RESUMEN
CYP3A4-mediated Phase I biotransformation is the rate-limiting step of elimination for many commonly used clinically agents. The modulatory effects of herbal medicines on CYP3A4 activity are one of the risk factors affecting the safe use of drug and herbal medicine. In the present study, the inhibitory effects of nearly hundred kinds of herbal medicines against CYP3A4 were evaluated based on a visual high-throughput screening method. Furthermore, biflavone components including bilobetin (7-demethylginkgetin, DGK), ginkgetin (GK), isoginkgetin (IGK), and amentoflavone (AMF) were identified as the main inhibitory components of Ginkgo biloba L. (GB) and Selaginella tamariscina (P. Beauv.) Spring (ST), which displayed very strong inhibitory effects toward CYP3A4. The inhibitory effects of these biflavones on clinical drugs that mainly undergo CYP3A4-dependent metabolism were evaluated. The IC 50 of GK toward tamoxifen, gefitinib and ticagrelor were found to be of 0.478 ± 0.003, 0.869 ± 0.001, and 1.61 ± 0.039 µM, respectively. These results suggest the potential pharmacokinetic interactions between the identified biflavones and clinical drugs undergoing CYP3A4-mediated biotransformation. The obtained information is important for guiding the rational use of herbal medicine in combination with synthetic pharmaceuticals.
RESUMEN
Seventeen triterpenoids including four new lanostane triterpenoids (1-3 and 5) were isolated from the fruiting bodies of Ganoderma lucidum by various chromatographic techniques. Their chemical structures were determined by extensive spectroscopic data, including 1D-NMR, 2D-NMR, and HRESIMS. In addition, the spectral data of compound 4 was reported for the first time. In an in vitro bioassay, most isolated triterpenoids could inhibit the hydrolysis activity of fatty acid amide hydrolase (FAAH). Furthermore, there is no cytotoxicity observed for these isolated triterpenoids. Therefore, G. lucidum showed the potential application for anti-neuroinflammation and more FAAH inhibitors may be explored from G. lucidum.
Asunto(s)
Ganoderma , Reishi , Triterpenos , Amidohidrolasas , Cuerpos Fructíferos de los Hongos/química , Ganoderma/química , Estructura Molecular , Reishi/química , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
Two undescribed ent-abietane-type diterpenoid dimers with nonacyclic backbone formed by intermolecular [4 + 2] cycloaddition into a spirocyclic skeleton, bisfischoids A (1) and B (2), along with a known one fischdiabietane A (3), were identified from Euphorbia fischeriana Steud. Their structures were elucidated by extensive spectroscopic analysis, ECD and NMR calculation combined with DP4+ probability analysis, as well as X-ray diffraction. The anti-inflammatory potential of dimers 1-3 were examined using their inhibitory effects on soluble epoxide hydrolase (sEH), which revealed that 1 and 2 exhibited promising activities with inhibition constant (Ki) of 3.20 and 1.95 µM, respectively. Further studies of molecular docking and molecular dynamics indicated that amino acid residue Tyr343 in the catalytic cavity of sEH was the key site for their inhibitory function.
Asunto(s)
Antiinflamatorios/farmacología , Medicamentos Herbarios Chinos/farmacología , Epóxido Hidrolasas/antagonistas & inhibidores , Euphorbia/química , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Epóxido Hidrolasas/metabolismo , Humanos , Medicina Tradicional China , Estructura Molecular , Relación Estructura-ActividadRESUMEN
Inhibition of soluble epoxide hydrolase (sEH) is considered to be an effective treatment for inflammation-related diseases, and small molecules origin from natural products show promising activity against sEH. Two undescribed protostanes, 3ß-hydroxy-25-anhydro-alisol F (1) and 3ß-hydroxy-alisol G (2) were isolated from Alisma orientale and identified as new sEH inhibitors with IC50 values of 10.06 and 30.45 µM, respectively. Potential lead compound 1 was determined as an uncompetitive inhibitor against sEH, which had a Ki value of 5.13 µM. In-depth molecular docking and molecular dynamics simulations revealed that amino acid residue Ser374 plays an important role in the inhibition of 1, which also provides an idea for the development of sEH inhibitors based on protostane-type triterpenoids.
Asunto(s)
Alisma/química , Inhibidores Enzimáticos/farmacología , Epóxido Hidrolasas/antagonistas & inhibidores , Triterpenos/farmacología , Inhibidores Enzimáticos/química , Epóxido Hidrolasas/química , Concentración 50 Inhibidora , Modelos Moleculares , Simulación del Acoplamiento Molecular , Simulación de Dinámica Molecular , Estructura Molecular , Farmacocinética , Extractos Vegetales/química , Extractos Vegetales/farmacología , Conformación Proteica , Triterpenos/químicaRESUMEN
As a genus of the Asteraceae, Inula is widely distributed all over the world, and several of them are being used in traditional medicines. A number of metabolites were isolated from Inula species, and some of these have shown to possess ranges of pharmacological activities. The genus Inula contains abundant sesquiterpenoids, such as eudesmanes, xanthanes, and sesquiterpenoid dimers and trimers. In addition, other types of terpenoids, flavonoids, and lignins also exist in the genus Inula. Since 2010, more than 300 new secondary metabolites, including several known natural products that were isolated for the first time from the genus Inula. Most of them exhibited potential bioactivities in various diseases. The review aimed to summarize the advance of recent researches (2010-2020) on phytochemical constituents, biosynthesis, and pharmacological properties of the genus Inula for providing a scientific basis and supporting its application and exploitation for new drug development.
Asunto(s)
Inula/química , Extractos Vegetales , Desarrollo de Medicamentos , Humanos , Estructura Molecular , Extractos Vegetales/biosíntesis , Extractos Vegetales/química , Extractos Vegetales/farmacologíaRESUMEN
Carboxylesterase 2 (CES 2), plays a pivotal role in endobiotic homeostasis and xenobiotic metabolism. Protostanes, the major constituents of the genus Alisma, display a series of pharmacological activities. Despite the extensive studies of pharmacological activities, the investigation on inhibitory effects of protostanes against CES 2 is rarely reported. In this study, the inhibitory activities of a library of protostanes (1-25) against human CES 2 were investigated for the first time, using 6,8-dichloro-9,9-dimethyl-7-oxo-7,9-dihydroacridin-2-yl benzoate (DDAB) as the specific fluorescent probe for human CES 2. Compounds 1, 2, 7, 8, 12, 13, 18, 19, and 25 showed strong inhibitory effects towards CES 2. For the most potent compounds 1, 7, 13, and 25, the inhibition kinetics were further investigated, and these four protostanes were all uncompetitive inhibitors against human CES 2 with the inhibition constant (Ki) values ranging from 0.89 µM to 2.83 µM. In addition, molecular docking and molecular dynamics stimulation were employed to analyze the potential interactions between these protostanes and CES 2, and amino acid residue Gln422 was identified to play a crucial role in the strong inhibition of protostanes towards CES 2.
Asunto(s)
Alisma/química , Carboxilesterasa/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/farmacología , Triterpenos/química , Triterpenos/farmacología , Acridinas/química , Benzoatos/química , Colorantes Fluorescentes/química , Concentración 50 Inhibidora , Cinética , Simulación del Acoplamiento Molecular , Simulación de Dinámica Molecular , Relación Estructura-ActividadRESUMEN
The genus Alisma contains 11 species distributed worldwide, of which at least two species (A. orientale [Sam.] Juzep. and A. plantago-aquatica Linn.) have been used as common herbal medicines. Secondary metabolites obtained from the genus Alisma are considered to be the material basis for the various biological functions and medicinal applications. In this review, we mainly focused on the recent investigations of secondary metabolites from plants of the genus Alisma and their biological activities, with the highlighting on the diversity of the chemical structures, the biosynthesis of interesting secondary metabolites, the biological activities, and the relationships between structures and bioactivities.
Asunto(s)
Alisma/química , Fitoquímicos/uso terapéutico , Plantas Medicinales/química , HumanosRESUMEN
The genus Uncaira (Rubiaceae) comprises of 34 species, many of which are usually used as traditional Chinese medicines (TCMs) to treat hypertension, fever, headache, gastrointestinal illness, and fungal infection. Over the past twenty years, Uncaira species have been paid the considerable attentions in phytochemical and biological aspects, and about 100 new secondary metabolites, including alkaloids, triterpenes, and flavonoids, have been elucidated. This review aims to present a comprehensive and up-to date overview of the biological source, structures and their biosynthetic pathways, as well as the pharmacological of the compounds reported in the genus Uncaria for the past two decades. It would provide an insight into the emerging pharmacological applications of the genus Uncaria.
Asunto(s)
Fitoquímicos/farmacología , Uncaria/química , Alcaloides/farmacología , Vías Biosintéticas , Flavonoides/farmacología , Medicina Tradicional China , Estructura Molecular , Metabolismo Secundario , Triterpenos/farmacologíaRESUMEN
Cardiovascular diseases, such as hypertension and cardiac failure, have become the most major and global cause for threatening human health in recent years. Uncaria rhynchophylla as a traditional Chinese medicine is widely used to treat hypertension for a long history, whereas its medicinal effective components and potential action mechanism are uncertain. Therefore, twenty-four alkaloids (1-24) isolated from U. rhynchophylla were assayed for their relaxant effects against phenylephrine (Phe)-induced contraction of rat mesenteric arteries. Among them, we surprisingly found that uncarialin A (21) exhibited most potent relaxation effect against Phe-induced contraction (IC50 = 0.18 µM) in the manner of independent on endothelium-derived vasorelaxing factors and endothelium. All the experiments including measurement of Ca2+ in vascular smooth muscle cells (VSMCs) by fluorescence microscopy, whole-cell path clamp, molecular docking, and molecular dynamics, demonstrated that uncarialin A (21) could significantly inhibit L-type calcium channel subunit alpha-1C (Cav1.2) via the hydrogen bond interaction with amino acid residue Met1186, allowing the inhibition of Ca2+ inward current. Our results suggested that uncarialin A (21) could be served as a potential L-type Cav1.2 blocker in the effective treatment of cardiovascular diseases.
Asunto(s)
Bloqueadores de los Canales de Calcio/farmacología , Canales de Calcio Tipo L/metabolismo , Medicamentos Herbarios Chinos/química , Vasodilatadores/farmacología , Alcaloides/análisis , Animales , Sitios de Unión , Células CHO , Bloqueadores de los Canales de Calcio/química , Canales de Calcio Tipo L/química , Células Cultivadas , Cricetinae , Cricetulus , Masculino , Arterias Mesentéricas/efectos de los fármacos , Ratones , Ratones Endogámicos C57BL , Miocitos del Músculo Liso/efectos de los fármacos , Unión Proteica , Ratas , Ratas Sprague-Dawley , Uncaria/química , Vasodilatadores/químicaRESUMEN
In this study, forty-nine kinds of traditional Chinese medicines (TCMs) were evaluated for their inhibitory activities against human carboxylesterase 2 (HCE 2) using a human liver microsome (HLM) system. Swertia bimaculata showed significant inhibition on HCE 2 at 10⯵g/mL among forty-nine kinds of TCMs. The extract of Swertia bimaculata was separated by preparative HPLC to afford demethylbellidifolin (1) identified by MS, 1H NMR, and 13C NMR spectra. Demethylbellidifolin (1) was assayed for its inhibitory HCE 2 effect by HCE 2-mediated DDAB hydrolysis, and its potential IC50 value was 3.12⯱â¯0.64⯵M. Demethylbellidifolin (1) was assigned as a mixed-type competitive inhibitor with the inhibiton constant Ki value of 6.87⯵M by Lineweaver-Burk and slope plots. Living cell imaging was conducted to corroborate its inhibitory HCE 2 activity. Molecular docking indicated potential interactions of demethylbellidifolin (1) with HCE 2 through two hydrogen bonds of the C-3 and C-5 hydroxy groups with amino acid residues Glu227 and Ser228 in the catalytic cavity, respectively.
Asunto(s)
Carboxilesterasa/antagonistas & inhibidores , Microsomas Hepáticos/efectos de los fármacos , Simulación del Acoplamiento Molecular , Extractos Vegetales/farmacología , Swertia/química , Xantenos/aislamiento & purificación , Xantenos/farmacología , Carboxilesterasa/metabolismo , Humanos , Hidrólisis , Microsomas Hepáticos/enzimología , Estructura MolecularRESUMEN
As a part of our searching for natural human carboxylesterase 2 (human CES 2) inhibitors from traditional Chinese medicine, we found that the extract of Alisma orientale significantly inhibited human CES 2 in vitro. The investigation on A. orientale led to the isolation of a new protostane-type triterpenoid alismanin I (1). Its structure was determined according to HRESIMS, 1D and 2D NMR spectra. Alismanin I (1) displayed significantly inhibitory activity against human CES 2 with IC50 value of 1.31⯱â¯0.09⯵M assayed by human CES 2-mediated DDAB hydrolysis. According to its inhibition kinetic result, compound 1 was a noncompetitive type inhibitor, and its Ki was 3.65⯵M. Its inhibitory effect was confirmed in living cell level through a visual manner. The potential interaction mechanism of compound 1 with human CES 2 was also analyzed by circular dichroism (CD) spectrum and molecular docking.
Asunto(s)
Alisma/química , Carboxilesterasa/antagonistas & inhibidores , Carboxilesterasa/metabolismo , Inhibidores Enzimáticos/farmacología , Simulación del Acoplamiento Molecular , Extractos Vegetales/farmacología , Carboxilesterasa/química , Dominio Catalítico , Dicroismo Circular , Inhibidores Enzimáticos/metabolismo , Humanos , Cinética , Extractos Vegetales/metabolismoRESUMEN
BACKGROUND: Carboxylesterases (CEs) belong to the serine hydrolase family, and are in charge of hydrolyzing chemicals with carboxylic acid ester and amide functional groups via Ser-His-Glu. Uncaria rhynchophylla (Miq.) Miq. ex Havil. is a famous traditional Chinese medicine used in managing hyperpyrexia, epilepsy, preeclampsia, and hypertension in China. HYPOTHESIS/PURPOSE: To discover the potential natural human carboxylesterase 2 (hCE 2) inhibitors from U. rhynchophylla. METHODS: Compounds were obtained from the hooks of U. rhynchophylla by silica gel and preparative HPLC. Their structures were elucidated by using HRESIMS, 1D and 2D NMR spectra. Their inhibitory activeties and inhibition kinetics against hCE 2 were assayed by the fluorescent probe, and potential mechanisms were also investigated by molecular docking. RESULTS: Twenty-three compounds, including a new phenolic acid uncariarhyine A (1), eight known triterpenoids (2-9), and ten known aromatic derivatives (10, 13-16, and 19-23), were isolated from U. rhynchophylla. Compounds 1-5, 7, 9, and 15 showed significant inhibitory activities against hCE 2 with IC50 values from 4.01⯠±â¯0.61 µM to 18.60⯱â¯0.21 µM, and their inhibition kinetic analysis results revealed that compounds 1, 5, 9, and 15 were non-competitive; compounds 3 and 4 were mixed-type, and compounds 2 and 7 were uncompetitive. Molecular docking studies indicated inhibition mechanisms of compounds 1-5, 7, 9, and 15 against hCE 2. CONCLUSION: Our present findings highlight potential natural hCE 2 inhibitors from U. rhynchophylla.
Asunto(s)
Carboxilesterasa/antagonistas & inhibidores , Medicamentos Herbarios Chinos/farmacología , Inhibidores Enzimáticos/farmacología , Fitoquímicos/farmacología , Triterpenos/farmacología , Uncaria/química , China , Cromatografía Líquida de Alta Presión , Humanos , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Cinética , Simulación del Acoplamiento Molecular , Estructura Molecular , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/farmacología , Triterpenos/química , Triterpenos/aislamiento & purificaciónRESUMEN
BACKGROUND/AIMS: Uncaria rhynchophylla, known as "Gou-teng", is a traditional Chinese medicine (TCM) used to extinguish wind, clear heat, arrest convulsions, and pacify the liver. Although U. rhynchophylla has a long history of being often used to treat central nervous system (CNS) diseases, its efficacy and potential mechanism are still uncertain. This study investigated neuroprotective effect and the underlying mechanism of U. rhynchophylla extract (URE) in MPP+-induced SH-SY5Y cells and MPTP-induced mice. METHODS: MPP+-induced SH-SY5Y cells and MPTP-induced mice were used to established Parkinson's disease (PD) models. Quantitative proteomics and bioinformatics were used to uncover proteomics changes of URE. Western blotting was used to validate main differentially expressed proteins and test HSP90 client proteins (apoptosis-related, autophagy-related, MAPKs, PI3K, and AKT proteins). Flow cytometry and JC-1 staining assay were further used to confirm the effect of URE on MPP+-induced apoptosis in SH-SY5Y cells. Gait analysis was used to detect the behavioral changes in MPTP-induced mice. The levels of dopamine (DA) and their metabolites were examined in striatum (STR) by HPLC-EC. The positive expression of tyrosine hydroxylase (TH) was detected by immunohischemical staining and Western blotting. RESULTS: URE dose-dependently increased the cell viability in MPP+-induced SH-SY5Y cells. Quantitative proteomics and bioinformatics results confirmed that HSP90 was an important differentially expressed protein of URE. URE inhibited the expression of HSP90, which further reversed MPP+-induced cell apoptosis and autophagy by increasing the expressions of Bcl-2, Cyclin D1, p-ERK, p-PI3K p85, PI3K p110α, p-AKT, and LC3-I and decreasing cleaved caspase 3, Bax, p-JNK, p-p38, and LC3-II. URE also markedly decreased the apoptotic ratio and elevated mitochondrial transmembrane potential (DΨm). Furthermore, URE treatment ameliorated behavioral impairments, increased the contents of DA and its metabolites and elevated the positive expressions of TH in SN and STR as well as the TH protein. CONCLUSIONS: URE possessed the neuroprotective effect in vivo and in vitro, regulated MAPK and PI3K-AKT signal pathways, and inhibited the expression of HSP90. U. rhynchophylla has potentials as therapeutic agent in PD treatment.
Asunto(s)
Medicamentos Herbarios Chinos/farmacología , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Proteínas HSP90 de Choque Térmico/biosíntesis , Sistema de Señalización de MAP Quinasas/efectos de los fármacos , Fármacos Neuroprotectores/farmacología , Trastornos Parkinsonianos , Uncaria/química , Animales , Línea Celular Tumoral , Medicamentos Herbarios Chinos/química , Humanos , Ratones , Fármacos Neuroprotectores/química , Trastornos Parkinsonianos/tratamiento farmacológico , Trastornos Parkinsonianos/metabolismo , Trastornos Parkinsonianos/patología , ProteómicaRESUMEN
BACKGROUND: Cholestasis is a clinical syndrome of liver damage that is caused by accumulation of bile acids in the liver and systemic circulation. Farnesoid X receptor (FXR) can regulate synthesis, metabolism, and excretion of bile acids. The rhizomes of Alisma orientale is a well-known traditional Chinese medicine to treat edema, obesity, gonorrhea, leukorrhea, diarrhea, hyperlipidemia, and diabetes in China. HYPOTHESIS/PURPOSE: We hypothesized Alisma orientale extract (AOE) to exert hepatoprotective effect against α-naphthylisothiocyanate (ANIT) induced cholestasis in rat. We aimed to investigate the mechanism of AOE. STUDY DESIGN: Male Sprague Dawley rats with intrahepatic cholestasis induced by ANIT were treated with AOE (150, 300, or 600â¯mg/kg). Rats receiving vehicle (0.5% CMC-Na) served as control. METHODS: 48â¯h after ANIT administration, rats were sacrificed. Blood was collected to obtain serum and livers were removed for histopathology and protein preparation. Biochemical indicators in serum were determined using commercial kits and triterpenoids were determined by liquid chromatography tandem Qtrap mass spectrometry. Proteomics was analyzed by liquid chromatography tandem ion-trap mass spectrometry. The differently expressed proteins were analyzed via the network database and verified by western blotting. The interaction between triterpenoids and FXR were evaluated by luciferase assay and molecular docking. RESULTS: AOE treatment significantly decreased the serum AST, ALT, TBIL, and intrahepatic TBA and improved the liver pathologic change induced by ANIT. Proteomics analysis indicated that AOE regulated proteins related to bile acid homeostasis via activating farnesoid X receptor (FXR) signaling pathway. Luciferase assay and molecular docking results indicated that triterpenoids could activate FXR, which resulting in ameliorative accumulation of bile acids in the liver by increase of metabolism and transportation for bile acids, and decrease of synthesis for bile acids. CONCLUSION: AOE protected against rat liver injury and cholestasis induced by ANIT by activation of farnesoid X receptor, suggesting that A. orientale could be regarded as a potential hepatoprotective drug.
Asunto(s)
Alisma/química , Colestasis Intrahepática/tratamiento farmacológico , Medicamentos Herbarios Chinos/farmacología , Receptores Citoplasmáticos y Nucleares/metabolismo , 1-Naftilisotiocianato/toxicidad , Alanina Transaminasa/sangre , Animales , Aspartato Aminotransferasas/sangre , Ácidos y Sales Biliares/metabolismo , Bilirrubina/metabolismo , China , Colestasis Intrahepática/inducido químicamente , Colestasis Intrahepática/patología , Medicamentos Herbarios Chinos/química , Homeostasis/efectos de los fármacos , Hígado/efectos de los fármacos , Hígado/patología , Masculino , Simulación del Acoplamiento Molecular , Sustancias Protectoras/farmacología , Ratas Sprague-Dawley , Transducción de Señal/efectos de los fármacosRESUMEN
The chemical constituent investigation of Alisma plantago-aquatica subsp. orientale has led to isolation and identification of thirteen compounds, including one new sesquiterpene, (10S)-11-hydroxy-ß-cyperone (1), three sesquiterpenes (2-4), five phenylpropanoids (5-9), and four alkaloids (10-13). We report herein, for the first time, the presence of compounds 2-13 in the genus Alisma. Their structures were established using 1D and 2D NMR and HRESIMS spectroscopic analyses. All the isolated compounds were assayed for their inhibitory activities against nitric oxide production in LPS-induced RAW 264.7 cells and antioxidant activities by DPPH scavenging assay. Compounds 1-13 displayed significant inhibitory effects against NO production at a certain concentration, while compound 5 showed antioxidant activity with IC50 of 55.28 µM. The interactions of compounds 1, 5, and 11 with iNOS were investigated using molecular docking.
Asunto(s)
Alisma/química , Antiinflamatorios/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Alcaloides/química , Alcaloides/aislamiento & purificación , Animales , Antiinflamatorios/farmacología , Antioxidantes/farmacología , Ratones , Simulación del Acoplamiento Molecular , Estructura Molecular , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Extractos Vegetales/química , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificaciónRESUMEN
The chemical characteristic of a well-known folk medicine Ganoderma lucidum has been investigated by a series of chromatographic technologies, which displayed the presences of 45 lanostane type triterpenoids, including two new nor-lanostane triterpenoids (40, 41). Their structures were identified on the basis of spectroscopic data analysis (UV, IR, HRESIMS, 1D, and 2D NMR). Notably, some triterpenoids displayed moderate inhibitory effects against AChE (acetylcholinesterase) by an in vitro screened experiment. Triterpenoid 2 displayed the potent inhibitory effect with IC50 10.8 and Ki 14.95 µM (inhibition kinetic). The preliminary SAR has been discussed by the docking analyses between ganoderic acids (1, 2) and AChE.
Asunto(s)
Inhibidores de la Colinesterasa/farmacología , Ganoderma/química , Triterpenos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Modelos Moleculares , Relación Estructura-Actividad , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
Chemical investigation has been performed on the roots of Euphorbia fischeriana, a traditional Chinese medicine. Three diterpenoids were obtained using various chromatographic techniques, and their structures were determined by spectroscopic data including HRESIMS, 1D NMR, 2D NMR, ECD, and calculated ECD, which gave two new diterpenoids, daphnane type (1) and ent-pimarene type (3). Additionally, the isolated compounds (1-3) displayed moderate inhibitory effects against α-glucosidase in an in vitro bioassay.