The bisabolane sesquiterpenoid endoperoxide, 3,6-epidioxy-1,10-bisaboladiene, isolated from Cacalia delphiniifolia inhibits the growth of human cancer cells and induces apoptosis

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2008-09, Vol.72 (9), p.2463-2466
• Main Authors: Nishikawa, K.(Iwate Univ., Morioka (Japan). Faculty of Agriculture), Aburai, N, Yamada, K, Koshino, H, Tsuchiya, E, Kimura, K
• Format: Article
• Language: English
• Subjects: 3,6-epidioxy-1,10-bisaboladiene; AGENTES ANTINEOPLASTICOS; ANTINEOPLASTIC AGENTS; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; APOPTOSE; APOPTOSIS; Apoptosis - drug effects; ASTERACEAE; Asteraceae - chemistry; Cacalia delphiniifolia; Cell Line, Tumor; EXTRACTOS VEGETALES; EXTRAIT D'ORIGINE VEGETALE; GENERO HUMANO; GENRE HUMAIN; Humans; Inhibitory Concentration 50; K562 Cells; LEUCEMIA; LEUCEMIE; LEUKAEMIA; Leukemia, Myelogenous, Chronic, BCR-ABL Positive - drug therapy; Leukemia, Myelogenous, Chronic, BCR-ABL Positive - metabolism; Leukemia, Myelogenous, Chronic, BCR-ABL Positive - pathology; Male; MANKIND; MEDICAMENT CYTOSTATIQUE; Molecular Structure; PLANT EXTRACTS; Prostatic Neoplasms - drug therapy; Prostatic Neoplasms - metabolism; Prostatic Neoplasms - pathology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; SESQUITERPENOIDE; SESQUITERPENOIDS; SESQUITERPENOS; Time Factors; α-curcumene
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.80266

In the course of our screening for a new anti-tumor substance, the bisabolane sesquiterpenoid endoperoxide, 3,6-epidioxy-1,10-bisaboladiene (EDBD), was isolated from the edible wild-plant, Cacalia delphiniifolia. EDBD showed cytotoxicity toward human chronic myelogenous leukemia K562 and human prostate carcinoma LNCaP cell lines with ICsub(50) values of 9.1 microM and 23.4 microM, respectively. DNA fragmentation and condensation of chromatin, the hallmarks of apoptosis, appeared in K562 cells after an 18-h treatment with EDBD. alpha-Curcumene, a bisabolane sesquiterpene that lacks the endoperoxide moiety of EDBD, also showed cytotoxicity toward both K562 and LNCaP cell lines at over a 10-times higher dose than that of EDBD. The results indicate the importance of the endoperoxide structure within EDBD to its anti-tumor activity in vitro.