Hamaudol

The herbs of Ledebouriella seseloides

Comparative analysis of the constituents in Saposhnikoviae Radix and Glehniae Radix cum Rhizoma by monitoring inhibitory activity of nitric oxide production.[Pubmed:26833192]

J Nat Med. 2016 Apr;70(2):253-9.

During the development of natural herbal medicines in Japan, Glehniae Radix cum Rhizoma (Hamabofu in Japanese) has been used as a substitute for Saposhnikoviae Radix (Bofu). Bofu and Hamabofu are blended differently in several Kampo formulae. For example, Bofu is included in Jumihaidokuto by a manufacturer, whereas Hamabofu is included instead of Bofu in the same formula by other manufacturers. Although both Bofu and Hamabofu are used for their expected anti-inflammatory effects, differences in their medicinal properties are not well characterized. In addition, there have been very few reports comparing the pharmacological activities of the constituents in Bofu and Hamabofu. In the present study, we investigated the anti-inflammatory effects of the extracts of Bofu and Hamabofu by monitoring levels of the inflammatory mediator nitric oxide (NO) produced in rat hepatocytes. Moreover, the chemical constituents responsible for the activity were investigated. Our results showed that ethyl acetate fractions of Bofu and Hamabofu extracts contain different compounds, although both fractions suppressed NO production in rat hepatocytes. The linear dihydropyranochromones from the Bofu extract (i.e., 3'-O-angeloylHamaudol, ledebouriellol and Hamaudol) suppressed NO production, whereas the coumarins from the Hamabofu extract (i.e., umbelliferone and scopoletin) also suppressed NO production. These results suggest that linear dihydropyranochromones and coumarins are responsible for the anti-inflammatory effects of Bofu and Hamabofu. It is plausible that Bofu and Hamabofu are blended differently in several Kampo formulae due to many constituents with as yet unidentified pharmacological activity.

[Quantitative analysis of five components in the rhizome of Angelica polymorpha by RP-HPLC under different UV wavelengths].[Pubmed:21174769]

Zhongguo Zhong Yao Za Zhi. 2010 Oct;35(19):2581-4.

A HPLC method was developed for simultaneouly quantitative analyses of aviprin (1), gosferol (2), 3'R-(+)-Hamaudol (3), 3'-O-acetylHamaudol (4) and iso-imperatorin (5) in the rhizome of Angelica polymorpha. The analysis was performed at 25 degrees C on an Agilent Eclipse XDB-C18 analytical column (4.6 mm x 250 mm, 5 microm) with the mobile phase of methanol and H2O in gradient elution [55:45 (0 min)-65:35 (25 min)-95:5 (35 min)]. And the flow rate was 1.0 mL min(-1) with the detection wavelengths of 312 nm (1), 306 nm (2), 300 nm (3), 294 nm (4) and 310 nm (5). Consequently, the reqresion equations were Y = 1.81 x 10(3) X + 7.93 x 10(2) (r = 0.9996), Y = 2.49 x 10(3) X - 2.17 x 10(2) (r = 0.9993), Y = 2.02 x 10(3) X - 1.42 x 10(2) (r = 0.9991), Y = 1.57 x 10(3) X - 0.66 x 10(2) (r = 0.999 7), Y = 2.65 x 10(3) X - 1.47 x 10(2) (r = 0.999 6). And the average recoveries were 99.7% (RSD 0.57%), 100.1% (RSD 1.3%), 100.0% (RSD 1.6%), 99.6% (RSD 1.3%), 99.2% (RSD 0.59%), respectively. The precision, repeatability and stability were all consistent with the request of quantitative analysis. The contents of compound 1-5 in A. polymorpha were determined as 0.525%, 0.044%, 0.046%, 0.043%, 0.15%, respectively. Accordingly, this quantitative analysis method is good for the quality control of A. polymorpha.

[Chemical constituents of roots of Saposhnikovia divaricata].[Pubmed:20815209]

Zhongguo Zhong Yao Za Zhi. 2010 Jun;35(12):1569-72.

OBJECTIVE: To study the chemical constituents in the dried roots of Saposhnikovia divaricata. METHOD: The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by IR, UV, MS and NMR evidences. RESULT: Eighteen compounds were obtained and identified as 3'-O-angeloylHamaudol (1), isobergapten (2), imperatorin (3), pentacosane acid (4), anomalin (5), decursin (6), 5-methoxy-7-(3,3-dimethylallyl- oxy)coumarin (7), decursinol angelate (8), xanthotoxin (9), bergapten (10), tectochrysin (11), scopoletin (12), Hamaudol (13), ledebouriellol (14), cimifugin (15), sec-O-glucosylHamaudol (16), 4'-O-beta-D-glucosyl-5-O-methylvisamminol (17), and prim-O-glucosylcimifugin (18). CONCLUSION: Compounds 2, 6-8, and 11 were isolated from the roots of S. divaricata for the first time. Compounds 1 and 13-18 were chromones, 2, 3, 5-10 and 12 were coumarins, 4 was fatty acid, and 11 was flavonoid.

[Isolation and structure identification of chemical constituents from Saposhnikovia divaricata (Turcz.) Schischk].[Pubmed:17703773]

Yao Xue Xue Bao. 2007 May;42(5):505-10.

Fourteen compounds were isolated from the ethanol extraction of Saposhnikovia divaricata (Turcz.) Schischk using column chromatographic methods after enrichment by macroporous adsorptive resins. They were identified as fangfengalpyrimidine (1), clemiscosin A (2), 5-hydroxy-8-methoxypsoralen (3), sec-O-glucosylHamaudol (4), Hamaudol (5), nodakenetin (6), prim-O-glucosylcimifugin (7), cimifugin (8), 4'-O-beta-D-glucosyl-5-O-methylvisamminol (9), 5-O-methylvisamminol (10), marmesin (11), adenosine (12), daucosterol (13) and beta-sitosterol (14) by physico-chemical properties and spectral data. Compound 1 is a new compound. Compounds 2 and 3 were isolated from umbelliferae plants and Saposhnikovia divaricata (Turcz.) Schischk for the first time respectively.

A new chromone, 11-hydroxy-sec-O-glucosylhamaudol from Ostericum koreanum.[Pubmed:17603202]

Chem Pharm Bull (Tokyo). 2007 Jul;55(7):1065-6.

From the ethyl acetate fraction of the roots of Ostericum koreanum, a new chromone, 11-hydroxy-sec-O-glucosylHamaudol (1) along with the known compounds: four chromones, three coumarins, six phenolic compounds, and three quinic acids were isolated. These compounds were assessed for antioxidant activities in the DPPH radical and superoxide anion radical scavenging assay systems. Among isolates, 4-(2-hydroxy-vinyl)-benzene-1,2-diol (12) showed the most potent DPPH radical scavenging activity (IC(50)=4.80+/-0.62 mug/ml) and superoxide anion radical scavenging activity (IC(50)=11.05+/-0.83 microg/ml) in the xanthine/xanthine oxidase system. The antioxidant activities of 12 were comparable to those of quercetin and luteolin.

[Simultaneous determination of six components in Yupingfeng Decoction by high-performance liquid chromatography].[Pubmed:17584662]

Nan Fang Yi Ke Da Xue Xue Bao. 2007 Jun;27(6):884-6.

OBJECTIVE: To establish a HPLC-based method for simultaneous determination of 2 classes of compounds (flavonoids and chromones) and 6 their effective components,(including prin-O-glucosylcimifugin, cimifugin, 4'-O-beta-D-glucosyl- 5-O-methylvisamminol, quercetin, sec-o-glucosylHamaudol and formononetin), in Yupingfeng Decoction. METHODS: HPLC-based separation of the agents was performed on Agilent Extend-C(18) column (4.6 mm x 250 mm, 5 microm) at 25 degrees with the mobile phase of MeOH-1% acetic acid water solution (gradient elution), flow rate of 0.8 ml/min and detection wavelength of 254 nm. RESULTS AND CONCLUSION: HPLC allowed simultaneous quantitative determination of the 6 components in Yupingfeng Decoction, and they showed good linear relationships when their sample amount ranged 90-1810 ng, 97-1940 ng, 190-1906 ng, 105-3144 ng, 88-2625 ng and 109-3279 ng, respectively, with correlation coefficients all beyond 0.9999 and average recovery rates of 98.2%, 99.1%, 97.3%, 97.8%, 98.8% and 99.2%, respectively. This simple and convenient method accommodated a broad linear range with high sensitivity and precise and reproducible results.

[Studies on the method for the processing roots of cultivated Saposhnikovia divaricata].[Pubmed:15139121]

Zhongguo Zhong Yao Za Zhi. 2003 May;28(5):402-4.

OBJECTIVE: To establishing a standard processing method for cultivated Saposhnikovia divaricata. METHOD: Crude drug was dried at different temperature, and the contents of prim-O-glucosyl-cimifugin,cimifugin,4'-O-beta-glucosyl-5-O-methylvisamminol, sec-O-glucosyl-Hamaudol in the processed crude drug were determined by HPLC. RESULT: Of the contents of the four compounds, the sample that heated by 45 degrees C was at the best level. Prim-O-glucosggl-cinmifugin was 0.636%, cimifugin was 0.043%, 5-O-methtlvsamminol was 0.598%, sec-O-glu-cosyl-Hamaudol was 1.85%, and total content was 1.302%. CONCLUSION: The best drying temperature for processing is 45 degrees C.

[Studies on chemical constituents of Peucedanum medium Dunn var. garcile Dunn ex Shan at Sheh].[Pubmed:12512437]

Zhongguo Zhong Yao Za Zhi. 2000 Apr;25(4):222-4.

OBJECTIVE: To study the chemical constitutents in Peucedanum medium var. gracile distributed in Guangxi. METHOD: Chromatography and spectral analysis were used to isolated and elucidate the constituents. RESULT: Eight compounds were isolated from the root of P. medium var. gracile and elucidated as isoimperatorin, phellopterin, bergapten, oxypeucedanin hydrate, byakangelicin beta-sitosterol, Hamaudol and mannitol. CONCLUSION: Seven compounds were obtained from this plant for the first time.

Analgesic components of saposhnikovia root (Saposhnikovia divaricata).[Pubmed:11217101]

Chem Pharm Bull (Tokyo). 2001 Feb;49(2):154-60.

By activity-oriented separation using the writhing method in mice, the analgesic components of Saposhnikovia root (Saposhnikovia divaricata Schischkin; Umbelliferae) were identified to be chromones, coumarins, polyacetylenes and 1-acylglycerols. Two new components, divaricatol and (3'S)-hydroxydeltoin, were also isolated. The most potent analgesia was observed in chromones such as divaricatol, ledebouriellol and Hamaudol, which inhibited writhing inhibition at an oral dose of 1 mg/kg in mice. Acylglycerols also showed inhibition significantly at a dose of 5 mg/kg. In some pharmacological tests using sec-O-glucosylHamaudol, the compound showed analgesia by the tail pressure and the Randall & Selitto methods, and its writhing inhibition was not reversed by naloxone.

Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica.[Pubmed:9987830]

Chem Pharm Bull (Tokyo). 1999 Jan;47(1):96-100.

The CHCl3 extract of the root of Angelica japonica showed high inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. From this extract, a new furanocoumarin named japoangelone and four furanocoumarin ethers of falcarindiol, named japoangelols A-D, were isolated together with caffeic acid methyl ester, four polyacetylenic compounds (panaxynol, falcarindiol, 8-O-acetylfalcarindiol, and (9Z)-1,9-heptadecadiene-4,6-diyne-3,8,11-triol), eight coumarins (osthol, isoimperatorin, scopoletin, byakangelicin, xanthotoxin, bergapten, oxypeucedanin methanolate, and oxypeucedanin hydrate), and two chromones (3'-O-acetylHamaudol, and Hamaudol). The structures of the new isolates were determined based on spectral evidence. The ED50 of isolates against MK-1, HeLa, and B16F10 cell lines are reported.

Coumarins and antiplatelet aggregation constituents from Formosan Peucedanum japonicum.[Pubmed:8821432]

Phytochemistry. 1996 Feb;41(2):525-30.

Four new khellactone esters, (-)-trans-3'-acetyl-4'-senecioylkhellactone, (+-)-cis-3'-acetyl-4'-tigloylkhellactone, (+-)-cis-4-tigloylkhellactone, (+)-trans-4'-tigloylkhellactone, together with 14 known coumarins, isoimperatorin, psoralen, bergapten, xanthotoxol, cnidilin, (-)-selinidin, (-)-deltoin, (+)-pteryxin, (+)-peucedanocoumarin III, xanthotoxin, imperatorin, (+)-marmesin, (+)-oxypeucedanin hydrate, (+)-peucedanol and three chromones, eugenin, (-)-Hamaudol, (+)-visamminol, have been isolated from the root of Formosan Peucedanum japonicum. The structures of the new compounds were elucidated by spectral data. The identities of (+)-trans-3'-tigloyl-4'-acetylkhellactone, formerly reported as a new compound, and (+)-cis-3'-angeloyl-4'-acetyl-khellactone, with the known (+)-peucedanocoumarin III and (+)-pteryxin, respectively, are discussed. Among the isolates, seven compounds, eugenin, (-)-selinidin, (+)-pteryxin, imperatorin, bergapten, cnidilin and (+)-visamminol, show strong antiplatelet aggregation activity in vitro.

Hamaudol is a chromone isolated from Saposhnikovia divaricata. Hamaudol shows significant inhibitory activity on cyclooxygenase (COX)-1 and COX-2 activities with IC50 values of 0.30, 0.57 mM, respectively, and has potent analgesia and anti-inflammary effects.

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