Triterpenoid saponins from Fatsia japonica

Five triterpenoid saponins isolated from the flowers, the mature fruits and the leaves of Fatsia japonica were identified as 3-O-[β-d-glucopyranosyl(1→4)-β-d-glucopyranosyl]-hederagenin (1), 3-O-[β-d-glucopyranosyl-(1→4)-α-l-arabinopyranosyl]-oleanolic acid (2), 3-O-[α-l-arabinopyranosyl]-hederagenin (3), 3-O-[β-d-glucopyranosyl]-hederagenin (4) and 3-O-[β-d-glucopyranosyl(1→4)-α-l-arabinopyranosyl]-hederagenin (5). The saponins 1 and 2 are new, naturally occurring, triterpenoid saponins. The distribution of the five saponins in three parts of the plant was investigated. Saponins 2, 3 and 5 were present in the flowers, saponins 1, 3, 4 and 5 were in the mature fruits and saponins 2, 3, 4 and 5 were in the leaves.     

Triterpenoid saponins from the flower buds of Fatsia japonica

Six triterpenoid saponins isolated from the flower buds of Fatsia japonica were identified as 3-O-[β-D-glucopyranosyl(1 → 4)-α-L-arabinopyranosyl]-oleanolic acid, 3-O-[α-L-arabinopyranosyl]-hederagenin, 3-O-[β-D-glucopyranosyl(1 → 4)-α-L-arabinopyranosyl]-hederagenin, 3-O-[α-L-arabinopyranosyl]-echinocystic acid, 3-O-[α-L-arabinopyranosyl]-16-epiechinocystic acid and 3-O-[α-L-arabinopyranosyl]-oleanolic acid. Of these saponins, three are new.     

Steroidal saponins from the leaves of Beaucarnea recurvata

Thirteen steroidal saponins were isolated from the leaves of Beaucarnea recurvata Lem. Their structures were established using one- and two-dimensional NMR spectroscopy and mass spectrometry. Six of them were identified as: 26-O-β-d-glucopyranosyl (25S)-furosta-5,20(22)-diene 1β,3β,26-triol 1-O-α-l-rhamnopyranosyl-(1 → 2) β-d-fucopyranoside, 26-O-β-d-glucopyranosyl (25S)-furosta-5,20(22)-diene 1β,3β,26-triol 1-O-α-l-rhamnopyranosyl-(1 → 2)-4-O-acetyl-β-d-fucopyranoside, 26-O-β-d-glucopyranosyl (25R)-furosta-5,20(22)-diene-23-one-1β,3β,26-triol 1-O-α-l-rhamnopyranosyl-(1 → 2) β-d-fucopyranoside, 26-O-β-d-glucopyranosyl (25S)-furosta-5-ene-1β,3β,22α,26-tetrol 1-O-α-l-rhamnopyranosyl-(1 → 4)-6-O-acetyl-β-d-glucopyranoside, 26-O-β-d-glucopyranosyl (25S)-furosta-5-ene-1β,3β,22α,26-tetrol 1-O-α-l-rhamnopyranosyl-(1 → 2) β-d-fucopyranoside, and 24-O-β-d-glucopyranosyl (25R)-spirost-5-ene-1β,3β,24-triol 1-O-α-l-rhamnopyranosyl-(1 → 2)-4-O-acetyl-β-d-fucopyranoside. The chemotaxonomic classification of B. recurvata in the family Ruscaceae was discussed.     

Molluscicidal saponins of Phytolacca dodecanra: Oleanoglycotoxin-A

The structure of one of the major molluscicidal saponins of the fruit of Phytolacca dodecandra has been elucidated as 3-[2,4-di-O-(β-d-glucopyranosyl)-β-d-glucopyranosyll-olean-12-ene-28-oic acid. The combined use of 300 Mc. PMR, MS and GC-MS led to this structural assignment.     

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).     

Steroidal saponins of Asparagus curillus

Three spirostanol and two furostanol glycosides were isolated from a methanol extract of the roots of Asparagus curillus and characterized as 3-O-[α-l-arabinopyranosyl (1→4)- β-d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, 3-O-[{α-l-rhamnopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β-d-glucopyranosyl]-(25S)-5β-spirostan- 3β-ol, 3-O-[{β-d-glucopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β- d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, 3-O-[{β-d-glucopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosyl]- 22α-methoxy-(25S)-5β-furostan-3β, 26-diol and 3-O-[{β-d-glucopyranosyl (1→2)} {α-l-arabinopyranosyl (1→4)}-β-d-glucopyranosyl]-26-O-[β-d-glucopyranosyl]- (25S)-5β-furostan-3β, 22α, 26-triol respectively.     

Steroidal saponins of Asparagus adscendens

From the methanol extract of the fruits of Asparagus adscendens sitosterol-β-d-glucoside, two spirostanol glycosides (asparanin A and B) and two furostanol glycosides (asparoside A and B) were isolated and characterized as 3-O-[β-d-glucopyranosyl (1→2)-β-d-glucopyranosyl]-(25S)-5β-spirostan-3β-ol, 3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl}-(25S)-5β-spirostan-3β-ol,3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl|} -26-O-(β- d-glucopyranosyl)-22α-methoxy-(25S)-5β-furostan-3β,26-diol and 3-O-{[β-d-glucopyranosyl(1→2)][α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranosyl}-26-O-(β-d-glucopyranosyl)- 25S)-5β-furostan-3β,22α, 26-triol, respectively.     

Structures of 3,28-O-bisglycosidic triterpenoid saponins of Fatsia japonica

Four novel 3,28-O-bisglycosidic triterpenoid saponins were isolated from the mature fruits of F. japonica. They were characterized as the 28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 4)-β- d-glucopyranosides of 3-O-α-l-arabinopyranosyl echinocystic acid, 3-O-α-l-arabinopyranosyl hederagenin, 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosyl oleanolic acid and 3-O-β- d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosyl hederagenin respectively.     

Triterpenoid saponins from leaves of Pittosporum undulatum

Two triterpenoid saponins obtained from the leaves of Pittosporum undulatum were characterized on the basis of chemical and spectral evidence as a     

Cold-induced fructosan synthesis in leaves of Dactylis glomerata

Dactylis glomerata accumulated fructosan more rapidly at 5° than at 15—20°. The pattern of incorporation of ¹⁴CO₂ into fructosan was determined in plants grown at 5°. During the major period of fructosan synthesis there was initial incorporation of label into mono- and disaccharides, and progressive synthesis of polymeric material occurred subsequently. Rates and levels of synthesis were much lower in leaf blades than in leaf bases. The MW distribution of the polymeric material in leaf bases differed from that in the blades and from that observed in plants which synthesize inulin.     

Phenolic compounds from Forsythia leaves

Four lignans, four lignan glucosides, one flavonoid and two caffeoyl glycosides of 3,4-dihydroxyphenethyl alcohol were identified variously in leaves of Forsythia suspensa, F. viridissima and F. koreana. The leaf patterns were broadly similar to those reported earlier for the fruits, except that suspensaside and β-hydroxyacteoside were not detected.     

Immunoregulatory effects of a glucogalactan from the root of Panax quinquefolium L.

In this research we purified one homogeneous glucogalactan from the roots of Panax quinquefolium, with a molecular weight of 54 kDa estimated by high-performance gel permeation chromatography (HPGPC). The monosaccharide composition of PPQ was composed of Glc (glucose) and Gal (galactose) in a molar ratio of 2.1:1, as determined by gas chromatography (GC). In order to evaluate the anti-lung carcinoma and immunoregulatory effects of this glucogalactan in mice, we established a Lewis lung carcinoma model in C57BL/6 mouse. The results showed that PPQ not only could inhibit the growth of lung tumor, but also enhance the thymus and spleen indices, as well as the level of IFN-γ, IL-10 and IL-2, indicating PPQ could have a possible cancer therapeutic potential.     

SIRT1 activator isolated from artificial gastric juice incubate of total saponins in stems and leaves of Panax ginseng

Panax ginseng as a traditional Chinese medicine has been extensively used for the treatment of many diseases, especially in prolonging life and anti-tumor. Dammarane-type triterpenoids from P. ginseng have diverse beneficial effects and their chemical structures can be modified in the gastrointestinal tract after oral administration. In this paper, the dammarane-type triterpenoids were isolated from artificial gastric juice incubate of total saponins in the stems and leaves of P. ginseng through column chromatographic methods and their chemical structures were determined based on spectral data. Two new dammarane-type triterpenoids named ginsenotransmetins B (1) and C (2), along with twenty-nine known compounds (3–31), were obtained. All 31 compounds isolated were investigated for their activities of SIRT1 using SIRT1 fluorometric drug discovery assay kit. Among them, compounds 11, 17, 18, 20, 23, 24, 28, and 29, which were found to be potential as SIRT1 activators, exhibited significant stimulation of SIRT1 activity. The results showed that these compounds may be considered to be a useful medicinal resource for prolonging life and anti-tumor. In addition, the results were helpful to explain the longevity effect of ginseng from the new field of view.     

Intracellular distribution of cardiac glycosides in leaves of Convallaria majalis

In order to investigate the intracellular distribution of the cardiac glycosides in leaves of Convallaria majalis, cell organelles were prepared by several methods. After mechanical disruption of the cells and differential centrifugation, the cardenolide content obtained was determined using the Baljet reaction. Most of the cardiac glycoside fraction was found in the soluble supernatant. However, a low but significant amount was also found in the 10 000g particles. Protoplasts and vacuoles were prepared by enzymic digestion of leaves. The cardenolide to protein ratio of vacuoles was far higher than that of protoplasts or the cytoplasmic fraction. The cardenolide content of isolated vacuoles relative to their number agreed well with the corresponding value obtained for protoplasts. This demonstrates clearly that cardiac glycosides are stored predominantly in the vacuoles of Convallaria majalis.     

Membrane-degrading enzymes in the leaves of Solanum tuberosum

When homogenates of potato leaves were prepared under conditions which are typical for organelle isolation (pH 7.5 and 4°), membrane lipids underwent rapid hydrolysis (17% of phosphatidylcholine was hydrolysed in 2 hr). Leaves of 41 potato cultivars were surveyed for phospholipase activity to determine whether certain cultivars might be more suitable for the preparation of organelles. Phospholipase activities ranged from 1.04 to 11.60, μmol/min · g fr. wt and p-nitrophenyl palmitate hydrolase activity ranged from 0.0119 to 0.0502,μmol/min · g fr. wt. These phospholipase values were several hundred-fold higher than previously reported for potato leaves and nearly as high as in potato tubers. Most of the phospholipase activity in leaves was soluble and not membrane-associated as previously reported.     

珠子参叶皂苷对脂肪酶抑制机制及降血脂研究

珠子参叶是五加科(Araliaca)植物珠子参(Panax japonicas var. major)的干燥带梗叶,为秦巴地区特色中药材。为合理开发利用珠子参叶并阐明其化学成分,该研究利用HPLC方法分析珠子参叶皂苷部位的主要化学成分,测定珠子参叶皂苷部位的脂肪酶抑制活性及抑制类型,通过分子对接及动物实验验证脂肪酶抑制机制及降血脂作用。结果表明:(1)珠子参叶皂苷部位主要成分为20(S)-人参皂苷Rg₂、20(R)-人参皂苷Rg₂、人参皂苷Rb₂、人参皂苷Rb₃、人参皂苷Rd、人参皂苷Rh₂。(2)珠子参叶皂苷部位、20(R)-人参皂苷 Rg₂对脂肪酶具有较强的抑制作用,其IC₅₀分别为0.14、2.30 μmol·L^-1。(3)珠子参叶皂苷部位、20(R)-人参皂苷Rg₂、人参皂苷Rb₃对脂肪酶的抑制为可逆性抑制,抑制类型为非竞争型抑制。(4)配体与ARG337B、ASP331B、ILE248B残基结合可能有助于提高配体的脂肪酶抑制活性。(5)珠子参叶总皂苷可以显著降低高脂血症小鼠血清中胆固醇和甘油三酯的含量。该研究为珠子参叶在降血脂方面的深入开发和利用提供了理论参考。     

Identification of pterostilbene as a phytoalexin from Vitis vinifera leaves

An inducible antifungal compound in grapevine leaves (Vitis vinifera L., cv Cabernet-Sauvignon) has been identified as trans-pterostilbene (3,5-dimethoxy-4′-hydroxy stilbene). It is only a minor component of the phytoalexin response of V. vinifera but its antifungal activity is relatively high by comparison with resveratrol and the viniferins, stress metabolites which have been identified previously in grapevine. Methods for the quantitative analysis of pterostilbene, resveratrol, ε- and α-viniferins by HPLC are described.     

C31,-secodammarane-type triterpenoid saponins from the male flowers of Alnus pendula

Six C₃₁-secodammarane-type triterpenoid saponins, in addition to alnustic acid, were isolated from the male flowers of Alnus pendula. Two of these saponins were new and were shown to be the 12-O-(2′-O-acetyl)-β-d-xylopyranoside and the 12-O-(2′-O-acetyl)-β-d-glucopyranoside of alnustic acid, respectively, on the basis of their physico-chemical data.     

New triterpenoid saponins from the roots of Gypsophila pacifica Kom.

Six new triterpenoid saponins (1-6) have been isolated from the roots of Gypsophila pacifica Kom. Their structures were established on the basis of extensive NMR (¹H, ¹³C, TOCSY, HSQC, and HMBC) and ESIMS studies.     

Triterpenoid saponins from the stem bark of Symplocos spicata

From the stem bark of Symplocos spicata a mixture of triterpenoid saponins was obtained. It behaved as a pure compound in TLC and HPLC, but heterogeneity was suspected on the basis of chemical and NMR spectral data. It was separated to give two analogous glycosides, which were identified as 3,28-O-bis-β-d-glucopyranosides of 19α-hydroxyarjunolic and 19α-hydroxyasiatic acids.