Planta Med 2011; 77 - PG58
DOI: 10.1055/s-0031-1282542

New sesquiterpene derivatives and anti-inflammatory constituents from Pachira aquatica

J Chen 1, L Cheng 2, C Liao 3, M Chung 2
  • 1Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan
  • 2Faculty of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
  • 3Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan

Pachira aquatica Aublet (Bombacaceae) is an evergreen tree, distributed in tropical America and introduced to Guangdong, Yunnan, and Taiwan as a cultivated plant [1]. Cadinane sesquiterpenoids, sesquiterpene lactones, and triterpenes are widely distributed in plants of the family Bombacaceae, and many of these compounds exhibit antiangiogenic, hypotensive, and antimicrobial activities. Investigation of n-hexane-soluble fraction of the stem of P. aquatica has led to the isolation of two new sesquiterpene derivatives, 11-hydroxy-2-O-methylhibiscolactone A (1) and O-methylhibiscone D (2), together with 18 known compounds, including 5-hydroxyauranetin (3), kaempferol-3,7,4'-trimethyl ether (4), santi-7-methyl ether (5), 3,5,6,7,8,3',4'-heptamethoxyflavone (6), calycopterin (7), retusin (8), 5,4'-dihydroxy-3,7-dimethoxyflavone (9), isohemigossylic acid lactone-7-methyl ether (10), hibiscolactone A (11), hibiscone C (12), hibiscone D (13), 2-O-methylisohemigossypolone (14), scopoletin (15), benzophenone (16), 2α,3β-dihydroxylupene (17), lupenone (18), 24-methylenecycloartenol (19), and (23E)-cycloart-23-ene-3β,25-diol (20). The structures of new compounds 1 and 2 were determined through spectroscopic and MS analyses. Among the isolates, 5-hydroxyauranetin (3) and isohemigossylic acid lactone-7-methyl ether (10) exhibited potent inhibition against N-formyl-L-methionyl-L-leucyl-L-phenylalanine-induced superoxide production with IC50 values of 28.84±2.26 and 12.77±2.48µM, respectively.

Figure 1: Structure of new compounds 1 and 2

Acknowledgement: This research was supported by grants from the National Science Council of the Republic of China (NSC 95–2320-B-127–001-MY3 and NSC 98–2320-B-127–001-MY3), awarded to Prof. J.-J. Chen.

References: 1. Tang Y et al. (1995) 'Bombacaceae' in 'Flora of China', Science Press, Beijing, China. Vol. 12, pp. 264–299