Steroidal saponins from the leaves of Cordyline fruticosa (L.) A. Chev. and their cytotoxic and antimicrobial activity

Three new steroidal saponins, spirosta-5,25(27)-diene-1β,3β-diol-1-O-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranoside (fruticoside H) 1, 5α-spirost-25(27)-ene-1β,3β-diol-1-O-α-l-rhamnopyranosyl-(1→2)-(4-O-sulfo)-β-d-fucopyranoside (fruticoside I) 2, and (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 1-O-β-galactopyranosyl-16-O-α-l-rhamnopyranoside (fruticoside J) 3, together with the known quercetin 3-O-β-d-glucopyranoside, quercetin 3-O-[6-trans-p-coumaroyl]-β-d-glucopyranoside, quercetin 3-rutinoside, apigenin 8-C-β-d-glucopyranoside and farrerol, were isolated from the leaves of Cordyline fruticosa. Their structures were elucidated by spectroscopic techniques (¹H NMR, ¹³C NMR, HSQC, ¹H–¹H COSY, HMBC, TOCSY, NOESY), mass spectrometry (HRESIMS, Tandem MS–MS), chemical methods and by comparison with published data. Compounds 1 and 2 showed moderate cytotoxic activity against MDA-MB 231 human breast adenocarcinoma cell line, HCT 116 human colon carcinoma cell line, and A375 human malignant melanoma cell line, while compound 3 was not active. Compound 2 also showed a moderate antibacterial activity against the Gram-positive Enterococcus faecalis.     

罗藦科马利筋亚科马利筋族植物C_(21)甾类成分研究进展

本文综述了 :到目前为止 ,从马利筋族植物中发现的 C2 1甾类成分及其分布 ,并介绍了一些化合物的药理作用。     

Occurrence of Potential Brassinosteroid Precursor Steroids in Seeds of Wheat and Foxtail Millet

Triticum aestivum L.) and foxtail millet (Setaria italica Beauv.) were found by GC-MS to contain, in addition to bulk sterols, 4-en-3-one steroids including 24-ethylcholesta-4,24(28)Z- dien-3-one (a new steroid), 24-methylcholest-4-en-3-one, 24-ethylcholesta-4,22E-dien-3-one and 24-ethylcholest-4-en-3-one, as well as 5α-steroidal 3-one compounds including 24-methyl-5α-cholestan-3-one, 24-ethyl-5α-cholestan-3-one and 24-ethyl 5α-cholest-22E-en-3-one (in S. italica only). Analysis of free sterol and steryl ester fractions indicated that campestanol and sitostanol were present at high levels in both seeds. These results suggest that the seeds of T. aestivum and S. italica synthesize campestanol from campesterol via 24-methylcholest-4-en-3-one and 24-methyl-5α-cholestan-3-one as has already been demonstrated in Arabidopsis thaliana L., and also produce sitostanol from sitosterol via 24-ethylcholest-4-en-3-one and 24-ethyl-5α-chotestan-3-one. Biosynthetic relationships of campestanol and sitostanol with C₂₈ and C₂₉ brassinosteroids are discussed. Received 4 September 1998/ Accepted in revised form 26 November 1998     

New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)

Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1–4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 μM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.     

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.     

Triterpene Saponins from Polygalaceae

The aim of this review is to give updated results on the chemistry and biological activities of Polygalaceae saponins from literature data and from authors’ studies. During the last decade the improvement of isolation and structure elucidation techniques allowed the characterization of about 150 complex triterpene saponins from Polygalaceae having mainly preatroxigenin, medicagenic acid and presenegenin as aglycone. The sequence 3-O-(β-d-glucopyranosyl)-presenegenin 28-[O-α-L-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl] ester with additional acylations with p-methoxy-, di- or trimethoxycinnamoyl groups at the position 4 of the fucopyranosyl moiety often encountered in the genera Polygala, Muraltia, Carpolobia, and Securidaca may represent a chemotaxonomic marker for the Polygalaceae family. The biological and pharmacological properties of some Polygalaceae species such as in vitro activity on the central nervous system, the hypoglycemic, cytotoxic, immunomodulatory activities and in vivo immunoadjuvant properties are highlighted.     

A spirostanol glycoside from Agave cantala

A new steroidal saponin has been isolated from the ethanolic extract of the roots of Agave cantata and shown to be 3-O-[β-d-glucopyranosyl]-6O-[β-d-glucopyranosyl]-(25R)-5α-22α-O- spirostan-3β, 6α-diol.     

Effects of different components of Mao Dongqing’s total flavonoids and total saponins on transient ischemic attack (TIA) model of rats

Objective: To study the effects of the different components of the total flavonoids and total saponins from Mao Dongqing's active site on the rats of TIA model, determine the optimal reactive components ratio of Mao Dongqing on the rats of TIA. Methods: TIA rat model was induced by tail vein injection of tert butyl alcohol, the blank group was injected with the same amount of physiological saline, then behavioral score wasevaluated.Determination the level of glutamic acid in serum, the activity of Na+-K+-ATP enzyme, CA⁺⁺-ATP enzyme and Mg⁺⁺-ATP enzyme in Brain tissue, observe the changes of hippocampus in brain tissue, the comprehensive weight method was used to evaluate the efficacy of each component finally. Results: The contents of total flavonoids and total saponins in the active part of Mao Dongqing can significantly improve the pathological changes of brain tissue in rats, improve the activity of Na⁺-K⁺-ATP enzyme, Ca⁺⁺-ATP enzyme and Mg⁺⁺-ATP enzyme in the brain of rats, and reduce the level of glutamic acid in serum. The most significant of the contents was the ratio of 10:6. Conclusion: The different proportions of total flavonoids and total saponins in the active part of Mao Dongqing all has a better effect on the rats with TIA, and the ratio of 10:6 is the best active component for preventing and controlling TIA.     

Chemical constituents isolated from the roots and rhizomes of Smilacina japonica

Phytochemical investigation of the roots and rhizomes of Smilacina japonica A. Gray led to the isolation of 16 compounds, including six steroidal saponins (1-6), one amide (7), one fatty alcohol (8), one steroidal sapogenin (9), two flavones (10-11), one glycoside (12), one phenol (13), one aliphatic acid (14), and two sterols (15-16). All of these compounds were isolated for the first time from the roots and rhizomes of S. japonica while compounds 1-13 were identified for the first time from the genus Smilacina, of which compounds 9, 11, and 13 were isolated from the Liliaceae family for the first time. Furthermore, the isolation of compound 9 was reported for the first time in plants. Their structures were identified by spectroscopic methods and compared previously published data. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Characterization of a membrane bound β-glucosidase responsible for the activation of oat leaf saponins

Oat leaves contain a β-glucosidase (= avenacosidase) specific for the cleavage of the C-26 bound glucose moiety of the oat saponins avenacosides A and B. This transformation activates the fungitoxicities of the avenacosides. Evidence is presented that this enzyme is bound to the tonoplast membrane. The solubilized enzyme showed a pH optimum of 6.0–7.0, a temperature optimum around 40°, a molecular weight of 68 000±3000 and a K_m of 183 (±16) μM. The enzyme is inhibited by Hg²⁺ (10^-2 M) but not by Cu²⁺ (10^-2 M).