sapogenins

Summary

Summary: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.

Top Publications

  1. Tohda C, Hashimoto I, Kuboyama T, Komatsu K. Metabolite 1 of protopanaxadiol-type saponins, an axonal regenerative factor, stimulates teneurin-2 linked by PI3-kinase cascade. Neuropsychopharmacology. 2006;31:1158-64 pubmed
    ..In addition, treatment with PI3-kinase inhibitor also reduced M1-induced axonal extension. These results suggest that M1 induces axonal outgrowth through the teneurin-2-PI3-kinase cascade. ..
  2. Yu Y, Zhou Q, Hang Y, Bu X, Jia W. Antiestrogenic effect of 20S-protopanaxadiol and its synergy with tamoxifen on breast cancer cells. Cancer. 2007;109:2374-82 pubmed
    ..In addition, aPPD synergistically enhances cytotoxicity of tamoxifen in an ER-independent fashion, probably by down-regulating Akt activity. ..
  3. Popovich D, Kitts D. Mechanistic studies on protopanaxadiol, Rh2, and ginseng (Panax quinquefolius) extract induced cytotoxicity in intestinal Caco-2 cells. J Biochem Mol Toxicol. 2004;18:143-9 pubmed
    ..These results show variable bioactive response in cultured intestinal cell to specific ginsenosides and an enriched Rh2 North American ginseng extract which may be explained on basis of hydrophobic/hydrophilic balance. ..
  4. Li G, Wang Z, Sun Y, Liu K, Wang Z. Ginsenoside 20(S)-protopanaxadiol inhibits the proliferation and invasion of human fibrosarcoma HT1080 cells. Basic Clin Pharmacol Toxicol. 2006;98:588-92 pubmed
    ..Ginsenoside 20(S)-protopanaxadiol, a metabolite of ginseng, may be applied as a potential therapeutic agent in the prevention and treatment of cancer. ..
  5. McAnuff M, Harding W, Omoruyi F, Jacobs H, Morrison E, Asemota H. Hypoglycemic effects of steroidal sapogenins isolated from Jamaican bitter yam, Dioscorea polygonoides. Food Chem Toxicol. 2005;43:1667-72 pubmed
    In this study, three steroidal sapogenins (Delta3 diosgenin, diosgenin, and pennogenin) and the phytosterols, stigmasterol and beta-sitosterol were isolated from Jamaican bitter yam, Dioscorea polygonoides...
  6. Li N, Huang Y, Xiao W, Liu J, Li X, Li P. Synthesis and cytotoxic activities of new fatty acid esters of 20(S)-protopanaxadiol. Z Naturforsch C. 2011;66:199-204 pubmed
  7. Lee M, Sorn S, Baek S, Jang S, Kim S. Antioxidant and apoptotic effects of korean white ginseng extracted with the same ratio of protopanaxadiol and protopanaxatriol saponins in human hepatoma HepG2 cells. Ann N Y Acad Sci. 2009;1171:217-27 pubmed publisher
  8. Xie H, Wang G, Chen M, Jiang X, Li H, Lv H, et al. Uptake and metabolism of ginsenoside Rh2 and its aglycon protopanaxadiol by Caco-2 cells. Biol Pharm Bull. 2005;28:383-6 pubmed
    ..Kinetic analysis of ppd showed a non-saturable component (Kd 0.78 nmol x h(-1) x mg(-1) protein). It was suggested that active extrusion of P-glycoprotein and drug degradation in the intestine may influence Rh2 bioavailability. ..
  9. Kang K, Kim H, Yoo H, Piao X, Ham J, Yang H, et al. Protective effect of ginseng sapogenins against 2,2'-azobis (1-aminopropane) dihydrochloride (AAPH)-induced LLC-PK? cell damage. Bioorg Med Chem Lett. 2012;22:634-7 pubmed publisher
    The effect of ginseng sapogenins, aglycone parts of ginsenosides, against oxidative damage by radical generator, 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPH), in renal epithelial LLC-PK(1) cells was investigated to identify the ..

More Information

Publications91

  1. Zhao J, Li N, Zhang H, Wu C, Piao H, Zhao Y. Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities. Bioorg Med Chem Lett. 2011;21:1027-31 pubmed publisher
    Three new dammarane-type sapogenins (1, 3, and 5) together with two known ones (2 and 4) were isolated from the total hydrolyzed saponins extracted from Panax ginseng berry...
  2. Choi J, Jung H, Lee K, Park H. Antinociceptive and anti-inflammatory effects of the saponin and sapogenins obtained from the stem of Akebia quinata. J Med Food. 2005;8:78-85 pubmed
    ..It has been reported that saponins in medicinal plants may act as bioactive components after biodegradation to sapogenins in the gastrointestinal tract. To find the active components, we obtained the methanol (MeOH) extract from A...
  3. Ming Y, Song G, Chen L, Zheng Z, Chen Z, Ouyang G, et al. Anti-proliferation and apoptosis induced by a novel intestinal metabolite of ginseng saponin in human hepatocellular carcinoma cells. Cell Biol Int. 2007;31:1265-73 pubmed
    ..These results provide significant insight into the anticarcinogenic action of IH-901. ..
  4. Lee J, Shin J, Chun K, Park K, Chung W, Bang Y, et al. Antitumor promotional effects of a novel intestinal bacterial metabolite (IH-901) derived from the protopanaxadiol-type ginsenosides in mouse skin. Carcinogenesis. 2005;26:359-67 pubmed
    ..Taken together, these findings suggest that IH-901 exerts anti-inflammatory effects by inhibiting TPA-induced COX-2 expression, which may contribute to its antitumor-promoting effects on mouse skin carcinogenesis. ..
  5. Wang W, Wang H, Rayburn E, Zhao Y, Hill D, Zhang R. 20(S)-25-methoxyl-dammarane-3beta, 12beta, 20-triol, a novel natural product for prostate cancer therapy: activity in vitro and in vivo and mechanisms of action. Br J Cancer. 2008;98:792-802 pubmed publisher
    ..In conclusion, our preclinical data indicate that 25-OCH3-PPD is a potential therapeutic agent against both androgen-dependent and androgen-independent prostate cancer. ..
  6. Tawab M, Bahr U, Karas M, Wurglics M, Schubert Zsilavecz M. Degradation of ginsenosides in humans after oral administration. Drug Metab Dispos. 2003;31:1065-71 pubmed
    ..These products are probably responsible for the action of ginseng in humans. In opposition to previous reports, G-Rb1 was identified in plasma and urine of one subject. ..
  7. Weissenberg M. Isolation of solasodine and other steroidal alkaloids and sapogenins by direct hydrolysis-extraction of Solanum plants or glycosides therefrom. Phytochemistry. 2001;58:501-8 pubmed
    ..Pure Solanum glycoalkaloids were also prepared and hydrolysed accordingly. The process has analytical applications too, and could be extended in a general way to glycosides in other series for preparation of their related aglycones. ..
  8. Usami Y, Liu Y, Lin A, Shibano M, Akiyama T, Itokawa H, et al. Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra. J Nat Prod. 2008;71:478-81 pubmed publisher
    ..We investigated the antiangiogenic effects of 20( S)-protopanaxadiol ( 1) and 20( S)-protopanaxatriol ( 2), the sapogenins of two major ginseng saponins, in an angiogenesis model of human umbilical vein endothelial cells (HUVECs)...
  9. Shibata S. Chemistry and cancer preventing activities of ginseng saponins and some related triterpenoid compounds. J Korean Med Sci. 2001;16 Suppl:S28-37 pubmed
    ..A. Meyer (Araliaceae). The genuine sapogenins of those saponins, 20(S)-protopanaxa-diol and -triol, were identified as 20(S) 12beta-hydroxy-and 20(S) 6alpha,..
  10. Liu H, Chou G, Wu T, Guo Y, Wang S, Wang C, et al. Steroidal sapogenins and glycosides from the rhizomes of Dioscorea bulbifera. J Nat Prod. 2009;72:1964-8 pubmed publisher
    Four new steroidal sapogenins (1-4), named diosbulbisins A-D, two new spirostane glycosides, diosbulbisides A (5) and B (6), one new cholestane glycoside, diosbulbiside C (7), and the known compounds 8-10 were isolated from rhizomes of ..
  11. Zhu G, Li Y, Tse A, Hau D, Leung C, Yu Z, et al. 20(S)-Protopanaxadiol, a metabolite of ginsenosides, induced cell apoptosis through endoplasmic reticulum stress in human hepatocarcinoma HepG2 cells. Eur J Pharmacol. 2011;668:88-98 pubmed publisher
    ..Taken together, we have identified ER as a molecular target of PPD and our data support the hypothesis that PPD induces HepG2 cell apoptosis through the ER stress pathway. ..
  12. Han M, Chen J, Chen S, Wang X. Development of a UPLC-ESI-MS/MS assay for 20(S)-protopanaxadiol and pharmacokinetic application of its two formulations in rats. Anal Sci. 2010;26:749-53 pubmed
  13. Dong H, Bai L, Wong V, Zhou H, Wang J, Liu Y, et al. The in vitro structure-related anti-cancer activity of ginsenosides and their derivatives. Molecules. 2011;16:10619-30 pubmed publisher
    ..The results clearly indicate the structure-related activities in which the compound with less polar chemical structures possesses higher cytotoxic activity towards cancer cells. ..
  14. Fauce S, Jamieson B, Chin A, Mitsuyasu R, Parish S, Ng H, et al. Telomerase-based pharmacologic enhancement of antiviral function of human CD8+ T lymphocytes. J Immunol. 2008;181:7400-6 pubmed
    ..Our study is the first to use a pharmacological telomerase-based approach to enhance immune function, thus directly addressing the telomere loss immunopathologic facet of chronic viral infection. ..
  15. Wang C, Yuan C. Potential role of ginseng in the treatment of colorectal cancer. Am J Chin Med. 2008;36:1019-28 pubmed
    ..This heat treatment process may increase the role of ginseng in treating colorectal cancer. ..
  16. Du G, Dai Q, Williams S, Wang C, Yuan C. Synthesis of protopanaxadiol derivatives and evaluation of their anticancer activities. Anticancer Drugs. 2011;22:35-45 pubmed publisher
    ..A flow cytometric assay indicated that compounds 1, 3, and 5 arrested cell cycle progression in the G1 phase and significantly induced apoptosis of cancer cells. ..
  17. Li L, Chen X, Li D, Zhong D. Identification of 20(S)-protopanaxadiol metabolites in human liver microsomes and human hepatocytes. Drug Metab Dispos. 2011;39:472-83 pubmed publisher
    ..The findings of this study strongly suggested that the formation of the 25-hydroxyl group is very important for the elimination of PPD. ..
  18. Kasai R, Hara K, Dokan R, Suzuki N, Mizutare T, Yoshihara S, et al. Major metabolites of ginseng sapogenins formed by rat liver microsomes. Chem Pharm Bull (Tokyo). 2000;48:1226-7 pubmed
    Incubation of ginseng sapogenins with microsomes from rat liver resulted in formation of their 20,24-epoxides as major metabolites. Identification of the metabolites was performed by HPLC, FAB-MS and EI-MS.
  19. Popovich D, Kitts D. Ginsenosides 20(S)-protopanaxadiol and Rh2 reduce cell proliferation and increase sub-G1 cells in two cultured intestinal cell lines, Int-407 and Caco-2. Can J Physiol Pharmacol. 2004;82:183-90 pubmed
    ..05) than for PT treatment at most time periods. These results show a specific structure-function relationship for bioactive ginsenosides in two contrasting intestinal cell types. ..
  20. Park M, Bae C, Lim S, Kim D, Lim J, Kim J, et al. Effect of protopanaxadiol derivatives in high glucose-induced fibronectin expression in primary cultured rat mesangial cells: role of mitogen-activated protein kinases and Akt. Arch Pharm Res. 2010;33:151-7 pubmed publisher
    ..In conclusion, ginsenoside Rb1 prevented high glucose-induced increase of fibronectin expression via the inhibition of MAPK-Akt signaling cascade. ..
  21. Liu G, Bu X, Yan H, Jia W. 20S-protopanaxadiol-induced programmed cell death in glioma cells through caspase-dependent and -independent pathways. J Nat Prod. 2007;70:259-64 pubmed
    ..These results showed that 20S-protopanaxadiol (1) induces different forms of programmed cell death, including both typical apoptosis and autophagy through both caspase-dependent and -independent mechanisms. ..
  22. Liu Y, Yang G, Bu X, Liu G, Ding J, Li P, et al. Cell-type-specific regulation of raft-associated Akt signaling. Cell Death Dis. 2011;2:e145 pubmed publisher
    ..Lipid rafts differ in different types of cells, which allows for the possibility of cell-type-specific targeting for which aPPD might prove to be a useful agent. ..
  23. Li T, Wang Y, Wang Y, Liang R, Zhang D, Zhang H, et al. Development of an SPE-HPLC-MS method for simultaneous determination and pharmacokinetic study of bioactive constituents of Yu Ping Feng San in rat plasma after oral administration. J Ethnopharmacol. 2013;145:784-92 pubmed publisher
    ..06-20.44h). This analytical method is a selective, sensitive, precise, accurate, and reliable assay for simultaneous determination of cycloastragenol, calycosin, formononetin, GMV, and cimifugin in rat plasma. ..
  24. Li W, Zhang M, Zheng Y, Li J, Wang Y, Wang Y, et al. Snailase preparation of ginsenoside M1 from protopanaxadiol-type ginsenoside and their protective effects against CCl4-induced chronic hepatotoxicity in mice. Molecules. 2011;16:10093-103 pubmed publisher
    ..Therefore, the results of this study show that PDG and G-M1 can be proposed to protect the liver against CCl(4)-induced oxidative injury in mice, and the hepatoprotective effect might be attributed to amelioration of oxidative stress. ..
  25. Lee J, Jeong S, Lee B, Kim D, Kim J, Kim J, et al. Differential effect of bovine serum albumin on ginsenoside metabolite-induced inhibition of alpha3beta4 nicotinic acetylcholine receptor expressed in Xenopus oocytes. Arch Pharm Res. 2003;26:868-73 pubmed
  26. Hong S, Kim J, Ahn H, Shin J, Kwon O. Panax ginseng extract rich in ginsenoside protopanaxatriol attenuates blood pressure elevation in spontaneously hypertensive rats by affecting the Akt-dependent phosphorylation of endothelial nitric oxide synthase. J Agric Food Chem. 2012;60:3086-91 pubmed publisher
  27. Wang Y, Liu H, Zhang X, Xiao Y, Lu B, Ma Z, et al. [Screening of pregnane X receptor activation from ginsenosides]. Yao Xue Xue Bao. 2013;48:144-8 pubmed
    ..Rg1 down-regulated CYP3A4 mRNA expression in a concentration-dependent manner. Activation of pregnane X receptor by ginsenosides may influence the metabolism of drug belong to CYP3A4 substrate, and cause ginseng-drug interactions. ..
  28. Li J, He C, Fang L, Yang L, Wang Z. Identification of Human UDP-Glucuronosyltransferase 1A4 as the Major Isozyme Responsible for the Glucuronidation of 20(S)-Protopanaxadiol in Human Liver Microsomes. Int J Mol Sci. 2016;17:205 pubmed publisher
    ..In conclusion, PPD-3-O-?-D-glucuronide was first identified as the principal glucuronidation metabolite of PPD in HLMs, which was catalyzed by UGT1A4. ..
  29. Francis G, Makkar H, Becker K. Effects of Quillaja saponins on growth, metabolism, egg production and muscle cholesterol in individually reared Nile tilapia (Oreochromis niloticus). Comp Biochem Physiol C Toxicol Pharmacol. 2001;129:105-14 pubmed
    ..The muscle cholesterol level in the S300 group was significantly higher than that of the C group. Possible mechanisms of action of the dietary saponins are discussed. ..
  30. Ramos Enríquez M, Vargas Romero K, Rárová L, Strnad M, Iglesias Arteaga M. Synthesis and in vitro anticancer activity of 23(23')E-benzylidenespirostanols derived from steroid sapogenins. Steroids. 2017;128:85-88 pubmed publisher
    ..synthesis including BF3·Et2O-catalyzed aldol condensation of several acetylated steroid sapogenins with benzaldehyde followed by saponification...
  31. Mathiyalagan R, Kim Y, Wang C, Jin Y, Subramaniyam S, Singh P, et al. Protopanaxadiol aglycone ginsenoside-polyethylene glycol conjugates: synthesis, physicochemical characterizations, and in vitro studies. Artif Cells Nanomed Biotechnol. 2016;44:1803-1809 pubmed
    ..Overall, results suggest that pH-dependent release of PPD, which expected in reduced cytotoxicity to non-targeted regions, may enhance the overall efficacy of PPD. ..
  32. Huang Z, Lin J, Cheng Z, Xu M, Huang X, Yang Z, et al. Production of dammarane-type sapogenins in rice by expressing the dammarenediol-II synthase gene from Panax ginseng C.A. Mey. Plant Sci. 2015;239:106-14 pubmed publisher
    ..LC/MS analysis confirmed production of PPD and PPT. These results indicate that a new "ginseng rice" germplasm containing dammarane-type sapogenins has been successfully developed by transforming the ginseng DS gene into rice.
  33. Lai L, Liu Y, Hao H, Wang G, Chen X, Ren H. Determination of 20(S)-ginsenoside Rh1 and its aglycone 20(S)-protopanaxatriol in rat plasma by sensitive LC-APCI-MS method and its application to pharmacokinetic study. Eur J Mass Spectrom (Chichester). 2009;15:57-65 pubmed publisher
    ..After intravenous administrations, the mean retention times of 20(S)-ginsenoside Rh1 and 20(S)-protopanaxatriol were 17.1 +/- 2.0 min and 3.46 +/- 0.33 h, respectively. ..
  34. Shin K, Oh H, Kim B, Oh D. Complete conversion of major protopanaxadiol ginsenosides to compound K by the combined use of ?-L-arabinofuranosidase and ?-galactosidase from Caldicellulosiruptor saccharolyticus and ?-glucosidase from Sulfolobus acidocaldarius. J Biotechnol. 2013;167:33-40 pubmed publisher
    ..This is the first report of the complete conversion of major protopanaxadiol ginsenosides to compound K. ..
  35. Camoutsis C, Trafalis D, Pairas G, Papageorgiou A. On the formation of 4-[N,N-bis(2-chloroethyl)amino]phenyl acetic acid esters of hecogenin and aza-homo-hecogenin and their antileukemic activity. Farmaco. 2005;60:826-9 pubmed
    ..These results support that the alkylating esters of hecogenin produce important antitumor activity as well as, indicate that the aza-homo-hecogenin ester exhibits significantly higher activity due to lactam group (-NHCO-) modification. ..
  36. Carelli M, Biazzi E, Panara F, Tava A, Scaramelli L, Porceddu A, et al. Medicago truncatula CYP716A12 is a multifunctional oxidase involved in the biosynthesis of hemolytic saponins. Plant Cell. 2011;23:3070-81 pubmed publisher
    ..The analysis of CYP716A12 expression in planta is reported together with the sapogenin content in different tissues and stages. This article provides evidence for CYP716A12 being a key gene in hemolytic saponin biosynthesis...
  37. Liu Q, Liang H, Zhao Y, Wang B, Yang W, Yu Y. Saikosaponin v-1 from roots of Bupleurum chinense DC. J Asian Nat Prod Res. 2001;3:139-44 pubmed
    ..Saikosaponin v-1 is a new compound, which was identified as 3beta,16alpha,23,28-tetrahydroxy-olean-11,13(18)-dien-30-oic acid-3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-fucopyranosyl-30-O-xylitol ester. ..
  38. Li W, Fuchs P. Polyphosphoric acid trimethylsilyl ester promoted intramolecular acylation of an olefin by a carboxylic acid: convenient construction of C-18-functionalized delta14-hecogenin acetate. Org Lett. 2003;5:4061-4 pubmed
    ..Studies led to the synthesis of C-18 functionalized steroidal compounds 5 and 9a-d with strict retention of the spiroketals. Isomerization of spiroketal 9e was studied. ..
  39. López Y, Ruíz Pérez K, Yépez R, Santillan R, Flores Alamo M, Iglesias Arteaga M. Mechanistic insights and new products of the reaction of steroid sapogenins with NaNO2 and BF3.Et2O in acetic acid. Steroids. 2008;73:657-68 pubmed publisher
    A detailed analysis of the course of the reaction of steroid sapogenins with NaNO(2) and BF(3).Et(2)O in acetic acid is presented and some evidences on the involved mechanism are provided...
  40. Mysterud I, Flåøyen A, Loader J, Wilkins A. Sapogenin levels in Narthecium ossifragum plants and Ovis aries lamb faeces during two alveld outbreaks in Møre og Romsdal, Norway, 2001. Vet Res Commun. 2007;31:895-908 pubmed
    ..Generally similar levels of sapogenins, determined after hydrolysis of parent plant saponins, were found in Narthecium leaves collected in June/July ..
  41. Nohara T, Okamoto K, Matsushita S, Fujiwara Y, Ikeda T, Miyashita H, et al. Mechanism for conversion of spirosolane derivative into pregnane. Chem Pharm Bull (Tokyo). 2008;56:1015-7 pubmed
    ..Its chemical mechanism including air oxidation is here described. ..
  42. Yang X, Wang Y, Liu Y, Tang X. Pharmacokinetics of salvianolic acids after intravenous injection, with and without Panax quinquefolium protopanaxadiol saponins, in rats. J Ethnopharmacol. 2008;117:408-14 pubmed publisher
    ..The results indicated that the PQDS extracts could delay the excretion of salvianolic acids as well as maintain the blood concentration higher than salvianolic acids extracts administered alone. ..
  43. Liu Y, Li W, Li P, Deng M, Yang S, Yang L. The inhibitory effect of intestinal bacterial metabolite of ginsenosides on CYP3A activity. Biol Pharm Bull. 2004;27:1555-60 pubmed
    ..This finding demonstrates that differences in their chemical structure might influence the effects of ginsenosides on CYP3A activity and that ginseng-derived products might have potential for significant ginseng-drug interactions. ..
  44. Al Sharif M, Alov P, Diukendjieva A, Vitcheva V, Simeonova R, Krasteva I, et al. Molecular determinants of PPARγ partial agonism and related in silico/in vivo studies of natural saponins as potential type 2 diabetes modulators. Food Chem Toxicol. 2018;112:47-59 pubmed publisher
    ..Saponins and sapogenins are considered as valuable natural products for ameliorating this pathology, possibly through the nuclear ..
  45. Chan L, Kwok H, Chan R, Peiris M, Mak N, Wong R, et al. Dual functions of ginsenosides in protecting human endothelial cells against influenza H9N2-induced inflammation and apoptosis. J Ethnopharmacol. 2011;137:1542-6 pubmed publisher
    ..This report further supports the traditional belief for immunomodulatory effects of ginseng, also demonstrated the partial protective mechanism of ginsenosides on avian influenza infection and its related endothelial dysfunction. ..
  46. Han H, Park S, Koh H, Nah S, Shin D, Choi H. Protopanaxatriol ginsenosides inhibit glucose uptake in primary cultured rabbit renal proximal tubular cells by arachidonic acid release. Kidney Blood Press Res. 1999;22:114-20 pubmed
    ..In conclusion, PT saponin inhibited, in part, alpha-MG uptake through the phospholipase A2 signal pathway in primary cultured rabbit renal PTCs. ..
  47. Alabdul Magid A, Voutquenne Nazabadioko L, Renimel I, Harakat D, Moretti C, Lavaud C. Triterpenoid saponins from the stem bark of Caryocar villosum. Phytochemistry. 2006;67:2096-102 pubmed
    ..The cytotoxic activity of saponins 2 and 3 was evaluated in vitro against human keratinocytes. The DOPA-oxidase inhibition and the lipolytic activities were evaluated ex vivo using an explant of human adipose tissue. ..
  48. Shao N, Jiang H, Wang X, Yuan B, Jin Y, Song M, et al. Stereoselective pharmacokinetics of 25-methoxyl-dammarane-3?,12?,20-triol and its active demethyl-metabolite epimers in rats after oral and intravenous administration. Fitoterapia. 2017;116:139-145 pubmed publisher
    ..25-OCH3-PPD) and 25-hydoxyprotopanaxadiol (25-OH-PPD) are novel protopanaxadiol-type (PPD) sapogenins. 25-OH-PPD was also the in vivo bioactive demethyl-metabolite of 25-OCH3-PPD...
  49. Chen G, Yang X, Zhai X, Yang M. Microbial transformation of 20(S)-protopanaxatriol by Absidia corymbifera and their cytotoxic activities against two human prostate cancer cell lines. Biotechnol Lett. 2013;35:91-5 pubmed publisher
    ..The metabolites 2, 6, 7, and 8 showed the more potent inhibitory effects against DU-145 and PC-3 cell lines than the substrate. ..
  50. Yim H, Jong H, Kim T, Choi H, Kim S, Song S, et al. Cyclooxygenase-2 inhibits novel ginseng metabolite-mediated apoptosis. Cancer Res. 2005;65:1952-60 pubmed
    ..In conclusion, IH-901 induced both G1 arrest and apoptosis, and this apoptosis could be inhibited by COX-2 induction. ..
  51. Fernández Herrera M, López Muñoz H, Hernández Vázquez J, Sánchez Sánchez L, Escobar Sánchez M, Pinto B, et al. Synthesis and selective anticancer activity of steroidal glycoconjugates. Eur J Med Chem. 2012;54:721-7 pubmed publisher
    The synthesis of glucosamine derivatives of the steroidal sapogenins diosgenin and hecogenin using the N-phthaloyl protected trichloroacetimidate of d-glucosamine as donor and TMSOTf as promoter is reported...
  52. Zhao Y, Bu L, Yan H, Jia W. 20S-protopanaxadiol inhibits P-glycoprotein in multidrug resistant cancer cells. Planta Med. 2009;75:1124-8 pubmed publisher
    ..It is also the first time that aPPD has showed a reversible nature of its P-gp inhibition. In addition to its pro-apoptotic nature, aPPD may be a potential new P-gp inhibitor for cancer treatment. ..
  53. Wang H, Guo Y, Guan Y, Zhou L, Lei P. The synthesis of cholestane and furostan saponin analogues and the determination of sapogenin's absolute configuration at C-22. Steroids. 2011;76:18-27 pubmed publisher
    ..The cytotoxicities of the synthetic analogues toward four types of tumor cells were shown also. ..
  54. Liao S, Wang Z, Wu Y, Zhang L, Li J, Wang A, et al. Report: structures and hepatocytotoxicity of co-occurring substances in oleanolic acid tablets. Pak J Pharm Sci. 2014;27:601-5 pubmed
    ..The results suggested that OA tablets of similar origin might not cause obvious cytotoxicity to the normal liver cell. The work may facilitate further SAR studies of OA-type triterpenoids. ..
  55. Manabe H, Fujiwara Y, Ikeda T, Ono M, Murakami K, Zhou J, et al. Saponins esculeosides B-1 and B-2 in Italian canned tomatoes. Chem Pharm Bull (Tokyo). 2013;61:764-7 pubmed
    ..To confirm that hypothesis, we refluxed esculeoside A with water for 6.5?h, providing esculeosides B-1 (1) and B-2 (2) in yields of 25.8% and 31.0%, respectively. ..
  56. Li K, Chen X, Xu J, Li X, Zhong D. Liquid chromatography/tandem mass spectrometry for pharmacokinetic studies of 20(R)-ginsenoside Rg3 in dog. Rapid Commun Mass Spectrom. 2005;19:813-7 pubmed
    ..This quantitation method was successfully applied to pharmacokinetic studies of Rg3 after both an oral and an intravenous administration to beagle dogs. No Rh2 and protopanaxadiol were detected in plasma. ..
  57. Wang Y, Chen J, Luo X, Zhang Y, Si M, Wu H, et al. Ginsenoside metabolite compound K exerts joint-protective effect by interfering with synoviocyte function mediated by TNF-α and Tumor necrosis factor receptor type 2. Eur J Pharmacol. 2016;771:48-55 pubmed publisher
    ..Our data suggest that CK exerts joint-protective effect by interfering with synoviocyte function mediated by TNF-α and TNFR2, and this effect may be mediated by GR. ..
  58. Wang T, Ruan J, Li X, Chao L, Shi P, Han L, et al. Bioactive cyclolanstane-type saponins from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao. J Nat Med. 2016;70:198-206 pubmed publisher
    ..Meanwhile, compounds 1-3, 5-9, and aleksandroside I (12) showed inhibitory effects on triglyceride accumulation in HepG2 cells. ..
  59. Danieli B, Falcone L, Monti D, Riva S, Gebhardt S, Schubert Zsilavecz M. Regioselective enzymatic glycosylation of natural polyhydroxylated compounds: galactosylation and glucosylation of protopanaxatriol ginsenosides. J Org Chem. 2001;66:262-9 pubmed
    ..GalT was also able to accept UDP-glucose as an activated sugar donor, giving rise to cellobiosyl derivatives of Rg1. ..
  60. Ming Y, Chen Z, Chen L, Tong Q, Zheng Z, Zheng G, et al. [Inhibitory effect of ginseng saponin IH901 on proliferation and metastasis of ECV304 cell line and its molecular mechanism]. Yao Xue Xue Bao. 2009;44:967-72 pubmed
    ..Therefore, IH901 dramatically suppresses cell proliferation and adhesion and migration of ECV304 cell line. ..
  61. Marciani D, Pathak A, Reynolds R, Seitz L, May R. Altered immunomodulating and toxicological properties of degraded Quillaja saponaria Molina saponins. Int Immunopharmacol. 2001;1:813-8 pubmed
  62. Yoo M, Yeom S, Park C, Lee K, Oh D. Production of aglycon protopanaxadiol via compound K by a thermostable ?-glycosidase from Pyrococcus furiosus. Appl Microbiol Biotechnol. 2011;89:1019-28 pubmed publisher
    ..5% and 1,610 mg l(-1) h(-1) at 1.2 h and were hydrolyzed completely to APPD with 300 mg l(-1) h(-1) after 6 h. The concentrations and productivities of compound K and APPD in the present study are the highest ever reported. ..
  63. Azerad R. Chemical structures, production and enzymatic transformations of sapogenins and saponins from Centella asiatica (L.) Urban. Fitoterapia. 2016;114:168-187 pubmed publisher
    ..of specific pentacylic triterpenoid saponins, mainly asiaticoside and madecassoside and the corresponding sapogenins. This review summarizes the updated knowledge about the chemical structures of about forty centelloids, found as ..
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    ..52, 4.34, and 6.57%, respectively. These results indicate that the BA for the inclusion complex was 1.9-fold higher than that for the pure IH901 powder. ..
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    ..The in vitro cytotoxic activities of metabolites against three human cancer cell lines were determined by the MTT method; compounds 8a, 9 and 10 had more potent inhibitory effects against HL-60 cell line than the substrate. ..
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    ..a facile protocol to obtain 22-substituted furostans and pseudosapogenins in high yields from (25R)- and (25S)-sapogenins. This method involves the treatment of the sapogenin with acetic-trifluoroacetic mixed anhydride and BF(3)·OEt(..
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    ..The results suggest that both saikosaponin a and TPA-induced HepG2 growth inhibition are associated with p-15(INK4a) and p-16(INK4b) gene expression and might be mediated by PKC signaling pathway. ..
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    ..Under these conditions, P. furiosus ?-glucosidase completely converted from R1 to Rg1 after 10 h, with a productivity of 0.4 g l?1 h?1 and completely converted Rf to Rh1 after 1.2 h, with a productivity of 2.74 g l?1 h?1. ..
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    ..These findings demonstrate that E2 exerts condition-dependent bidirectional effects on NMDA receptor-mediated transmission and, thus, synaptic plasticity via ER? and ER? in the dentate gyrus of juvenile male rats. ..
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    Dammarane Sapogenins (DS), with main ingredients of protopanaxatriol (PPT, 33%) and protopanaxadiol (PPD, 16%), is an alkaline hydrolyzed product of ginsenosides and had significant activities in improving learning and memory and ..
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    ..However, given that the varied contribution of these two UGT isoforms towards drug metabolism and the influence of herb complexity and individual difference, the explanation of these results should be paid more caution. ..
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    ..These findings support a crucial role of gut bacterial conversion of AIV in the traditional application of Astragali herb and warrant further investigational emphasis on CA and CA-iso. ..
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    ..Thus, CYP716A47 is a dammarenediol 12-hydroxylase that produces protopanaxadiol from dammarenediol-II. ..
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