Two New Triterpene Saponins from Eryngium campestre (original) (raw)

Two Triterpene Saponins from Achyranthes bidentata

CHEMICAL & PHARMACEUTICAL BULLETIN, 2001

In the search for new saponins possessing the ability to potentiate in vitro the cisplatin cytotoxicity in human cancer colon cells, we have previously isolated three known oleanolic acid glycosides 1) and one new triterpene saponin, bidentatoside I, 2) from Achyranthes bidentata BLUME (Amaranthaceae). Furthermore, as part of our ongoing studies, we report here the isolation, structure elucidation and influence on the potentiation of cisplatin cytotoxicity in human colon cancer cells of one new further triterpene saponin, bidentatoside II (1) and chikusetsusaponin V methyl ester (2).

Triterpene saponins from Alternanthera repens

Phytochemistry, 1999

Four new triterpene saponins were isolated from the methanol extract of the aerial parts of Alternanthera repens. Their structures have been elucidated using a combination of 1D and 2D NMR techniques as 2a,3b-dihydroxyurs-12,20 -dien-28 oic acid 3-O-{O-b-D-glucopyranosyl-(1 4 2)-O-a-L-arabinopyranosyl-(1 4 2)-O-[b-D-xylopyranosyl-(1 4 3)]b-D-glucopyranoside}; 2a,3b-dihydroxyurs-12,20(30)-dien-28 oic acid 3-O-{O-b-D-quinovopyranosyl-(1 4 2)-O-a-L-arabinopyranosyl-(1 4 2)-O-[b-Dxylopyranosyl-(1 4 3)]b-D-glucopyranoside}; 2a,3b-dihydroxyurs-12,20(30)-dien-28 oic acid 3-O-{O-a-L-arabinopyranosyl-(1 4 2)-O-[b-D-xylopyranosyl-(1 4 3)]b-D-glucopyranoside}; 2a,3b-dihydroxyurs-12,20(30)-dien-28 oic acid 3-O-{O-b-D-xylopyranosyl-(1 4 3)-b-D-glucopyranoside}. #

Triterpene saponins from Billia rosea

Phytochemistry, 2017

Five previously undescribed triterpene saponins, billiosides A-E, and a known analogue, were isolated from the seeds of Billia rosea (Planch. & Linden) C. Ulloa & P. Jørg. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments ((1)H, (13)C, DEPT, COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC) and mass spectrometry as (3β,21β,22α)-3-[(2-O-β-D-glucopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21-[((2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl)oxy]-22-(acetyloxy)-24-hydroxyolean-12-en-28-oic acid, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranoside, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-xylopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-β-D-glucopyranoside, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-β-D-gluco...

Saponins and acylated saponins from Dizygotheca kerchoveana

Phytochemistry, 2004

Four new triterpenoid saponins were isolated from the leaves and stem of branches of Dizygotheca kerchoveana along with seven known ones. The new saponins were respectively characterized as 3-O-[b-D D-glucopyranosyl-(1 ! 3)]-[b-D D-glucopyranosyl-(1 ! 2)]a-L L-arabinopyranosyl echinocystic acid, 3-O-[b-D D-glucopyranosyl-(1 ! 3)]-[b-D D-glucopyranosyl-(1 ! 2)]-a-L L-arabinopyranosyl echinocystic acid 28-O-[a-L L-rhamnopyranosyl-(1 ! 4)-b-D D-glucopyranosyl-(1 ! 6)-b-D D-glucopyranosyl] ester, 3-O-[b-D D-3-O-transp-coumaroyl-glucopyranosyl-(1 ! 3)]-[b-D D-glucopyranosyl-(1 ! 2)]-a-L L-arabinopyranosyl echinocystic acid 28-O-[a-L L-rhamnopyranosyl-(1 ! 4)-b-D D-glucopyranosyl-(1 ! 6)-b-D D-glucopyranosyl] ester and 3-O-[b-D D-3-O-cis-p-coumaroyl-glucopyranosyl-(1 ! 3)]-[b-D D-glucopyranosyl-(1 ! 2)]-a-L L-arabinopyranosyl echinocystic acid 28-O-[a-L L-rhamnopyranosyl-(1 ! 4)-b-D D-glucopyranosyl-(1 ! 6)-b-D D-glucopyranosyl] ester. Their structures were elucidated by 1D and 2D NMR experiments, FAB-MS as well as chemical means.

A New Triterpene Glycoside from the Roots of Symphytum officinale

Journal of Natural Products, 1993

Amrucr.Ahemica1 investigation of the EtOH-soluble portion of SVmphVum o f i i d e roots has resulted in the isolation of a new pentacyclic triterpene glycoside of oleanolic acid. Its structure was elucidated by spectroscopic studies, including 2D nmr, and chemical evidences as 3-O-@-~-glucopyranosyl-(1~4)-&~-glucopyranosy1-(1~4)-a-~-arabinopyranosyl]~leanolic acid [I]. Sympbytum officinale L. (Boraginaceae), commonly known as "comfrey," is widely distributed in North Asia, England, and Europe, and is found abundantly in Turkey. The EtOH extract of the roots of the plant are used extensively in the indigenous medicine for the treatment of various ailments (1,2). No work has apparently been carried out on the saponin constituents of the roots of S. officitule. The present study describes the isolation and structure determination of a new pentacyclic triterpenoid saponin, 3-O-[fb~-glucopyranosyl-(1H4)-P-D-glucopyranosyl-(1~4)-a-~-arabinopyranosyl)oleanolic acid [l) from the roots of S. officinale. RESULTS AND DISCUSSION Compound 1 was purified by repeated cc on Si gel followed by hplc on a reversedphase column (RP-8) with MeOH-H,O (70:30) as the mobile phase: {a}'*D-I-22.86 (c= 0.14, MeOH). The ir spectrum showed carboxylic (1700 cm-') together with strong hydroxyl (3400 cm-') absorption bands. The uv spectrum showed only end absorption. The 13C nmr (Table 1) was assigned on the basis of BB, DEPT, 2D direct "/ mlz 749 .,-* mlz 455

Novel Triterpene Saponins from Zizyphus joazeiro

Helvetica Chimica Acta, 2000

Two dammarane-type saponins with a novel aglycone derived from the parent 16,22-epoxy-24methylidenedammarane and lotoside A, a new lotogenin derivative, were isolated from the MeOH extract of the stem bark of the Brazilian medicinal plant Zizyphus joazeiro, in addition to the known saponin 3b-{{O-[O-[a-l-arabinofuranosyl-(1 3 2)]-O-[b-d-glucopyranosyl-(1 3 3)]]-a-l-arabinopyranosyl}oxy}jujubogenin (1). The structures of the new compounds were determined as 16,22-epoxy-3b-[(b-d-glucopyranosyl)oxy]-24methylidenedammarane-15a,16a,20b-triol (2), 16,22-epoxy-3b-{{O-[O-[b-d-glucopyranosyl-(1 3 2)]-O-[b-dapiofuranosyl-(1 3 3)]]-b-d-glucopyranosyl-(1 3 2)-a-l-arabinopyranosyl}oxy}-24-methylidenedammarane-15a,16a,20b-triol (3), and 3b-{{O-[O-[b-d-glucopyranosyl-(1 3 2)]-O-[b-d-apiofuranosyl-(1 3 3)]]-b-d-glucopyranosyl-(1 3 2)-a-l-arabinopyranosyl}oxy}lotogenin (4) by means of 1D-and 2D-NMR spectroscopy, as well as FAB mass spectrometry. For the novel aglycone, we propose the name joazeirogenin and, for the new saponins, joazeiroside A (2) and B (3). Joazeirogenin was found to be 16,22-epoxy-24-methylidenedammarane-3b,15a,16a,20b-tetrol.

Triterpene Saponins from Cyclamen coum var. coum

Planta Medica, 1997

From the tubers of Cyclamen coum (Primulaceae) three new saponins, cydaminorin (1), cyclacoumin (3) and mirabilin lactone (4) were isolated together with a known saponin, deglucocyclamin (2). The structures of the new compounds were established as 1 3/J,28-epoxy-3j1-{{[fi-o-glucopyranosyl-(1-'2)]-[Jl-t-glucopyranosyl-(1-4)]-a-i-arabinopyranosyl}oxy} 1 6a-hydroxy-olean-30-aI (1). 1 3p,28-epoxy-311-{{[jJ-o-xylopyranosyl-(1-*2)-D-glucopyranosyI-(1-4)]-[-D-gIucopyranosyI-(1-2)]a-L-arabinopyranosyl}oxy)-1 6a,23-dihydroxy-olean-30-aI (3) and 1 6a-hydroxy-3/l-{ ({[fl-D-xylopyranosyl-(1-2)]-[/J-o-gIucopyranosyl-1-6)]-/1D-glucopyranosyJ-(1-4)}-[JJ-D-gIucopyranosyI-(1-2)1-a-i-arabinopyranosyI}-oxy}oIean-1 2-eno-30,28-lactone (4). Structure elucidations were accomplished using both spectral (NMR, MS, IR) and chemical methods.