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Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A‒C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A‒C, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β-d-xylopyranosyl-(1→3)-β-d-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC 50  = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC 50 value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

The fresh leaves of Metapanax delavayi (Araliaceae) have been used as a common wild vegetable for salad and soup, and also herbal tea by the local people living in its growing areas of Yunnan province, China. Detailed chemical investigation led to the identification of a new triterpenoid saponin, 3- O - α -L-arabinopyranosyl-28- O - β -D-glucopyranosyl-(1→6)- O - β -D-glucopyranosyl-3 β -hydroxyolean-12-ene-28,29-dioic acid ( 1 ) from the fresh leaves, together with 11 known compounds, including six triterpenoid saponins ( 2 - 7 ), two caffeoylquinic acid derivatives ( 8 - 9 ), and three flavonoid glycosides ( 10 - 12 ). Their structures were determined on the basis of spectroscopic analysis and acidic hydrolysis. Compounds 3 - 5 and 8 - 12 were isolated from M. delavayi for the first time. Moreover, the known saponins 3- O - β -D-xylopyranosyl-3 β -hydroxyolean-12-ene-28,29-dioic acid ( 3 ) and yiyeliangwanoside IV ( 5 ) exhibited protective effects on HepG2 cells damaged by the alcohol intakes, at a concentration of 1.0 µg/mL. The results indicated M. delavayi is an ideal dietary vegetable and herbal tea with potential hepatoprotective activity.[Formula: see text].

Further phytochemical investigation of the steaming treated roots of Panax notoginseng (Araliaceae) led to the identification of two new dammarane-type triterpenoid saponins, notoginsenoside SP20 (1) and SP21 (2). In addition, a pair of new phenolic glycosides (3a and 3b) was also isolated together with two known compounds. Their structures were elucidated by HRESIMS, 1D- and 2D-NMR spectra. Compounds 1 and 2 showed no in vitro cytotoxicity against five human cancer cell lines (HL-60, SMMC-7712, A-549, MCF-9 and SW480).

Two new oleanane-type triterpenoid saponins (1 and 2) were isolated from the methanolyzed total saponins of the seeds of Momordica cochinchinensis (Lour.) Spreng, together with 16 known compounds (3-18). Their structures were elucidated on the basis of detailed spectroscopic, including 1D and 2D NMR, mass spectrometric, methanolysis and LC-MS analysis. All the isolates were tested for their cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7721, PANC-1, A-549, and SW-480) and the glucose uptake activity. The known compound 6 exhibited toxic effects against HL-60 with an IC50 value of 18.1 μM, while 10 showed cytotoxicity against SMMC-7721 and A-549 cell lines, with IC50 values of 34.4 and 32.8 μM, respectively. In addition, the new compound 2 showed glucose uptake activity with a glucose consumption value of 0.29 μM at 10 μM concentration.

The roots of Panax notoginseng, an important Chinese medicinal plant, have been used traditionally in both the raw and processed forms, due to the different chemical constituents and bioactivities found. Thirty-eight dammarane-type triterpenoid saponins were isolated from the steam-processed roots of P. notoginseng, including 18 new substances, namely, notoginsenosides SP1-SP18 (1-18). The structures of 1-18 were determined on the basis of spectroscopic analysis and acidic hydrolysis. The absolute configuration of the hydroxy group at C-24 in 1-4, 19, and 20 was determined in each case by Mo2(AcO)4-induced circular dichroism. The new compounds were found to feature a diversity of highly oxygenated side chains, formed by hydrolysis of the C-20 sugar moiety followed by dehydration, dehydrogenation, epoxidation, hydroxylation, or methoxylation of the main saponins in the raw roots. The new saponins 1, 2, 6-8, 14, and 17 and the known compounds 20-27 showed promoting effects on the differentiation of PC12 cells, at a concentration of 10 μM.

Nine new minor dehydrogenated and cleavaged dammarane-type triterpenoid saponins, namely notoginsenosides ST6-ST14 (1-9) were isolated from the steamed roots of Panax notoginseng, together with 14 known ones. Among them, 5-7 and 21-22 were protopanaxadiol type and the left 18 compounds, including 1-4, 8-20, and 23 were protopanaxatriol type saponins. Their structures were identified by extensive analysis of MS, 1D and 2D NMR spectra, and acidic hydrolysis. Resulted from the side chain cleavage, the new saponins 1 and 2 featured in a ketone group at C-25, and 3-5 had an aldehyde unit at C-23. The known saponins 12, 16 and 18 displayed the enhancing potential of neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM, while 20 exhibited acetyl cholinesterase inhibitory activity, with IC50 value of 13.97 μM., (Copyright © 2015 Elsevier B.V. All rights reserved.)

A collection of 70 randomly selected three-year-old Panax notoginseng plants was analyzed to evaluate the germplasmic resources of cultivated notoginseng. The results obtained indicated that the individual plants of P. notoginseng were greatly diversified not only in saponin contents, but also in morphological features. It was further proven that, after hundreds years of cultivation, notoginseng has become a mixed farm cultivar with very large variations occurring. This high variance in saponin contents implies the possibility for breeding of this medicinal plant in order to obtain cultivars with higher saponin production. Statistic analysis of correlation between morphologic variation and chemical variation suggests that some morphological characters, such as root weight, plant height and peduncle length, can be correlated with saponin contents and can be used as important selective traits for selective breeding., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

• Notoginsenoids T1−T7, a new class of hexa-nortriterpenoids, were obtained. • Spectral, single-crystal X-ray, Mo 2 (AcO) 4 -induced CD and ECD analyzes were applied. • T1-T7 possess an unprecedented 9-en-5-ketone tricyclic hexa-nordammar skeleton. • A plausible biotransformed pathway for T1−T7 by degradation from PNS was proposed. • T1−T5 showed growth inhibitory effects on probiotic and pathogenic fungi of sanqi. Notoginsenoids T1−T7, a new class of hexa-nortriterpenoids including two dimers and five monomers, possessing an unprecedented 9-en-5-ketone tricyclic hexa-nordammar skeleton and a variable side chain at C-17, were obtained from biotransformation of PPD-type dammarane saponins by the soil harvested with Panax notoginseng (Araliaceae), a famous traditional Chinese medicinal herb. Their structures were unambiguously determined by spectroscopic, single-crystal X-ray diffraction, Mo 2 (AcO) 4 -induced CD and ECD analyzes. A plausible biotransformed pathway for T1−T7 was proposed. Notoginsenoids T1−T5 showed growth inhibitory effects on the probiotic and pathogenic fungi of P. notoginseng. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract: Notoginseng, the root of Panax notoginseng (Burk.) F. H. Chen (Araliaceae), a famous traditional Chinese medicine, has been used in both raw and processed forms due to their different therapeutic functions. In this study, HPLC analyses on saponin composition of processed notoginseng were conducted, which revealed that, during the steaming process, the five main saponin constituents (ginsenosides Rg1, Rb1, Rd, and Re, and notoginsenoside R1) in raw notoginseng decreased gradually and some other new saponins were formed. Among these, eight newly converted ginsenosides were identified as 20(S)-Rh1, 20(R)-Rh1, Rk3, Rh4, 20(S)-Rg3, 20(R)-Rg3, Rk1 and Rg5. Different processing methods, including steaming and baking, were studied, along with the correlative dynamic curves of the transformation of saponins. The results indicated that the moisture content and temperature were the determinant effecting factors in the preparing process, and water content was necessary and high temperature was helpful for saponin transformation. [Copyright &y& Elsevier]

Phytochemical investigation of the rhizomes of Panax japonicus C. A. Meyer (Araliaceae) resulted in the isolation of two new dammarane-type triterpenoid saponins, yesanchinoside R1 ( 1) and yesanchinoside R2 ( 2), together with one new natural product, 6′′′- O-acetylginsenoside Re ( 3). In addition, 25 known compounds, including 23 triterpenoid saponins, 4- 26, β-sitosterol 3- O- β- D-glucopyranoside ( 27), and ecdysterone ( 28), were also identified. The known saponins 12, 15, and 18- 22 were reported for the first time from the title plant. Their structures were elucidated on the basis of detailed spectroscopic analyses, including 1D- and 2D-NMR techniques, as well as acidic hydrolysis. [ABSTRACT FROM AUTHOR]