Studies on the Fruits of Annona squamosa-Chemical Constituents and Biological Activities

• Main Author: 洪毓春
• Other Authors: 吳永昌
• Format: Others
• Language: zh-TW
• Published: 1994
• Online Access: http://ndltd.ncl.edu.tw/handle/70798665678292592001

碩士 === 高雄醫學大學 === 天然藥物研究所 === 82 === As a result of our continuing search for novel plant bioactive agents. The methanolic extracts of the fresh fruits of Annona squamosa (Annonaecae), was found to show significant cytotoxicity against in vitro tissue culture cells in human A-549 lung carcinoma, murine P-388 lymphocytic and HIV replication in H9 lymphocyte cells. Bioactivity-guided chromatographic fractionation led to the isolation and characterization of fourteen kaurane diterpenoids: (-)-kaur-16-en-19-oic acid (1), 16β, 17-dihydrxoy-(-)-kauran-19-oic acid (2), 16β(-)-kauran-16, 17, 19-triol (3), mixture of 17-hydroxy-16β-(-)-(-)-kauran-19-oic acid and 17-hydroxy-16α-(-)-kauran-19-oic acid (4)/(5), (-)-kaur-16-en-19-ol (6), 16α, 17-dihydroxy-(-)-kauran-19-oic acid (7), 17-acetoxy-16β-(-)-kauran-19-oic acid (8), (-)-kauran-19-al-17-oic acid (9), 16β, 17-dihydroxy-(-)-kauran-19-al (10), 17-hydroxy-16β-(-)-kauran-19-al (11), 16β-hydroxy-17-acetoxy-(-)-kauran-19-al (12), 19-nor-(-)-kauran-4α-ol-17-oic acid (13), 19-nor-(-)-kauran-4α, 16β, 17-triol (14). Among them, 16β-hydroxy-17-acetoxy-(-)-kauran-19-al (12) and 19-nor-(-)-kauran-4α, 16β, 17-triol (14) are new compounds and compounds 2, 3, 4/5, 7, 8, 9 and 10 are isolated for the first time from Annona squamsoa. The structural elucidation of the isolates were established by spectroscopic and chemical evidences. Compound 2 showed significant cytotoxicity against P-388 and A-549 cancer cells with ED50 values of 0.41 and 0.13μg/ml, respectively. Compounds 1, 2 and 3 inhibited HIV replication in H9 lymphocyte cells. Especially, compound 2 showed potent anti-HIV activity in H9 lymphocyte cells with an ED50 of 0.8μg/ml. All of the compounds did not show significant effective inhibition against human immunodeficiency virus reverse transcriptase (HIV-RT).