Bioassay-guided isolation of prenylated xanthones and polycyclic acylphloroglucinols from the leaves of Garcinia nujiangensis.

Bioassay-guided fractionation of the acetone extract of the leaves of Garcinia nujiangensis resulted in the isolation of two new prenylated xanthones, nujiangexanthones A (1) and B (2), three new polycyclic polyprenylated acylphloroglucinols, nujiangefolins A-C (3-5), and 10 known related analogues. The structures of compounds 1-5 were elucidated by interpretation of their spectroscopic data. Compounds 3 and 4 are unusual polycyclic polyprenylated acylphloroglucinols in which the enol hydroxy group forms a six-membered ring with a benzene ring carbon. The compounds isolated were evaluated for their cytotoxic effects against 11 cancer cell lines and immortalized MIHA normal liver cells, and the test substances demonstrated selectivity toward the cancer cells. Isojacareubin (6) was found to be the most potent cytotoxic compound of those tested.

[1]  David J Newman,et al.  Natural products as sources of new drugs over the 30 years from 1981 to 2010. , 2012, Journal of natural products.

[2]  A. Kinghorn,et al.  Absolute configuration of (-)-gambogic acid, an antitumor agent. , 2011, Journal of natural products.

[3]  Yan Zhou,et al.  Apoptotic effects of polyprenylated benzoylphloroglucinol derivatives from the twigs of Garcinia multiflora. , 2010, Journal of natural products.

[4]  Hui-Chi Huang,et al.  Cytotoxic polyisoprenyl benzophenonoids from Garcinia subelliptica. , 2010, Journal of natural products.

[5]  Ge Lin,et al.  Cytotoxic acylphloroglucinol derivatives from the twigs of Garcinia cowa. , 2010, Journal of natural products.

[6]  D. Lantvit,et al.  Cytotoxic xanthone constituents of the stem bark of Garcinia mangostana (mangosteen). , 2009, Journal of natural products.

[7]  A. Carroll,et al.  Guttiferones O and P, prenylated benzophenone MAPKAPK-2 inhibitors from Garcinia solomonensis. , 2009, Journal of natural products.

[8]  J. Ngoupayo,et al.  Antimicrobial and immunomodulatory properties of prenylated xanthones from twigs of Garcinia staudtii. , 2009, Bioorganic & medicinal chemistry.

[9]  T. Hwang,et al.  Benzophenone derivatives from the fruits of Garcinia multiflora and their anti-inflammatory activity. , 2009, Journal of natural products.

[10]  Marcy J. Balunas,et al.  Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity. , 2008, Journal of natural products.

[11]  David J Newman,et al.  Natural products as leads to potential drugs: an old process or the new hope for drug discovery? , 2008, Journal of medicinal chemistry.

[12]  A. Kinghorn,et al.  Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen). , 2008, Phytochemistry.

[13]  D. Cunningham,et al.  Adjuvant therapy in colon cancer--what, when and how? , 2006, Annals of oncology : official journal of the European Society for Medical Oncology.

[14]  R. B. Grossman,et al.  Polycyclic polyprenylated acylphloroglucinols. , 2006, Chemical reviews.

[15]  F. Mahuteau‐Betzer,et al.  Oblongifolins A-D, polyprenylated benzoylphloroglucinol derivatives from Garcinia oblongifolia. , 2006, Journal of natural products.

[16]  A. Kinghorn,et al.  Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen). , 2006, Journal of agricultural and food chemistry.

[17]  Paul Cos,et al.  Antiparasitic activity of some xanthones and biflavonoids from the root bark of Garcinia livingstonei. , 2006, Journal of natural products.

[18]  V. Barone,et al.  Structural revision of clusianone and 7-epi-clusianone and anti-HIV activity of polyisoprenylated benzophenones , 2005 .

[19]  Y. Ohizumi,et al.  Prenylated xanthones from Garcinia xanthochymus. , 2003, Chemical & pharmaceutical bulletin.

[20]  Tetsuro Ito,et al.  Induction of apoptosis by xanthones from mangosteen in human leukemia cell lines. , 2003, Journal of natural products.

[21]  Michiho Ito,et al.  Benzoylphloroglucinol derivatives from Hypericum scabrum. , 2002, Journal of natural products.

[22]  Q L Wu,et al.  Xanthones from Hypericum japonicum and H. henryi. , 1998, Phytochemistry.

[23]  J. Krungkrai,et al.  Antimalarial xanthones from Garcinia cowa. , 1998, Planta medica.

[24]  F. Monache,et al.  Vismione H and prenylated xanthones from Vismia guineensis , 1986 .

[25]  D. Chang,et al.  Bioassay-guided isolation of xanthones and polycyclic prenylated acylphloroglucinols from Garcinia oblongifolia. , 2009, Journal of natural products.

[26]  C. Moretti,et al.  Antiplasmodial benzophenones from the trunk latex of Moronobea coccinea (Clusiaceae). , 2009, Phytochemistry.

[27]  Chun-Nan Lin,et al.  Phloroglucinols with prooxidant activity from Garcinia subelliptica. , 2008, Journal of natural products.

[28]  M. Boyd,et al.  Guttiferone F, the first prenylated benzophenone from Allanblackia stuhlmannii. , 1999, Journal of natural products.