Methyl angolensate and mexicanolide-type limonoids from the seeds of Cipadessa baccifera

• Published in: Phytochemistry (Oxford) Vol. 98; pp. 174 - 182
• Main Authors: Siva, Bandi, Poornima, B., Venkanna, A., Prasad, K. Rajendra, Sridhar, B., Lakshma Nayak, V., Ramakrishna, Sistla, Babu, K. Suresh
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.02.2014; Elsevier
• Subjects: Animals; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biochemistry & Molecular Biology; Cancer cell lines; Cell Line, Tumor; Cell Proliferation - drug effects; Cipadessa baccifera; Crystallography, X-Ray; Cytotoxic activity; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HT29 Cells; Humans; Life Sciences & Biomedicine; Limonins - chemistry; Limonins - isolation & purification; Limonins - pharmacology; Limonoids; Magnetic Resonance Spectroscopy; MCF-7 Cells; Meliaceae - chemistry; Mice; Models, Molecular; Molecular Conformation; Plant Sciences; Science & Technology; Seeds - chemistry; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship; Triterpenes - chemistry; Triterpenes - isolation & purification; Triterpenes - pharmacology; Cipadessa baccifera; Cancer cell lines; Limonoids; Cytotoxic activity; TETRANORTRITERPENOIDS; MANGROVE; LEAVES
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2013.11.006

Six new methyl angolensate type (1–6) and three new mexicanolide-type (7–9) limonoids, along with six known limonoids (10–15), were isolated from the seeds of Cipadessa baccifera. The structures of all these compounds were established by extensive 1D, 2D NMR, and HRESIMS experiments. •Nine new compounds were isolated from seeds of Cipadessa baccifera.•Six known compounds were isolated.•All the isolates were tested for their cytotoxic activities using MTT assay.•The cell lines A549, MCF7, ME-180, HT-29, B-16, ACHN were used for this study. Six new methyl angolensate type (1–6) and three new mexicanolide-type (7–9) limonoids, along with six known limonoids (10–15), were isolated from the seeds of Cipadessa baccifera. The structures of all these compounds were established by extensive 1D, 2D NMR, and HRESIMS experiments, and structures of 11 and 13 were further confirmed by a single crystal X-ray diffraction analysis, which are reported for the first time. The cytotoxic activities of these isolates were also studied against A549, MCF7, ME-180, HT-29, B-16, ACHN cancer cell lines using MTT assay, and results indicated that compounds 4, 10, and 14 displayed potent cytotoxic activity against B-16, ACHN cell lines with an IC50 values of 8.51 and 7.0μg/mL, respectively.