A new triterpenoid saponin and other saponins from Salicornia europaea

Abstract

ester (5), was isolated from Salicornia europaea Linn. Their structures were elucidated on the basis of spectral analysis.Salicornia europaea Linn., marshfire glasswort, is a halophytic plant belonging to the family Chenopodiaceae growing on the sea coasts of temperate and subtropic zones, which has been used in Chinese folk medicine for the treatment of hypertension, cephalalgia, and scurvy [1]. Previous researches of chemical constituents of this plant resulted in the isolation of nine flavonoid compounds and four chromone compounds [2][3][4][5]. In the current research, a new triterpenoid saponin, namely 3E,29-dihydroxy-olean-12-en-28-oic acid 28-O-E-D-glucopyranosyl ester, was isolated from Salicornia europaea Linn., together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-E-D-glucopyranoside (2), 3-O-(methyl-E-D-glucuronopyranosiduronoate)-28-O-E-D-glucopyranosyl oleanolate (chikusetsusaponin IVa methyl ester) (3), 3-O-E-D-glucuronopyranosyl oleanolic acid (calenduloside E) (4), and oleanolic acid 3-O-6c-O-methyl-E-D-glucuronopyranoside (calenduloside E 6c-methyl ester) (5). Their structures were established by spectral analysis. Compound 1 was isolated as a white amorphous powder, [D] 25 D +31.3q (c 0.11, MeOH). Its molecular formula was identified as C 36 H 58 O 9 by HR-ESI-MS at m/z 657.3991 [M + Na] + (calcd 657.3979), indicating the presence of eight degrees of unsaturation. Its 1 H NMR spectrum showed the presence of six tertiary methyl groups (G 0.91, 1.01, 1.08, 1.13, 1.20, and 1.25), a trisubstitued olefinic proton (5.48, t-like), and an anomeric proton signal (6.33, d, J = 8.1 Hz). 1: R = CH 2 OH 2: R = CH 3 3: R 1 = CH 3 , R 2 = Glc 4: R 1 = R 2 = H 5: R 1 = CH 3 , R 2 = H O CH 2 OH OH OH H R HO O O HO

Preparative mass‐spectrometry profiling of minor concentrated metabolites in Salicornia gaudichaudiana Moq by high‐speed countercurrent chromatography and off‐line electrospray mass‐spectrometry injection

“…These compounds are frequent in Chenopodiaceae and occurring aglycones are triterpenes such as oleanolic acid, akebonic acid, hederagenin, gypsogenin, phytolaccagenic acid and serjanic acid substituted at C‐3 and/or C‐28 with one or two sugar chains . Linked sugars with acetal and alkyl residues are also reported.…”

“…In Salicornia , oleanolic acid‐ O ‐glycosides were isolated from S. europaea, S. herbaceae , and S. bigelovii . Nor ‐derivatives of oleanolic acid, hederagenin, and gypsogenin were found in S. herbaceae and S. bigelovii .…”

Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>

“…The leaves of D. maritima extracted with MeOH and the MeOH extracts were separated by solvent partition according to the polarity of the constituents. The relatively polar 1-BuOH-soluble fraction was separated by various kinds of chromatography to afford four new triterpene saponins (1)(2)(3)(4) and two new megastigmanes (5,6), together with two known flavonol glycosides (7,8). The structures of new triterpene derivatives were elucidated using one-and two-dimensional spectroscopies.…”

“…It is known that the fruits contain a toxic naphthoquinone derivative, plumbagin, and their constituents have been extensively investigated by Higa et al [2][3][4] Recently, from the leaves and branches of a related Thai medicinal plant, D. mollis, the isolation of naphthoquinone glycosides was reported. 5) In our continuing work on Okinawan resource plants, the constituents of the leaves of D. maritima were investigated to give eight ent-kaurane-type diterpenoid glycosides, called diosmariosides A-H. 6) Further extensive work resulted in the isolation of four new triterpene saponins, named ebenamariosides A-D (1-4) and two megastigmanes (5,6), along with two known flavonol glycosides, kaempferol 3-O-β-D-(2″,6″-di-O-α-L-rhamonopyranosyl) glucopyranoside (7) 7) and 3-O-β-D-(2″,6″-di-α-L-rhamonopyranosyl) galactopyranoside (8) 8) (Fig. 1).…”

Phytochemical composition of some common coastal halophytes of the United Arab Emirates

“…No studies have been performed on the phytochemical composition of S. sinus-persica to date, but S. europaea was found to contain alkaloids, saponins, flavonoids and other phenolic compounds (Lellau and Liebezeit, 2001). Four triterpenoid saponins extracted from S. europaea have been identified in a new study (Yin et al, 2012). These include oleanolic acid glucoside, chikusetsusaponin methyl ester, calenduloside E and calenduloside E 6'-methyl ester, in addition to a newly discovered dihydroxyoleanenoic acid glucopyranosyl ester.…”