Four New Lignans from Viburnum foetidum var. foedidum

Abstract

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...

Sesquiterpenoids and Lignans from the Roots of <i>Syringa pinnatifolia</i>

“…[11][12][13][14][15] Oxidant stress plays an important role in the pathogenesis of many cardiovascular diseases (CVDs), and the use of antioxidant supplements is very benefit to the prevention of coronary artery diseases. 16) Due to the bioactivity of S. pinnatifolia related to the cardiovascular system, all the lignans isolated from this plant in our present studies were tested for their anti-oxidant activity.…”

Flavones and lignans from the stems of Wikstroemia scytophylla diels

“…The structures of compounds 1-12 [ Figure 1 ] were identified as wikstrol B (1),[ 6 7 ] apigenin 7- O -methyl ether (2),[ 8 ] apigenin 5, 7-dimethyl ether (3),[ 9 ] luteolin 7, 4’-dimethyl ether (4),[ 10 ] 5, 7-di- O -methylquercetin(5),[ 11 ] 3’-hydroxy-4’, 5, 7-trimethoxy-flavone (6),[ 12 ] 3-(1, 3-benzodioxol-5-ylmethyl)-4-[(3, 4-dimethoxyphenyl)methyl]dihydro-, (3 S -cis)-2(3H)-furanone (7),[ 13 14 ] 4-[( R )-1, 3-benzodioxol-5-ylhydroxymethyl]-3-(1, 3-benzodioxol-5-ylmethyl)dihydro-, (3 S , 4 R )-2(3H)-furanone (8),[ 14 15 ] (-)-dihydrosesamin (9),[ 16 ] phenol, 4, 4’-[(2 R , 3 S , 4 S )-tetrahydro-2-methoxy-3, 4-furandiyl]bis(methylene)]bis[2-methoxy- (10),[ 17 ] 4, 4’-dihydroxy-3, 3’, 9-trimethoxy-9, 9’-epoxylignan (11),[ 17 ] (+)-1-hydroxypinoresinol (12),[ 18 19 ] respectively, by analysis of mass spectrometry and nuclear magnetic resonance (NMR) data, and comparison with those in the literature.…”

Recent Advance on Chemistry and Bioactivities of Secondary Metabolites from Viburnum Plants: An Update

“…Lignan constituents isolated from Viburnum plants can be classified into lignans, neolignans, norneolignans and norlignans. Compounds 189 – 194 found in V. foetidum and V. lancifolium were assigned to be the 3,4‐dibenzyltetrahydrofuran lignans, [39,53,54] which can be reduced to dibenzylbutane lignans via corresponding reductase, possessing the chemical skeleton as that of compounds 195 – 197 isolated from V. setigerum [55] . A pair of aryltetralin‐type lignans 199 and 200 , which were similar to (+)‐isolariciresinol ( 198 ) and aviculin ( 201 ), [11,47] along with four neolignans 202 , 212 , 213 and 215 were obtained from the stems of V. erosum [17,56] .…”

“…In addition, the other epoxylignans including thirteen 2‐aryl‐4‐benzyltetrahydrofuran lignans ( 230 – 242 ) and one 2,5‐diaryltetrahydrofuran ( 243 ) were reported in Viburnum plants [31,53,55,56,61–63] . (+)‐9′‐ O ‐Senecioyllariciresinol ( 231 ) from V. odoratissmum var.…”