Botanical Supplements Research Articles

Ecological and Chemotypic Analysis for Improved Growth and Management of Naturally Occurring Black Cohosh (<i>Actaea racemosa</i> L.) Populations in Western Maryland

Black cohosh (Actaea racemosa L.) is a perennial herb native to deciduous woodlands in eastern North America with an extensive history of traditional use, most commonly for rheumatoid arthritis and female reproductive issues. Modern clinical research has maintained this herb’s relevance into the 21st century with a majority of authentic black cohosh raw material still harvested from naturally occurring populations in Appalachian woodlands for use in botanical supplements. Increased use and interest in black cohosh have led to increased wild harvesting, reports of adulteration, and stress on this important natural resource. In an effort to study this significant medicinal plant as part of an ecosystem, and to understand factors that would contribute to the more effective growth and maintenance of black cohosh, key chemical, physiological, and ecological aspects of two occurring populations in western Maryland were surveyed. Rhizomes were harvested from six populations of naturally occurring black cohosh in two state forests located in the Allegheny Plateau and Ridge and Valley physiogeographic provinces of Maryland. The concentrations of five medicinal compounds found in black cohosh extracts, actein, 23-epi-26-deoxyactein, cafeic acid, ferulicacid, and N-methylserotonin, were compared with plant reproductive status as well as accompanying overstory and under story species, soil moisture, and soil pH at each site. Compound levels showed a complex dependence on physiography but were independent of reproductive state. The findings provide clues to guide efforts at effective growth and management of wild populations of black cohosh and other threatened medicinal plants.

Essential oil chemotypification and secretory structures of the neglected vegetable Smyrnium olusatrum L. (Apiaceae) growing in central Italy

AbstractAs part of our research on local plants, including neglected horticultural crops to be rediscovered as culinary vegetables, we focused on Smyrnium olusatrum, a biennal herb used in cuisine for many centuries by Romans that has now been replaced by celery. We investigated the essential oil compositions of different plant organs collected in 18 populations of central Italy (Marche, Umbria, Abruzzo, Tuscany and Latium) by gas chromatography (GC) with a flame ionization detector and GC with mass spectrometry (MS) to identify the main chemotypes that occur. Owing to the presence of thermosensitive molecules such as isofuranodiene, curzerene and germacrone undergoing Cope‐rearrangement during the GC run, a truthful quantitative determination of these constituents was accomplished by high‐performance liquid chromatography with a diode‐array detector (HPLC‐DAD). Chemical data were supported by a chemometric technique in the form of principal component analysis, which allowed identification of chemical differences among organs. Furanosesquiterpenoids were the main fraction of the oils, with isofuranodiene as the most abundant in flowers and roots, furanoeremophil‐1‐one in leaves and roots and 1‐β‐acetoxyfuranoeudesm‐4(15)‐ene in fruits. To complete the phytochemical analysis, polar compounds such as chlorogenic acid, isoquercitin, 3‐indoleacetic acid and saccharose were isolated from the ethanolic extracts of the plant by column chromatography and structurally elucidated by nuclear magnetic resonance. Moreover, a morphological and histochemical survey on the secretory structures was performed, with the special aim to localize the sites of terpenes biosynthesis in both above‐ and belowground organs. Overall, the results can be considered important in the light of the recent interest in neglected edible plants for botanical food supplements and functional foods market. Copyright © 2014 John Wiley & Sons, Ltd.

LTC4 synthase polymorphism modifies efficacy of botanical seed oil combination in asthma.

Botanical seed oils reduce the generation of leukotrienes in patients with asthma.Our objective was to determine the efficacy of a botanical seed oil combination against airflow obstruction in asthma, and to determine the pharmacogenomic effect of the leukotriene C4 synthase (LTC4S) polymorphism A-444C.We conducted a randomized, double-blind, placebo-controlled, cross-over clinical trial in mild to moderate asthmatics to determine the change in FEV1 after 6 weeks of therapy with borage and echium seed oils versus corn oil placebo. We also examined the effect of the variant LTC4S -444C allele on the change in lung function.We did not identify a difference in FEV1 in the study cohort as a whole (n = 28), nor in the group of A homozygotes. In the C allele carriers (n = 9), FEV1 improved by 3% after treatment with borage and echium seed oils and declined by 4% after placebo corn oil (p = 0.02). All 9 C allele carriers demonstrated an improvement in their FEV1 on active treatment compared to placebo as compared to only 7 out of 19 A allele homozygotes (p = 0.007). We observed transient differences in ex vivo leukotriene generation from circulating basophils and granulocytes. We did not observe significant differences in urinary LTE4 levels.We conclude that compared to corn oil, a combination of borage and echium seed oils improves airflow obstruction in mild to moderate asthmatics who carry the variant allele in the LTC4S gene (A-444C). Botanical oil supplementation may have therapeutic potential in asthma if used in a personalized manner.Trial registration: This trial was registered at http://www.clinicaltrials.gov as NCT00806442.

Phytochemical modulators of human drug metabolism: An introduction to clinically relevant herb-drug interactions

Over the past two decades, an upsurge in botanical supplement usage, particularly within the United States, has engendered concerns among health care professionals regarding herb-drug interactions. Two general categories of herb-drug interactions have been recognized: pharmacodynamic and pharmacokinetic. Pharmacodynamic herb-drug interactions are those in which a botanical supplement can either enhance or diminish a drug's pharmacological activity without affecting its metabolism or transport. Pharmacokinetic herb-drug interactions involve phytochemical-mediated alterations in a drug's metabolism and/or transport. One mechanism that appears to underlie many herb-drug interactions is the modulation of human cytochrome P450 drug metabolizing enzyme (CYP450) activity. CYP450 s are heme-containing monooxygenases located in the small intestine, liver, and other tissues that play pivotal roles in the detoxification and bioactivation of diverse xenobiotics. Phytochemical-mediated changes in the activity of specific CYP450 isoforms (e.g., CYP3A4, CYP2D6) may significantly alter the efficacy or toxicity of conventional medications whose biotransformation pathways are dependent on these isoforms. Modulation of drug transport protein activity (e.g., P-glycoprotein, organic anion transporting polypeptide) is another mechanism by which phytochemicals can affect the pharmacokinetic profile of conventional medications. The purpose of this presentation is to provide an introduction to herb-drug interactions using clinically relevant examples of each category.

How America’s Flawed Supplement Law Creates the Mirage of Weight Loss Cures

Dr. Mehmet Oz, “America’s Doctor,” recently testified before Congress on why he was promoting supplements containing Garcinia cambogia, raspberry ketones, green coffee extract and other unproven ingredients as weight loss miracles. He acknowledged that “sometimes they don’t have the scientific muster to pass as fact.” In fact, there is no legal over-the-counter botanical supplement that has demonstrated clinical efficacy as a diet pill. [The only herbal treatment that can lead to modest weight loss is ephedra combined with caffeine, but this cocktail can also cause strokes, heart attacks and sudden death; hence, ephedra was banned in 2004.]

Effectiveness of a novel herbal agent MB-6 as a potential adjunct to 5-fluoracil–based chemotherapy in colorectal cancer

Natural products, such as fermented soybeans, have been used to treat various physical conditions, including cancer. MB-6 is a botanical preparation composed of fermented soybean extract, green tea extract, Antrodia camphorata mycelia, spirulina, grape seed extract, and curcumin extract. Based on this, we hypothesized that MB-6 would increase the effectiveness of chemotherapy in patients with colon cancer. In a rodent study, MB-6, in combination with leucovorin/5-fluorouracil chemotherapy, increased the survival rate and life span of colon cancer tumor-bearing BALB/c mice as compared with treatment with chemotherapy alone. In a proof-of-concept clinical study, 72 patients with metastatic colorectal cancer were randomized to receive leucovorin, 5-fluorouracil, and oxaliplatin in combination with either MB-6 or placebo for 16 weeks. The primary outcome was the best overall response, and secondary outcomes included progression-free survival, overall survival, and adverse effects. Up to 77 weeks after treatment, there was follow-up with the patients. No significant difference in the best overall response rate and overall survival was observed between the 2 groups. Patients in the MB-6 group had a significantly lower disease progression rate than patients in the placebo group, during the study period (0.0% vs 15.8%, P = .026). The placebo group had a significantly higher incidence of adverse events at least grade 4 compared with the MB-6 group (28.9% vs 2.9%, respectively, P = .004) and a significantly higher occurrence of increased serum creatinine compared with the MB-6 group (29% vs 5.9%, P = .014). MB-6 is a promising botanical supplement that may increase the effectiveness of chemotherapy in patients with metastatic colorectal cancer.

Artemisia scoparia enhances adipocyte development and endocrine function in vitro and enhances insulin action in vivo.

BackgroundFailure of adipocytes to expand during periods of energy excess can result in undesirable metabolic consequences such as ectopic fat accumulation and insulin resistance. Blinded screening studies have indicated that Artemisia scoparia (SCO) extracts can enhance adipocyte differentiation and lipid accumulation in cultured adipocytes. The present study tested the hypothesis that SCO treatment modulates fat cell development and function in vitro and insulin sensitivity in adipose tissue in vivo.Methods In vitro experiments utilized a Gal4-PPARγ ligand binding domain (LBD) fusion protein-luciferase reporter assay to examine PPARγ activation. To investigate the ability of SCO to modulate adipogenesis and mature fat cell function in 3T3-L1 cells, neutral lipid accumulation, gene expression, and protein secretion were measured by Oil Red O staining, qRT-PCR, and immunoblotting, respectively. For the in vivo experiments, diet-induced obese (DIO) C57BL/6J mice were fed a high-fat diet (HFD) or HFD containing 1% w/w SCO for four weeks. Body weight and composition, food intake, and fasting glucose and insulin levels were measured. Phospho-activation and expression of insulin-sensitizing proteins in epididymal adipose tissue (eWAT) were measured by immunoblotting.ResultsEthanolic extracts of A. scoparia significantly activated the PPARγ LBD and enhanced lipid accumulation in differentiating 3T3-L1 cells. SCO increased the transcription of several PPARγ target genes in differentiating 3T3-L1 cells and rescued the negative effects of tumor necrosis factor α on production and secretion of adiponectin and monocyte chemoattractant protein-1 in fully differentiated fat cells. DIO mice treated with SCO had elevated adiponectin levels and increased phosphorylation of AMPKα in eWAT when compared to control mice. In SCO-treated mice, these changes were also associated with decreased fasting insulin and glucose levels.ConclusionSCO has metabolically beneficial effects on adipocytes in vitro and adipose tissue in vivo, highlighting its potential as a metabolically favorable botanical supplement.

English

Noni (Morinda citrifolia L.) is a tropical plant belonging to the family, Rubiaceae. It is a small evergreen tree or shrub growing to a height of 3 to 6 m. Fruits are multiple, oblong, 5 to 7 cm long, soft, watery with a cheesy aroma. Fruits contain more than 150 compounds having nutraceutical properties. The major compounds isolated are scopoletine, octaanoic acid, vitamin C, terpenoids, alkaloids, anthraquinones, beta sitosterol, carotene, vitamin A, amino acids, acubin, etc. Xeronine is a miracle ingredient responsible for all therapeutic properties of noni and it is reported to exist in noni as its precursor prexeronine. Noni is most important botanical and dietary supplement traded in international market. The fruit is marketed in different forms such as fermented and pasteurized noni juice, noni powder, noni capsules, etc. Noni is a valuable medicinal plant and it may prove to be one of the more diversely valuable agents in nature’s medicine chest, and an enduring dietary supplement which serves the health needs of our country. Based on its ethnobotany, phytochemistry, production, processing and value addition as a highly nutritious medicinal plant, noni is discussed in detail. Key words: Noni, medicinal plant, nutritious, fermented, pasteurized.

Measuring Botanical Supplement Use among Hispanics/Latinos in the United States: A Comparison of Methods in the Hispanic Community Health Study/Study of Latinos (HCHS/SOL)

The Journal of Alternative and Complementary MedicineVol. 20, No. 5 Research MethodologyMeasuring Botanical Supplement Use among Hispanics/Latinos in the United States: A Comparison of Methods in the Hispanic Community Health Study/Study of Latinos (HCHS/SOL)Keturah Faurot, Anna-Maria Siega-Riz, Paula Gardiner, José O. Rivera, Laura Young, Hector González, Janice Barnhart, Sheila Casteneda, Diana Chirinos, Martha Daviglus, Rebeca Espinoza, Gregory Talavera, Linda Van Horn, Eric Whitsel, and M. Larissa Avilés-SantaKeturah FaurotSearch for more papers by this author, Anna-Maria Siega-RizSearch for more papers by this author, Paula GardinerSearch for more papers by this author, José O. RiveraSearch for more papers by this author, Laura YoungSearch for more papers by this author, Hector GonzálezSearch for more papers by this author, Janice BarnhartSearch for more papers by this author, Sheila CastenedaSearch for more papers by this author, Diana ChirinosSearch for more papers by this author, Martha DaviglusSearch for more papers by this author, Rebeca EspinozaSearch for more papers by this author, Gregory TalaveraSearch for more papers by this author, Linda Van HornSearch for more papers by this author, Eric WhitselSearch for more papers by this author, and M. Larissa Avilés-SantaSearch for more papers by this authorPublished Online:7 May 2014https://doi.org/10.1089/acm.2014.5364.abstractAboutSectionsView articleView Full TextPDF/EPUB Permissions & CitationsPermissionsDownload CitationsTrack CitationsAdd to favorites Back To Publication ShareShare onFacebookTwitterLinked InRedditEmail View article"Measuring Botanical Supplement Use among Hispanics/Latinos in the United States: A Comparison of Methods in the Hispanic Community Health Study/Study of Latinos (HCHS/SOL)." The Journal of Alternative and Complementary Medicine, 20(5), p. A136FiguresReferencesRelatedDetails Volume 20Issue 5May 2014 InformationCopyright 2014, Mary Ann Liebert, Inc.To cite this article:Keturah Faurot, Anna-Maria Siega-Riz, Paula Gardiner, José O. Rivera, Laura Young, Hector González, Janice Barnhart, Sheila Casteneda, Diana Chirinos, Martha Daviglus, Rebeca Espinoza, Gregory Talavera, Linda Van Horn, Eric Whitsel, and M. Larissa Avilés-Santa.Measuring Botanical Supplement Use among Hispanics/Latinos in the United States: A Comparison of Methods in the Hispanic Community Health Study/Study of Latinos (HCHS/SOL).The Journal of Alternative and Complementary Medicine.May 2014.A136-A136.http://doi.org/10.1089/acm.2014.5364.abstractPublished in Volume: 20 Issue 5: May 7, 2014PDF download

Quantitation of Selected Polyphenols in Plant-Based Food Supplements by Liquid Chromatography–Ion Trap Mass Spectrometry

A high-performance liquid chromatography method with electrospray ionization mass spectrometric detection (HPLC-ESI-MS/MS) for the determination of some of the most important polyphenols present in botanical supplements has been developed. The target analytes were five flavonoids (diosmin, hesperidin, quercetin, rutin and troxerutin) and the flavolignan silybin. The extraction of the analytes from the supplements was carried out by ultrasound-assisted extraction using 100 % dimethyl sulfoxide (or methanol) for 15 min. After centrifugation, 1 μL of the diluted supernatant was injected in the HPLC system and the quantitation was performed by ESI-MS using the negative ionization mode, with methylparaben as internal standard. The validation of the method was performed with recovery experiments, observing recoveries in the range of 85–112 %, and relative standard deviations lower than 10 % for the complete analytical procedure, including the extraction. The limits of detection were in the 2.5–120 μg L−1 range.

Artemisia supplementation differentially affects the mucosal and luminal ileal microbiota of diet-induced obese mice

ObjectiveThe gut microbiome has been implicated in obesity and metabolic syndrome; however, most studies have focused on fecal or colonic samples. Several species of Artemisia have been reported to ameliorate insulin signaling both in vitro and in vivo. The aim of this study was to characterize the mucosal and luminal bacterial populations in the terminal ileum with or without supplementation with Artemisia extracts. MethodsFollowing 4 wk of supplementation with different Artemisia extracts (PMI 5011, Santa or Scopa), diet-induced obese mice were sacrificed and luminal and mucosal samples of terminal ileum were used to evaluate microbial community composition by pyrosequencing of 16 S rDNA hypervariable regions. ResultsSignificant differences in community structure and membership were observed between luminal and mucosal samples, irrespective of diet group. All Artemisia extracts increased the Bacteroidetes to Firmicutes ratio in mucosal samples. This effect was not observed in the luminal compartment. There was high interindividual variability in the phylogenetic assessments of the ileal microbiota, limiting the statistical power of this pilot investigation. ConclusionsMarked differences in bacterial communities exist depending on the biogeographic compartment in the terminal ileum. Future studies testing the effects of Artemisia or other botanical supplements require larger sample sizes for adequate statistical power.

Efficacy of a Botanical Supplement with Concentrated Echinacea purpurea for Increasing Aerobic Capacity.

The present investigation evaluated the efficacy of a botanical supplement that delivered a concentrated dose of Echinacea purpurea (8 grams day−1). The participants were 13 apparently healthy, recreationally active college students (VO2 max: 51 mL O2/kg∗min). The participants were provided with a 30-day supplementation regime. Data regarding maximum aerobic capacity was collected through pre- and posttesting surrounding the 30-day supplementation regime. The participants were instructed to maintain normal levels of physical activity and exercise during the experimental period. The levels of physical activity and exercise were monitored via the Leisure and Physical Activity Survey. The participants did not report any significant increases in aerobic physical activity or exercise during the supplementation period. Paired samples t-test analysis did not reveal a significant difference in maximum aerobic capacity, t(12) = 0.67, P = .516. Presupplementation maximum aerobic capacity (M = 51.0, SD = 6.8) was similar to postsupplementation values (M = 51.8, SD = 6.5). This study suggests that botanical supplements containing a concentrated dose of Echinacea purpurea is not an effective intervention to increase aerobic capacity of recreationally active individuals.

The Need for a Legal Distinction of Nutraceuticals

The nutraceutical and botanical terms are often used by the lay press or for marketing purposes to describe health beneficial food, food supplements or herbs. However, there is no common definition of nutraceuticals or botanicals and moreover a lack of regulation that classifies this category. Concerning their health value, it is unclear if they belong to drugs or food. Currently, they fall into a legal limbo between both. This regulatory lack can lead to misuse of claims indicating a health benefit or the misleading of the consumer. This review will focus on current definitions of nutraceutical, botanical, functional food and food supplements with special emphasis on the differences between the US and European legislation. Some special considerations will be given for Germany, one of the main markets for food supplements in Europe.

St. John's Wort Has Metabolically Favorable Effects on Adipocytes In Vivo.

In addition to serving as a storage site for reserve energy, adipocytes play a critical role in whole-body insulin sensitivity and glucose metabolism. St. John's Wort (SJW) is a botanical supplement widely used as an over-the-counter treatment of depression and a variety of other conditions associated with anxiety and nerve pain. Previous studies in our laboratory demonstrated that SJW inhibits insulin-stimulated glucose uptake and adipocyte differentiation in cultured murine and mature human adipocytes. To investigate the effects of SJW on adipocyte function in vivo, we utilized C57BL/6J mice. In our studies, mice were administered SJW extract (200 mg/kg) once daily by gavage for two weeks. In contrast to our in vitro studies, mice treated with SJW extract showed increased levels of adiponectin in white adipose tissue in a depot specific manner (P < 0.01). SJW also exerted an insulin-sensitizing effect as indicated by a significant increase in insulin-stimulated Akt serine phosphorylation in epididymal white adipose tissue (P < 0.01). Food intake, body weight, fasting blood glucose, and fasting insulin did not differ between the two groups. These results are important as they indicate that SJW does not promote metabolic dysfunction in adipose tissue in vivo.

A new problem. Contamination of botanicals by phthalates. Rapid detection tests

The purity of solvents used in medical, herbal and food products is an essential prerequisite. This communication is focused on the possible occurrence of phthalates contaminant derived from the utilisation of plastic containers for solvents instead of glass containers. The contamination must be detected also in the derived marketed extracts, like botanical food supplements.

Isolation, purification and characterisation of selenium-containing polysaccharides and proteins in selenium-enriched Radix puerariae

Selenium (Se) is an essential dietary mineral and Radix puerariae (RP) (the dried root of Pueraria lobata Willd.) is a botanical supplement widely used as a nutraceutical. Food enriched with Se provides a feasible and economic approach for production of organic Se compounds. However, little is known about Se-enriched RP and the structure of Se-containing polysaccharides and proteins derived from Se-enriched RP. The organic form of Se accounted for 82.42% of total content. Purification by DEAE-52 and Sephadex G-100 column chromatography yielded three single fractions--RP-SeP-11, RP-SeP-22 and RP-SeP-33--with Se contents of 0.9562 × 10⁻³, 0.6113 × 10⁻³ and 0.3827 × 10⁻³ g kg⁻¹, respectively. RP-SeP-11 (3.5 kDa) was made of glucose, RP-SeP-22 (19.6 kDa) was composed of xylose and glucose, and RP-SeP-33 (97.9 kDa) was made up galactose, mannose and glucose. Two Se-containing proteins were obtained with Se content of 3.175 × 10⁻³ and 4.328 × 10⁻³ g kg⁻¹, respectively. One appeared as three subunits with molecular masses of 43.0, 29.0 and 17.8 kDa while the other appeared as two subunits with molecular masses of 43.0 and 26.3 kDa. The results provide a basis for promoting the utilisation of RP resources enriched with Se as a promising tool for the food industry and are significant for its contribution to Se biochemistry in plants.

Why do we have for health claims different criteria between plant based food supplements and herbal medicinal products?

It seems obvious for most of the people that there are strong differences between botanical food supplements and herbal medicinal products, especially because consumers as well as treatment goals are not the same. However, some main convergences can be observed as for example quality and safety. A key question today is why for a given plant and the same preparation, the requirements imposed by the official European authorities (EMEA) are less severe in terms of clinical assessments to get a marketing authorization for a food product in comparison to a medicinal product? In the EU, traditional herbal medicinal products having a long history of prior human usage can be registered under a special, simplified registration procedure without the necessity of providing some proofs of efficacy with clinical trials. This is the consequence of a specific legal framework known as Directive 2004/24/EC. On the contrary, regarding food products, EFSA requires randomized clinical trials on healthy subjects and under such requirements no “traditional claims” will obtain a positive opinion from this Authority. Furthermore, it is really difficult to understand that for a drug, designed for a targeted disease and focused on a given pharmacological activity, the proof of its efficacy is not required in a contrary to a food supplement, used to maintain the homeostasis status and to help in minor troubles, where the efficacy proof is required. The dosage of a plant extract being lower for a food supplement than for a drug reinforces the difficulty to get the validation. How can we demonstrate such efficacy on a person without evident pathology but having only some well-being problems? In a scientific perspective, this clinical approach is adapted to pure active substances as vitamins but not to the complexity of plant extracts. Many years ago, a group of experts at the Council of Europe proposed some recommendations to differentiate the requirements necessary for food supplements and for herbal drug medicine, taking into consideration for example the individual impact and the final aim of the product. Unfortunately, this proposal has not been retained. In conclusion, we consider today that the requirements necessary to get a validated health claim for botanical food supplements and botanical preparations are not appropriate, leading to an insoluble situation. European harmonization is more and more necessary.

Efficacy and safety regulations and scientific criteria applicable to traditional botanical food supplements and herbal medicinal products marketed in the European Union

Efficacy and safety regulations and scientific criteria applicable to traditional botanical food supplements and herbal medicinal products marketed in the European Union

Health claims for botanical food supplements: approach and consequences for the regulatory framework

Health claims for botanical food supplements: approach and consequences for the regulatory framework

Evaluation of Estrogenic Activity of Licorice Species in Comparison with Hops Used in Botanicals for Menopausal Symptoms

The increased cancer risk associated with hormone therapies has encouraged many women to seek non-hormonal alternatives including botanical supplements such as hops (Humulus lupulus) and licorice (Glycyrrhiza spec.) to manage menopausal symptoms. Previous studies have shown estrogenic properties for hops, likely due to the presence of 8-prenylnarigenin, and chemopreventive effects mainly attributed to xanthohumol. Similarly, a combination of estrogenic and chemopreventive properties has been reported for various Glycyrrhiza species. The major goal of the current study was to evaluate the potential estrogenic effects of three licorice species (Glycyrrhiza glabra, G. uralensis, and G. inflata) in comparison with hops. Extracts of Glycyrrhiza species and spent hops induced estrogen responsive alkaline phosphatase activity in endometrial cancer cells, estrogen responsive element (ERE)-luciferase in MCF-7 cells, and Tff1 mRNA in T47D cells. The estrogenic activity decreased in the order H. lupulus > G. uralensis > G. inflata > G. glabra. Liquiritigenin was found to be the principle phytoestrogen of the licorice extracts; however, it exhibited lower estrogenic effects compared to 8-prenylnaringenin in functional assays. Isoliquiritigenin, the precursor chalcone of liquiritigenin, demonstrated significant estrogenic activities while xanthohumol, a metabolic precursor of 8-prenylnaringenin, was not estrogenic. Liquiritigenin showed ERβ selectivity in competitive binding assay and isoliquiritigenin was equipotent for ER subtypes. The estrogenic activity of isoliquiritigenin could be the result of its cyclization to liquiritigenin under physiological conditions. 8-Prenylnaringenin had nanomolar estrogenic potency without ER selectivity while xanthohumol did not bind ERs. These data demonstrated that Glycyrrhiza species with different contents of liquiritigenin have various levels of estrogenic activities, suggesting the importance of precise labeling of botanical supplements. Although hops shows strong estrogenic properties via ERα, licorice might have different estrogenic activities due to its ERβ selectivity, partial estrogen agonist activity, and non-enzymatic conversion of isoliquiritigenin to liquiritigenin.