Triterpene saponins from Lysimachia christinae

Seven triterpene saponins were isolated from Lysimachia christinae and identified as lysichriside A (1), lysichriside B (2), primulanin (3), lysikokianoside 1 (4), anagallisin C (5), ardisiacrispin A (6), and ardisicrenoside B (7). Compounds 1 and 2 are new triterpene saponins, compounds 3, 5, and 7 were isolated from this genus, and compounds 4 and 6 were isolated from this species for the first time. Their structures were elucidated by means of 1D and 2D NMR experiments.     

中国产山茶种子中总皂苷的分离与鉴定

目的 研究中国产山茶（Camellia sinensis）种子中皂苷类化学成分。方法 采用反复制备HPLC法分离纯化,通过理化常数测定和光谱分析鉴定其化学结构。结果 从中国产山茶种子中分离得到了7个茶皂苷类化合物,即茶叶皂苷I foliatheasaponinⅠ(1),阿萨姆皂苷A assamsaponin A （2）,阿萨姆皂苷B assamsaponin B（3）,阿萨姆皂苷C assamsaponin C（4）,阿萨姆皂苷D assamsaponin D（5）,阿萨姆皂苷F assamsaponin F（6）,阿萨姆皂苷I assamsaponin I（7）。结论 化合物1为首次从茶种子中分离得到。对中国产山茶种子化学成分的研究尚属首次。     

Antimalarial compounds from the root bark of Garcinia polyantha Olv

Eight compounds were isolated from the roots of Garcinia polyantha, and identified. Two of them, the xanthone garciniaxanthone I (1), and the triterpene, named garcinane (2), are reported as new natural products. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR spectroscopic studies. The structure of compound 1 was confirmed by X-ray crystallography. Among the remaining six known compounds, three were known xanthones [smeathxanthone A (3), smeathxanthone B (4), and chefouxanthone (5)], one benzophenone [isoxanthochymol (6)], one triterpene [magnificol], and one sterol [beta-sitosterol]. The in vitro antimalarial activity of isoxanthochymol (6) against Plasmodium falciparum shows strong chemosuppression of parasitic growth.     

人参叶中三萜皂苷类成分的研究

目的 研究人参叶中的微量皂苷类化合物.方法 利用正相硅胶柱层析和反相硅胶制备色谱技术,分离人参叶中的微量成分,并运用质谱和核磁共振技术鉴定其结构.结果 从人参叶中分离得到5个微量成分,分别鉴定为:人参皂苷Rk1(Ⅰ)、Rk3(Ⅱ)、Rh4(Ⅲ)、RgS(Ⅳ)和Rg6(Ⅴ).结论 化合物Ⅰ～Ⅳ为首次从人参叶中分离得到.     

桔梗中远志酸型皂苷的化学研究

目的分离、鉴定桔梗［Platycodon grandiflorum (Jacq.)A.DC］根中的远志酸型皂苷类化学成分。方法 采用乙醇提取、乙酸乙酯萃取，大孔树脂柱色谱、硅胶柱色谱及高效液相色谱等方法进行分离，得到3个化学成分，运用IR，MS，¹H NMR和¹³C NMR等光谱法鉴定化合物的结构。结果分离鉴定了3种三萜皂苷：3-O-β-D-laminaribiosyl polygalacic acid (I)，3-O-β-D-glucopyranosyl polygalacic acid (II)及polygalacin D (III)。结论化合物I是新化合物，II，III为已知化合物。化合物II为首次从该植物中分得，化合物I和II也是首次从桔梗中分离得到的单糖链糖苷。     

Triterpenes and triterpenoid saponins from the leaves of Ilex kudincha

One new triterpene, kudinchalactone A (1), and four new triterpenoid saponins, ilekudinchosides A-D (2- 5), were isolated from the leaves of Ilex kudincha C.?J. Tseng along with eight known triterpenoids. These new compounds were elucidated by spectroscopic methods including 1D and 2D NMR, HR-TOF-MS, and CD spectra. Compounds 2, 3, 12, and 13 showed antibacterial activities against Staphylococcus aureus (SA) and methicillin-resistant Staphylococcus aureus (MRSA).     

Five new triterpene glycosides from Lysimachia foenum-graecum and evaluation of their effect on the arachidonic acid metabolizing enzyme

Five new oleanane-type triterpene saponins, named foenumosides A ( 1), B ( 2), C ( 3), D ( 4) and E ( 5), were isolated from the aerial parts of Lysimachia foenum-graecum Hance. Their structures were identified on the basis of 1D and 2D NMR techniques, including H-H COSY, HMQC, HMBC, HMQC-TOCSY, ROESY experiments as well as chemical methods. We have evaluated the cytotoxity of 1 - 5 against rat and human polymorphonuclear leukocytes and the effect of 5 on the arachidonic acid metabolizing enzyme. All compounds showed a high degree of toxicity except for compound 5, while 5 notably reduced the production of leukotriene B (4) (LTB (4)) from rat peritoneal leukocytes with an IC (50) value of 74 microM without inhibiting human elastase. Compound 5 also reduced the production of 12-HHTrE and 12-HETE by 14 % and 50 % as a measurement for cyclooxygenase-1 and 12-lipoxygenase inhibition at 100 microM.     

Two unusual oleanane saponins from Anemone anhuiensis

From the rhizomes of Anemone anhuiensis (Ranunculaceae), two new triterpene saponins, anhuienosides A (1) and B (2), were isolated. These compounds are glycosylated at C-23 and their structures were elucidated as hederagenin 23-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside (1) and 23-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester (2) on the basis of chemical and spectral evidence.     

A new triterpene glycoside from Asterias rollentoni

A new triterpene glycoside, rollentoside A, has been isolated from Asterias rollentoni Bell and identified as 3beta-O-{3-O-methyl-beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-quinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl}-16-beta-acetoxy-23S-acetoxy-holost-7-ene (1), together with a new natural product, rollentoside B (2). The structures of compounds1 and 2 were elucidated by extensive 1D and 2D NMR investigation (1H-1H COSY, TOCSY, HSQC, HMBC, NOESY).     

Anticomplement activities of oleanolic acid monodesmosides and bisdesmosides isolated fromTiarella polyphylla

Seven known oleanolic acid glycosides (1-7) were isolated from the MeOH extract of Tiarella polyphylla. The structures were identified to be 3-O-(beta-D-glucopyranosyl) oleanolic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl] oleanolic acid (3), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester (4), 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester (5), 3-O-[a-L-rhamnopyranosyl-(1-->3)-beta-D-glucuronopyranosyl] oleanolic acid (6), and 3-O-[alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucuronopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester (7) on the basis of physicochemical and spectral data. These triterpene glycosides were tested for the anticomplement activity and hemolytic activity. Bisdesmosidic saponins, 4, 5, and 7, showed anticomplement activity; in contrast, monodesmosidic saponins, 1-3, and 6, showed direct hemolytic activity. Methyl esterified monodesmosidic saponins showed anticomplement activity at a low concentration and hemolytic activity at a high concentration.     

Bioactive constituents of oleanane-type triterpene saponins from the roots of Glycyrrhiza glabra

Three new oleanane-type triterpene saponins, namely licorice-saponin M3 (1), licorice-saponin N4 (2), and licorice-saponin O4 (3), an artificial product (4), as well as five known triterpene glucuronides (5–9), were isolated from the roots of Glycyrrhiza glabra L. Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry, and by comparison with spectroscopic data reported in the literature. The inhibitory effects of the selected compounds on neuraminidase were evaluated, and the preliminary structure–activity relationship was also predicted.     

Metabolite profiling of the leaves of the Brazilian folk medicine Sideroxylon obtusifolium

Sideroxylon obtusifolium (Roem. & Schult.) T. D. Penn. (family Sapotaceae) is a tree native to Central and South America. Infusions of the bark and the leaves are used in Brazilian folk medicine as an anti-inflammatory remedy. However, information on the constituents of S. obtusifolium remains scarce, and only common pentacyclic triterpenoids have been previously reported. HPLC-DAD/MS analyses revealed that saponins and flavonoids were the main constituents of the leaves. From the butanol-soluble fraction of an ethanolic extract, a total of four saponins and ten flavonol glycosides were isolated by a combination of chromatographic methods including Sephadex LH-20, MPLC, and HPLC. Their structures were established by acid hydrolysis and spectroscopic methods, mainly MS (n), 1D and 2D NMR experiments. The compounds include the new triterpene glycoside 3-O-( β-D-glucopyranosyl)-protobassic acid 28-O- β-D-apiofuranosyl-(1 → 3)-O-[O- β-D-apiofuranosyl-(1 → 3)- β-D-xylopyranosyl-(1 → 4)]-O- α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester ( 1), as well as the new flavonol glycosides, quercetin-3-O-(O- α-L-rhamnopyranosyl-(1→ 2)-O-[ β-D-glucopyranosyl-(1 → 3)]- β-D-galactopyranoside) ( 6) and kaempferol-3-O-(O- α-L-rhamnopyranosyl-(1 → 2)-O-[ β-D-glucopyranosyl-(1 → 3)]- β-D-galactopyranoside) ( 8). In addition, catechin and a glycerogalactolipid, gingerglycolipid A, were obtained from the ethyl acetate-soluble fraction. The isolated compounds could be used in the future as chemical markers for quality control of this herbal drug.     

Structure-activity relationships for saponins from Allium hirtifolium and Allium elburzense and their antispasmodic activity

A phytochemical study of Allium hirtifolium Boiss flowers has led to the isolation of high amounts of six new furostanol and spirostanol saponins, named hirtifoliosides A1/A2 (1a/ 1b), B (2), C1/C2 ( 3a/ 3b), and D(4) along with three known spirostanol saponins, alliogenin 3- O-beta-D-glucopyranoside, gitogenin 3- O-beta-D-glucopyranosyl-(1-->4)- O-beta-D-glucopyranoside, and agapanthagenin 3- O-beta-D-glucopyranoside. High concentrations of the following known flavonol glycosides have been isolated from both flowers and bulbs: kaempferol 3- O-beta-D-rhamnopyranosyl-(1-->2)-glucopyranoside, kaempferol 3- O-beta-D-glucopyranosyl-(1-->4)-glucopyranoside, kaempferol 3-O-glucopyranoside, kaempferol 7-O-glucopyranoside. The isolated saponins along with the four saponins elburzensosides A1/A2 and C1/C2 and the sapogenin agapanthagenin, previously described from A. elburzense, have been subjected to biological assays for evaluating possible antispasmodic activity in the guinea-pig isolated ileum. The obtained results served as a basis for the establishment of structure-activity relationships within this class of antispasmodic agents. They highlight the positive effects of a hydroxyl group at position 5 and of a glucose unit at position 26 and demonstrate the detrimental effects of both a hydroxyl group at position 6 and of a glucose unit at position 3. Among the tested compounds, elburzensosides C1/C2 and agapanthagenin showed the highest activity in reducing induced contractions as measured by the reduction of histamine release by about 50 %. The observed effect therefore contributes to the explanation of the traditional use of onion and garlic in the treatment of disturbances of the gastrointestinal tract.     

Saponins from the roots ofPulsatilla koreana

From the roots ofPulsatilla koreana, three monodesmosides(pulsatilla saponins A, B and D) and two bisdesmosides(pulsatilla saponins F and H) were isolated. The structure of these saponins have been determined as hederagenin 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranoside(A), hederagenin 3-O-β-D-glucopyranosyl(1→4)-α-L-arabinopyranoside(B), hederagenin 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-glucopyranosyl(1→4)]-α-L-arabinopyranoside(D), 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester (F) and 3-O-α-L-rhamnopyranosyl(1→2)-[β-D-glucopyranosyl(1→4)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester(H) on the basis of chemical and spectral studies. Pulsatilla saponin B is the first report of its presence in plants but saponins A, D, F, and H have recently been isolated from the same genusP. cernua.     

Cycloartane triterpenoids from Cassia occidentalis

A phytochemical investigation of the whole plants of Cassia occidentalis led to the isolation of two new cycloartane triterpenoids, cycloccidentalic acids A and B (1 and 2), and five new related saponins, cycloccidentalisides I-V (3-7), together with sixteen known compounds. The structures of the isolated compounds were elucidated through detailed spectroscopic analyses, including 1D and 2D NMR techniques, and chemical methods. Compounds 2 and 5 showed modest anti-HIV-1 activities with EC?? values of 2.23 μM and 4.36 μM, respectively, in comparison to the positive control.     

Two new triterpenoid saponins from the leaves of Ilex kudingcha

Two new triterpene saponins, ilekudinchosides F (1) and G (2), along with three known saponins were isolated from the leaves of Ilex kudingcha C. J. Tseng. The new compounds were characterized as 3β,19α-dihydroxy-12α-ethoxy-urs-13(18)-ene-28,20β-lactone-3-O-[β-D-glucopyranosyl(1 → 3)]-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (1) and 3β,19α-dihydroxy-12α-methoxy-urs-13(18)-ene-28,20β-lactone-3-O-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (2). The new structures were elucidated by spectroscopic methods including 1D and 2D NMR, HR-TOF-MS, and CD spectrometry, and the known compounds were identified by the comparison of their NMR and HR-TOF-MS data with those reported in the literature.     

Four new triterpenoid saponins from Ardisia gigantifolia Stapf. and their cytotoxic activity

Four new oleanane-type triterpenoid saponins, cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (1), cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-glucopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (2), cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-6-O-acetylglucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (3) and 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside]-16,28-dihydroxy-30-acetoxyoleana-12-en (4), along with one known triterpene saponin and ardisiacrispin A (5) were isolated from the rhizome of Ardisia gigantifolia. Their structures were established with the help of extensive spectroscopic techniques. Furthermore, the inhibitory effects of compounds on tumor cells (MTT based) in vitro were evaluated, and compounds 1, 2, and 5 showed potent anti-tumor activities.     

Isolation of a new saponin and cytotoxic effect of saponins from the root of Platycodon grandiflorum on human tumor cell lines

A novel triterpenoid saponin, deapioplatycoside E (1) was isolated from the root extract of Platycodon grandiflorum, together with the seven known saponins 2 - 8, i. e., platycoside E (2), deapioplatycodin D3 (3), platycodin D3 (4), polygalacin D2 (5), platycodin D2 (6), deapioplatycodin D (7) and platycodin D (8). The structure of the new saponin 1 was determined on the basis of spectral analysis and chemical evidence. The crude saponin fraction (ED50: ca. 10 - 15 microg/mL) and compounds 6 - 8 (ED50: ca. 4 - 18 microg/mL) exhibited significant inhibition on the proliferation of five kinds of cultured human tumor cell lines, i. e., A549 (non-small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT-15 (colon), in vitro.     

Antimicrobially active hederagenin glycosides from Cephalaria elmaliensis

A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their structures were identified by extensive spectroscopic techniques (1D and 2D NMR, HR ESIMS) and chemical evidence. The antimicrobial activity of the extracts and the pure compounds was evaluated by the MIC method. According to the results, all pure compounds including the new ones were found to be very active against both gram-positive and gram-negative bacteria.     

Antioxidant and urease inhibitory C-glycosylflavonoids from Celtis africana

Two new C-glycosylflavonoids celtisides A (1) and B (2) have been isolated from n-butanol-soluble fraction of Celtis africana, along with five known C-glycosylflavonoids vitexin (3), orientin (4), isoswertiajaponin (5), isoswertisin (6), and 2″-O-rhamnosyl vitexin (7) reported for the first time from this species. Their structures were assigned from 1D and 2D NMR spectra. These compounds were investigated for biological activities and showed significant antioxidant and urease inhibitory activities.