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Regular Articles Flavonol Glycosides from Epimedium pubescens F. Tu, Y. Dai, Z. Yao, X. Wang, X. Yao, and L. Qin pp. 1317–1321 Simultaneous Determination of Ten Flavonoids from Viscum coloratum Grown on Different Host Species and Different Sources by LC-MS Y. Zhao, Z. Yu, R. Fan, X. Gao, M. Yu, H. Li, H. Wei, and K. Bi pp. 1322–1328 Oleanene Glycosides of the Aerial Parts and Seeds of Bupleurum falcatum and the Aerial Parts of Bupleurum rotundifolium, and Their Evaluation as Anti-hepatitis Agents Y. Nakahara, M. Okawa, J. Kinjo, and T. Nohara pp. 1329–1339 Garlicnin A from the Fraction Regulating Macrophage Activation of Allium sativum M. El-Aasr, Y. Fujiwara, M. Takeya, M. Ono, D. Nakano, M. Okawa, J. Kinjo, T. Ikeda, H. Miyashita, H. Yoshimitsu, and T. Nohara pp. 1340–1343 ii CHEMICAL & PHARMACEUTICAL BULLETIN Vol. 59, No. 11 November 2011 © Copyright, 2011, by the Pharmaceutical Society of Japan. Contents

CHEMICAL & PHARMACEUTICAL BULLETIN · M. S. Alam, L. Liu, and D. U. Lee pp. 1413–1416 Oleanolic Triterpene Saponins from the Roots ... in which halogen atoms or a nitro group was

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Page 1: CHEMICAL & PHARMACEUTICAL BULLETIN · M. S. Alam, L. Liu, and D. U. Lee pp. 1413–1416 Oleanolic Triterpene Saponins from the Roots ... in which halogen atoms or a nitro group was

Regular Articles

Flavonol Glycosides from Epimediumpubescens

F. Tu, Y. Dai, Z. Yao, X. Wang, X. Yao, and L. Qin

pp. 1317–1321

Simultaneous Determination of Ten Flavonoidsfrom Viscum coloratum Grown on DifferentHost Species and Different Sources by LC-MS

Y. Zhao, Z. Yu, R. Fan, X. Gao, M. Yu, H. Li, H. Wei, and K. Bi

pp. 1322–1328

Oleanene Glycosides of the Aerial Parts andSeeds of Bupleurum falcatum and the AerialParts of Bupleurum rotundifolium, and TheirEvaluation as Anti-hepatitis Agents

Y. Nakahara, M. Okawa, J. Kinjo, and T. Nohara

pp. 1329–1339

Garlicnin A from the Fraction RegulatingMacrophage Activation of Allium sativum

M. El-Aasr, Y. Fujiwara, M. Takeya, M. Ono, D. Nakano, M. Okawa, J. Kinjo, T. Ikeda, H. Miyashita, H. Yoshimitsu, and T. Nohara

pp. 1340–1343

ii

CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 59, No. 11 November 2011 © Copyright, 2011, by the Pharmaceutical Society of Japan.

Conten t s

Page 2: CHEMICAL & PHARMACEUTICAL BULLETIN · M. S. Alam, L. Liu, and D. U. Lee pp. 1413–1416 Oleanolic Triterpene Saponins from the Roots ... in which halogen atoms or a nitro group was

Neolignans from Schisandra wilsoniana andTheir Anti-human Immunodeficiency Virus-1Activities

G.-Y. Yang, R.-R. Wang, H.-X. Mu, Y.-K. Li, W.-L. Xiao, L.-M. Yang, J.-X. Pu, Y.-T. Zheng, andH.-D. Sun

pp. 1344–1347

Three New Nortriterpene Glycosides and TwoNew Triterpene Glycosides from the Bulbs ofScilla scilloides

M. Ono, D. Toyohisa, T. Morishita, H. Horita, S. Yasuda, Y. Nishida, T. Tanaka, M. Okawa, J. Kinjo, H. Yoshimitsu, and T. Nohara

pp. 1348–1354

Photochemical Cleavage Reaction of 8-Quinolinyl Sulfonates That Are Halogenatedand Nitrated at the 7-Position

S. Ariyasu, K. Hanaya, M. Tsunoda, M. Kitamura,M. Hayase, R. Abe, and S. Aoki

pp. 1355–1362

Androgen Receptor Antagonists and Anti-prostate Cancer Activities of Some Synthesized Steroidal Candidates

S. A. Bahashwan, M. A. Al-Omar, E. Ezzeldin, M. M. Abdalla, A. A. Fayed, and A.-G. E. Amr

pp. 1363–1368

Discovery of a Novel Acyl-CoA: CholesterolAcyltransferase Inhibitor: The Synthesis,Biological Evaluation, and Reduced AdrenalToxicity of (4-Phenylcoumarin)acetanilideDerivatives with a Carboxylic Acid Moiety

M. Ogino, Y. Nakada, N. Negoro, S. Itokawa, S. Nishimura, T. Sanada, T. Satomi, S. Kita, K. Kubo, and S. Marui

pp. 1369–1375

Chemical & Pharmaceutical Bulletin Vol. 59, No. 11

iii

A nobel series of steroid derivatives were synthesized and theirandrogen receptor (AR) antagonist acyivities and in vivoantiandrogenic were evaluated.

Page 3: CHEMICAL & PHARMACEUTICAL BULLETIN · M. S. Alam, L. Liu, and D. U. Lee pp. 1413–1416 Oleanolic Triterpene Saponins from the Roots ... in which halogen atoms or a nitro group was

Synthesis and Pharmacological Evaluation of1-Alkyl-N-[(1R)-1-(4-fluorophenyl)-2-methyl-propyl]piperidine-4-carboxamide Derivativesas Novel Antihypertensive Agents

S. Watanuki, K. Matsuura, Y. Tomura, M. Okada, T. Okazaki, M. Ohta, and S. Tsukamoto

pp. 1376–1385

Antitumor Effect of Liposomal HistoneDeacetylase Inhibitor-Lipid Conjugates in Vitro

Y. Hattori, Y. Nagaoka, M. Kubo, H. Yamasaku, Y. Ishii, H. Okita, H. Nakano, S. Uesato, and Y. Maitani

pp. 1386–1392

Notes

Two New Flavone C-Glycosides from Trollius ledebourii

L.-Z. Wu, H.-F. Wu, X.-D. Xu, and J.-S. Yang

pp. 1393–1395

Chemical Constituents from Sambucus adnataand Their Protein–Tyrosine Phosphatase 1BInhibitory Activities

T. Sasaki, W. Li, H. Morimura, S. Li, Q. Li, Y. Asada, and K. Koike

pp. 1396–1399

Adsorption of Cadmium Ions by Wheat BranTreated with Pectinase

F. Ogata, H. Tominaga, M. Kangawa, and N. Kawasaki

pp. 1400–1402

Two new flavone C-glyco-sides, trollisin A and B, were isolated from the flowers of Trollius ledebourii REICHB.

Chemical & Pharmaceutical Bulletin Vol. 59, No. 11

iv

Page 4: CHEMICAL & PHARMACEUTICAL BULLETIN · M. S. Alam, L. Liu, and D. U. Lee pp. 1413–1416 Oleanolic Triterpene Saponins from the Roots ... in which halogen atoms or a nitro group was

New Solanocapsine-Type Tomato Glycosidefrom Ripe Fruit of Solanum lycopersicum

M. Ohno, M. Ono, and T. Nohara

pp. 1403–1405

Efficient Improved Extraction of TomatoSaponin Using Shock Waves

H. Manabe, A. Takemoto, H. Maehara, M. Ohno, Y. Murakami, S. Itoh, and T. Nohara

pp. 1406–1408

New Cannabinoid-Like Chromane andChromene Derivatives from Rhododendron anthopogonoides

N. Iwata and S. Kitanaka

pp. 1409–1412

Cytotoxicity of New 5-Phenyl-4,5-dihydro-1,3,4-thiadiazole Analogues

M. S. Alam, L. Liu, and D. U. Lee

pp. 1413–1416

Oleanolic Triterpene Saponins from the Rootsof Panax bipinnatifidus

N. H. Tung, T. H. Quang, N. T. T. Ngan, C. V. Minh,B. K. Anh, P. Q. Long, N. M. Cuong, and Y. H. Kim

pp. 1417–1420

Chemical & Pharmaceutical Bulletin Vol. 59, No. 11

v

Page 5: CHEMICAL & PHARMACEUTICAL BULLETIN · M. S. Alam, L. Liu, and D. U. Lee pp. 1413–1416 Oleanolic Triterpene Saponins from the Roots ... in which halogen atoms or a nitro group was

Secolignans, Neolignans and Phenylpropanoidsfrom Daphne feddei and Their BiologicalActivities

Q.-F. Hu, H.-X. Mu, H.-T. Huang, H.-Y. Lv, S.-L. Li,P.-F. Tu, and G.-P. Li

pp. 1421–1424

Bioactive Phenolic Constituents from the Seedsof Pharbitis nil

K. H. Kim, S. K. Ha, S. U. Choi, S. Y. Kim, and K. R. Lee

pp. 1425–1429

Sesquiterpenes from the SecondaryMetabolites of Streptomyces sp. (YIM 56130)

Z. Yang, Y. Yang, X. Yang, Y. Zhang, L. Zhao, L. Xu, and Z. Ding

pp. 1430–1433

Chemical & Pharmaceutical Bulletin Vol. 59, No. 11

vi

About the cover: Photochemical bond-cleavage reactions are potentially useful in chemistry, bioorganic chemistry andmedicinal chemistry. We previously reported on a photochemical cleavage reaction of 8-quinolinyl sulfonate (8-QS)derivatives in aqueous solution at neutral pH, which we proposed to proceed via an excited triplet state. In this report, wereport on the synthesis of some new photocleavable 8-QS derivatives, in which halogen atoms or a nitro group was introducedat the 7-position, in an attempt to improve photoreactive properties and to produce a red-shift in the irradiation wavelength. Itwas found that 7-nitro-8-QS absorbs at �360 nm, and, as a result, the S–O bond of this compound can be cleaved byphotoirradiation with a fluorescent lamp in aqueous solution and on silicon surface. See the article by Ariyasu et al. on page1355 of this issue.