Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest

• Published in: Journal of natural products (Washington, D.C.) Vol. 78; no. 7; pp. 1543 - 1547
• Main Authors: Liu, Yixi, Young, Kelly, Rakotondraibe, L. Harinantenaina, Brodie, Peggy J, Wiley, Jessica D, Cassera, Maria B, Callmander, Martin W, Rakotondrajaona, R, Rakotobe, Etienne, Rasamison, Vincent E, TenDyke, Karen, Shen, Yongchun, Kingston, David G. I
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 24.07.2015; Amer Chemical Soc
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemistry; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Cell Proliferation - drug effects; Chemistry, Medicinal; Dioxoles - chemistry; Drug Screening Assays, Antitumor; Forests; HCT116 Cells; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; Lignans - chemistry; Lignans - isolation & purification; Lignans - pharmacology; Madagascar; Malpighiaceae - chemistry; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Leaves - chemistry; Plant Sciences; Plasmodium falciparum - drug effects; Science & Technology; Stereoisomerism; Madagascar; SEEDS; HERNANDIA-OVIGERA L; ABSOLUTE-CONFIGURATION; OPTICAL-ROTATORY DISPERSION; NATURAL-PRODUCTS; MEDICINAL-PLANT; ARYLTETRALIN LIGNANS; CONSTITUENTS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np501020m

The two new lignans 3α-O-(β-d-glucopyranosyl)­desoxypodophyllotoxin (1) and 4-O-(β-d-glucopyranosyl)­dehydropodophyllotoxin (2) were isolated from Cleistanthus boivinianus, together with the known lignans deoxypicropodophyllotoxin (3), (±)-β-apopicropodophyllin (4), (−)-desoxypodophyllotoxin (5), (−)-yatein (6), and β-peltatin-5-O-β-d-glucopyranoside (7). The structures of all compounds were characterized by spectroscopic techniques. Compounds 1, 4, and 5 showed potent antiproliferative activities against the A2780 ovarian cancer cell line, with IC50 values of 33.0 ± 3.6, 63.1 ± 6.7, and 230 ± 1 nM, respectively. Compounds 2 and 7 showed only modest A2780 activities, with IC50 values of 2.1 ± 0.3 and 4.9 ± 0.1 μM, respectively, while compounds 3 and 6 had IC50 values of >10 μM. Compound 1 also had potent antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 value of 20.5 nM, and compound 4 exhibited modest antiproliferative activity against the A2058 human caucasian metastatic melanoma and MES-SA human uterine sarcoma cell lines, with IC50 values of 4.6 and 4.0 μM, respectively.