Bioactive Constituents of the Seeds of Brucea javanica

Bao-Ning Su; Leng Chee Chang; Eun Jung Park; Muriel Cuendet; Bernard D. Santarsiero; Andrew D. Mesecar; Rajendra G. Mehta; Harry H. S. Fong; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1055/s-2002-33798

Planta Medica, Table of Contents

Planta Med 2002; 68(8): 730-733
DOI: 10.1055/s-2002-33798

Original Paper

Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Bioactive Constituents of the Seeds of Brucea javanica

Bao-Ning Su¹ , Leng Chee Chang¹ , Eun Jung Park¹ , Muriel Cuendet¹ , Bernard D. Santarsiero² , Andrew D. Mesecar² , Rajendra G. Mehta³ , Harry H. S. Fong¹ , John M. Pezzuto¹ , A. Douglas Kinghorn¹

¹Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, U.S.A.
²Center for Pharmaceutical Biotechnology, College of Pharmacy, University of Illinois at Chicago, IL, U.S.A.
³Department of Surgical Oncology, College of Medicine, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL, U.S.A.

Abstract

A new quassinoid, yadanziolide S (1), was isolated from the seeds of the traditional Chinese medicinal herb, Brucea javanica, along with ten known compounds, flazin, bruceine D, yadanziolide B, bruceoside A, yadanziolide S, yadanzigan, glycerol 1,3-bisoleate, azelaic acid, (±)-8-hydroxyhexadecanoic acid, and vanillin. Compound 1 is the first quassinoid to have been isolated from B. javanica without a methyleneoxy bridge between C-8 and C-13, and its structure was determined using spectroscopic methods, and confirmed by single-crystal X-ray diffraction. All isolates were evaluated for their potential to induce human promyelocytic leukemia (HL-60) cell differentiation, and to inhibit cyclooxygenase-1 (COX-1), -2 (COX-2), and 7,12-dimethylbenz[a]anthracene (DMBA)-induced lesions in a mouse mammary organ culture model.

Key words

Simaroubaceae - Brucea javanica - quassinoid - yadanziolide S - X-ray analysis - human promyelocytic leukemia (HL-60) - cyclooxygenase-1 (COX-1) and -2 (COX-2) - mouse mammary organ culture assay

Full Text

References

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Prof. A. Douglas Kinghorn,Ph. D., D.Sc.

Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy

College of Pharmacy

University of Illinois at
Chicago

833 South Wood Street (M/C 781)

Chicago

IL 60612

U.S.A.

Phone: +1-312-996-0914

Fax: +1-312-996-7107

Email: kinghorn@uic.edu