Research Update:Alisma orientalis.

  seminal trace...Alismatis.Alisma orientalis.Oriental Waterplantain Rhizome.Alisma plantago-aquatica.Oriental Water plantain.Rhizoma Alismatis.5:1,10:1Extract.Alisol A,Alisol B,Alisol A monoacetate,Alisol B monoacetate,Alisol C monoacetate,Sulfoorientalol A,Sulfoorientalol B,Sulfoorientalol C,Sulfoorientalol D,Orientatol A,Orientatol B,Orientatol C,Epialisol A;11-deoxyalisol C;Alisol D monoacetate;Alismoxide;Triterpenoid;Orientalos A;Orientalos B;Orientalos C;Sulfoorientalols A,Sulfoorientalols B,Sulfoorientalols C,Sulfoorientalols D,Lactose polyphosptate sodium salt;Alisol E 24-acetate;13,17-epoxyal-isol A 24-acetate;alisol E 23-acetate;13Beta,17Beta-epoxyalisol A;11-deoxyalisol A.Orientalol E;Alismoxide;Alismol;Ent-kaurane Diterpenoid compound;Kaurane-2,12-dione;Oriediterpenol;Oriediterpenoside...

 


   Phytochemical info of Alisma orientalis:

 Product Name:
 Synonym:
 Definition:Alisma orientalis are majorly composed of
 Chemical information disclosed as following table:


   Research Update:Alisma orientalis:

  Two new sesquiterpenes from Alisma orientalis.:Chem Pharm Bull.2007 Jun;55(6):905-7.Jiang ZY, Zhang XM, Zhou J, Zhang FX, Chen JJ, L¨¹ Y, Wu L, Zheng QT.State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Yunnan, PR China.

 Two new sesquiterpenoids named alismorientols A (1) and B (2) were isolated from the rhizomes of Alisma orientalis collected in Sichuan province, People's Republic of China. Their structures were elucidated based on spectroscopic analyses (1D and 2D NMR data including HSQC, HMBC, COSY, and ROESY) and X-ray crystallographic analysis. Anti-hepatitis B virus (HBV) bioassay revealed that compound 1 showed moderate anti-HBV activity in vitro with IC50 for HBsAg: 1.1 microM, for HBeAg: 14.7 microM.
 

  Protective effects of the Alisma orientalis extract on the experimental nonalcoholic fatty liver disease.:J Pharm Pharmacol. 2006 Oct;58(10):1391-8.Hong X, Tang H, Wu L, Li L.Institute of Chinese Herb Medicine, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang, 310031, PRC.

 The aim of this investigation was to evaluate the efficacy of Alisma orientalis methanolic extract (AOME) on the experimental nonalcoholic fatty liver disease (NAFLD) induced by high-fat diet. Rats were fed with high-fat diet for six weeks and then gavaged the AOME for another six weeks. Typical pathological symptoms of NAFLD occurred in the high-fat diet rats. Administration with the AOME (150,300 and 600 mg kg (-1)) markedly decreased the serum and liver lipids; the high level of fasting serum glucose was reduced and insulin resistance was improved. The AOME treatment was also helpful in preventing the oxidative stress by lessening lipid peroxidation and activating antioxidant enzymes. Markers of the liver injury, aminotransferase abnormalities and hepatomegaly were improved and morphological changes, such as liver steatosis, mixed inflammation and collagen deposition, were lessened in rats treated with the AOME. These results suggested that the AOME showed hepatoprotective effects on NAFLD and may be a potential clinical application for treatment of this chronic liver disease.
 

  A new triterpene and anti-hepatitis B virus active compounds from Alisma orientalis.:Planta Med. 2006 Aug;72(10):951-4. Epub 2006 Jul 20.Jiang ZY, Zhang XM, Zhang FX, Liu N, Zhao F, Zhou J, Chen JJ.State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, The Chinese Academy of Sciences, Kunming, Yunnan, PR China.

 A new triterpenoid named alisol O ( 1) was isolated from the rhizomes of Alisma orientalis, together with six known compounds: alisol A 24-acetate ( 2), 25-anhydroalisol A ( 3), 13 beta,17 beta-epoxyalisol A ( 4), alisol B 23-acetate ( 5), alisol F ( 6), and alisol F 24-acetate ( 7). Based on 1D and 2D-NMR data (HMQC, HMBC, COSY, ROESY), the structure of the new compound was deduced to be 11-dehydroxy-12-dehydroalisol F-24-acetate ( 1). Compounds 2 - 7 exhibited inhibitory activity in vitro on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line with IC (50) values of 2.3, 11.0, 15.4, 14.3, 0.6 and 7.7 microM, and on HBV e antigen (HBeAg) secretion with IC (50) values of 498.1, 17.6, 41.0, 19.9, 8.5 and 5.1 microM, respectively.
 

  Reversal of multidrug resistance in cancer cells by Rhizoma Alismatis extract.:Phytomedicine. 2007 Feb;14(2-3):160-5. Epub 2006 May 18.Fong WF, Wang C, Zhu GY, Leung CH, Yang MS, Cheung HY.Bioactive Products Research Group, Department of Biology and Chemistry, City University of Hong Kong, Kowloon, Hong Kong SAR, China. bhwffong@cityu.edu.hk

 Prolonged chemotherapy may lead to the selective proliferation of multidrug resistant (MDR) cancer cells. In MDR HepG2-DR and K562-DR cells that over-expressed P-glycoprotein (Pgp), the extract of the rhizomes of Alisma orientalis (Sam) Juzep. showed a synergistic growth inhibitory effect with cancer drugs that are Pgp substrates including actinomycin D, puromycin, paclitaxel, vinblastine and doxorubicin. At the same toxicity levels the herbal extract was more effective than verapamil, a standard Pgp inhibitor, in enhancing cellular doxorubicin accumulation and preventing the efflux of rhodamin-123 from the MDR cells. The extract restored the effect of vinblastine on the induction of G(2)/M arrest in MDR cells. Our data suggest that A. orientalis may contain components that are effective inhibitors of Pgp.
 

  Antioxidant and antiplatelet effects of dang-gui-shao-yao-san on human blood cells.:Am J Chin Med. 2005;33(5):747-58.Shen AY, Wang TS, Huang MH, Liao CH, Chen SJ, Lin CC.Basic Medical Science Education Center, Fooyin University Ta-Liao, Kaohsiung County, Taiwan.

 Dang-Gui-Shao-Yao-San (DGSYS) is a mixture of medicinal herbs, which has long been used in traditional Chinese medicine for treating anemia and ovulary disorders. Its preparation comprises Angelicae sinensis (Oliv.) Diels, Ligustucum chuanxiong Hort, Paeonia lactiflora pall, Poria cocos (Schw.) Wolf, Atractylodis macrocephala Koidz and Alisma orientalis (Sam.) Juzep. The present study examined the anti-superoxide formation, free radical scavenging and anti-lipid peroxidation activities of DGSYS by xanthine oxidase inhibition, cytochrome C system with superoxide anion released by the fMLP or PMA activating pathway in human neutrophils, and FeCl2 ascorbic acid-induced lipid peroxidation effects on lipids in rat liver homogenate, respectively. DGSYS showed anti-superoxide formation and free radical scavenging activity in a concentration-dependent manner. It also inhibited PMA- but not fMLP-induced superoxide anion released from human neutrophils. These antioxidant actions of DGSYS showed beneficial cytoprotective effects against lipid peroxidation in rat liver homogenate, human platelet aggregation induced by arachidonic acid (AA) and adenosine diphosphate (ADP) and mitomycin C-mediated hemolytic in human erythrocytes.
 

 

  Quality evaluation of Alisma orientalis from different habitats:Zhong Yao Cai. 2004 Nov;27(11):799-801.Chen J, Zhang L, Chen Y, Zheng W, Liu B, Zhang Q, Zhu B, Cai X, Yang Z.Institute of Pomology, Fujian Academy of Agricultural Sciences, Fuzhou.

 OBJECTIVE: To study the seed quality of Alisma orientalis (Sam.) Juzep. METHOD: Collecting seeds from different habitats and studying the thousand-grain weight, moisture content, purity and germination percentage. RESULT: The seeds reaped in summer friom Pengshan, Sichuan province are better than those from other habitats. Its thousand-grain weight is 0.4682 g, moisture content is 12.48%, purity of seeds is 89.18% and germination percentage is above 95%. CONCLUSION: The cause of qualitative differences in seeds of Alisma orientalis from different habitats were analysed in this paper.

  An experimental study of effect of different extracts of Alisma orientalis on urinary calcium oxalate stones formation in rats:Zhongguo Zhong Yao Za Zhi. 2003 Nov;28(11):1072-5.Cao ZG, Liu JH, Radman AM, Wu JZ, Ying CP, Zhou SW.Department of Urology, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei, China. zgcao2002@hotmail.com

 OBJECTIVE: To study the effect of different extracts of Alisma orientalis on urinary calcium oxalate stone formation in rats and to identify the effective constituents. METHOD: Different extracts were administered through a stomach tube to rats of different groups with renal calcium oxalate stones induced by ethylene glycol (EG) and ammonium chloride (AC). RESULT: In the rats administered with ethyl acetate elution of ethyl acetate extract, blood Cr, BUN, renal tissue calcium content, urinary calcium excretion and crystals deposition in renal tissue were significantly lower than those of the stone formation group. CONCLUSION: The ethyl acetate elution of ethyl acetate fraction extract of Alisma orientalis can significantly inhibit urinary calcium oxalate stone formation in rats and be the most effective constituent of Alisma orientalis.
 

  The effects of the active constituents of Alisma orientalis on renal stone formation and bikunin expression in rat urolithiasis model:Zhonghua Yi Xue Za Zhi. 2004 Aug 2;84(15):1276-9.Cao ZG, Liu JH, Zhou SW, Wu W, Yin CP, Wu JZ.Department of Urology, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.

 OBJECTIVE: To evaluate the effects of the active constituents of Alisma orientalis on the expression of bikunin mRNA in rat urolithiasis model, and explore the mechanism of this traditional Chinese medicine on prevention of urinary calculi. METHODS: Modern phytochemistry and bioactivity guided isolation techniques were applied to extract the active constituents of Alisma orientalis. Hyperoxaluria and the renal oxalate calcium stone formation were induced in rats by infusion into the stomach with 1% ethylene glycol and 2% ammonium chloride. 30 adult male Wistar rats were randomized into 3 groups of 10 rats: control group, infused into the stomach with running water; stone-forming group, infused into the stomach with 1% ethylene glycol and 2% ammonium chloride so as to make into renal oxalate calcium stone model; and group of Alisma orientalis, infused into the stomach with 2% ammonium chloride and the constituents of Alisma orientalis. Four weeks after the rats were killed and their kidneys were taken out. Reverse transcription polymerase chain reaction technique was used to examine the bikunin mRNA expression levels in the rat renal tissues. The calcium oxalate deposits in the kidneys were detected by microscopy. The serum creatinnine and blood urea nitrogen levels, renal tissue calcium content, 24 h urinary calcium and oxalate excretion were also detected. RESULTS: In the group administered with the active constituents of Alisma orientalis, calcium oxalate deposits in the kidney, serum creatinnine and blood urea nitrogen levels, the bikunin mRNA expression levels, renal tissue calcium content and 24 h urinary calcium excretion were all significantly lower than those in the model group (the bikunin mRNA expression levels: 0.53 +/- 0.17 vs 0.71 +/- 0.25, P < 0.05; renal tissue calcium content: 4.70 mg/g +/- 0.08 mg/g vs 9.49 mg/g +/- 0.45 mg/g, P < 0.01; 24 h urinary calcium excretion: 37 micromol +/- 2 micromol vs 62 micromol +/- 2 micromol, P < 0.01). CONCLUSION: The active constituents of Alisma orientalis can down-regulate the bikunin mRNA expression, decrease the calcium oxalate formation in rat kidney, and inhibit the renal stone formation in rat urolithiasis model.
 

  Guaiane-type sesquiterpenoids from Alisma orientalis.:Phytochemistry. 2003 Aug;63(8):877-81.Peng GP, Tian G, Huang XF, Lou FC.Nanjing University of Traditional Chinese Medicine, 210029 Nanjing, PR China. guopingpeng@sohu.com

 Two guaiane-type sesquiterpenoids named orientalol E (1) and orientalol F (3) were isolated from the rhizome of Alisma orientalis (SAM) JUZEP together with two known guaiane-type sesquiterpenoids alismol (2) and alismoxide (4). Their relative stereostructures were elucidated by spectroscopic methods, whereas absolute stereostructures were determined on the basis of chemical correlation.

  The identification of Alisma orientalis and Alisma canaliculatum by UV and IR spectrum:Zhong Yao Cai. 2002 Dec;25(12):871-4.Wu Q, Wang L, Duqian.Pharmacy College, Nanjing University of Traditional Chinese Medicine, Nanjing 210029, China.

 The paper reported that UV and IR spectrum were used to identify Alisma orientalis and A. canaliculatum. The results of determination showed that the solution of methanol extraction of A. orientalis absorbed in 204.1 +/- 0.5 nm, but which of Alisma canaliculatum absorbed in 205.7 nm and 285 nm in UV spectrum. The dry substance of water extraction of A. orientalis absorbed in 3402, 2933, 1642, 1054 and 926 cm-1 in IR spectrum. IR spectrum of A. orientalis is different from which of Alisma canaliculatum in fingerprint.

 

  Effect of wu lin powder and its ingredients on atrial natriuretic factor level in mice:Zhongguo Zhong Xi Yi Jie He Za Zhi. 1995 Jan;15(1):36-7.Zhou L, Chen ZX, Chen JY.Guangzhou College of TCM.

 Wu Lin powder (WLP) is a prescription that causes urination to remove dampness. In order to elucidate its mechanism of action, the effect of WLP on atrial natriuretic factor (ANF) was observed. The results showed that the level of ANF was significantly higher in the plasma of mice after giving WLP as well as giving Alisma orientalis or Cinnamomum cassia orally, compared with control, P < 0.05, 0.01 and 0.001 respectively. The effect was most evident at 45 minute after giving WLP (P < 0.05). It is suggested that ANF might play an important role in therapeutic action of WLP.

  Screening of herbal extracts for activation of the human peroxisome proliferator-activated receptor.:Pharmazie. 2006 Nov;61(11):952-6.Rau O, Wurglics M, Dingermann T, Abdel-Tawab M, Schubert-Zsilavecz M.Johann Wolfgang Goethe University Frankfurt, Institute of Pharmaceutical Chemistry/ZAFES, Frankfurt/Main, Germany.

 The peroxisome proliferator-activated receptors play a pivotal role in metazoan lipid and glucose homeostasis. Synthetic activators of PPARalpha (fibrates) and PPARgamma (glitazones) are therefore widely used for treatment of dislipidemia and diabetes, respectively. There is growing evidence for herbal compounds to influence nuclear receptor signalling e.g. the PPARs. We recently reported carnosic acid and carnosol, both being diterpenes found in the labiate herbs sage and rosemary, to be activators of PPARgamma. The subsequent screening of a variety of ethanolic extracts, obtained from traditionally used herbs, for PPAR activation, led to an exceptionally high hit rate. Among 52 extracts nearly the half significantly activated PPARgamma and 14 activated PPARalpha in addition, whereas three of them were pan-PPAR activators, which also activated PPARdelta. The most active extracts, for which a concentration dependent effect could be shown, were the extracts of Alisma plantago aquatica (ze xie/european waterplantain), Catharanthus roseus (madagascar periwinkle), Acorus calamus (sweet calamus), Euphorbia balsamifera (balsam spurge), Jatropha curcas (barbados nut), Origanum majorana (marjoram), Zea mays (corn silk), Capsicum frutescens (chilli) and Urtica dioica (stinging nettle). The results of the present study provide a possible rationale for the traditional use of many herbs as antidiabetics.
 

  Effects of liuwei dihuang decoction and its compositions on blood sugar and glycogen in mice:Zhongguo Zhong Yao Za Zhi. 1991 Jul;16(7):437-8, 448 proceeding.Liu B, Wen W, Zhu D, Jiang Y.China Pharmaceutical University, Nanjing.

 We have studied the effects of liuwei dihuang decoction (LDD) and its compositions on blood sugar and glycogen in mice, and found that sanbu, shanzhuyu-danpi and shanyao-fuling matched pairs can reduce the level of blood sugar, while LDD, sanbu, shudi-zexie and shanzhuyu-danpi matched pairs can increase the content of glycogen in liver. The present study is only a preliminary research on the effects of LDD and its compositions on the metabolism of sugar in the body.

  Experimental and natural weed host-virus relations.:Commun Agric Appl Biol Sci. 2004;69(3):53-60.Kazinczi G, Horv¨¢th J, Tak¨¢cs AP, G¨¢borj¨¢nyi R, B¨¦res I.Office for Academy Research Groups Attached to Universities and Other Institutions, Virological Group, University of Veszpr¨¦m, Georgikon, Faculty of Agricultural Sciences, H-8361 Keszthely, P.O. Box 71, Hungary.

 Weeds, as alternative hosts of plant viruses and nutrient plants of virus vectors play important role in virus ecology and epidemiology. The aim of our study was to discover new weed-virus relations. Therefore some weed species were mechanically inoculated with 28 viruses (strains or isolates) maintained in our glasshouse. Different weed species with and without visible symptoms were collected from agro-, water ecosystems and wastelands of Hungary between 1997 and 2003. Virus infections were evaluated by biotests, DAS ELISA serological methods, electronmicroscopy and immunosorbent electronmicroscopy (ISEM). Under glasshouse conditions Ambrosia artemisifolia was considered as a virophob species, showing resistance to all viruses listed above. A series of new artificial (Chenopodium album--SoMV (LH+SH)*, AMV (LH+SH); C. berlandieri--PVY(NTN) (LH), AMV (LH+SH), CMV (LH), SoMV (LH+SH), ObPV (LH+SH), ZYMV-10 (LH): C. ugandae--ObPV (LH), SoMV (L); C. glaucum--ObPV (LH), SoMV (L); Echinocystis lobata--PVX (L), ZYMV (LH+SH); Solanum nigrum--MYFV (LH+SH), PVY(N) (L), PVY(NTN) (LH+SH), SoMV (LH), TMV (SH), CMV (SH); S. dulcamara--CMV-U/246 (SH), PVY(NTN) (LH), SoMV-H (L), TMV-O (L); S. luteum--PVY(N) (SH), PVY(NTN) (LH+L), TMV(SH).) and natural (Asclepias syriaca--TMV, AMV, TSWV; Alisma plantago-aquatica--PVY, SoMV; Ambrosia artemisiifolia--CMV; Chenopodium album--CMV, PVS, PLRV; C. hybridum--CMV; Cirsium canum--CMV, PVM; Carex vulpina--CMV; Comium maculatum--PVY; Datura stramonium--PVA, PVX, PVS, PVM, CMV, TMV; Lysimachia vulgaris--ArMV, BNYVV, CMV, TMV; Lythrum salicaria--ArMV; Malva neglecta--CMV; Mercurialis annua--SoMV; Solanum nigrum--CMV, PVY, PVY(N); Solidago gigantea--CMV, RpRSV, BNYVV; Stenactis annua--PVM, PVA) weed--virus relations were detected. The epidemiological role of perennial hosts (A. syriaca, A. planlago aquatica, C. canurm, L. vulgaris, L. salicaria, S. gigantea) is especially high, because they can serve as infection sources as well as overwintering hosts of different plant viruses.
 

  Screening the wetland plant species Alisma plantago-aquatica, Carex rostrata and Phalaris arundinacea for innate tolerance to zinc and comparison with Eriophorum angustifolium and Festuca rubra Merlin.:Environ Pollut. 2005 Mar;134(2):343-51.Matthews DJ, Moran BM, Otte ML.Wetland Ecology Research Group, Department of Botany, University College Dublin, Belfield, Dublin 4, Ireland. davematt00@hotmail.com

 Several wetland plant species appear to have constitutive metal tolerance. In previous studies, populations from contaminated and non-contaminated sites of the wetland plants Typha latifolia, Phragmites australis, Glyceria fluitans and Eriophorum angustifolium were found to be tolerant to high concentrations of metals. This study screened three other species of wetland plants: Alisma plantago-aquatica, Carex rostrata and Phalaris arundinacea for innate tolerance to zinc. The degree of tolerance was compared to known zinc-tolerant E. angustifolium and Festuca rubra Merlin. It was found that A. plantago-aquatica and P. arundinacea did not posses innate tolerance to zinc, but that C. rostrata was able to tolerate elevated levels of zinc, at levels comparable to those tolerated by E. angustifolium and F. rubra Merlin. The findings support the theory that some wetland angiosperm species tend to be tolerant to exposure to high levels of metals, regardless of their origin.

 

  Aquatic and terrestrial plant species with potential to remove heavy metals from storm-water.:Int J Phytoremediation. 2003;5(3):211-24.Fritioff A, Greger M.Dept. of Botany, Stockholm University, S-10691 Stockholm, Sweden. fritioff@botan.su.se

 Remediation of storm-water polluted with heavy metals should be possible in percolation systems, ponds, or wetlands. The aim of this work was to find plant species for such systems that are efficient in the uptake of Zn, Cu, Cd, and Pb. Plants were collected from percolation and wetland areas and analyzed for heavy metal concentrations. Results showed that submersed and free-floating plants had the capacity to take up high levels of Cu, Zn, and Pb into their shoots. With roots having a concentration factor above 1, the terrestrial plants show efficient stabilization of Cd and Zn and emergent plants show corresponding stabilisation of Zn. In addition, Potamogeton natans, Alisma plantago-aquatica, and Filipendula ulmaria were used in a controlled experiment. The shoots of P. natans and the roots of A. plantago-aquatica were found to accumulate even higher concentrations of Zn, Cu, and Pb than found in the field-harvested plants. Similar results were found for Cd in shoots and Pb in roots of F. ulmaria. Our conclusion is that submersed plant species seem to be the most efficient for removal of heavy metals from storm-water.

  Effect of alisol B acetate, a plant triterpene, on apoptosis in vascular smooth muscle cells and lymphocytes.:Eur J Pharmacol. 2001 May 11;419(2-3):127-38.Chen HW, Hsu MJ, Chien CT, Huang HC.Office for Medical Research, National Taiwan University Hospital, Taipei.

 Glucocorticoid-induced apoptosis is a well-recognized physiological regulator of T-cell number and function. Alisol B acetate, a triterpene from Alisma Plantago-aquatica, has a glucocorticoid-like structure, and may have a similar function like glucocorticoid-induced apoptosis in both vascular smooth muscle cell line (A7r5) and human acute lymphoblastic leukemia cell line (CEM cells). For exploring its mechanism, mitochondria membrane potential and apoptosis-related gene expression were discussed. Alisol B (10(-6)-10(-4) M) inhibited serum-stimulated DNA synthesis in a concentration-dependent manner (IC50) = 4.0 +/- 0.8 x 10(-6) M in A7r5 and 2.1 +/- 1.2 x 10(-6) M in CEM cells). The cell viability was reduced at 10(-4) M of alisol B. Similar results were seen in dexamethasone treatment (a synthetic glucocorticoid, 10(-6) M, 48 h). Apoptosis was induced after the cells were exposed to 10(-5)-10(-4) M alisol B or 10(-6) M dexamethasone for 48 h. The mitochondrial membrane potential (delta psi(m)) was significantly reduced after the alisol B treatment, indicating that the mitochondria might play a role in the alisol B induced cell apoptosis. Alisol B (10(-5)-10(-4) M) increased the levels of c-myc and bax mRNA and proteins, but not on the anti-apoptotic proto-oncogene, bcl-2, in A7r5 and CEM cells. In contrast, dexamethasone (10(-6) M) treatment only caused significant increase in c-myc mRNA levels. These results suggest that the increased ratio of Bax/Bcl-2 and the decreased mitochondrial membrane potential might be involved in the mechanisms of alisol B-induced cell apoptosis.
 

  11-Deoxyalisol C and Alisol D: New Protostane-Type Triterpenoids from Alisma plantago-aquatica.:Planta Med. 1988 Oct;54(5):445-7.

 New protostane-type triterpenes, 11-deoxyalisol C and alisol D, have been isolated from the rhizomes of ALISMA PLANTAGO-AQUATICA, and their structures have been elucidated on the basis of spectral and chemical data.

  Anti-complementary activity of protostane-type triterpenes from Alismatis rhizoma.:Arch Pharm Res. 2003 Jun;26(6):463-5.Lee SM, Kim JH, Zhang Y, An RB, Min BS, Joung H, Lee HK.Laboratory of Immunomodulator, Korea Research Institute of Bioscience, Biotechnology, P.O. Box 115, Yusong, Daejeon 305-333, Korea.

 Four protostane-type triterpenes, alisol B 23-acetate (1a), alisol C 23-acetate (2a), alisol B (3a), and alisol A 24-acetate (4a), were isolated from the rhizome of Alismatis plantago-aquatice L. var. orientale Samuelson (Alismataceae) and eleven protostane derivatives (compounds 1-11) were obtained by selective modification from alisol B 23-acetate (1a). These compounds were investigated for their anti-complement activity against the classical pathway of the complement system. Alisol B (3a) and alisol A 24-acetate (4a) exhibited anti-complement activity with IC50 values of 150 and 130 microM. Among the synthetic derivatives, the tetrahydroxylated protostane triterpene (9) showed moderate inhibitory activity with IC50 value of 97.1 microM. Introduction of an aldehyde group at C-23 (10; IC50 value, 47.7 microM) showed the most potent inhibitory effect on the complement system in vitro.

  Cytotoxic triterpenoides from Alismatis Rhizoma.:Arch Pharm Res. 2001 Dec;24(6):524-6.Lee S, Kho Y, Min B, Kim J, Na M, Kang S, Maeng H, Bae K.Korea Research Institute of Bioscience and Biotechnology, Taejon.

 Four prostane-type triterpenes were isolated from a methanol extract of Alismatis Rhizoma by bioassay-guided isolation using in vitro cytotoxic assay. The compounds were identified as alisol B 23-acetate (1), alisol C 23-acetate (2), alisol B (3), alisol A 24-acetate (4) by spectroscopic methods. Amongst the compounds, alisol B (3) showed significant cytotoxicity against SK-OV3, B16-F10, and HT1080 cancer cell lines with ED50 values of 7.5, 7.5, 4.9 microg/ml, respectively.

 

  Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate.:Bioorg Med Chem Lett. 1999 Nov 1;9(21):3081-6.

 The methanolic extract from a Chinese herbal medicine, the rhizome of Alisma orientale, was found to exhibit inhibitory activity of nitric oxide (NO) production in lipopolysaccharide (LPS)activated macrophages. Novel triterpenes, alismaketones-B 23-acetate and -C 23-acetate, were isolated from the active extract together with eight sesquiterpenes and eighteen protostane-type triterpenes. The absolute stereostructures of new triterpenes were characterized on the basis of chemical and physicochemical evidence, which included the chemical correlations with known triterpenes. The guaiane-type sesquiterpenes (alismol, orientalols A and C) and protostane- and seco-protostane-types triterpenes (alisols C monoacetate, E-23-acetate, F, H, I, L-23-acetate, and M-23-acetate, alismaketones-B 23-acetate and -C 23-acetate, alismalactone 23-acetate, and 3-methylalismalactone 23-acetate) inhibited LPS-induced NO production (IC50 = 8.4-68 microM). Other triterpenes (alisols A, A monoacetate, B, B monoacetate, E, G, K-23-acetate, and N-23-acetate and 11-deoxyalisol B) also showed the potent inhibitory activity, but they showed cytotoxic effects more than 30 microM (MTT assay). In addition, alismol and alisol F were found to suppress iNOS induction.

  Studies on Alismatis Rhizoma. II. Anti-complementary activities of methanol extract and terpene components from Alismatis Rhizoma (dried rhizome of Alisma orientale).:Biol Pharm Bull. 1998 Dec;21(12):1317-21.

 A methanol extract (TMe-ext) from the dried rhizome of Alisma orientale was screened for anti-complementary activity in experimental models. In the animal models, it was found that TMe-ext inhibits zymosan-induced hind paw edema in rats and zymosan-activated rat serum (ZAS)-induced vascular permeability in mice. TMe-ext showed an inhibitory effect on complement-induced hemolysis through both the classical pathway and the alternative pathway. And TMe-ext inhibited hypotonic shock-induced hemolysis, but this effect was weak compared with the anti-complementary activities of TMe-ext. Four triterpenes (alisol A, alisol A monoacetate, alisol B and alisol B monoacetate) isolated from the rhizome also inhibited the complement-induced hemolysis through the classical pathway, but two sesquiterpenes (alismol and alismoxide) were ineffective. These results indicate that Alismatis Rhizoma shows anti-complementary activity, and its anti-complementary components are partially attributable to the terpene components mentioned above.
 

  Studies on Alismatis rhizoma. I. Anti-allergic effects of methanol extract and six terpene components from Alismatis rhizoma (dried rhizome of Alisma orientale).:Biol Pharm Bull. 1997 May;20(5):511-6.

 Methanol and aqueous extracts (TMe-ext and TAq-ext) from dried rhizomes of Alisma orientale have been screened for activity in experimental models of type I-IV allergies. In the type III allergic model, TMe-ext at oral doses of 50, 200 mg/kg showed an inhibitory effect on the direct passive Arthus reaction (DPAR) in rats, while TAq-ext did not. Four triterpenes (alisol A, alisol B, alisol A monoacetate and alisol B monoacetate) and two sesquiterpenes (alismol and alismoxide) isolated from TMe-ext also exhibited this inhibitory effect. In a type I allergic model, TMe-ext inhibited 48-h homologous passive cutaneous anaphylaxis (PCA) in rats. In a type II allergic model, it was found that TMe-ext inhibits reversed cutaneous anaphylaxis (RCA) in rats. Furthermore, in a type IV allergic model, TMe-ext had an inhibitory effect on the induction phase in picryl chloride-induced contact dermatitis (PC-CD) in mice. These results indicate that Alismatis Rhizoma not only inhibits antibody-mediated allergic reactions but also influences cell reactions and should be recognized as a material for the treatment of allergic reactions, and the anti-type III allergic components are partially attributable to the terpenes mentioned above.

  Crude drugs from aquatic plants. III. Quantitative analysis of triterpene constituents in alismatis rhizoma by means of high performance liquid chromatography on the chemical change of the constituents during alismatis rhizoma processing:

 As a series of study on the evaluation of Alismatis Rhizoma and the chemical characterization of the processing, a quantitative method by high performance liquid chromatography (HPLC) for ten triterpene constituents, alisols A, A monoacetate, B, B monoacetate, E 23-acetate, F, and G and 13,17-epoxyalisol A, 11-deoxyalisols B and B 23-acetate, has been developed. By the use of this HPLC method, the contents of these triterpenes in various Alismatis Rhizoma and the fresh rhizoma of Alisma oriental JUZEPC, originated from in China, Taiwan, and Japan were examined. Furthermore, the chemical change of the triterpene constituents during the drying process of the rhizoma of Alisma oriental has been investigated and it was found that the bioactive triterpenes of Alismatis Rhizoma such as alisol A and alisol A monoacetate were artificially formed during the drying process.
 

  Alisol B acetate, a triterpene from Alismatis rhizoma, induces Bax nuclear translocation and apoptosis in human hormone-resistant prostate cancer PC-3 cells.:Cancer Lett. 2006 Jan 18;231(2):270-8.Huang YT, Huang DM, Chueh SC, Teng CM, Guh JH.Pharmacological Institute, College of Medicine, National Taiwan University, No. 1, Jen-Ai Road, Sect. 1, Taipei, Taiwan, ROC.

 The anti-tumor potential of components from Chinese herbal medicines has been greatly concerned. Alisol B acetate, a triterpene from Alismatis rhizoma, induced apoptotic cell death in human hormone-resistant prostate cancer PC-3 cells in a time- and concentration-dependent manner. A good correlation between loss of mitochondrial membrane potential and apoptotic cell death was apparent indicating the participation of mitochondria-related mechanism. Alisol B acetate induced Bax up-regulation and nuclear translocation; it also induced the activation of initiator caspase-8 and caspase-9, and executor caspase-3, suggesting the involvement of both extrinsic and intrinsic apoptosis pathways. Taken together, it is suggested that alisol B acetate induces apoptosis in PC-3 cells via a mitochondria-mediated mechanism with activation of caspase-8, -9 and -3. Furthermore, the Bax activation and translocation from the cytosol to nucleus might be a crucial response to the apoptotic effect.

 

  Reversal of P-glycoprotein-mediated multidrug resistance by Alisol B 23-acetate.:Biochem Pharmacol. 2004 Sep 1;68(5):843-55.Wang C, Zhang JX, Shen XL, Wan CK, Tse AK, Fong WF.Department of Biology and Chemistry, Bioactive Products Research Group, City University of Hong Kong, Kowloon, Hong Kong SAR, China.

 Herbal drugs were screened for their activity in reversing multidrug resistance (MDR) in P-glycoprotein (P-gp) over-expressing cancer cells. Through bio-assay guided fractionation an active compound was isolated from Rhizoma Alismatis, the underground part of Alisma orientale and the chemical structure of the isolate compound was confirmed by HPLC, LC-MS and NMR as Alisol B 23-acetate (ABA). ABA restored the sensitivity of MDR cell lines HepG2-DR and K562-DR to anti-tumor agents that have different modes of action but are all P-gp substrates. It restored the activity of vinblastine, a P-gp substrate, in causing G2/M arrest in MDR cells. In a dose-dependent manner, ABA increased doxorubicin accumulation and slowed down the efflux of rhodamin-123 from MDR cells. ABA inhibited the photoaffinity labeling of P-gp by [125I]iodoarylazidoprazosin and stimulated the ATPase activity of P-gp in a concentration-dependent manner, suggesting that it could be a transporter substrate for P-gp. In addition, ABA was also a partial non-competitive inhibitor of P-gp when verapamil was used as a substrate. Our results suggest that ABA may be a potential MDR reversal agent and could serve as a lead compound in the development of novel drugs.

  Pharmacological evaluation of several major ingredients of Chinese herbal medicines in human hepatoma Hep3B cells.:Eur J Pharm Sci. 2003 Aug;19(5):403-12.Chou CC, Pan SL, Teng CM, Guh JH.Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan.

 Long-dan-tan (Chinese name) is one of the most common herbal medicines used by Chinese people with chronic liver disease. Accumulated anecdotal evidence suggests that Long-dan-tan may show a beneficial effect in patients with hepatocellular carcinoma. Long-dan-tan is made from five plants: Gentiana root, Scutellaria root, Gardenia fruit, Alisma rhizome, and Bupleurum root. In this study, we have examined the cytotoxic effects of the five major ingredients isolated from the above plants, i.e. gentiopicroside, baicalein, geniposide, alisol B acetate and saikosaponin-d, respectively, on human hepatoma Hep3B cells. Annexin V immunofluorescence detection, DNA fragmentation assays and FACScan analysis of propidium iodide-staining cells showed that gentiopicroside, baicalein, and geniposide had little effect, whereas alisol B acetate and saikosaponin-d profoundly induced apoptosis in Hep3B cells. Alisol B acetate, but not saikosaponin-d, induced G2/M arrest of the cell cycle as well as a significant increase in caspase-3 activity. Interestingly, baicalein by itself induced an increase in H(2)O(2) generation and the subsequent NF-kappaB activation; furthermore, it effectively inhibited the transforming growth factor-beta(1) (TGF-beta(1))-induced caspase-3 activation and cell apoptosis. We suggest that alisol B acetate and saikosaponin-d induced cell apoptosis through the caspase-3-dependent and -independent pathways, respectively. Instead of inducing apoptosis, baicalein inhibits TGF-beta(1)-induced apoptosis via increase in cellular H(2)O(2) formation and NF-kappaB activation in human hepatoma Hep3B cells.

  Content variety of alisol B 23-acetate in Rhiozma Alismatis reaped at different time:Zhong Yao Cai. 1998 Dec;21(12):595-6.Wen H, Li W, Peng G, Chi Y.Nanjing University of Traditional Chinese Medicine, Nanjing 210029.

 Alisol B 23-acetate in Rhizoma Alismatis reaped at different time was determinated by RP-HPLC. The result indicated that the content of those reaped in April is obviously higher than those reaped from Jan. to March.

  Chemical modification of alisol B 23-acetate and their cytotoxic activity.:Arch Pharm Res. 2002 Oct;25(5):608-12.Lee S, Min B, Bae K.Korea Research Institute of Bioscience and Biotechnology, Daejon.

 The twelve-protostane analogues were synthesized from alisol B 23-acetate and assessed for their in vitro antitumor activity against six different human and murine tumor cell lines. Of the compounds synthesized, 23S-acetoxy-24R(25)-epoxy-11beta,23S-dihydroxyprotost-13(17)-en-3-hydroxyimine (12) exhibited significant cytotoxic activities against A549, SK-OV3, B16-F10, and HT1080 tumor cells with ED50 values of 10.0, 8.7, 5.2, and 3.1 microg/ml, respectively. Furthermore, 23S-acetoxy-13(17),24R(25)-diepoxy-11beta-hydroxyprotost-3-one (5), 13(17),24R(25)-diepoxy-11beta,23S-dihydroxyprotostan-3-one (6), 24R,25-epoxy-11beta,23S-dihydroxyprotost-13(17)-en-3-one (7), and 11beta,23S,24R,25-tetrahydroxyprotost-13(17)-en-3-one (9) showed moderate cytotoxic activities against B16-F10 and HT1080 tumor cells. These results mean that a hydroxyimino group at C-3 position in the protostane-type terpene enhances cytotoxic activity.

  In vitro inducible nitric oxide synthesis inhibitors from Alismatis Rhizoma.:Biol Pharm Bull. 1999 Oct;22(10):1147-9.Kim NY, Kang TH, Pae HO, Choi BM, Chung HT, Myung SW, Song YS, Sohn DH, Kim YC.College of Pharmacy, Wonkwang University, Iksan, Chonbuk, Korea.

 Bioassay-guided fractionation of an aqueous extract of Alismatis Rhizoma has furnished two inducible nitric oxide synthase (iNOS) inhibitory compounds, alismol (1) and alisol B monoacetate (2), together with an inactive triterpene, alisol C monoacetate (3). Compounds 1 and 2 inhibited nitric oxide (NO) synthesis in a dose-dependent manner in murine macrophage-like RAW 264.7 cells stimulated with interferon-gamma (IFN-gamma) plus lipopolysaccharide (LPS). The inhibitory effects of 1 and 2 on NO synthesis were partly due to suppression of iNOS mRNA expression as determined by Northern blotting.

 

  Sairei-to inhibits the production of endothelin-1 by nephritic glomeruli(2): alisols, possible candidates as active compounds:Nippon Jinzo Gakkai Shi. 1998 Feb;40(2):33-41.

 We have previously reported that Sairei-to (TJ-114), a Japanese herbal medicine, prevented the production of endothelin-1 in anti-GBM nephritic rats, and that Alismatis Rhizoma (Takusha in Japanese), one of the twelve herbs composing TJ-114, might be responsible for the action. In order to further clarify the antinephritic components of TJ-114, we investigated the effects of Takusha extracts on various parameters, including endothelin-1 production of glomeruli in vitro and in vivo using anti-GBM nephritic rats. MeOH-100% MeOH and MeOH-50% MeOH fractions (31.3 microgram/ml or higher) strongly inhibited an increase in endothelin-1 concentration in culture medium when they were added to a culture of glomerular cells derived from nephritic rats. In addition, oral administration of the MeOH-100% MeOH fraction (30 mg/kg) ameliorated the proteinuria, increase in systolic blood pressure and changes in histopathological parameters in nephritic rats. Oral administration of the MeOH-100% MeOH fraction inhibited increase in endothelin-1 expression in the glomeruli of nephritic rats and in endothelin-1 production by a culture of glomerular cells derived from the nephritic rats. Alisols A and B, the main constituents of the MeOH-100% MeOH fraction, inhibited in vitro endothelin-1 production by glomerular cells derived from the nephritic rats. Oral administration of alisol B (30 mg/kg) prevented the endothelin-1 expression by glomeruli and the increase in endothelin-1 production by cultured nephritic glomerular cells. Oral administration of alisol B also ameliorated the proteinuria, the increase in systolic blood pressure and the changes in histopathological parameters in the nephritic rats. These results indicate that the antinephritic action of TJ-114, resulting from the inhibition of endothelin-1 production, may be attributed to the alisols in Takusha

  Crude drugs from aquatic plants. V. On the constituents of alismatis rhizoma. (3). Stereostructures of water-soluble bioactive sesquiterpenes, sulfoorientalols a, b, c, and d, from Chinese alismatis rhizoma.:Chem Pharm Bull. 1994 Dec;42(12):2430-5.

 From the water-soluble portion of Chinese Alismatis Rhizoma, four bioactive sesquiterpenes, sulfoorientalols a, b, c, and d, were isolated and their structures having a sulfonic acid function were established on the basis of chemical and physicochemical evidence. In addition, two sulfoorientalol congeners were derived from alismol by sulfonation of the exo-methylene moiety. Sulfoorientalols and the synthetic congeners were found to inhibit the carbachol-induced contraction of isolated bladder smooth muscle of guinea pig.

  Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide.:J Org Chem. 2006 Sep 29;71(20):7866-9.Blay G, Garc¨ªa B, Molina E, Pedro JR.Departament de Qu¨ªmica Org¨¤nica, Facultat de Qu¨ªmica, Universitat de Val¨¨ncia, Dr. Moliner 50, E-46100, Burjassot, Val¨¨ncia, Spain.

 The first total syntheses of (+)-alismoxide and (+)-4-epi-alismoxide are reported. Formal chemo-, regio-, and stereoselective addition of water to 10alpha-acetoxy-1alphaH,5betaH-guaia-3,6-diene afforded the target compounds after reduction. The absolute stereochemistry of (+)-alismoxide has been established. The low [alpha](D) +8.6 value indicates that significant amounts of alismoxide result from biosynthetic processes. Furthermore, the structure of the natural guaienediol isolated from Silphium perfoliatum has been corrected to (-)-alismoxide.


  Scientific References:

  1.Research Update:Alisma orientalis.