Pomolic acid and its glucopyranose ester promote apoptosis through autophagy in HT-29 colon cancer cells.

BACKGROUND: Colon cancer remains a leading cause of death globally. Pomolic acid (PA) can be separated from the ethyl acetate fraction of achyrocline satureioides. AIM: To determine the effects of PA and its glucopyranose ester, pomolic acid-28-O-ß-D-glucopyranosyl ester (PAO), on colon cancer HT-29 cells. METHODS: 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide assay was used to measure cell viability. Apoptosis was detected via hoechst 33342 staining. PI single staining was identified by flow cytometry to determine the cycle and scratch assay was used to observe the migration of HT-29 cells. The levels of mRNA and proteins were evaluated by q polymerase chain reaction and western blotting, respectively. RESULTS: PA and PAO considerably inhibited the growth of the HT-29 cell line in a time and dose-dependent manner. After the administration of PA and PAO for 24 and 48 h, cell apoptosis was significantly promoted and HT-29 cells were arrested in the G0/G1 stage. The Bax/Bcl2 ratio was also increased, which activated cysteinyl aspartate specific proteinase 3, leading to apoptosis; it also increased the expression of light chain 3 II/I and Beclin1, which activated autophagy and caused cell death. This in turn increased the expression of p62 to promote cell apoptosis, inhibiting the levels of signal transducer and activator of transcription 3 (STAT3) and p-STAT3, suppressing the level of Bcl2, and promoting cell. CONCLUSION: Both PA and PAO provide novel therapeutic strategies for treating colorectal cancer.

Recent Advances Regarding the Molecular Mechanisms of Triterpenic Acids: A Review (Part II).

Triterpenic acids are a widespread class of phytocompounds which have been found to possess valuable therapeutic properties such as anticancer, anti-inflammatory, hepatoprotective, cardioprotective, antidiabetic, neuroprotective, lipolytic, antiviral, and antiparasitic effects. They are a subclass of triterpenes bearing a characteristic lipophilic structure that imprints unfavorable in vivo properties which subsequently limit their applications. The early investigation of the mechanism of action (MOA) of a drug candidate can provide valuable information regarding the possible side effects and drug interactions that may occur after administration. The current paper aimed to summarize the most recent (last 5 years) studies regarding the MOA of betulinic acid, boswellic acid, glycyrrhetinic acid, madecassic acid, moronic acid, and pomolic acid in order to provide scientists with updated and accessible material on the topic that could contribute to the development of future studies; the paper stands as the sequel of our previously published paper regarding the MOA of triterpenic acids with therapeutic value. The recent literature published on the topic has highlighted the role of triterpenic acids in several signaling pathways including PI3/AKT/mTOR, TNF-alpha/NF-kappa B, JNK-p38, HIF-α/AMPK, and Grb2/Sos/Ras/MAPK, which trigger their various biological activities.

[Retracted] Antitumor­ and apoptosis­inducing effects of pomolic acid against SK­MEL­2 human malignant melanoma cells are mediated via inhibition of cell migration and sub­G1 cell cycle arrest.

Following the publication of the above paper, a concerned reader drew to the Editor's attention that several figures (Figs. 3­8 inclusive) contained apparent anomalies, including repeated patternings of data within the same figure panels. After having conducted an independent investigation in the Editorial Office, the Editor of Molecular Medicine Reports has determined that the above paper should be retracted from the Journal on account of a lack of confidence concerning the originality and the authenticity of the data. The authors were asked for an explanation to account for these concerns, but the Editorial Office never received any reply. The Editor regrets any inconvenience that has been caused to the readership of the Journal. [the original article was published on Molecular Medicine Reports 17: 1035­1040, 2018; DOI: 10.3892/mmr.2017.7977].

Pomolic acid in persimmon peel suppresses the increase in glycerol-3 phosphate dehydrogenase activity in 3T3-L1 adipocytes.

Persimmon peels, though usually discarded, are useful sources of nutraceuticals. In this study, persimmon peel-derived pomolic acid was found to suppress the increase in the activity of glycerol-3 phosphate dehydrogenase, a neutral fat synthesis-related enzyme, in 3T3-L1 adipocytes, whereas oleanolic and ursolic acids did not exert this effect. Therefore, persimmon peel may be an effective functional food material.

In vitro activities of crude extracts and triterpenoid constituents of Dichapetalum crassifolium Chodat against clinical isolates of Schistosoma haematobium.

Dichapetalum crassifolium Chodat (Dichapetalaceae) is widely distributed in Africa, Tropical Asia and Latin America. As part of our quest for potential bioactive lead compounds for various neglected tropical diseases, we report the anti-schistosomal potential of the crude extracts and chemical constituents of the stems and roots of Dichapetalum crassifolium. Column chromatography of extracts of the stems and roots led to the isolation and identification of three oleanane-type triterpenoids, friedelan-3ß-ol (1), friedelan-3-one (2), and maslinic acid (3); the ursane-type tritepenoid, pomolic acid (4) and the dammarane-type tetracyclic triterpenoids, dichapetalin A (5) and dichapetalin M (6). Dichapetalin A was isolated from only the roots. Isolated compounds were identified by comparison of their physico-chemical and spectral data with published data. The highest in vitro anti-schistosomal activity (IC50) of the crude extracts against clinical isolates of Schistosoma haematobium (Bilharz 1852) was 248.6 µg/ml for the ethyl acetate extract of the root while dichapetalin A gave the highest activity at 151.1 µg/ml among the compounds compared with the 15.5 µg/ml for the standard drug, praziquantel. The rest of the compounds showed activities in the order 177.9, 191.0, and 378.1 µg/ml respectively for mixture of ß-sitosterol/stigmasterol, dichapetalin M and friedelan-3-one. The least active extract was the methanol extract of the stem (893.7 µg/ml). The constituents of D. crassifolium showed activity against the S. haematobium that are below praziquantel. It is envisaged that the presence of multiple layers and the minute sizes of pores in the egg shells, may preclude penetration of eggs by the compounds.

Pomolic acid reduces contractility and modulates excitation-contraction coupling in rat cardiomyocytes.

Pomolic acid (PA) isolated from Licania pittieri has hypotensive effects in rats, inhibits human platelet aggregation and elicits endothelium-dependent relaxation in rat aortic rings. The present study was designed to investigate the effects of PA on cardiomyocytes. Trabeculae and enzymatically isolated cardiomyocytes from rats were used to evaluate the concentration-dependent effects of PA on cardiac muscle tension and excitation-contraction coupling (ECC) by recording Ca2+ transients reported with Fluo-3 and Fura-2, as well as L-type Ca2+ currents (LTCC). PA reduced the contractile force in rat cardiac trabeculae with an EC50 = 14.3 ±â€¯2.4 µM. PA also reduced the amplitude of Ca2+ transients in a concentration-dependent manner, with an EC50 = 10.5 ±â€¯1.3 µM, without reducing sarcoplasmic reticulum (SR) Ca2+ loading. PA decreased the half width of the Ca2+ transient by 31.7 ±â€¯3.3% and increased the decay time and decay time constant (τ) by 7.6 ±â€¯2.7% and 75.6 ±â€¯3.7%, respectively, which was associated with increased phospholamban (PLN) phosphorylation. PA also reversibly reduced the macroscopic LTCC in the cardiomyocyte membrane, but did not demonstrate any effects on skeletal muscle ECC. In conclusion, PA reduces LTCC, Ca2+ transients and cardiomyocyte force, which along with its vasorelaxant effects explain its hypotensive properties. Increased PLN phosphorylation protected the SR from Ca2+ depletion. Considering the effects of PA on platelet aggregation and the cardiovascular system, we propose it as a new potential, multitarget cardiovascular agent with a demonstrated safety profile.

A new caffeoyl glucoside from Hedyotis caudatifolia with antitumor activity / 中草药

Objective To study the chemical constituents of Hedyotis caudatifolia. Methods These compounds were isolated from H. caudatifolia and purified by repeated silica gel, polyamine, Sephadex LH-20 column chromatography and other methods. Their structures were identified by NMR, MS, and physico-chemical properties. Results Ten compounds were isolated and elucidated as hedycaffeoylglucoside A (1), β-sitosterol (2), 5α-stigmastane-3,6-dione (3), 7-hydroxy-6-methoxycoumarin (4), oleanolic acid (5), ursolic acid (6), pomolic acid (7), 3α,19α-dihydroxyurs-12-en-24,28-dioic acid (8), 2α,3β,24-trihydroxyolean-12-en-28-oic acid (9), and 2α,3α-dihydroxyolean-12-en-28-oic acid (10), respectively. Conclusion Compound 1 is a new caffeoyl glucoside and compounds 7-10 are isolated from this plant for the first time. Compound 1 exhibits cytotoxicity against four tumor cells.

Pomolic Acid Ameliorates Fibroblast Activation and Renal Interstitial Fibrosis through Inhibition of SMAD-STAT Signaling Pathways.

Fibrosis is a common pathological feature in most kinds of chronic kidney disease. Transforming growth factor ß1 (TGF-ß1) signaling is the master pathway regulating kidney fibrosis pathogenesis, in which mothers against decapentaplegic homolog 3 (SMAD3) with signal transducer and activator of transcription 3 (STAT3) act as the integrator of various pro-fibrosis signals. We examine the effects of pomolic acid (PA) on mice with unilateral ureteral obstruction (UUO) and TGF-ß1 stimulated kidney fibroblast cells. UUO mice were observed severe tubular atrophy, and tubulointerstitial fibrosis and extracellular matrix (ECM) deposition at seven days postoperatively. However, PA-treated UUO mice demonstrated only moderate injury, minimal fibrosis, and larger reductions in the expression of ECM protein and epithelial-mesenchymal transition (EMT) progress. PA inhibited the SMAD-STAT phosphorylation in UUO mice. PA effects were also confirmed in TGF-ß1 stimulated kidney fibroblast cells. In this study, we first demonstrated that PA ameliorates fibroblast activation and renal interstitial fibrosis. Our results indicate that PA may be useful as a potential candidate in the prevention of chronic kidney disease.

Antitumor Effect of Pomolic Acid in Acute Myeloid Leukemia Cells Involves Cell Death, Decreased Cell Growth and Topoisomerases Inhibition.

BACKGROUND: Acute myeloid leukemia (AML) represents the largest number of annual deaths from hematologic malignancy. In the United States, it was estimated that 21.380 individuals would be diagnosed with AML and 49.5% of patients would die in 2017. Therefore, the search for novel compounds capable of increasing the overall survival rate to the treatment of AML cells is urgent. OBJECTIVES: To investigate the cytotoxicity effect of the natural compound pomolic acid (PA) and to explore the mechanism of action of PA in AML cell lines with different phenotypes. METHODS: Three different AML cell lines, HL60, U937 and Kasumi-1 cells with different mechanisms of resistance were used to analyze the effect of PA on the cell cycle progression, on DNA intercalation and on human DNA topoisomerases (hTopo I and IIα) in vitro studies. Theoretical experiments of the inhibition of hTopo I and IIα were done to explore the binding modes of PA. RESULTS: PA reduced cell viability, induced cell death, increased sub-G0/G1 accumulation and activated caspases pathway in all cell lines, altered the cell cycle distribution and inhibited the catalytic activity of both human DNA topoisomerases. CONCLUSION: Finally, this study showed that PA has powerful antitumor activity against AML cells, suggesting that this natural compound might be a potent antineoplastic agent to improve the treatment scheme of this neoplasm.

Study on triterpenoids and their glycosides chemical constituents of Camellia sinensis / 中草药

Objective To investigate the chemical constituents from the leaf of Camellia sinensis. Methods The chemical constituents were isolated and purified by repeated silica gel column chromatography, Sephadex LH-20 gel column chromatography, ODS column chromatography, high pressure flash chromatography and semi-preparative HPLC, and their structures were elucidated on the basis of physico-chemical constants and spectral analysis. Results Nine compounds were separated from C. sinensis, among them, four compounds were identified as triterpenoids and named as 21β-hydroxyl pomolic acid (1), pomonic acid (2), pomolic acid (3), and ursolic acid (4); The other five compounds were idetified as triterpenoid saponins and named as 3-O-α-L-arabinopyranosyl pomolic acid (5), 3β-[(α-L-arabinopyranosyl)oxy]-urs-12,19 (20)-dien-28-oic acid (6), oleanolic acid-3-O-α-L-arabinopyranoside (7), 3β-[(α-L-arabinopyranosyl) oxy]-urs-12,18-dien-28-oic acid (8), and 20-epi-urs-12,18-dien-28-oic acid 3β-O-α-L-arabinopyranoside (9). Conclusion Compound 1 is a new compound, compounds 2, 3, 5-9 are obtained from this genus for the first time.

A new seco-triterpene from roots of Rosa laevifgata / 中草药

Objective Seven triterpenes were isolated from the methanol extract of the roots of Rosa laevifgata. Methods The compounds were isolated and purified by a combination of various chromatographic approaches, including silica gel, Sephadex LH-20, semipreparative HPLC and so on. Their structures were identified on the basis of pfysicochemiscal and spedtroscopic analysis. The in vitro anti-inflammatory activity test was investjgated. Results On the basis of spectroscopic data analysis, their structures were identified as 18,19-seco-2α,3β,23α-trihydoxyl-19-oxo-urs-11,13(18)-dien-28-oic acid (1), (2R,19R)-methyl 2-acetyloxy-19-hydroxyl-3-oxo-urs-12-en-28- oic acid (2), pomonic acid (3), cecropiacic acid 3-methyl ester (4), 2-acetyl tormentic acid (5), pomolic acid (6), and 2α,3α-dihydroxyurs-12,18-dien-28-oic acid (7). Conclusion Among them, compound 1 named as rosasecotriterpene A is a new triterpene. The anti-inflammatory activities of compounds 1—7 are tested in vitro. The results show that all the isolated compounds have obvious inhibitory effects on the release of NO from RAW264.7 cells induced by LPS. The inhibitory effects of compounds 1 and 7 are more significant, showing good anti-inflammatory activity in vitro.

[Apoptosis as the basic mechanism of cytotoxic action of ursolic and pomolic acids in glioma cells].

Pentacyclic triterpene acids are of great interest as compounds that exhibit selective cytotoxicity against malignant tumor cells. If earlier studies were carried out mainly in cancer cells of epithelial origin, in the present work the cytotoxic effect of ursolic and pomolic acids on the primary and permanent glioma cell lines was analyzed. Both compounds are toxic to oncotransformed cells and induce apoptosis in U-87 MG line. Using molecular docking, it has been shown that Akt1 and MDM2 may be potential targets of the studied triterpene acids. It has been suggested that ursolic and pomolic acids induce apoptosis in glioma cells through inhibition of the PI3K/Akt signaling pathway, and they can be considered as potentially promising agents for the treatment of glioblastoma.

Pomolic acid suppresses HIF1α/VEGF-mediated angiogenesis by targeting p38-MAPK and mTOR signaling cascades.

BACKGROUND: Pomolic acid (PA), an active triterpenoid from Euscaphis japonica, inhibits the proliferation of a variety of cancer cells, but the molecular mechanisms of the anti-angiogenic potential of PA have not been fully elucidated in breast cancer cells. HYPOTHESIS/PURPOSE: We investigated the molecular mechanisms underlying the anti-angiogenic effect of PA in epidermal growth factor (EGF)-responsive human breast cancer cells, MCF-7 and MDA-MB-231, and human umbilical vascular endothelial cells (HUVEC). STUDY DESIGN/METHODS: Effects of PA on EGF-induced HIF1α/VEGF expression in MCF-7, MDA-MB-231 and HUVEC were assayed. As to the mechanisms, EGF-mediated MAPKs, PI3K/Akt, and mTOR signaling pathway were performed. Wound healing and invasion assay, tube formation assay, immunoblot assay, real-time PCR, luciferase gene assay, electrophoretic mobility shift assay and immunofluorescence staining were used for assessment. RESULTS: PA significantly and selectively suppressed EGF-induced HIF1α/VEGF expression, whereas it did not affect the expression of HIF1ß in MCF-7 and MDA-MB-231. Furthermore, PA inhibited EGF-induced angiogenesis in vitro and downregulated HIF1α/VEGF expression in HUVEC. Mechanistically, we found that the inhibitory effects of PA on HIF1α/VEGF expression are associated with inhibition of HIF1α/VEGF expression through an EGF-dependent mechanism. In addition, PA suppressed the EGF-induced phosphorylation of p38-MAPK and mTOR. CONCLUSION: PA suppresses EGF-induced HIF1α protein translation by inhibiting the p38-MAPK and mTOR kinase signaling pathways and plays a novel anti-angiogenic role.

Isolation, characterization, and anthelminthic activities of a novel dichapetalin and other constituents of Dichapetalum filicaule.

CONTEXT: Dichapetalum filicaule Breteler (Dichapetalaceae) is a rare species occurring only in Côte d'Ivoire and Ghana. Although research on several species of the genus has produced interesting bioactive compounds, particularly the Dichapetalins, a novel class of triterpenoids with antineoplastic properties, there is virtually no information on the ethnobotanical uses and chemical constituents of D. filicaule. OBJECTIVE: The phytochemical and anthelminthic activities of the constituents of D. filicaule were investigated. MATERIALS AND METHODS: Chemical constituents of the petroleum ether, chloroform-acetone, and methanol root extracts of D. filicaule were isolated by column chromatography and characterized by their physico-chemical properties, 1-D and 2-D NMR spectroscopy and mass spectrometry. In vitro anthelminthic activity of the extracts and compounds against the human hookworm, Necator americanus, Stiles 1902 (Nematoda: Ancylostomatidae) was determined within a concentration range of 2500-250 µg/ml using the Egg Hatch Inhibition (EHI) Assay. The hookworm species were identified using a published polymerase chain reaction (PCR) method. RESULTS: A new dichapetalin, dichapetalin X (1), together with the known dichapetalin A (2), pomolic acid (3), glycerol monostearate (4), D:A-friedooleanan-3ß-ol (5), and D:A-friedooleanan-3-one (6) were isolated. Compounds 1, 2, and 4 exhibited EHI with IC50 values of 523.2, 162.4, and 306.0 µg/ml, respectively, against the hookworm. The positive control albendazole gave an IC50 value of 93.27 µg/ml. DISCUSSION AND CONCLUSION: This is the first report of the phytochemical investigation of D. filicaule. The study has yielded a new dichapetalin and also demonstrated the potential anthelminthic properties of the constituents.

Triterpenoids from roots of Rosa laevigata / 中草药

Objective: To study the triterpenoids from the roots of Rosa laevigata. Methods: The silica gel column chromatography was used to extract and separate the chemical constituents from the roots of R. laevigata. HPLC was used to analyze its purity, chemical and spectroscopy methods were used to determine their structures. Results: Thirteen constituents were isolated and identified as niga-ichigosides F2 (1), rosamultin (2), arjunetin (3), kaji-ichigoside F1 (4), auscaphic acid (5), cecropiacic acid 3-methyl ester (6), 2-acetyl tormentic acid (7), pomolic acid (8), 2α,3α-dihydroxyurs-12,18-dien-28-oic acid (9), 3β-E-feruloyl corosolic acid (10), fupenzic acid (11), 2-O-acetyl euscaphic acid (12), and 12,13-dihydromicromeric acid (13). Conclusion: Compounds 3, 6, 7 and 9-13 are obtained from this plant for the first time. Compounds 10, 12 and 13 are obtained from the plants of Rosa L. for the first time.

Secondary Metabolites from Leaves of Manilkara subsericea (Mart.) Dubard.

BACKGROUND: Manilkara subsericea (Sapotaceae) is a species widely spread in the sandbanks of Restinga de Jurubatiba National Park (Rio de Janeiro, Brazil). It is commonly known as "maçaranduba", "maçarandubinha" and "guracica", being used in this locality as food, and timber. However, M. subsericea remains almost unexplored regarding its chemical constituents, including secondary metabolites from the leaves. OBJECTIVE: Identify the chemical constituents from the leaves of M. subsericea. MATERIALS AND METHODS: Leaves were macerated with ethanol (96% v/v), and dried crude ethanolic extract was sequentially washed with the organic solvents in order to obtain an ethyl acetate fraction. Substances from this fraction were identified by different techniques, such as negative-ion electrospray ionization Fourier and (1)H and (13)C nuclear magnetic resonance (NMR). Fresh leaves from M. subsericea were also submitted to hydrodistillation in order to obtain volatile substances, which were identified by gas chromatograph coupled to mass spectrometer. RESULTS: NMR(1)H and (13)C spectra allowed for the identification of the compounds myricetin, quercetin, and kaempferol from the ethyl acetate fraction. The negative-ion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry mass spectrum also revealed the presence in this fraction of a polyhydroxytriterpene acid (pomolic acid), and some flavonoids, such as quercitrin, and myricitrin. In all 34 volatile compounds were identified by gas chromatography-mass spectrometry, including monoterpenes, sesquiterpenes, and long chain hydrocarbons. CONCLUSION: This study describes the first reports concerning the phytochemical information about leaves from M. subsericea. SUMMARY: Manilkara subsericea fruits proved to be a rich source of triterpenes. However, no phytochemical studies were carried out with leaves. Thus, we described identification of volatile substances from its essential oils, in addition to non-reported triterpene and flavonoids from this species.

Chemical Constituents in Charred Sanguisorbae Radix / 中草药·英文版

Objective: To study the chemical constituents in the effective fractions of charred Sanguisorbae Radix. Methods: The compounds were isolated and purified by column chromatography and their structures were identified on the basis of physicochemical properties and spectral analysis. Results: Five compounds were isolated and identified as 3β-hydroxy-28-norurs-17,19,21-trien (1), 3β-hydroxy-28-norurs-12,17-dien (2), 3β,19α-dihydroxyurs-13(18)-en-28-oic acid (3), 3β-[(α-L-arabin-opyranosyl) oxy]-28-norurs-12,17-dien (4), and pomolic acid (5). Conclusion: Compounds 1, 3, and 4 are novel compounds belong to triterpenoids and triterpenoid saponins, named as sanguisorbigenins Z, Y1, and Y2, respectively. © 2013 Tianjin Press of Chinese Herbal Medicines.

Triterpenoid components from Rosa cymosa / 中草药

Objective: To study the triterpenoid components of Rosa cymosa. Methods: Compounds were isolated by repeated chromatography on silica gel column. The structures were elucidated by chemical and spectroscopic methods. Results: Thirteen triterpenoids were isolated and identified as 2-oxo-pomolic acid (1), 2α, 19α-dihydroxy-3-oxo-12-ursen-28-oic acid (2), 2-acetyl tormentic acid (3), pomolic acid (4), euscaphic acid (5), arjunic acid (6), myrianthic acid (7), arjunetin (8), rosamultin (9), kaji-ichigoside F1 (10), 2α, 3α, 19α, 23-tetrahydroxy-12-ursen-28-O-β-D-glucoside (11), fupenzic acid (12), and cecropiacic acid 3-methyl ester (13). Conclusion: Compounds 1-4, 7, and 11-13 are obtained from this plant for the first time.

Chemical constituents from cane of Pileostegia viburnoides / 中草药

Objective: To study the chemical constituents from the cane of Pileostegia viburnoides. Methods: The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography. Their structures were identified on the basis of their physicochemical properties and spectroscopic data. Results: Thirteen compounds were isolated from the cane of P. viburnoides and their structures were identified as friedelin (1), 3-oxo-nofriedelin-28-al (2), stigmast-4-en-3-one (3), stigmasterol (4), (24R)-5A- stigmastane-3, 6-dione (5), tetracosyl amine (6), ursolic acid (7), pomolic acid (8), oleanolic acid (9), umbelliferone (10), 4-hydroxymellein (11), cleomiscosin A (12), and daucosterol (13), respectively. Conclusion: Compound 6 is obtained as a natural product for the first time; Compounds 2-5, 7-9, 11, and 12 are obtained from this genus for the first time and all the compounds are obtained from P. viburnoides for the first time.

Chemical constituents from charred Sanguisorbae Radix / 中草药

Objective: To study the chemical constituents from charred Sanguisorbae Radix. Methods: The compounds were isolated and purified by column chromatography and their structures were identified on the basis of physicochemical properties and spectral analysis. Results: Five compounds were isolated and identified as 3β-hydroxy-28-norurs-17, 19, 21-trien (1), 3β-hydroxy-28- norurs-12, 17-dien (2), 3β-[(α-L-arabinofuranosyl) oxy]-28-norurs-12, 17-dien 3β, 19α-dihydroxyurs-13(18)-en-28-oic acid (3), 3β- [(α-L-arabinopyranosyl)oxy]-28-norurs-12, 17-dien (4), and pomolic acid (5). Conclusion: The compounds 1, 3, and 4 are novel compounds which belong to triterpenoids and triterpenoid saponins, named sanguisorbigenin Z, sanguisorbin Y1, and sanguisorbin Y2, respectively.