds (4-10), were isolated from the leaves of Viburnum chingii. The structures of compounds 1-3 were elucidated by means of spectroscopic methods including exte...

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Oleanane-type triterpenes from Viburnum awabuki

Cited by 22 publications

References 9 publications

Fatty Acid Esters of Triterpenes from Erythroxylum passerinum

Fatty Acid Esters of Triterpenes from Erythroxylum passerinum

Four New Lignans from Viburnum foetidum var. foedidum

Triterpenoids and Diterpenoids from Viburnum chingii

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