A New Benzoylphloroglucinol Derivative with an Adamantyl Skeleton and Other Constituents from Garcinia multiflora : Effects on Neutrophil Pro- Inflammatory Responses by Chia-Wei Ting a ), Tsong-Long Hwang b ), Ih-Sheng Chen a ), Ming-Hong Yen* a ), and Jih-Jung Chen* c ) a )Faculty of Pharmacy, KaohsiungMedical University, Kaohsiung 807, Taiwan b )Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan c )Graduate Institute of Pharmaceutical Technology & Department of Pharmacy, Tajen University, Pingtung 907, Taiwan (phone: þ 886-8-7624002 (ext. 2827); fax: þ 886-8-7624002 (ext. 5121); e-mail: jjchen@mail.tajen.edu.tw) A novel benzoylphloroglucinol derivative, garcimultiflorone D (1), with an unusual adamantyl- caged skeleton was isolated from the fruits of Garcinia multiflora, together with four known compounds. The structure of 1 was determined through extensive 1D/2D-NMR and mass-spectrometric analyses. Garcimultiflorone D (1) exhibited inhibitory activities with IC 50 values of 7.21  1.07 and 6.01  0.37 mg/ ml against fMLP/CB-induced superoxide anion generation and elastase release, respectively. Introduction. – Garcinia multiflora Champ. is a small evergreen tree, distributed in South China, Hong Kong, and Taiwan [1]. The genus Garcinia (Guttiferae) comprises ca. 400 species with pantropical distribution. In Taiwan, the genus Garcinia is represented by three species, G. linii, G. multiflora, and G. subelliptica. Plants of this genus contain a variety of secondary metabolites including xanthones [2–6], benzophenones [7][8], phloroglucinols [7][9][10], terpenoids [9][10], biflavonoids [11], and their derivatives. Many of these compounds exhibit antioxidant [2] [3] [8], trypanocidal [4], cytotoxic [5][7][8], antitubercular [6], anti-inflammatory [9][10], and anti-HIV [11] activities. As part of our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro inhibitory activity on neutrophil pro- inflammatory responses. In the course of this screening, an AcOEt-soluble fraction of the fruit of G. multiflora exhibited inhibitory activities with IC 50 values of 7.21  1.07 and 6.01  0.37 mg/ml, against fMLP/CB-induced superoxide anion generation and elastase release, respectively. Investigation of the active fraction afforded a novel benzoylphloroglucinol derivative, garcimultiflorone D (1) , with an unusual adamantyl- caged skeleton and four known compounds. Here, we describe the structure elucidation of 1 and the inhibitory activities of the isolates on superoxide generation and elastase release by neutrophils. Results and Discussion. – Structure Elucidation. Chromatographic purification of the AcOEt-soluble fraction of the MeOH extract of fruits of G. multiflora by silica-gel column chromatography and preparative TLC afforded a new, 1, and four known CHEMISTRY & BIODIVERSITY – Vol. 9 (2012) 99  2012 Verlag Helvetica Chimica Acta AG, Zürich