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Alisma plantago-aquatica is a hairless plant that grows in shallow water, consists of a fibrous root, several basal long stemmed leaves 15–30 cm long, and a triangular stem up to 1 m tall. It has branched inflorescence bearing numerous small flowers, 1 cm across, with three round or slightly jagged, white or pale purple petals. The flowers open in the afternoon. There are 3 blunt green sepals, and 6 stamens per flower. The carpels often exist as a flat single whorl. It flowers from June until August.
Plants from Alisma species belong to the genus of Alisma Linn. in Alismataceae family. The tubers of A. orientale (Sam.) Juzep, also known as Ze Xie in Chinese and Takusha in Japanese, have been used in traditional medicine for a long history. Triterpenoids are the main secondary metabolites isolated from Alisma species, and reported with various bioactive properties, including anticancer, lipid-regulating, anti-inflammatory, antibacterial, antiviral and diuretic activities. In this brief review, we aimed to summarize the phytochemical and pharmacological characteristics of triterpenoids found in Alisma, and discuss their structure modification to enhance cytotoxicity as well. Starting from 1968, triterpenoids have been isolated from Alisma genus successively (Murata et al., 1968). All these compounds contain protostane tetracyclic skeleton with the structural characteristics of trans-fusions for A/B, B/C and C/D rings, α-methyl submitted at C-8, β-methyl at C-10, β-methyl at C-14 and side chain at C-17. At present there are 101 protostane triterpenoids, 12 nor-protostanes, and 5 seco-protostanes reported from Alisma. According to the changes of side chains submitted at C-17, protostane triterpenoids from Alisma are divided into four classes, including open aliphatic chains, epoxy aliphatic chains, spiro hydrocarbon at C-17, and epoxy at C-16, C-23 or C-16, C-24. The individual triterpenoids were detailed in Table 1.
Eight protostanes with spiro hydrocarbon at C-17 (82–89) have been isolated from the genus of Alisma as shown in Figure 3. Oxaspiro-nonane moiety is generated between D ring and its side chain with C-17 as spiro hydrocarbon. Methyl group substituted at C-20 with α- (82) (Xin et al., 2016) or β- (85) (Jin et al., 2019) conformation. Alisol U (83) differs from alisol V (84) by forming an epoxy at C-24 and C-25.Twelve nor-protostanes (102–113) have been found in Alisma, including two demethyl-protostanes (102, 103) and ten tetranorprotostanes (104–113). Among C-2 may be submitted by carbanyl group (109) (Mai et al., 2015). The configuration of C-17 is determined (107, 108) (Xin et al., 2018). (Source: www.ncbi.nlm.nih.gov)