A New Glycosidic Acid, Muricatic Acid D, and Resin Glycosides, Muricatins X and XI, from the Crude Resin Glycoside Fraction of the Seeds of Ipomoea muricata.

Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3S-hydroxybutyric acid. Two new genuine resin glycosides with macrolactone structures (jalapins), muricatins X and XI, were also isolated from the fraction. Their structures were determined using spectroscopic data and chemical evidence.

Hepta-, hexa-, penta-, tetra-, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines.

Six new partially acylated resin glycosides were isolated from convolvulin of Ipomoea purga, Ipomoea stans, and Ipomoea murucoides (Convolvulaceae). The structures of compounds 1-6 were elucidated by a combination of NMR spectroscopy and mass spectrometry. The structure of jalapinoside B (1) consists of a hexasaccharide core bonded to an 11-hydroxytetradecanoic (convolvulinic) acid forming a macrolactone acylated by a 2-methylbutanoyl, a 3-hydroxy-2-methylbutanoyl, and a quamoclinic acid B units. Purginoic acid A (2) contains a hexasaccharide core bonded to a convolvulinic acid acylated by a 3-hydroxy-2-methylbutanoyl unit. Stansin A (4) is an ester-type heterodimer, and consists of two stansoic acid A (3) units, acylated by 2-methylbutanoic and 3-hydroxy-2-methylbutanoic acids. The site of lactonization was located at C-3 of Rhamnose, and the position for the ester linkage of the monomeric unit B on the macrolactone unit A was established as C-4 of the terminal rhamnose. Compounds 5 and 6 are glycosidic acids. Murucinic acid II (5) is composed of a pentasaccharide core bonded to an 11-hydroxyhexadecanoic (jalapinolic) acid, acylated by an acetyl unit. Stansinic acid I (6) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by 2-methylbutanoyl and 3-hydroxy-2-methylbutanoyl units. Preliminary testing showed the cytotoxicity of compounds 1-6 toward OVCAR and UISO-SQC-1 cancer cell lines. In addition, compound 1 showed an antiproliferative activity on glioma C6 and RG2 tumor cell lines. Copyright © 2016 John Wiley & Sons, Ltd.

Multidrug resistance-reversal effects of resin glycosides from Dichondra repens.

Investigation of hydrophobic extract of Dichondra repens (Convolvulaceae) led to the isolation of three new resin glycosides dichondrins A-C (1-3), and three known resin glycosides cus-1, cus-2, and cuse 3. All the isolated resin glycosides with an acyclic core were evaluated for their multidrug resistance reversal activities, and the combined use of these compounds at a concentration of 25µM increased the cytotoxicity of vincristine by 1.03-1.78-fold.

Synthesis of key macrolactone structure of resin glycosides using a Keck macrolactonization method.

We present in this paper the efficient synthesis of three macrocyclic lactone units which are core structures of natural resin glycosides by the use of a Keck macrolactonization approach.

Evaluation of the neuroprotective activity of stansin 6, a resin glycoside from Ipomoea stans.

Stansin 6 a tetrasaccharide resin glycoside isolated from the root of Ipomoea stans was evaluated as anticonvulsant and neuroprotective in kainic acid-induced seizures of rats. Intraperitoneal injection of kainic acid (10 mg/kg) induced typical behavioral seizures such as wet dog shakes and limbic seizures, and histopathological changes in the hippocampus (degeneration and loss of pyramidal cells in CA1 to CA4 areas). Stansin 6 (10-80 mg/kg) had no effect on the behavior of rats and did not induce hippocampal damage. Pretreatment with stansin 6 inhibited convulsions in rats from kainic acid-induced seizures, reduced the degeneration pattern in the CA3 region, decreased astrocytic reactivity, and reduced the expression of IL-1ß and TNF-α induced by kainic acid. These results suggest that stansin 6 possesses neuroprotective and anticonvulsant activities.

Isolation and structural characterization of eight new resin glycosides, calyhedins XVI-XXIII, from the rhizomes of Calystegia hederacea.

Biological effects attributed to resin glycosides, including cytotoxicity against cancer cells and antibacterial, multidrug resistance-modulating, and antiviral activities have been documented. Penta-glycosides composed of calysolic acid A or calyhedic acid A, which are glycosidic acid components of the crude resin glycoside fraction of Calystegia hederacea, have not yet been isolated from this plant. In this study, eight new resin glycosides, termed calyhedins XVI (1)-XXIII (8), were isolated from the rhizomes of C. hederacea. Compounds 1-8 are penta- or hexa-glycosides with macrolactone structures, and their sugar moieties are partially acylated by five organic acids, including 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R-methyl-3R-hydroxybutyric acids. Compounds 1-5 are the first identified macrocyclic resin glycosides with five monosaccharides obtained from this plant, and 2 and 4 are the first to be characterized as containing calyhedic acid A as the glycosidic acid component. Compounds 1-8 were of the four following macrolactone types: one with a 22-membered ring (5), another with a 23-membered ring (6-8), the third with a 27-membered ring (1, 3), and the fourth with a 28-membered ring (2, 4). Compounds 2-8 exhibited cytotoxic activity against HL-60 human promyelocytic leukemia cells comparable to that of the positive control, cisplatin.

Identification and characterization of organic and glycosidic acids in the crude resin glycoside fraction of Ipomoea alba seeds.

Resin glycosides act as laxatives in crude drugs derived from plants of the Convolvulaceae family. These compounds have exhibited antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug resistance-modulating properties, as well as cytotoxicity against cancer cells. This study investigated the organic acid, hydroxyl fatty acid, monosaccharide, and glycosidic acid components of the crude resin glycoside fraction obtained from the methanol extract of Ipomoea alba L. (Convolvulaceae) seeds, which was subjected to alkaline and acidic hydrolysis. The alkaline hydrolysis yielded acetic, isobutyric, (E)-2-methylbut-2-enoic, and 2S-methyl-3S-hydroxybutyric acids as organic acid components, along with a glycosidic acid fraction. The acidic hydrolysis of the glycosidic acid fraction resulted in the isolation of 11S-hydroxytetradecanoic and 11S-hydroxyhexadecanoic acids as hydroxyl fatty acid components, as well as d-glucose, d-quinovose, d-fucose, d-xylose, and l-rhamnose as monosaccharide components. In addition, 10 new glycosidic acid methyl esters were isolated from the glycosidic acid fraction treated with trimethylsilyldiazomethane-hexane, along with one known glycosidic acid methyl ester. Of these, eight compounds contained new glycans. Four of these compounds were unusual natural glycosides with four glycosidic linkages to one monosaccharide. Their structures were determined using MS and NMR spectral analyses, which provided valuable insights into the unique glycosidic composition of I. alba seeds.

Four new resin glycosides from Ipomoea muricata seeds: muricatins XIV-XVII.

Ipomoea muricata (L.) Jacq. seeds (Convolvulaceae) are used as a traditional laxative and carminative medicine. Muricatins XIV (1), XV (2), XVI (3), and XVII (4), were isolated from I. muricata seeds as four new resin glycosides, along with seven known compounds, three of which were isolated for the first time as natural products; their structures were determined using MS and NMR spectroscopy. Compounds 1-4 are macrolactones (jalapins); the sugar moieties of 1, 2, and 4 are partially acylated with 2S-methylbutyric acid, while that of 3 is esterified with 2S-methylbutyric and 2S-methyl-3S-hydroxybutyric acids. In addition, the antiviral activities of the seven compounds obtained in this study, together with five known compounds obtained in our previous study into resin glycosides from I. muricata seeds, were evaluated against herpes simplex virus type 1 (HSV-1); their cytotoxicities against HL-60 human promyelocytic leukemia cells were also investigated. All examined jalapins exhibited similar or slightly weaker anti-HSV-1 activities than acyclovir, the positive control; however, the glycosidic acid of 4 was inactive, while its methyl ester was weakly active. On the other hand, cytotoxicity testing against HL-60 cells showed similar results to those observed during anti-HSV-1 activity testing, with the exception that one jalapin was less active.

Identification and characterization of organic and glycosidic acids in the crude resin glycoside fraction of Ipomoea lacunosa seeds.

Resin glycosides are commonly found in plants belonging to the Convolvulaceae family. Ipomoea lacunosa L. (Convolvulaceae) is an herbaceous vine native to the United States. The resin glycosides of this plant have not been studied in detail. In this study, the components of the crude resin glycoside fraction extracted from the seeds of I. lacunosa are characterized. Alkaline hydrolysis of the crude resin glycoside fraction obtained from methanolic extract of the seeds yielded three organic acids, namely, 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R-methyl-3R-hydroxybutyric acids, and a glycosidic acid fraction. Acidic hydrolysis of the glycosidic acid fraction yielded hydroxyl fatty acid components, including 7S-hydroxydecanoic, 11S-hydroxytetradecanoic, 11S-hydroxyhexadecanoic, 3S,11S-dihydroxytetradecanoic, 3S,11S-dihydroxyhexadecanoic, and 3S,12S-dihydroxyhexadecanoic acids, as well as monosaccharide components, including d-glucose, d-quinovose, d-fucose, and l-rhamnose. Trimethylsilyldiazomethane-hexane treatment of the glycosidic acid fraction further yielded eleven previously undescribed glycosidic acid methyl esters and two known glycosidic acid methyl esters. The structures of the obtained compounds were characterized using various spectral techniques. Four of the undescribed compounds were hexaglycosides, five were heptaglycosides, and two were octaglycosides. The aglycone of these compounds was either methyl 11S-hydroxytetradecanoate, methyl 3S,11S-dihydroxytetradecanoate, or methyl 3S,11S-dihydroxyhexadecanoate. Among the undescribed compounds identified, eight contained novel glycans, and three were rare bisdesmosides with sugar linkages at the C-3 and C-11 positions of methyl 3S,11S-dihydroxytetradecanoate.

Four new resin glycosides, calyhedins VII-X, from the rhizomes of Calystegia hederacea.

Four new resin glycosides with macrolactone structures (jalapins), namely, calyhedins VII (1)-X (4), were isolated from the rhizomes of Calystegia hederacea Wall. (Convolvulaceae). The structures of 1-4 were determined based on spectroscopic data. They were classified into three ring types: a 27-membered ring (1), a 22-membered ring (2, 3), and a 23-membered ring (4). Their sugar moieties were partially acylated using five organic acids, including (E)-2-methylbut-2-enoic acid, 2S-methylbutyric acid, and 2 R-methyl-3R-hydroxybutyric acid. Compound 4 was the first genuine resin glycoside with calyhedic acid F as the glycosidic acid component. Additionally, the cytotoxic activities of 1, 2, and 4 towards HL-60 human promyelocytic leukaemia cells were evaluated. All compounds demonstrated almost the same activity as the positive control, cisplatin.

Five new resin glycosides, calyhedins XI-XV, from Calystegia hederacea.

Calystegia hederacea Wall. (Convolvulaceae) is a perennial herbaceous vine that grows widely in India and East Asia. All parts of this plant are used to treat various disorders such as menoxenia and gonorrhea. Four new resin glycosides, calyhedins XI (1)-XIV (4), were isolated from the rhizomes of C. hederacea. A new glycoside, calyhedin XV (5), was isolated from its leaves and stems. Alkaline hydrolysis of 1 and 2 furnished a new glycosidic acid, calyhedic acid G (1a), from 1 and a new acid, calyhedic acid H (2a), from 2 along with 2S-methylbutyric acid and 2R-methyl-3R-hydroxybutyric (2R,3R-nilic) acid. The structures of 1-5, 1a, and 2a were determined using MS and NMR spectral analyses. Compounds 1a and 2a had the same sugar moiety, ß-D-glucopyranosyl-(1 → 6)-O-ß-D-glucopyranosyl-(1 → 6)-O-ß-D-glucopyranosyl-(1 → 3)-[O-ß-D-glucopyranosyl-(1 → 3)-O-α-L-rhamnopyranosyl-(1 → 2)]-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-fucopyranose, while their aglycones were 11S-dihydroxyhexadecanoic acid and 12S-dihydroxyhexadecanoic acid, respectively. These compounds are the first glycosidic acids, with fucose as the monosaccharide component obtained from the resin glycosides of C. hederacea. Compounds 1-5, comprising either 1a or 2a, were heptaglycosides with macrolactone structures, and their sugar moieties were partially acylated with 5 mol of organic acids comprising 2S-methylbutyric, (E)-2-methylbut-2-enoic, and 2R,3R-nilic acids. Compounds 1 and 5 had 22-membered rings, while 2-4 had 28-membered rings. In addition, 1 and 5 exhibited cytotoxic activity against HL-60 human promyelocytic leukemia cells, comparable to that of the positive control cisplatin.

Identification and characterization of organic and glycosidic acids in the crude resin glycoside fraction from the leaves and stems of Calystegia japonica.

The alkaline hydrolysis of the crude resin glycoside fraction from the leaves and stems of the plant Calystegia japonica Choisy (Convolvulaceae) yielded organic acid and glycosidic acid fractions. The organic acid fraction was esterified with p-bromophenacyl bromide to obtain p-bromophenacyl 2R-methyl-3R-hydroxybutyrate (1) and p-bromophenacyl (E)-2-methylbut-2-enoate (2). By treating the glycosidic acid fraction with trimethylsilyldiazomethane-hexane, seven new methyl esters of glycosidic acids, namely calyjaponic acid A methyl ester (3) calyjaponic acid B methyl ester (5), calyjaponic acid C methyl ester (6), calyjaponic acid D methyl ester (7), calyjaponic acid E methyl ester (8), calyjaponic acid F methyl ester (9), and calyjaponic acid G methyl ester (10), were isolated along with one known ester (4). Their structures were characterized based on spectroscopic and chemical analyses. Compounds 3-8 had the same sugar moiety, α-L-rhamnopyranosyl-(1 → 2)-O-ß-D-glucopyranosyl-(1 → 2)-[O-α-L-rhamnopyranosyl-(1 → 6)]-O-ß-D-glucopyranose, and the aglycones of 3-8 were methyl 3S,11S-dihydroxyhexadecanoate, methyl 3S,12S-dihydroxyhexadecanoate, methyl 11S-hydroxyhexadecanoate, methyl 11S-hydroxypentadecanoate, methyl 3S,11S-dihydroxypentadecanoate, and methyl 3S,12S-dihydroxypentadecanoate, respectively. Compounds 9 and 10 were derivatives of 3 and 4, respectively, in which the C-6 of the second glucosyl residue was methylated. Compounds 6-8 contained methyl esters of unusual odd-carbon fatty acids as aglycones. The cytotoxicity of the crude resin glycoside fraction and 3 against HL-60 human promyelocytic leukemia cells was evaluated further; both were either weakly active or inactive compared to the positive control, cisplatin.

Two new glycosidic acids, calyhedic acids E and F, in crude resin glycoside fraction from Calystegia hederacea.

Two new glycosidic acids, calyhedic acids E (1a) and F (2a), were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the crude resin glycoside fraction obtained from whole plants of Calystegia hederacea Wall. Compounds 1a and 2a were characterised as 11S-hydroxyhexadecanoic acid 11-O-ß-D-glucopyranosyl-(1→6)-O-ß-D-glucopyranosyl-(1→6)-O-ß-D-glucopyranosyl-(1→3)-[O-α-L-rhamnopyranosyl-(1→2)]-O-ß-D-glucopyranosyl-(1→2)-ß-D-quinovopyranoside and an isomer of 1a, in which the 11S-hydroxyhexadecanoyl residue of 1a was replaced by a 12S-hydroxyhexadecanoyl residue, respectively, on the basis of spectroscopic data.

Evaluation of the Role of Merromoside from Ipomoea aquatica Forsskal Hydroalcoholic Extract in the Downregulation of ROS Species in Overcoming MDR in Breast Cancer.

PURPOSE: The medicinal plant Ipomoea aquatica belonging to convulvulaceae family is an effective natural herb for treatment of various ailments and possesses effective anticancer activity. The aim of the work is to characterize a secondary metabolite merromoside (a resin glycoside) for anti-breast cancer activity through down regulation of ROS species. METHODS: The Extract of the whole plant has been prepared by maceration method using 50%v/v ethanol in distilled water to get a hydroalcoholic extract. The phytochemical evaluation reveals that the active secondary metabolite was isolated by using column chromatographic technique. The isolated compound was evaluated for its anticancer properties through invitro method such as 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay on Michigan Cancer Foundation-7 Cell lines. The purity and structural characterization were done by high-performance thin layer chromatography, Fourier Transform Infrared Spectroscopy, Proton and13C Nuclear Magnetic Resonance spectroscopy and Liquid Chromatography-Mass Spectrometry. RESULTS: The isolated compound (W04) from the derived extract showed Rf value of 0.79 that showed IC50 of 182.8µg/ml. The chemical structure of W04 has been confirmed as [4,5-dihydroxy-6-[5-hydroxy-2-methyl-4-(2-methylpropanoyloxy)-6-[(24,25,26-trihydroxy-5,23-dimethyl-9-oxo-19-pentyl-2,4,8,20,22-pentaoxatricyclo[19.2.2.13,7]hexacosan-6-yl)oxy]oxan-3-yl]oxy-2-methyloxan-3-yl] 2-methyl propanoate with the molecular weight of 979.15268. The isolated compound merromoside from hydroalcoholic extract of Ipomoea aquatica has been evaluated for anti-breast cancer properties. The down regulation of ROS species will prevent reverse signalling and angiogenesis. This indicates that merromoside will overcome MDR in breast cancer especially DOX-resistant.

Two new resin glycosides, muricatins XII and XIII, from the seeds of Ipomoea muricata.

Two new resin glycosides, muricatins XII (1) and XIII (2), were isolated from the crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae), along with three known ones, muricatins V (3), VI (4), and IX (5). Compounds 1 and 2 contained new glycosidic acids, muricatic acids E (1a) and F (2a), respectively. The structures of these compounds were determined using data obtained from spectroscopy measurements and chemical evidence. The results suggested that 1 and 2 have macrolactone structures (jalapins). Furthermore, the cytotoxic activity of the crude resin glycoside fraction and 3-5 against HL-60 human promyelocytic leukaemia cells was evaluated. All tested samples demonstrated cytotoxic activities.

Sweet potato extract alleviates high-fat-diet-induced obesity in C57BL/6J mice, but not by inhibiting pancreatic lipases.

Scope and aim: Sweet potato is widely consumed as a healthy and nutritive vegetable containing bioactive constituents for health promotion. This study investigated the beneficial impact of white-fleshed sweet potato extract (SPE) on high fat diet (HFD)-induced obese mice. Methods and results: First, SPE, in which resin glycoside was found as the dominant constituent, was suggested as a potential anti-obesity agent, because 20-70% pancreatic lipase (PL) inhibition was measured with SPE by in vitro turbidity assay and pNPP assay. Hence, next, the effect of SPE on obese mice was detected by oral administration of HFD supplemented with 6% SPE on C57BL/6J mice for 9 weeks. Surprisingly, being the opposite of what was typically observed from a lipase inhibitor such as orlistat, the fecal fat content in SPE-fed obese mice was decreased (p < 0.01). Meanwhile, 6% SPE supplement indeed significantly ameliorated HFD-induced obesity in mice, including body weight gain, fat accumulation, adipocyte enlargement, insulin resistance, and hepatic steatosis (p < 0.05). The improved liver steatosis was found associated with a down-regulating action of SPE on nuclear factor kappa B activation in HFD-fed mice. The anti-obesity influence of SPE was also confirmed on the HepG2 cell model for non-alcoholic fatty liver disease (NAFLD). Conclusion: These results indicate that SPE, as a dietary supplement, has the great potential for weight control and treating hepatic steatosis, possibly through a different action mechanism from that of orlistat.

Different effects on the tonus of colon and ileum isolated from mouse by resin glycoside (pharbitin) of Pharbitidis Semen.

BACKGROUND: Pharbitidis Semen (the seeds of Pharbitis nil), traditionally used as a purgative in Japan, China and Korea, contains a resin glycoside fraction named pharbitin, which is known as a purgative ingredient. Due to the complex nature of pharbitin, little is known about either the action on intestinal tension caused by resin glycoside itself or by its components. METHODS: In this study, we investigated the effects of pharbitin, the glycosidic acid fraction (pharbitic acid) and the aglycone fraction (phar-genin) generated from pharbitin on peristalsis of colon and ileum isolated from mice with the Magnus method. RESULTS: We demonstrated that pharbitin (3-30 µg/mL) concentration-dependently increased tonus of mice colon via acetylcholine receptors, its components phar-genin (1.27-12.7 µg/mL) and pharbitic acid (10-1000 µg/mL) also had the increment on colon tonus. On the other hand, ileum tension decreased in the presence of pharbitin. CONCLUSIONS: The effects of resin glycoside of Pharbitidis Semen on colon tonus are different with those on ileum tonus isolated from mice. In the next step it is necessary to investigate details of its pharmacological mechanism.

Isolation of evolvulic acids B and C, two new components of crude resin glycoside fraction from Evolvulus alsinoides.

Two new glycosidic acids, evolvulic acids B and C (1 and 2), along with a known one, evolvulic acid A (3), were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of crude resin glycosides from Evolvulus alsinoides whole plants. Their structures were characterized by the spectroscopic data and chemical evidences. Compounds 1 and 2 are both defined as tetrasaccharides, composed of D-fucose, D-glucose, L-rhamnose or D-galactose units. Their aglycones are identified to be a distinctive 3S,11R,14R-trihydroxyhexadecanoic acid, which is only discovered from E. alsinoides up to now. The cytotoxic and anti-migration activities of compounds 1-3 were also tested.

Calyhedins I-VI: Resin glycosides from the rhizomes of Calystegia hederacea.

Six previously undescribed resin glycosides, calyhedins I-VI, were isolated from the rhizomes of Calystegia hederacea Wall., which are the first genuine resin glycosides isolated from C. hederacea. The structures of calyhedins I-VI were determined based on spectroscopic data and chemical evidence. All the compounds have macrolactone structures (jalapins), and their sugar moieties were partially acylated by five organic acids. Calyhedins I, II-V, and VI have 27-, 28-, and 23-membered rings, respectively, and calyhedins IV-VI are the first jalapins with a sugar chain consisting of seven monosaccharides. Additionally, the cytotoxic activity of calyhedins II and III toward HL-60 human promyelocytic leukemia cells was evaluated. Both compounds demonstrated almost the same activity as the positive control, cisplatin.

Identification and characterization of organic and glycosidic acids in crude resin glycoside fraction from Calystegia hederacea.

Resin glycosides are well known as the purgative ingredients, which are characteristic of convolvulaceous plants. Calystegia hederacea Wall. is a perennial herbaceous vine that is widespread throughout India and East Asia. All parts of this plant are used for the treatment of menoxenia, gonorrhea, etc. Alkaline hydrolysis of the crude resin glycoside fraction of the whole plants of C. hederacea yielded four new glycosidic acids, calyhedic acids A, B, C, and D, along with two known glycosidic acids, calysolic acids A and C, and three known organic acids, 2S-methylbutyric, tiglic, and 2R,3R-nilic acids. Their structures were characterized on the basis of spectroscopic data and chemical evidence. Calyhedic acids A, B, and D were penta-, hexa-, and hepta-glycosides of 12S-hydroxyhexadecanoic acid, respectively, and cayhedic acid C was an isomer of calyhedic acid D, in which the 12S-hydroxyhexadecanoyl residue of calyhedic acid D was replaced by a 11S-hydroxyhexadecanoyl residue. Additionally, cytotoxic activity toward HL-60 human promyelocytic leukemia cells of the crude resin glycoside fraction, the glycosidic acid fraction, calyhedic acid A, and calysolic acid A from C. hederacea was evaluated. Furthermore, to clarify the structure-activity relationship of resin glycosides, the activities of six genuine resin glycosides with calysolic acid A or calysolic acid C as the glycosidic acid, which were isolated from C. soldanella, were examined. Among them, the crude resin glycoside fraction and five genuine resin glycosides with macrolactone structures demonstrated clear cytotoxic activities, while the glycosidic acid fraction, calyhedric acid A, calysolic acid A, and a genuine non-macrolactone-type resin glycoside were either inactive or exhibited weaker activity than the tested macrolactone-type resin glycosides.