Planta Med 2008; 74 - PB116
DOI: 10.1055/s-0028-1084461

Three new tyramine and two new phenolic constituents from Limonia acidissima

KH Kim 1, MC Yang 1, KH Lee 1, IK Lee 1, SK Ha 2, P Choi 3, W Bae 3, SY Kim 2, KR Lee 1
  • 1Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University, Suwon 440–746, Korea
  • 2Graduate School of East-West Medical Science, Kyung Hee University, Yongin 449–701, Korea
  • 3R and D institute, Miwon Commercial, Co., LTD. 405–3, Mongnae-dong, Ansan-shi, Gyeonggi, Korea

The wood apple (Limonia acidissima L., Rutaceae) is a tropical fruit distributed in dry warm regions of Burma, India, Malaya, and Sri Lanka [1], and used for its medicinal properties. 'Thanaka,' a root paste made from the pulp of L. acidissima, is a facial cosmetic and also used to remove small spots and lesions that appear on the skin [2]. The extracts contain several coumarins, triterpenoids, benzoquinones, and tyramine derivatives [3–4]. In continuing our search for potential lead compounds for drug development from medicinal plant sources, we performed a phytochemical investigation of this herb. Dried barks of L. acidissima (3kg) were extracted with 85% EtOH at 85oC temperature. The EtOH extract (250g) was dissolved in water and partitioned with EtOAc to give an EtOAc extract (50g). Purification of the EtOAc soluble fraction by repeated column chromatography led to the isolation of three new tyramine derivatives, acidissimina A (1), acidissimina B (2), and acidissimina B epoxide (3), and two new phenolic compounds, oxiranyl-(3,5-dimethoxy-4-hydroxy-phenyl)-methanol (4) and oxiranyl-(3,4,5-trimethoxy-phenyl)-methanol (5). The identification and structural elucidation of these compounds were based on 1D- and 2D-NMR spectral data. The absolute configurations of 4 and 5 were determined by a convenient Mosher ester procedure carried out in an NMR tube.

References: 1. Allen, B. M. (1967) Malayan Fruits. Donald Moore Press Ltd. Singapore.

2. Chopra, R. N. et al. (1956) Glossary of Indian Medicinal Plants. CSIR. New Delhi.

3. Ghosh, P. et al. (1982) Phytochemistry 240.

4. Ghosh, P. et al. (1991)J. Nat. Prod. 54:1389.