Studies on the Constituents of Lonicera Species. X. Neolignan Glycosides from the Leaves of Lonicera gracilipes var. glandulosa MAXIM.

Matsuda, Noriko; Kikuchi, Masao

doi:10.1248/cpb.44.1676

Cited by 103 publications

(72 citation statements)

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“…J = 8.0 Hz) of threo configuration. 17,18 The absolute configurations of C-7 and C-8 were confirmed, by a negative cotton effect at 239 nm in the CD spectrum, as being 7S and 8R configuration. 18,19 Therefore, 1 was determined to be 7S,8R-3,4,7,9,9'-pentahydroxy-3'-methoxy-8-O-4'-neolignan, and this compound was isolated for the first time as a natural product.…”

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confidence: 84%

A New Neolignan from Cephalotaxus koreana

Yoon¹,

Chin²,

Kim³

2010

Bulletin of the Korean Chemical Society

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confidence: 84%

A New Neolignan from Cephalotaxus koreana

Yoon¹,

Chin²,

Kim³

2010

Bulletin of the Korean Chemical Society

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“…3) In this paper, seven new saponins (1-4, 6-8) and a new lignan glucoside (14) were isolated from the extract of C. barbinervis, together with echinocystic acid 3-β-d-glucuronopyranoside (5), 4) hemsganoside B (9), 5,6) scheffleraside II (10), 5) rotundic acid (11), 7) barbinervic acid (12), 8) clethric acid (13), 9,10) 8-O-4′ neolignan 7-O-β-glucopyranoside (15), 11) rourinoside (16), 12) epicatechin (17), 13) pavetannin A (18), 14) 2-phenylethyl β-glucopyranoside (19), 15) 2-phenylethyl O-α-larabinofuranosyl-(1→ 6)-β-d-glucopyranoside (20), 16) 2-phenylethyl O-α-l-rhamnopyranosyl-(1→ 6)-β-d-glucopyranoside (21), 17) and methyl salicylate β-primeveroside (22) 18) (Figs. 1, 2).…”

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confidence: 99%

Triterpene Saponins from <i>Clethra barbinervis</i> and Their Hyaluronidase Inhibitory Activities

et al. 2013

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An extract of Clethra barbinervis with an inhibitory effect on hyaluronidase activity was fractionated guided by the results of an assay. From the active fractions, seven new triterpene saponins (1-4, 6-8) and a new lignan glycoside (14) were isolated together with 14 known compounds (5, 9-13, 15-22). Some of the saponins (2, 3, 9) were revealed as hyaluronidase inhibitors similar to epicatechin (17). Key words Clethra barbinervis; hyaluronidase inhibitor; triterpene saponinHyaluronidase has important roles in the body. It degrades and helps turnover hyaluronic acid in organs and tissues. Moreover, it has been imprecated in inflammatory reactions. Previously, we tested Lamiaceae plant extracts using a hyaluronidase inhibitory assay to identify anti-allergic and antiaging compounds.

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“…side (17, 0.00008%), 20) eugenyl vicianoside (18,0.00096%), 21) 2,6-dimethoxy-4-(2-propenyl)phenol 6-O-b -D-glucopyranosyl-b-D-glucopyranoside (19, 0.00011%), 22) coniferin (20, 0.00024%), 23) syringin (21, 0.0032%), 24) cis-syringin (22, 0.00024%), 25) dihydrosyringin (23, 0.00024%), 26) trans-psinapoyl-b-D-glucopyranoside (24, 0.00068%), 27) (E)-coumaroyl-1-O-b-D-glucopyranoside (25, 0.00026%), 28) 1-[(2Z)-3-(4-hydroxyphenyl)-2-propenoate]-b -D-glucopyranoside (26, 0.00005%), 28) myzodendrone (27, 0.00024%), 29,30) hovetrichoside A (28, 0.00010%), 31) 4,7,9-trihydroxy-3,3Ј-dimethoxy-8-O-4Ј-neolignan-9Ј-O-b -D-glucopyranoside[7S, 8R-erythro form] (29, 0.00019%), 32) syringaresinol mono-b-D-glucopyranoside (30, 0.00049%), 33) eleutheroside E 2 (31, 0.00017%), 34) 7R,8S-dihydrodehydrodiconiferyl alcohol 4-Ob-D-glucopyranoside (32, 0.00028%), 35) (2S)-2,3-O-di-(9,12, 15-octadecatrienoyl)-glyceryl-b -D-galactopyranoside (33, 0.0066%), 36) and 1,2-di-9,12,15-octadecatrienoyl-sn-glycerol (34, 0.00023%). 37) Structures of Foliachinenosides, E, F, G, H, and I, and Foliasalaciosides J, K, and L Foliachinenoside E (1) was obtained as a colorless amorphous powder with positive optical rotation ([a] D 27 ϩ9.8°in MeOH).…”

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Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis

Nakamura

Zhang

Matsuda

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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In the course of our characterization studies on bioactive constituents from Salacia species (Hippocrateaceae), [1][2][3][4][5][6] we have reported the isolation and absolute stereostructure elucidation of 13 megastigmane glycosides, 7 phenolic glycosides, and 11 triterpenes from the leaves of Salacia chinensis collected in Thailand together with 40 known constituents. 7-11)As a continuning study on the leaves of Salacia chinensis, the methanolic (MeOH) extract was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the MeOH extract, eight new glycosides, named foliachinenosides E, F, G, H, and I, and foliasalaciosides J, K, and L, were isolated together with 26 known constituents. Furthermore, we examined the hepatoprotective effects of the isolated compounds on D-galactosamine-induced cytotoxicity. In this paper, we describe the isolation and structure elucidation of the new constituents (1-8) and the hepatoprotective effects of isolated compounds from the leaves of Salacia chinensis.The dried leaves of S. chinensis, which were collected at Nakhon Si Thammarat province, Thailand, were finely cut and extracted with MeOH to furnish a MeOH extract (13.0%). The MeOH extract was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish an EtOAc-soluble fraction (4.1%) and an aqueous phase. The aqueous phase was further extracted with n-BuOH to give an n-BuOH-soluble fraction (2.4%) and a H 2 O-soluble fraction (6.6%). The n-BuOH-soluble fraction was subjected to Diaion HP-20 column chromatography (H 2 O→MeOH) to give the water-and MeOHeluted fractions as previously reported.7) The EtOAc-soluble fraction and the MeOH-eluted fraction were respectively subjected to normal-and reversed-phase silica gel column chromatographies, and finally HPLC to give eight new compounds, foliachinenosides E (1, 0.00009%), F (2, 0.00013%), G (3, 0.00017%), H (4, 0.00048%), and I (5, 0.0018%), and foliasalaciosides J (6, 0.00017%), K (7, 0.00016%), and L (8, 0.00007%), together with 26 known compounds, 3-methyl-2-but-2-en-1-ol 6-O-a-L-arabinopyranosyl-b-D-glucopyranoside (9, 0.0017%), 12) (3Z)-3-hexen-1-ol 6-O-a-L-arabinopyranosyl-b-D-glucopyranoside (10, 0.0014%), 13) 2,4,6-trimethoxyphenol 1-O-b-D-glucopyranoside (11, 0.00016%), 14) benzyl alcohol b-D-glucopyranoside (12, 0.00003%), 15) benzyl alco- Yamashina-ku, Kyoto 607-8412, Japan: and b Pharmaceutical Research and Technology Institute, Kinki University; 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Received April 27, 2011; accepted May 26, 2011; published

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Studies on the Constituents of Lonicera Species. X. Neolignan Glycosides from the Leaves of Lonicera gracilipes var. glandulosa MAXIM.

Cited by 103 publications

References 0 publications

A New Neolignan from Cephalotaxus koreana

A New Neolignan from Cephalotaxus koreana

Triterpene Saponins from <i>Clethra barbinervis</i> and Their Hyaluronidase Inhibitory Activities

Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis

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