Five naphthoquinones including 4 compounds with new absolute configurations, (–)-2' S-trypethelone methyl ether (1), (–)-2' S-8-methoxytrypethelone methyl ether (2), (–)-(2' S,3' S)-4'-hydroxytrypethelone (3), and (–)-(2' S,3' R)-4'-hydroxy-8-methoxy trypethelone methyl ether (5), together with a known compound, (–)-2' S-trypethelone (4), were isolated from cultured mycobiont of Marcelaria cumingii. These compounds were structurally elucidated by high-resolution mass spectra, nuclear magnetic resonance, circular dichroism, optical rotation, and single-crystal X-ray analysis. The cytotoxicity against several cancer cell lines of the isolated compounds were tested. (–)-2' S-Trypethelone methyl ether (1) showed selective inhibition of HCT116 and A549 cell lines with half-maximal inhibitory concentration values of 0.32 ± 0.03 and 1.05 ± 0.12 µM, respectively. The binding conformation and molecular interactions including the effect of substituent modification were also revealed.

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Context: Triphala is a traditional herbal formulation consisting of dried fruits from three plants namely, Terminalia bellirica, Terminalia chebula and Phyllanthus emblica. Its traditional used to treat many ailments, including various types of cancers, health promotion, and longevity. Aims: To evaluate the ability of an aqueous extract Triphala (TPL) to inhibit the growth of Hepatocellular carcinoma cells (HepG2) and in mice. Methods: The anticancer activity of TPL and its composite extracts was assessed in vitro by MTT assay with HepG2 cells. The mice were inoculated with HepG2 cells and then divided randomly into six groups (6 mice/group): control group, positive control group (intraperitoneal with 3 mg/kg body weight doxorubicin), and TPL treatment groups (oral administrated with 50, 100, and 200 mg/kg body weight TPL, respectively). Anticancer activity based on body weight, tumor growth volumes, survival time, relative organ weight, and hematological parameters was determined after administrating the TPL for 14 consecutive days. Results: The results demonstrated that the TPL extract exhibited antiproliferative activity against HepG2 cells in a time-dependent manner of treatment. The selectivity index (SI) showed that TPL is highly selective (SI>3) against the HepG2 cell line and has no activity against non-tumor cells. Oral administration with TPL extract at the dose of 200 mg/kg body weight inhibited tumor growth volume and increase the survival time. No abnormality of hematological parameters, relative organ weight, body weight, and morphology of organs were observed. Conclusions: The TPL extract at the test doses was a non-toxic drug. Our finding reveals the anticancer efficacy of TPL extract.