Changes in the organization of the mouse egg plasma membrane upon fertilization and first cleavage: Indications from the lateral diffusion rates of fluorescent lipid analogs

Using the technique of fluorescence photobleaching recovery, we have measured the lateral diffusion of the lipid analogs 3,3′-diacylindocarbocyanine iodides of acyl chain lengths, n = 14 to 22 in the plasma membranes of unfertilized and fertilized CD-1 mouse eggs and two-cell embryos. Mean diffusion coefficients ranged from (3.4 to 7.9) × 10^?9 cm²/sec and mean percentage diffusing ranged from 65 to 82%. Within 10% diffusing fractions are independent of chain length and unaffected by fertilization or first cleavage. In unfertilized and fertilized eggs the diffusion coefficients show relative maxima at n = 16 and 20. In two-cell embryos the relative maximum at n = 16 is suppressed. As was observed by D. E. Wolf, W. Kinsey, W. Lennarz, and M. Edidin (1981, Develop. Biol.81, 133) on sea urchin eggs, the effect of fertilization on diffusion coefficients is chain length dependent. Little change is observed for n = 14 and 18; a slight increase is observed for n = 16; and small decreases are observed for n = 20 and 22. This is interpreted in terms of a reordering of the lipid domains in the plasma membrane upon fertilization and first cleavage.     

Prolactin Levels Do Not Rise Among Transgender Women Treated With Estradiol and Spironolactone

Objective: Existing transgender treatment guidelines suggest that there is a need to monitor prolactin levels in patients receiving transfeminine hormone treatment. Also, recent studies suggest that use of cyproterone acetate as an adjunctive anti-androgen during transgender hormone treatment may elevate serum prolactin. We sought to determine whether the reported relationship between transfeminine estradiol treatment and hyperprolactinemia would be evident when the regimen used spironolactone as the adjunctive anti-androgen.Methods: Estradiol levels, testosterone levels, prolactin levels, body mass index (BMI), and prescribed spironolactone dosage were extracted from the electronic medical records of 98 de-identified transgender women treated with estrogen therapy at the Endocrinology Clinic at Boston Medical Center (BMC). Up to 6 years of data were available for some patients.Results: We found no statistically significant relationship between prolactin and any of the other measures. No estrogen dose-associated elevations in prolactin were found. None of the patients were diagnosed with prolactinoma.Conclusion: Our data suggest that there may be no significant rise in prolactin when transgender women are treated with estrogen along with spironolactone as the adjunct anti-androgen. It may be unnecessary to monitor prolactin in patients on this treatment combination.Abbreviations: BMI = body mass index; BMC = Boston Medical Center; HT = hormone therapy     

Chemical constituents of Medinilla septentrionalis (W. W. Sm.) H. L. Li (Melastomataceae)

Our phytochemical investigation of the whole plants of Medinilla septentrionalis (W. W. Sm.) H. L. Li led to the isolation of five tannins (1–5), five phenolic acids and phenolic acid derivatives (6–10), four flavonoids (11–14), two triterpenes (15 and 16), and one hydantoin derivative (17). The structures of the obtained compounds were identified using spectrometric methods (¹H NMR, ¹³C NMR and MS). This is the first study reporting on the chemical constituent of M. septentrionalis and the chemotaxonomic relationships between Medinilla and other genera of Melastomataceae.     

Are cadmium effects on plasma gonadotropins, prolactin, ACTH, GH and TSH levels, dose-dependent?

It is well established that cadmium affects plasma levels of the pituitary hormones studied. However, whether the effects of the metal are dose dependent needs to be clarify. This work was designed to evaluate the possible changes in plasma levels of gonadotropins, prolactin, ACTH, GH and TSH after oral cadmium exposure in adult male rats. Plasma levels of these hormones were measured in adult male rats exposed to cadmium chloride (CdCl₂) in the drinking water at the doses of 5, 10, 25, 50 or 100 ppm for one month. The lower dose of cadmium increased plasma prolactin levels and higher doses of the metal (25 or 50 ppm) decreased them. There was a continuous increase of plasma ACTH levels from the lower to 25 ppm dose of CdCl₂ and decreased them after to basal values with the highest dose. Plasma GH levels were increased with the dose of cadmium of 10 ppm, although the doses of 5, 25 and 50 ppm decreased them. Plasma LH levels were only reduced with the dose of 50 ppm of CdCl₂, whereas those of FSH increased. Plasma TSH levels were increased with the doses of 5, 25 and 100 ppm of CdCl₂. Cadmium concentration increased in pituitary with the doses of 125, 50 and 100 ppm of CdCl₂. These data suggest that cadmium differentially affects the secretory mechanisms of the pituitary hormones studied depending on the dose used. The effects of the metal on prolactin and ACTH are dose-dependent.     

A comparative study of the susceptibility of inbred strains of mice to infection with Mesocestoides corti

White T. R., Thompson R. C. A. and Penhale W. J. 1982. A comparative study of the susceptibility of inbred strains of mice to infection with Mesocestoides corti. International Journal for Parasitology12: 29–33. The susceptibility of 6 strains of inbred mice to infection with Mesocestoides corti was studied following both intraperitoneal and oral inoculation of tetrathyridia. The greatest degree of resistance was seen in C57BL/6 mice and this resistance was independent of route of inoculation. The proliferation of the parasite in C57BL/6 mice was compared with a more susceptible strain (CBA/H) on 7, 14, 21, 35 and 60 days post-infection. Although both strains harboured significantly different parasite burdens during the initial period following infection, these differences were no longer apparent by day 60.     

Effects of serotonergic agents on plasma prolactin levels in pyridoxine-deficient adult male rats

Plasma concentration of prolactin was significantly reduced in pyridoxine-deficient as compared to control (pyridoxine-supplemented) adult male rats. Administration of pyridoxine to deficient rats resulted in a significant increase in plasma prolactin. The reduction in plasma prolactin in pyridoxine-deficient rats corresponded with the significantly reduced hypothalamic contents of pyridoxal phosphate and serotonin in pyridoxine-deficient rats. Plasma prolactin concentrations were also measured in response to serotonergic agents in both groups of rats. The administration of the 5HT_1A agonist (8-hydroxy 2-n-dipropylamino tetralin) resulted in a significant increase in plasma prolactin and that of the specific 5HT_1A antagonist spiroxatrine had the opposite effect. The results suggest that the hypothalamic serotonergic regulation of prolactin release is impaired in pyridoxine deficiency.     

The Effect of Raloxifene on Serum Prolactin Level in Patients with Prolactinoma

Objective: To evaluate the effect of raloxifene on prolactin (PRL) levels in addition to dopamine agonist (DA) therapy in patients with prolactinoma.Methods: We conducted a retrospective chart review of 14 patients with prolactinoma on stable dose of DA for 6 months who received raloxifene 60 mg daily, as PRL could not be normalized despite being on fairly high doses of DA. Patients were informed that raloxifene is not approved by the Food and Drug Administration for prolactinoma treatment. PRL level was measured at 1 to 6 months after starting raloxifene and at 1 to 3 months following its discontinuation. Raloxifene was stopped in 8 out of 14 patients after 2 (1 to 6) months of treatment as the absolute change in PRL level was felt to be small.Results: The median age and female/male sex ratios were 50 years (range 18 to 63 years), 6/8 respectively. The baseline DA dose was 3 mg/week (0.5 to 7 mg/week) for cabergoline and 15 mg/day for bromocriptine. Ten patients had an absolute and percentage decrease in PRL of 8.3 ng/mL (1.5 to 54.2 ng/mL) and 25.9% (8 to 55%) from baseline, respectively, after 1 to 6 months on raloxifene treatment. Among 10 patients with a decrease in PRL level, 2 (20%) achieved PRL normalization. Two patients had no change in PRL and two patients had an increase in PRL level by 22.8 ng/mL and 8.8 ng/mL (47% and 23.6%), respectively.Conclusion: Raloxifene was associated with a 25.9% (8 to 55%) decrease in PRL level in 10/14 (71%) patients with prolactinoma who were on stable doses of DA including 2 patients (14%) who achieved normoprolactinemia.Abbreviations: CV = coefficient of variation; DA = dopamine agonist; FSH = follicule-stimulating hormone; LH = luteinizing hormone; PRL = prolactin; PTTG = pituitary tumor transforming gene     

Comparative electron microscope study of pellicular structures in coccidia (Sarcocystis, besnoitia and Eimeria)

D'Haese J., Mehlhorn H. and Peters W. 1977. Comparative electron microscope study of pellicular structures in coccidia (Sarcocystis, Besnoitia and Eimeria). International Journal for Parasitology7: 505–518. Negatively stained zoites of Sarcocystis ovifelis (= S. tenella pro parte) and Besnoitia jellisoni and sporozoites of Eimeria falciformis were studied by means of electron microscopy and compared with results obtained by other techniques. A new concept for the pellicle of motile coccidia was achieved, which throws some light on the mechanism of motility of these parasites,     

Two cytotoxic stereoisomers of malyngamide C, 8-epi-malyngamide C and 8-O-acetyl-8-epi-malyngamide C,from the marine cyanobacterium Lyngbya majuscula

Two epimers of malyngamide C, 8-O-acetyl-8-epi-malyngamide C (1) and 8-epi-malyngamide C (3) have been isolated along with known compounds 6-O-acetylmalyngamide F (5), H (6), J (7) K (8), and characterized from a Grenada field collection of the marine cyanobacterium Lyngbya majuscula. The structures of these compounds were deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. Absolute configurations were determined by a combination of CD-spectroscopy, chemical degradation and the variable temperature Mosher’s method. Compounds 1–5, 7 and 8 displayed moderate cytotoxicity to NCI-H460 human lung tumor and neuro-2a cancer cell lines, with IC₅₀ values ranging between 0.5 and 20 μg/mL.     

Effect of central injection of bradykinin and bradykinin potentiating factor upon release of anterior pituitary hormones in ovariectomized female rats

The effects of third ventricular (IVT) injection of 25 μg of bradykinin (BK) upon plasma levels of LH, FSH, TSH, GH and prolactin were investigated in conscious ovariectomized female rats bearing indwelling jugular cannulae. Some animals were pretreated with bradykinin potentiating factor (BPF). Intravenous administration of BK had no effect upon hormone levels. IVT injection of BK significantly depressed plasma prolactin levels at 15 and 30 min post-drug, with levels returning to control values by 60 min. Pretreatment of animals with BPF (75 μg/3 μl) prolonged the prolactin suppression induced by BK for up to two hours. Plasma LH, FSH, TSH and GH levels in BK-rats were not significantly different from those of saline-injected animals at any time point measured. Neither BPF alone nor in conjunction with BK had any effects upon plasma levels of TSH; however, BK plus BPF suppressed FSH concentrations at 75 min post-BPF, while BPF alone appeared to increase GH levels at 45 min. In vitro incubation of hemipituitaries with 0.083, 0.83 or 8.33 μg/ml BK had no effect upon the release of LH, TSH or prolactin compared to control values. However, the secretion of GH and FSH was suppressed by the lowest dose of BK tested. These results suggest that BK may play a physiological inhibitory role in the regulation of prolactin, which can be augmented by preventing its degradation, i.e. via BPF. The effect of the peptide seems to be mediated by the CNS since neither intravenous injection of BK nor in vitro incubation of pituitaries with the peptide modified prolactin release.     

Competition for dietary fructose between Moniliformis (acanthocephala) and growing rats

Crompton D. W. T., Singhvi A., Nesheim M. C. and Walters D. E. 1981. Competition for dietary fructose between Moniliformis (Acanthocephala) and growing rats. International journal for Parasitology11: 457–461. The food intake, weight gain and blood sugar of young rats, fed on diets containing growth-limiting amounts of fructose and infected with Moniliformis dubius (Acanthocephala) for 6 weeks, were measured and compared with values obtained from similar uninfected rats which had been treated in the same manner. The growth of the rats was closely related to the fructose content of the diet. However, on average, the infected rats gained less weight than their uninfected counterparts. Significant differences between the values for blood sugar from infected and uninfected rats were not detected when the diet contained 2% fructose. The blood sugar of infected rats fed on a diet containing 4% fructose was found to be significantly less than that of similar uninfected rats. Information was also obtained about the numbers, sex, dry weight and location of the Moniliformis in the small intestines of their hosts. Male and female Moniliformis from rats fed on the 4% fructose diet were found to be heavier than those from rats fed on the 2% fructose diet. The results can be interpreted to suggest that the reduction in the growth rate of the infected rats is due to competition for fructose between Moniliformis and the rat.     

III. Prolactin and calcium metabolism in the rat

The relation between plasma prolactin and plasma calcium was investogated in normoprolactinemic and hyperprolactinemic adult male rats. Hyperprolactinemia was induced by implantation of a pituitary underneath the kidney capsule in intact males. Hyperprolactinemia did not affect the concentration of calcium in the plasma. It did neither affect food and water consumption, nor urine production and urinary sodium excretion, indicating that prolactin is not important for osmoregulation. However, in hyperprolactinemic rats urinary calcium excretion was markedly increased. 90 Min of intravenous infusion of CaCl₂ induced a similar rise of plasma calcium in normoprolactinemic and hyperprolactinemic rats. Infusiion of EGTA during 60 min induced no change in total plasma calcium in normo- and hyperprolactinemic rats. although probably ionized plasma calcium was considerably decreased. Plasma prolactin, however, was not changed during these infusions. It is concluded that in the adult male rat prolactin has no function in the short term regulation of calcium homeostasis. However, when plasma prolactin is considerably increased duing prolonged periods, the hormone may affect calcium metabolism.     

Hyperthyroidism and Hyperprolactinemia: Is There any Association?

Objective: To compare the serum prolactin level in hyperthyroid and normal control females. Hyperthyroidism is a common disease. Although a direct association has been demonstrated between hypothyroidism and increased prolactin levels, this association has not been established for hyperthyroidism.Methods: Cross-sectional study in cases and control groups. Control subjects were chosen from those participating in the Kerman Coronary Artery Disease Risk Factors study. To select the cases, all women referred to the laboratories of Kerman with a thyroid-stimulating hormone (TSH) level ≤0.5 mIU/L who met the inclusion criteria were entered in the study. A total of 231 women aged 15 to 50 years were enrolled. The case group included 71 hyperthyroid women, and the control group included 160 women with normal thyroid function matched by age.Results: The mean (SD) serum level of prolactin was 16.56 (0.97) ng/mL (95% confidence interval [CI], 15.41 ng/mL to 15.71 ng/mL) in the controls and 23.07 (1.49) ng/mL (95% CI, 22.7 ng/mL to 23.4 ng/mL) in the case subjects. Hyperprolactinemia was more common in the hyperthyroid group (16.5 [0.97] ng/mL versus 23.07 [1.49] ng/mL; P<.001). The prolactin level decreased with age. Hyperthyroidism and estradiol increased the prolactin level. After adjusting for age and estradiol, hyperthyroidism increased the serum prolactin level (P<.001).Conclusion: The results of this study revealed that hyperprolactinemia is more frequent in hyperthyroid females. Serum prolactin level can be increased in hyperthyroidism.Abbreviations:PRL = prolactinT4 = thyroxineTRH = thyrotropin-releasing hormoneTSH = thyroid-stimulating hormone     

Plasma prolactin, thyroxine, triiodothyronine, testosterone, and luteinizing hormone during a photoinduced reproductive cycle in mallard drakes

The temporal relationships between plasma concentrations of prolactin, thyroxine (T4) and triiodothyronine (T3) were determined in a group of six wild mallard drakes during the development and maintenance of long-day refractoriness after transfer from 6 h light: 18 h darkness (6L:18D) to 20L:4D for 24 weeks. As shown by changes in the plasma concentrations of luteinizing hormone (LH) and testosterone, the birds came into breeding condition and then became long-day refractory within 5 weeks of photostimulation. Long-day refractoriness was maintained for the remainder of the study. Plasma prolactin began to increase immediately after photostimulation, although not as fast as the increases in plasma LH and testosterone. The concentration of plasma T4 also increased after photostimulation but, as shown by decreased plasma LH and testosterone levels, only after the birds had become long-day refractory. The development of long-day refractoriness was thus directly correlated with an increased plasma prolactin and not with a change in plasma concentration of T4. Plasma T3 decreased after photostimulation but returned to prestimulation values as the birds became long-day refractory and remained stable for the remainder of the study. Concentrations of plasma T4 and prolactin returned to baseline values after about 15 weeks photostimulation showing that the long-term maintenance of long-day refractoriness is not directly related to continuously high plasma concentrations of either hormone.     

Short-term effects of vasoligation upon plasma follicle-stimulating hormone, luteinizing hormone, and prolactin in the adult rat: further evidence for a direct neural connection between the testes and the central nervous system

The purpose of these experiments was to determine whether bilateral vasoligation of adult male rats had any short-term effects upon plasma levels of follicle-stimulating hormone (FSH), luteinizing hormone (LH), and prolactin. Adult male rats (250-300 g) were either bilaterally vasoligated or sham vasoligated, and blood samples were obtained by cardiac puncture preoperatively and at 24 h and 7 days following surgery. Plasma levels of both FSH and LH were significantly (P less than 0.01) decreased at 24 h following vasoligation compared to preoperative levels and those of sham-operated controls. However, the response was differential since, at 7 days following vasoligation, plasma FSH was still significantly decreased while LH was returning to control levels. Conversely, plasma prolactin levels were significantly (P less than 0.01) increased at 24 h compared to preoperative values and those in sham-operated controls, and at 7 days prolactin had returned to preoperative control levels. Sham vasoligation did not significantly change plasma levels of FSH, LH, or prolactin at any of the time intervals investigated. These results provide further evidence that suggests that there may be a direct connection between the testis and central nervous system that may be involved in the short-term regulation of gonadotropin and prolactin secretion.     

Dependence upon temperature of corrected sedimentation coefficients measured in a Beckman analytical ultracentrifuge

The corrected sedimentation coefficient (s_{20, w}) has been examined as a function of temperature for bovine liver catalase and for a small linear duplex DNA in a Beckman Model E analytical ultracentrifuge. These measurements were carried out using both the standard Beckman rotor temperature indicator and control system and a modified version of this system which was designed to reduced thermal gradients in the rotor [Hearst, J. E., and Gray, H. B., Jr. (1968) Anal. Biochem.24, 70–79)]. The temperature dependence of s_{20, w} for both the protein and the DNA were identical between the two systems. The slight increase of s_{20, w} with increasing temperature observed for the DNA is in agreement with that predicted on the basis of the temperature dependence of the Kuhn statistical length for DNA. Intrinsic viscosity measurements as a function of temperature were also carried out for the DNA in a low-shear viscometer. These data indicate a slight decrease of intrinsic viscosity with increasing temperature. Previous investigations, which have suggested that the actual temperature of the ultracentrifuge cell is substantially higher [Incardona, N. L., Notarius, H., and Flanegan, J. B. (1971) Anal. Biochem.40, 267–280] or lower [Rowe, A. J., and Khan, G. M. (1972) Anal. Biochem.45, 488–497] than that indicated by the temperature monitoring system of the Model E centrifuge at temperatures below ambient, are not supported by the present studies. Discrepancies between the actual temperature of the sedimenting sample and the indicated temperature are thus shown in this work not to be an inherent problem of the design of the Beckman instrument.     

The withanolides of Withania somnifera chemotypes I and II

Seven steroidal lactones of the withanolide series have been isolated as minor constituents of the leaves of Withania somnifera Dun. (Solanaceae) chemotype I, along with the major component withaferin A. Structures have been assigned to the new compounds: withanolide N (17α,27-dihydroxy-1-oxo-20R,22R-witha-2,5,14,24-tetraenolide) (6a) and withanolide O (4β,17α-dihydroxy-1-oxo-20R,22R-witha-2,5,8(14),24-tetraenolide) (7a). Similarly the leaves of W. somnifera chemotype II afforded three new withanolides along with the major component withanolide D (9a) and trace amounts of withanolide G (10). The new compounds are: 27-hydroxywithanolide D(4β,20α,27-trihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide) (11a), 14α-hydroxywithanolide D (4β,14α,20α-trihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide) (12a) and 17α-hydroxywithanolide D (4β,17β,20α-trihydroxy-1-oxo-5β,6β-epoxy-20S,22R-witha-2,24-dienolide) (13a). Whereas all the withanolides of chemotype I are unsubstituted at C-20 (20α-H), those of chemotype II possess an OH at this position (20α-OH).     

Cytotoxic,larvicidal, nematicidal,and antifeedant activities of piperidin-connected 2-thioxoimidazolidin-4-one derivatives

The objective of this study was to investigate brine shrimp cytotoxicity, larvicidal, nematicidal, and antifeedant activities of novel piperidin-connected 2-thioxo-imidazolidin-4-one derivatives. The activities of target compounds were compared with some naturally occurring (?)-pinidinol, hydantocidin, and positive controls. Target compounds were synthesized via cyclocondensation method. The compounds were synthesized and then characterized by infrared spectroscopy, ¹H NMR, ¹³C NMR, mass spectral, and elemental analyses. Brine shrimp cytotoxicity assay was investigated using freshly hatched, free-swimming nauplii of Artemiasalina. Larvicidal screening was performed against urban mosquito larvae (Culex quinquefasciatus). Nematicidal activity was evaluated using juvenile nematodes of Meloidogyne javanica. Regarding antifeedant activity, marine-acclimated Oreochromis mossambicus fingerlings were used. Compounds 3a-c (piperidin-connected 2-thioxoimidazolidin-4-one) were found to be lethal to the second instar larvae of mosquito, which produced LD₅₀ values of 1.37, 6.66, 6.51 μg/mL, compared to compounds (?) pinidinol and hyantocidin LD₅₀ values of 18.28 and 22.11 μg/mL respectively. Compound 3a-c was found to kill 100% of fish fingerlings within 6 h at 20 µg/mL, with LD₅₀ values of 1.54, 1.79, 1.52 µg/mL, compared to compounds (?) pinidinol and hyantocidin with LD₅₀ values of 10.21 and 21.05 μg/mL respectively. Compound 3c with LD₅₀ value of 1.57 μg/mL demonstrated high nematicidal activity compared to compound 3a, 3b, (?) Pinidinol and Hyantocidin LD₅₀ values of 6.45, 2.42, 14.25, 26.30 μg/mL respectively. Therefore, the 2-thioxoimidazolidin-4-one with piperidin ring showed high potential cytotoxic, larvicidal, nematicidal, and antifeedent activities.     

Voulkensin C–E,new 11-oxocassane-type diterpenoids and a steroid glycoside from Caesalpinia volkensii stem bark and their antiplasmodial activities

A bioassay guided isolation of potential antimalarial molecules from the stem bark of Caesalpinia volkensii Harms (Fabaceae) achieved three new 11-oxocassane-type diterpenoids named voulkensin C (1), D (2) and E (3) together with one steroid glycoside named 3-O-[β-glucopyranosyl(1→2)-O-β-xylopyranosyl]-stigmasterol (4) and seven other known compounds including stigmasterol (5), β-sitosterol (6), oleanolic acid (7), 3-β-acetoxyolean-12-en-28-methyl ester (8), voucap-5-ol (9), caesadekarin C (10), deoxycaesaldekarin C (11). The structures of the new compounds were determined on the basis of extensive spectroscopic data (IR, MS, ¹H and ¹³C NMR and 2D NMR) analyses. The polar extracts revealed moderate to good antiplasmodial activities against chloquine-sensitive (D6) and -resistant strains (W2) of Plasmodium falciparum. Whereas the pure isolates exhibited limited to moderate antiplasmodial activities with compound 4 showing the highest antiplasmodial activities (IC₅₀ values of 4.44 ± 0.88 and 2.74 ± 1.10 μM against D6 and W2 strains, respectively). These results suggest a possible contribution of phytochemicals from C. volkensii stem bark towards inhibition of plasmodial parasites’ growth hence potential antimalarial.     

Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities

Five flavonols (3, 5, and 9–11) were isolated from Rhodiola rosea, and compared with commercially available flavonoids (1, 2, 4, 6–8, and 12–14) to facilitate analysis of their structure–activity relationship (SAR). All compounds (1–14) showed neuraminidase inhibitory activities with IC₅₀ values ranging from 0.8 to 56.9 μM. The in vitro anti-influenza virus activities of flavonoids 1–6, 8–12, and 14 were evaluated using two influenza viral strains, H1N1 (A/PR/8/34) and H9N2 (A/Chicken/Korea/MS96/96), testing their ability to reduce virus-induced cytopathic effect (CPE) in MDCK cells. We found that the activity of these compounds ranged from 30.2 to 99.1 μM against H1N1- and 18.5 to 133.6 μM against H9N2-induced CPE. Of compounds 1–14, gossypetin (6) exhibited the most potent inhibitory activity, with IC₅₀ values of 0.8 and 2.6 μM on neuraminidases from Clostridium perfringens and recombinant influenza virus A (rvH1N1), respectively. In contrast, kaempferol (3) exhibited the highest activity against two influenza viruses, H1N1 and H9N2 with EC₅₀ values of 30.2 and 18.5 μM, respectively. Activity depended on the position and number of hydroxy groups on the flavonoids backbone. In kinetic studies, all isolated compounds behaved as noncompetitive inhibitors.