Cytotoxic Aryltetralin Lignans from Fruits of Cleistanthus
                    indochinensis

Van Trinh Thi Thanh; Van Cuong Pham; Huong Doan Thi Mai; Marc Litaudon; Françoise Guéritte; Van Hung Nguyen; Van Minh Chau

doi:10.1055/s-0034-1368505

Planta Medica, Table of Contents

Planta Med 2014; 80(08/09): 695-702
DOI: 10.1055/s-0034-1368505

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Aryltetralin Lignans from Fruits of Cleistanthus indochinensis

Van Trinh Thi Thanh

¹Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam

,

Van Cuong Pham

¹Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam

,

Huong Doan Thi Mai

¹Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam

,

Marc Litaudon

²Institut de Chimie des Substances Naturelles, Gif-sur Yvette, France

,

Françoise Guéritte

²Institut de Chimie des Substances Naturelles, Gif-sur Yvette, France

,

Van Hung Nguyen

¹Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam

,

Van Minh Chau

¹Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam

› Author Affiliations

Abstract

Eight new aryltetralin lignans, cleisindosides A–F (1–6), picroburseranin (7), and 7-hydroxypicropolygamain (8), were isolated from the fruits of Cleistanthus indochinensis (Euphorbiaceae). The structures of the isolates were established on the basis of their one- and two-dimensional NMR spectral data, as well as their mass spectrometric data. Compound 7 was found to have potent cytotoxicity against oral epidermoid carcinoma cells with an IC₅₀ value of 0.062 µM, whereas glycosylation to 3 (IC₅₀ 7.5 µM) and stereochemical changes to 8 (IC₅₀ 10.8 µM) led to marked decreases in biological activity. Thus, it was determined that the C-7 and C-8′ positions are critical for the biological activity of the lignans from this plant.

Key words

Euphorbiaceae - Cleistanthus indochinensis - lignans - glycosides - cytotoxicity

Full Text

References

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