Anti-human Immunodeficiency Virus-1 Constituents of the Bark of Poncirus trifoliata

Abstract

Poncirus trifoliata (L.) RAF., a 1-5 m tree in the family Rutaceae, is widely distributed in P. R. China.1) Its dried immature fruit has been traditionally used for uterine contraction and relaxation, and treating gastrointestinal and cardiovascular diseases.2) The crude extract also has reported for anti-inflammatory, anti-bacterial and anti-mucin releasing activities. [3][4][5] Previous study on the roots and fruits of this plant reported lots of coumarins, [6][7][8][9][10][11][12] flavonoids, 2) and nortriterpenoids. 13,14) However, the chemical constituent of the stem bark of this plant was seldom reported. As part of searching for novel and bioactive compounds, now we report the result of a phytochemical investigation on the stem bark of P. trifoliata. Results and DiscussionsThe chemical investigation on a MeOH extact of the stem bark of P. trfoliata led to the isolation of 36 compounds (1-36) including flavonoids, coumarins, triterpenoids, steroids, and lignans. Compounds 1-3 are new prenylated flavonoids which were elucidated as (Ϫ)-5, 4Ј-dihydroxy-7,8-[(3Љ,4Љ- limonin ( 4, 102.8, 104.7, 121.2, 155.8, 158.7, 160.3, 161.2, 163.8, 181.9) (Table 1). Of them, five carbon signals at d C 21.3 (q), 26.4 (q), 60.5 (d), 71.1 (d), and 79.4 (s) constructed a prenyl group on the basis of heteronuclear multiple bond correlation (HMBC) correlations (Fig. 1). Subsequently, a 2Љ,2Љ-dimethyldihydropyran moiety with hydroxy substitutes at C-3Љ and C-4Љ was established according to the 2D-NMR data and MS analysis (Fig. 1). In the 1 H-NMR spectrum (Table 1)

Characteristics and chemical compositions of propolis from Ethiopia

“…Therefore, the major source of triterpenoids is terrestrial vegetation (Hernández-Vázquez et al 2010; Manguro et al 2009; Moreau et al 2009; Ramadan et al 2009). They are found in plant leaves (Ramadan et al 2009; van Maarseveen & Jetter 2009; Silva et al 2009), bark (Hernández-Vázquez et al 2010; Rosas-Acevedo et al 2011; Feng et al 2010; Vouffo et al 2010), resins (Hernández-Vázquez et al 2010; Manguro et al 2009; Wang et al 2011), and oils (Moreau et al 2009; Akihisa et al 2010; Bakowska-Barczak et al 2009; Wesolowska et al 2011). Their concentrations vary and depend on the plant species.…”

The Chemistry and Pharmacology of Citrus Limonoids

“…Limonin has also recently been found in Citrus genus plant bark [25,116,117], and root [118], tissues. In addition to the above reported plants, 1 has been isolated from numerous non-Citrus species such as the endemic Brazilian species Raulinoa echinata [119], Glycosmis parva (a wild small shrub distributed in Thailand) [120], Poncirus trifoliata (a tree that is widely distributed in China) [121], and Dictamnus angustifolius [27,122,123]. From a biosynthetic point of view ( Figure 3), 1 has nomilin (2) as its most accredited parent compound in an enzymatic route possibly passing through obacunone (3), obacunoic acid (29), and ichangin (8).…”

A systematic review on biological activities of prenylated flavonoids

“…0 -Dihydroxy-7,8-[(3 00 -hydroxy-4 00 -one)-2 00 ,2 00 -dimethylpyrano]-flavone from Poncirus trifoliata L. (Rutaceae) showed significant anti-HIV-1 activity with high therapeutic index (TI) of 143.65 (Feng et al, 2010). On the other hand, lonchocarpol A with two prenyl groups on both C-5 and C-6 showed a notable antimalarial activity (IC 50 ¼ 1.6 mg/ml), but two other prenylflavonoids with a cycle on ring A showed no antimalarial activity (Khaomek et al, 2008).…”