Phenolic compounds and rare polyhydroxylated triterpenoid saponins from Eryngium yuccifolium

Phytochemical investigation on the whole plant of Eryngium yuccifolium resulted in the isolation and identification of three phenolic compounds (1-3) and 12 polyhydroxylated triterpenoid saponins, named eryngiosides A-L (4-15), together with four known compounds kaempferol-3-O-(2,6-di-O-trans-p-coumaroyl)-β-d-glucopyranoside (16), caffeic acid (17), 21β-angeloyloxy-3β-[β-d-glucopyranosyl-(1→2)]-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyloxyolean-12-ene-15α,16α,22α,28-tetrol (18), and saniculasaponin III (19). This study reports the isolation of these compounds and their structural elucidation by extensive spectroscopic analyses and chemical degradation.     

Triterpenoid saponins from a cytotoxic root extract of Sideroxylonfoetidissimum subsp. gaumeri

Evaluation of the cytotoxicity of an ethanolic root extract of Sideroxylonfoetidissimum subsp. gaumeri (Sapotaceae) revealed activity against the murine macrophage-like cell line RAW 264.7. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which four saponins were isolated. Use of 1D (¹H, ¹³C, DEPT135) and 2D (COSY, TOCSY, HSQC, and HMBC) NMR, mass spectrometry and sugar analysis gave their structures as 3-O-(β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, 3-O-β-d-glucopyranosyl-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, 3-O-(β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, and the known compound, 3-O-β-d-glucopyranosyl-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-protobassic acid. Two further saponins were obtained from the same fraction, but as a 5:4 mixture comprising 3-O-(β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid and 3-O-(β-d-apiofuranosyl-(1 → 3)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, respectively. This showed greater cytotoxicity (IC₅₀ = 11.9 ± 1.5 μg/ml) towards RAW 264.7 cells than the original extract (IC₅₀ = 39.5 ± 4.1 μg/ml), and the saponin-containing fraction derived from it (IC₅₀ = 33.7 ± 6.2 μg/ml).     

New triterpenoid saponins from the roots of Gypsophila perfoliata Linn

Nine new triterpenoid saponins (1–9) have been isolated from the roots of Gypsophila perfoliata Linn. Their structures were established on the basis of extensive NMR (¹H, ¹³C, HSQC and HMBC) and ESIMS studies.     

Triterpenoid saponins with antifeedant activities from stem bark of Catunaregam spinosa (Rubiaceae) against Plutella xylostella (Plutellidae)

Seven triterpenoid saponins, including four new compounds, catunarosides A–D (1–4), and three known compounds, swartziatrioside (5), aralia-saponin V (6), araliasaponin IV (7) were isolated from the stem bark of Catunaregam spinosa, a Chinese mangrove associate. Their structures were elucidated on the basis of their spectral data and hydrolysis experiments. The antifeedant activities of compounds 1–7 against Plutella xylostella were also evaluated.     

金银花花蕾中的新三萜皂甙

从金银花 (LonicerajaponicaThunb .)花蕾中分离得六个化合物 (A—F) ,据化学降解和波谱数据 ,推定了它们的化学结构 ,其中F为一新化合物 ,命名为新常春皂甙F ,其化学结构为 :3-氧 - β -D -葡萄吡喃糖基 (1→ 4 ) - β -D -葡萄吡喃糖基 (1→ 3) -α -L -鼠李吡喃糖基 (1→ 2 )α -L -阿拉伯吡喃糖基 -常春皂甙元 - 2 8-氧 - β -D -葡萄吡喃糖基 (1→ 6 ) -β -D -葡萄吡喃糖基酯 (F)。其它五个化合物的结构分别为 :常春皂甙元 - 3-氧 -α -L -鼠李吡喃糖基 (1→ 2 ) -α -L -阿拉伯吡喃糖甙 (A) ,3-氧 -α -L -鼠李吡喃糖基 (1→ 2 ) -α-L -阿拉伯吡喃糖基 -常春皂甙元 - 2 8-氧 - β -D -吡喃木糖基 (1→ 6 ) - β -D -葡萄吡喃糖基酯 (B) ,3-氧 -α -L -鼠李吡喃糖基 (1→ 2 ) -α -L -阿拉伯吡喃糖基 -常春皂甙元 -2 8-氧 - β -D -葡萄吡喃糖基 (1→ 6 ) - β -D -葡萄吡喃糖基酯 (C) ,3-氧 -α -L -鼠李吡喃糖基 (1→ 2 ) -α -L -阿拉伯吡喃糖基 -常春皂甙元 - 2 8-氧 -α -L -鼠李吡喃糖基 (1→2 ) [β -D -吡喃木糖基 (1→ 6 ) ]- β -D -葡萄吡喃糖基酯 (D) ,3-氧 - β -D -葡萄吡喃糖基 (1→ 3) -α -L -鼠李吡喃糖基 (1→ 2 )α -L -阿拉伯吡喃糖基 -常春皂甙元 - 2 8-氧 - β-D -葡萄吡     

广东冬青中的三萜及三萜皂甙成分

从广东冬青（Ｉｌｅｘ ｋｗａｎｇｔｕｎｇｅｎｓｉｓ）的叶中分离得到四个三萜皂甙和三个三萜成分,通过光谱解析及化学方法,三个三萜成分分别鉴定为齐墩果酸（１）、熊果酸（２）和常春藤皂甙元（３）;四个三萜皂甙成分分别鉴定为齐墩果酸３－Ｏ－β－Ｄ－吡喃葡萄糖基－（１→３）－α－Ｌ－吡喃阿拉伯糖甙（４）、齐墩果酸３－Ｏ－β－Ｄ－吡喃葡萄糖基－（１→２）－α－Ｌ－吡喃阿拉伯糖甙（５）、齐墩果酸３－Ｏ－β－Ｄ－     

Structural Identification of Kudinchagenin I

A novel triterpenoid, kudinchagenin Ⅰ was isolated from the leaves of Ilex kudincha C. J. Tseng and its structure was determined to be 3β-hydroxy- 11 (12), 13 ( 18 ), 19 ( 29 ) - triene-28,20β-lactonic-ursane by a combination of spectroscopic methods and single crystal X-ray analysis.     

The Isolation and Structures of Kaji-lchigoside Fl and Rosamultin

Two epimers of triterpenoid saponins, kajiichigoside F1 (R-8) and rosamultin (R-9) were isolated from the fruits of Rosa roxburghii Tratt. R-8 was obtained as white needle crystal with mp 205–207℃ and [a]D18 + 10.5˚ (C = 0.0953, absolute ethanol); R-9 was white crystal with mp 214–216℃ and [a]D18 + 9.5 (C=0.1050, absolute ethanol). The structures of the two compounds were elucidated on the basis of spectroscopic analysis ,(UV, IR, 1H-, 13C-NMR, MS) and chemical methods.     

The Isolation and Characterization of Triterpenoid Constituents from Maytenus confertiflora Lou et Chen

A new triterpenoid confertiflorol along with other two triterpenoids(canophyllol and wieforlide A) have been isolated from the stems of Maytenus conferti-flora Luo et Chen (Celastraceae). The chemical structure of confertifiorol, as 28, 29-dihydroxyfriedelan-3-one, has been confirmed on the basis of chemical studies and spectrometric analysis.     

Chemical constituents from the leaves of Ilex urceolatus

Eighteen compounds, including four hemiterpene glycosides (1–4), three triterpenoid saponins (5–7), four triterpenes (8–11), five sterols (12-16) and two monoterpene glucosides (17 and 18), were isolated from the leaves of Ilex urceolatus C. B. Shang, K. S. Tang et D. Q. Du, which was identified as a new species belonging to the genus Ilex. Among them, compounds 14–18 were firstly isolated from the genus Ilex, others were obtained from I. urceolatus for the first time. This work represented the initially phytochemical study on this plant. The isolated compounds have significant chemotaxonomic characteristics with the other species from this genus.