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Anti-HIV and cytotoxic biphenyls, benzophenones and xanthones from stems, leaves and twigs of Garcinia speciosa.
Phytochemistry. 2018 Mar; 147:68-79.P

Abstract

Eleven previously undescribed compounds, including four benzophenones (garciosones A-D), four xanthones (garciosones E-H) and three biphenyls (garciosines A-C), along with eighteen known compounds were isolated from the stems, leaves and twigs of Garcinia speciosa Wall. (Clusiaceae). Their structures were established by extensive spectroscopic analysis. For garciosines A-C, the structures were confirmed by single crystal X-ray diffraction analysis. Most of the isolated compounds were evaluated for their cytotoxic activity and anti-HIV-1 activity using the syncytium inhibition assay and HIV-1 reverse transcriptase (RT) assay. The known compounds, 4,6,3',4'-tetrahydroxy-2-methoxybenzophenone and macluraxanthone, displayed significant cytotoxic activity with the ED50 in the range of 1.85-11.76 μM. 1,5-Dihydroxyxanthone exhibited the most potent anti-HIV activity against syncytium formation with EC50 < 17.13 μM (SI > 25.28) and 2-(3,3-dimethylallyl)-1,3,7-trihydroxyxanthone was the most active compound in the HIV-1 reverse transcriptase assay with IC50 value of 58.24 μM. Structure-activity relationship of some isolated compounds were also discussed.

Authors+Show Affiliations

Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. Electronic address: vichai.reu@mahidol.ac.th.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29304383

Citation

Pailee, Phanruethai, et al. "Anti-HIV and Cytotoxic Biphenyls, Benzophenones and Xanthones From Stems, Leaves and Twigs of Garcinia Speciosa." Phytochemistry, vol. 147, 2018, pp. 68-79.
Pailee P, Kuhakarn C, Sangsuwan C, et al. Anti-HIV and cytotoxic biphenyls, benzophenones and xanthones from stems, leaves and twigs of Garcinia speciosa. Phytochemistry. 2018;147:68-79.
Pailee, P., Kuhakarn, C., Sangsuwan, C., Hongthong, S., Piyachaturawat, P., Suksen, K., Jariyawat, S., Akkarawongsapat, R., Limthongkul, J., Napaswad, C., Kongsaeree, P., Prabpai, S., Jaipetch, T., Pohmakotr, M., Tuchinda, P., & Reutrakul, V. (2018). Anti-HIV and cytotoxic biphenyls, benzophenones and xanthones from stems, leaves and twigs of Garcinia speciosa. Phytochemistry, 147, 68-79. https://doi.org/10.1016/j.phytochem.2017.12.013
Pailee P, et al. Anti-HIV and Cytotoxic Biphenyls, Benzophenones and Xanthones From Stems, Leaves and Twigs of Garcinia Speciosa. Phytochemistry. 2018;147:68-79. PubMed PMID: 29304383.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Anti-HIV and cytotoxic biphenyls, benzophenones and xanthones from stems, leaves and twigs of Garcinia speciosa. AU - Pailee,Phanruethai, AU - Kuhakarn,Chutima, AU - Sangsuwan,Chanyapat, AU - Hongthong,Sakchai, AU - Piyachaturawat,Pawinee, AU - Suksen,Kanoknetr, AU - Jariyawat,Surawat, AU - Akkarawongsapat,Radeekorn, AU - Limthongkul,Jitra, AU - Napaswad,Chanita, AU - Kongsaeree,Palangpon, AU - Prabpai,Samran, AU - Jaipetch,Thaworn, AU - Pohmakotr,Manat, AU - Tuchinda,Patoomratana, AU - Reutrakul,Vichai, Y1 - 2018/01/02/ PY - 2017/09/11/received PY - 2017/12/18/revised PY - 2017/12/19/accepted PY - 2018/1/6/pubmed PY - 2018/3/14/medline PY - 2018/1/6/entrez KW - Anti-HIV KW - Benzophenones KW - Biphenyls KW - Clusiaceae KW - Cytotoxicity KW - Garcinia speciosa KW - Xanthones SP - 68 EP - 79 JF - Phytochemistry JO - Phytochemistry VL - 147 N2 - Eleven previously undescribed compounds, including four benzophenones (garciosones A-D), four xanthones (garciosones E-H) and three biphenyls (garciosines A-C), along with eighteen known compounds were isolated from the stems, leaves and twigs of Garcinia speciosa Wall. (Clusiaceae). Their structures were established by extensive spectroscopic analysis. For garciosines A-C, the structures were confirmed by single crystal X-ray diffraction analysis. Most of the isolated compounds were evaluated for their cytotoxic activity and anti-HIV-1 activity using the syncytium inhibition assay and HIV-1 reverse transcriptase (RT) assay. The known compounds, 4,6,3',4'-tetrahydroxy-2-methoxybenzophenone and macluraxanthone, displayed significant cytotoxic activity with the ED50 in the range of 1.85-11.76 μM. 1,5-Dihydroxyxanthone exhibited the most potent anti-HIV activity against syncytium formation with EC50 < 17.13 μM (SI > 25.28) and 2-(3,3-dimethylallyl)-1,3,7-trihydroxyxanthone was the most active compound in the HIV-1 reverse transcriptase assay with IC50 value of 58.24 μM. Structure-activity relationship of some isolated compounds were also discussed. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/29304383/Anti_HIV_and_cytotoxic_biphenyls_benzophenones_and_xanthones_from_stems_leaves_and_twigs_of_Garcinia_speciosa_ DB - PRIME DP - Unbound Medicine ER -