Bioactive constituents of the seeds of Brucea javanica.
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.
Su
Bao-Ning
BN
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Chang
Leng Chee
LC
Park
Eun Jung
EJ
Cuendet
Muriel
M
Santarsiero
Bernard D
BD
Mesecar
Andrew D
AD
Mehta
Rajendra G
RG
Fong
Harry H S
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D032269:Brucea / Q000737:chemistry*; D002454:Cell Differentiation / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D009924:Organ Culture Techniques; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry* / Q000494:pharmacology*; D012639:Seeds / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D010936:Plant Extracts; D011714:Pyrans; C467918:standishinal