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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.

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Authors+Show Affiliations

Pailee P
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Kuhakarn C
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Sangsuwan C
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Hongthong S
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Piyachaturawat P
Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Suksen K
Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Jariyawat S
Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Akkarawongsapat R
Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Limthongkul J
Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Napaswad C
Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Kongsaeree P
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Prabpai S
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Jaipetch T
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Pohmakotr M
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Tuchinda P
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Reutrakul V
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.

MeSH

AnimalsAnti-HIV AgentsAntineoplastic Agents, PhytogenicBenzophenonesBiphenyl CompoundsCell Line, TumorCell ProliferationCell SurvivalDose-Response Relationship, DrugDrug Screening Assays, AntitumorGarciniaHIV InfectionsHIV-1HumansMiceMolecular StructurePlant LeavesPlant StemsRatsStructure-Activity RelationshipXanthones

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 -