Dimeric phthalides from an aqueous extract of the Angelica sinensis root head / 药学学报

Ten dimeric phthalide racemates (1-10) were isolated from an aqueous extract of the Angelica sinensis root head (Guitou) by separation techniques of column chromatography over macroporous adsorbent resin, MCI resin, silica gel, and Sephadex LH-20, together with preparative thin-layer chromatography and reversed phase HPLC. The racemates were further separated into (+)-/(-)-1-(+)-/(-)-10 with chiral HPLC. Their structures including absolute configurations were elucidated by comprehensive analysis of spectroscopic data, combined with electronic circular dichroism (ECD) and NMR calculations as well as single crystal X-ray diffractions. Compounds (+)-/(-)-1-(+)-/(-)-10 are either new structure or new natural product, named (+)-/(-)-angelidipthalidic acids A-H [(+)-/(-)-1-(+)-/(-)-8] and (+)-/(-)-angelidipthalidols A and B [(+)-/(-)-9 and (+)-/(-)-10], respectively. Meanwhile, dimeric phthalide mono- and bis-lactone derivatives with 3.3′a,8.6′- and 3.6′,8.3′a-coupling patterns as well as determination of their relative configurations are discussed.

Monoterpenes from an aqueous extract of the Angelica sinensis root head / 药学学报

Eleven monoterpenes including seven new chemical structures or new natural products covering two pairs of scalemic enantiomers, together with four known analogues, were isolated from an aqueous extract of the Angelica sinensis root head (Guitou) by separation techniques of column chromatography over macroporous adsorbent resin, MCI resin, silica gel, Sephadex LH-20, and Toyopearl HW-40C, together with preparative thin-layer chromatography as well as reversed phase and chiral HPLC. Their structures were determined by spectroscopic data analysis, combined with theoretic calculation of electronic circular dichroism (ECD) spectra and single crystal X-ray diffraction. The new structures or new natural products named (+)-/(-)-angelinones A and B [(+)-/(-)-1 and (+)-/(-)-2], angelinones C and D (3 and 4), and angelinol A (5), respectively, while the known analogues were 6β,9-dihydroxy-(+)-α-pinene (6), 1,1,5-trimethyl-2-hydroxymethyl-cyclohexa-2,5-dien-4-one (7), jasminol E (8), and (+)-trans-sobrerol (9). All the isolates were reported in this plant for the first time, except for the previously reported 6 from an ethanol extract of the aerial parts of A. sinensis, of which the structure was confirmed by X-ray crystallography in this study.

Ethnobotany, Phytochemistry, and Pharmacology of Angelica decursiva Fr. et Sav

Angelica decursiva Fr. et Sav. (Umbelliferae) has traditionally been used to treat different diseases due to its antitussive, analgesic, and antipyretic activities. It is also a remedy for thick phlegm, asthma, and upper respiratory infections. Recently, the leaf of A. decursiva has been consumed as salad without showing any toxicity. This plant is a rich in different types of coumarin derivatives, including dihydroxanthyletin, psoralen, dihydropsoralen, hydroxycoumarin, and dihydropyran. Its crude extracts and pure constituents possess anti-inflammatory, anti-diabetic, anti-Alzheimer disease, anti-hypertension, anti-cancer, antioxidant, anthelmintic, preventing cerebral stroke, and neuroprotective activities. This valuable herb needs to be further studied and developed not only to treat these human diseases, but also to improve human health. This review provides an overview of current knowledge of A. decursiva metabolites and their biological activities to prioritize future studies.

Medicinal properties of Angelica archangelica root extract: Cytotoxicity in breast cancer cells and its protective effects against in vivo tumor development / 中西医结合学报

OBJECTIVE@#Although Angelica archangelica is a medicinal and aromatic plant with a long history of use for both medicinal and food purposes, there are no studies regarding the antineoplastic activity of its root. This study aimed to evaluate the cytotoxicity and antitumor effects of the crude extract of A. archangelica root (CEAA) on breast cancer.@*METHODS@#The cytotoxicity of CEAA against breast adenocarcinoma cells (4T1 and MCF-7) was evaluated by a 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay. Morphological and biochemical changes were detected by Hoechst 33342/propidium iodide (PI) and annexin V/PI staining. Cytosolic calcium mobilization was evaluated in cells staining with FURA-4NW. Immunoblotting was used to determine the effect of CEAA on anti- and pro-apoptotic proteins (Bcl-2 and Bax, respectively). The 4T1 cell-challenged mice were used for in vivo assay.@*RESULTS@#Using ultra-high-performance liquid chromatography-mass spectrometry analysis, angelicin, a constituent of the roots and leaves of A. archangelica, was found to be the major constituent of the CEAA evaluated in this study (73 µg/mL). The CEAA was cytotoxic for both breast cancer cell lines studied but not for human fibroblasts. Treatment of 4T1 cells with the CEAA increased Bax protein levels accompanied by decreased Bcl-2 expression, in the presence of cleaved caspase-3 and cytosolic calcium mobilization, suggesting mitochondrial involvement in breast cancer cell death induced by the CEAA in this cell line. No changes on the Bcl-2/Bax ratio were observed in CEAA-treated MCF7 cells. Gavage administration of the CEAA (500 mg/kg) to 4T1 cell-challenged mice significantly decreased tumor growth when compared with untreated animals.@*CONCLUSION@#Altogether, our data show the antitumor potential of the CEAA against breast cancer cells in vitro and in vivo. Further research is necessary to better elucidate the pharmacological application of the CEAA in breast cancer therapy.

Chuanliguspirolide, a new butylphthalide derivative from Chuanxiong Rhizoma and its inhibition on NO production in LPS-activated RAW264.7 and BV2 cell lines / 中草药

Objective: To study the chemical constituents of 95% ethanol aqueous extract of Chuanxiong Rhizoma and the bioactivities of inhibition on nitric oxide (NO) production in lipopolysaccharides (LPS)-activated murine macrophage RAW264. 7 and mouse microglia BV2 cell lines. Methods: The compounds were separated and purified by silica gel column and high performance liquid chromatographies, and their structures were determined by spectroscopic data analysis. Using LPS-activated RAW264. 7 and BV2 cell line models in vitro, all of the isolated compounds were evaluated for the inhibition against NO production. Results: Three butylphthalide derivatives were obtained and identified as Z-3', 8', 3'a, 7'a-tetrahydro-6, 3', 7, 7'a-diligustilide-8'-one (1), Z, Z'-3.3'a, 7. 7'a-diligustilide (2), and chuanliguspirolide (3), respectively. For the inhibition of NO production in the LPS-activated two cell lines, the half inhibitory concentration (IC50) values of compounds 1-3 and indomethacin as a positive control drug in RAW 264. 7 cell line model were (31.60 ± 2.62), (21.20 ± 0.61), (30.12 ± 2.90), and (54.62 ± 7.53) μmol/L, respectively, while IC50 values of compounds 1-3 and curcumin as a positive control drug in BV2 cell line model were (21.99 ± 4.40), (15.43 ± 1.34), (12.20 ± 3.40), and (10.58 ± 1. 41) μmol/L, respectively. Conclusion: Compound 3 named as chuanliguspirolide is a new one. The results of bioactivity assays indicated that compounds 1-3 are potential anti-inflammatory agents.

Larvicidal, pupicidal and oviposition deterrent activities of essential oils from Umbelliferae plants against house fly Musca domestica

Objective:To evaluate the toxicity against house fly Musca domestica L. (M. domestica)-larvicidal, pupicidal, and oviposition deterrent activities of essential oils (EOs) from five plants: Anethum graveolens L. (A. graveolens), Centratherum anthelminticum L. (C. anthelminticum), Foeniculum vulgare Mill. (F. vulgare), Pimpinella anisum L. (P. anisum), and Trachyspermum ammi L. (T. ammi) Sprague.Methods:Dipping, topical and dual-choice assays were performed by using each EO at three concentrations (1%, 5% and 10%) as well as cypermethrin (positive control) and ethyl alcohol (negative control) in order to determine their larvicidal, pupicidal and oviposition deterrent activities against M. domestica mortality rate and morphogenic abnormality of larvae and pupae were recorded after 3 and 10 days of incubation. Oviposition deterrent activity was recorded for 5 consecutive days from the beginning of the assay.Results:All EOs at the highest concentration (10%) were highly effective in oviposition deterrent with 100% effective repellency and an oviposition activity index of -1.00. Ten percent of F. vulgare oil exhibited the highest efficacy against the larvae with 89.6% mortality rate at 3 days and an LCConclusions:These results indicate that F. vulgare, A. graveolens and T. ammi EOs are effective larvicidal, pupicidal and oviposition deterrent agents against house fly M. domestica.

Larvicidal, pupicidal and oviposition deterrent activities of essential oils from Umbelliferae plants against house fly Musca domestica

Objective: To evaluate the toxicity against house fly Musca domestica L. (M. domestica)-larvicidal, pupicidal, and oviposition deterrent activities of essential oils (EOs) from five plants: Anethum graveolens L. (A. graveolens), Centratherum anthelminticum L. (C. anthelminticum), Foeniculum vulgare Mill. (F. vulgare), Pimpinella anisum L. (P. anisum), and Trachyspermum ammi L. (T. ammi) Sprague. Methods: Dipping, topical and dual-choice assays were performed by using each EO at three concentrations (1%, 5% and 10%) as well as cypermethrin (positive control) and ethyl alcohol (negative control) in order to determine their larvicidal, pupicidal and oviposition deterrent activities against M. domestica mortality rate and morphogenic abnormality of larvae and pupae were recorded after 3 and 10 days of incubation. Oviposition deterrent activity was recorded for 5 consecutive days from the beginning of the assay. Results: All EOs at the highest concentration (10%) were highly effective in oviposition deterrent with 100% effective repellency and an oviposition activity index of -1.00. Ten percent of F. vulgare oil exhibited the highest efficacy against the larvae with 89.6% mortality rate at 3 days and an LC

Chemical constituents from Chuanxiong Rhizoma in standardization implantation / 中草药

Objective: To study the chemical constituents in 95% ethanol aqueous extract of Chuanxiong Rhizoma. Methods: The compounds were separated and purified by repeated column chromatography on silica gel and high performance liquid chromatography, and their structures were determined by spectroscopic data analyses. Results: Forty-one compounds were obtained. Among them, 34 compounds were identified as xanthotoxin (1), 3-butylidenephthalide (2), Z-ligustilide (3), senkyunolide A (4), senkyunolide H (5), senkyunolide I (6), coniferyl alcohol (7), 3-propylanisole (8), epoxyligustilide (9), 5-hydroxy-3-butylene-phthalide (10), chuanxiongdiolide R1 (11), neocnidilide (12), Z'-3,8-dihydro-6.6',7.3'a-diligustilide (13), tokinolide B (14), ansaspirolide (15), bergaptol (16), senkyunolide D (17), 4-hydroxy-3-butyl-phthalide (18), 5-hydroxymethylfurfural (19), vanillin (20), levistolide A (21), trans-ferulic acid (22), 4-hydroxy-3-methoxypropiophenone (23), ethyl ferulate (24), falcarindiol (25), oplopandiol (26), senkyunolide E (27), stigmasterol (28), pregnenolone (29), isopimpinellin (30), β-sitosterol (31), dibutylphthalate (32), diisobutylphthalate (33), and coniferyl aldehyde (34), respectively. Conclusion: Compounds 1, 8, 16, 23, 26, and 30 are isolated from Chuanxiong Rhizoma for the first time.

Guaiane-type sesquiterpenes from the fruits of Fructus carotae / 药学学报

To study the chemical constituents of the fruits of Fructus carotae, silica gel column chromatog­raphy and preparative HPLC were used to isolate and purify the extract of Fructus carotae. The structures of obtained compounds were elucidated on the basis of physicochemical property and spectral data. Nine guaiane-type sesquiterpenes were isolated and identified as 8β-angeloyloxy-11-hydroxy-4-guaien-3-one(1), 11-acetoxy-4-guaien-3-one(2), 11-acetoxy-8β-isobutyryl-4-guaien-3-one(3), 11-acetoxy-8β-propionyl-4-guaien-3-one(4), 11-hydroxy-4-guaien-3-one(5), 11-acetoxy-8β-angeloyloxy-1β-hydroxy-4-guaien-3-one(6), 11-acetoxy-8β-angeloyloxy-4-guaien-3-one(7), 11-acetoxy-8β-hydroxy-4-guaien-3-one(8)and 8β,11-dihydroxy-4-guaien-3-one(9). Compound 1 is a new compound, compound 5 is a new natural product, and compounds 2-4 were isolated from this genus for the first time.

Advance in studying early bolting of Umbelliferae medicinal plant / 中国中药杂志

The early bolting has become one of the key issues affecting the Umbelliferae herbs production. The early bolting does not only reduce herbs production but also affect the active ingredients of plants. The concept of early bolting, physiological theory, induce factors of the quality of medicine and, control technology about the early bolting of Umbelliferae are integrative reviewed in the paper. Its occurrence mechanism include: genetic factors, environmental and ecological factors, endogenous hormones, sowing, fertilizer and other production management measures. For the above occurring mechanism, the proposed prevention measures are as follows: preferably germplasm, sowing, rational fertilization, exogenous hormones, shading, reed head cut off, cut fall the leaves, reasonable planting density and other agronomic measures can reduce its bolting rate. And the early bolting problem focused for future research are mentioned, including: development of authentic ingredients cultivation technical specifications, screened early bolting hormone inhibitor, in-depth study of the mechanism of early bolting, reveal its early bolting gene and key ecological factors. The research of vernalization gene, gene regulation of flowering early bolting will solve the problem of quality and production reducing fundamentally caused by the early bolting.

Molecular Cloning and Expression of Squalene Epoxidase from a Medicinal Plant, Bupleurum chinense / 中草药·英文版

Objective: In plant, squalene epoxidase (SE) catalyzes the first oxygenation step in the biosynthetic pathway of triterpenoid and phytosterol, representing one of the rate-limiting enzymes in this pathway. Bupleurum chinense is an important medicinal herb with its major active constituents such as triterpenoid saponins and saikosaponins. In order to obtain the series of enzymatic genes involved in saikosaponin biosynthesis, a cDNA of SE, designated BcSE1, was cloned from B. chinense. Methods: The BcSE1 gene was cloned by homology-based PCR and 5'/3' RACE methods from the adventitious roots of B. chinense. The physical and chemical parameters of BcSE1 protein were predicted by protparam. In order to discover hints in amino acid sequences on the dominant functions in the biosynthesis of saponin or phytosterol, sequences of SE from other plants were downloaded from NCBI for sequences alignment and phylogenetic analysis. BcSE1 was cloned into a yeast mutant KLN1 (MATa, erg1::URA3, leu2, ura3, and trp1) to verify the enzyme activity of BcSE1. Additionally, the tissue-specific expression and methyl jasmonate (MeJA) inducibility of BcSE1 were investigated using quantitative real-time PCR. Results: The predicted protein of BcSE1 is highly similar to SEs from other plants sharing amino acid sequence identities of up to 88%. The BcSE1 can functionally complement with yeast SE gene (ERG1) when expressed in the KLN1 mutant (MATa, erg1::URA3, leu2, ura3, and trp1). Using as controls with β-amyrin synthase (β-AS) which is presumed to catalyze the first committed step in saikosaponin biosynthesis and a cycloartenol synthase (CAS) relating to the phytosterol biosynthesis, the transcript of BcSE1 was significantly elevated by MeJA in adventitious roots of B. chinense and the transcript of BcSE1 was most abundant in the fruits and flowers of plants, followed by that in the leaves and roots, and least in stems. Conclusion: It is the first time to illustrate the molecular information of SE in B. chinense and to clone the full-length SE gene in plants of genus Bupleurum L.

The Application of DNA Chip Technology to Identify Herbal Medicines: an Example from the Family Umbelliferae

Comparative molecular analysis has been frequently adopted for the authentication of herbal medicines as well as the identification of botanical origins. Roots and rhizomes of the family Umbelliferae have been used as traditional herbal medicines to relieve various symptoms such as inflammation, neuralgia and paralysis in countries of East Asia. Since most herbal medicines of the Umbelliferae roots or rhizomes are generally supplied in the form of dried slices, morphological examination does not often provide sufficient evidence to identify the botanical origin. Using species-specific probes developed by the comparative analysis of nrDNA ITS sequences, a DNA chip was developed to identify herbal medicines for 13 species in the Umbelliferae. The developed DNA Chip proves its potential as a rapid, sensitive and effective tool for authenticating herbal medicines in future.

Diuretic and hipotensive activity of aqueous extract of parsley seeds (Petroselinum sativum Hoffm) in rats / Atividade diurética e hipotensora do extrato aquoso da semente de salsa (Petroselinum sativum Hoffm) em ratos

PURPOSE: the vegetal specie, Petroselinum sativum Hoff., known as parsley, is widely used in the Brazilian folk medicine as diuretic. The objective of this study is to verify if Brazilian use of parsley aqueous extract has similar effects with investigations that show a diuretic effect of P. sativum in rats. METHODS: 19 rats were anesthetized and we cannulated the trachea, left carotid artery (for arterial pressure measurement) and urinary bladder (to collect urine). After 40 minutes of adaptive surgery conditions, anesthetized rats were administrated as related with their group: control (CON), oral administration with 1.0 mL of filtered water, and treated group (AE), oral administration with aqueous extract of seeds of parsley 20 percent (AE). Urine was collected three times (30 minutes each) and then this material was used for sodium and potassium determinations, to evaluate the amount excreted of these ions. Blood pressure was measured by mercury manometer for 9 times. All data were statistically evaluated. RESULTS AND CONCLUSION: in the analyzed parameters, CON group did not show any differences; but AE group showed an increased of urinary flow and sodium and potassium amount excreted, and also decreased arterial pressure. All the parameters presented these modifications after 30 minutes of administration of AE (p<0.05). These results show that the treatment with the AE results in natriuretic and hypotensive effects in anesthetized Wistar rats, confirming the use of Brazilian population of this herb as diuretic.

A espécie vegetal, Petroselinum sativum Hoff, conhecida como salsa, é amplamente utilizada na medicina popular brasileira como diurético. O objetivo desse estudo é verificar se o uso brasileiro do extrato aquoso da salsa tem efeitos semelhantes com investigações que mostram o efeito diurético da P. sativum em ratos. MÉTODOS: 19 Ratos foram anestesiados e canulamos a traquéia, artéria carótida esquerda (para a medição da pressão arterial) e bexiga urinária (para coletar urina). Depois de 40 minutos para adaptação das condições cirúrgicas, ratos anestesiados foram administrados de acordo com seus grupos: controle (CON), administração oral com 1.0 mL de água filtrada, e grupo tratado (AE), administração oral com extrato aquoso de sementes de salsa 20 por cento (AE). Urina foi coletada três vezes (de 30 em 30 minutos) e então esse material foi utilizado para determinações de sódio e potássio, para avaliar a quantidade excretada desses íons. Pressão arterial foi medida pelo manômetro de mercúrio por 9 vezes. Todos os dados foram estatisticamente avaliados. RESULTADOS E CONCLUSÃO: nos parâmetros anestesiados, o grupo CON não mostrou nenhuma diferença; mas o grupo AE mostrou um aumento do fluxo urinário e da quantidade excretada de sódio e potássio, e também uma diminuição da pressão arterial. Todos os parâmetros apresentaram essas modificações após 30 minutos de administração do AE (p<0,05). Esses resultados mostram que o tratamento com o AE leva a efeitos natriurético e hipotensor em ratos Wistar anestesiados, confirmando o uso da população brasileira dessa erva como diurético.

Coumarins from the aerial parts of Prangos uloptera (Apiaceae) / Cumarinas das partes aéreas de Prangos uloptera (Apiaceae)

Phytochemical studies on the aerial parts of Prangos uloptera, an endemic Iranian species of the genus Prangos, yielded five coumarins, xanthotoxin (1), prangenin (2), scopoletin (3), deltoin (4) and prangolarin (5). The structures of these coumarins were elucidated by spectroscopic means, and the antioxidant potential of 1-5 was evaluated by the DPPH assay. The chemotaxonomic significance of 1-5 is also discussed.

Os estudos fitoquímicos das partes aéreas de Prangos uloptera, uma espécie do gênero Prangos endêmica do Irã, forneceram cinco cumarinas, xantotoxina (1), prangenina (2), escopoletina (3), deltoína (4) e prangolarina (5). As estruturas destas cumarinas foram elucidas através de métodos espectroscópicos e o potencial antioxidante de 1-5 foi avaliado pelo ensaio de DPPH. O significado quimiotaxonômico de 1-5 também é discutido.

Chromones from Angelica morri Hayata / 中国药科大学学报

AIM:Bioactive constituents were expected to be obtained from the roots of Angelica morri Hayata. METHOD:They were extracted with 95% alcohol and isolated by using column chromatography and recrystallization methods. The structures were elucidated by means of physico-chemical data and UV,IR,1HNMR, 13CNMR,and EIMS. The inhibitory effect on the constriction of rat aortic rings was induced by K+ or Ca2+. RESULT:3′S-(-)-hamaudol,3′S-(-)-Ο-acetylhamaudol,3′R-(+)-hamaudol,and (±)-hamaudol were isolated from the pieces of Radix Angelica Morri. The inhibitory rate of 3′S-(-)-Ο-acetylhamaudol and (±)-hamaudol on the above pharmacologic model appears the relation of quantity response. CONCLUSION:All the above compounds were found in this species for the first time,and(±)-hamaudol is a new. One of effect mechanisms of 3′S-(-)-Ο-acetylhamaudol and (±)-hamaudol diluted aorta could contribute to be inhibiting Ca2+ influx of vascular smooth muscle.

Chemical constituents from root and rhizome of Glehnia littoralis / 中草药

Object To study the chemical constituents of the underground part of Glehnia littoralis Fr. Schimidt ex Miq. Methods Eight compounds were isolated from EtOAc-soluble fraction of ethanol extract of G. littoralis by repeated chromatography over silica gel. Their structures were determined on the basis of their spectral data. Results They were identified as falcalindiol (Ⅰ), (8E)-1, 8-heptadecadiene-4, 6-diyne-3, 10-diol (Ⅱ), bergapten (Ⅲ), cnidilin (Ⅳ), xanthotoxin (Ⅴ), salicylic acid (Ⅵ), vanillic acid (Ⅶ), ferulic acid (Ⅷ). Conclusion Compounds Ⅱ and Ⅵ-Ⅷ were isolated from this plant for the first time.