A new triterpenoid, madhunolic acid, from the seeds of Madhuca latifolia

A new triterpenoid, madhunolic acid, along with the three known constituents stigmasterol, 4-hydroxymethyl benzoate, and hydroquinone were isolated from the fruit seeds of Madhuca latifolia. The structure of the new compound was elucidated as 2beta,3beta,23-trihydroxyurs-5,12,20-trien-28-oic acid (1) on the basis of spectral data and chemical evidence.     

A new triterpenoid from Entodon okamurae Broth

One new triterpenoid, entokamurol (1), was isolated from Entodon okamurae Broth, together with other nine compounds, namely dryocrassol (2), chrysophamol (3), physcion (4), 10-nonacosamnol (5), n-hexadecanol (6), phthalic acid isodibutyl ester (7), curcumol (8), β-sitosterol (9) and daucosterol (10). Their structures were elucidated on the basis of extensive NMR (DEPT, DQF-COSY, HMQC, HMBC and NOESY), IR and MS studies. All the compounds were isolated and identified from the genus of Entodon for the first time, and it is also the first report of a guaiane-type sesquiterpenoid and compounds with anthraquinone skeleton in mosses.     

九子参中一个新三萜皂苷

运用硅胶、SephadexLH-20、0DD以及高效液相色谱法,从九子参的根中分离得到一个新三萜皂苷和一个已知三萜皂苷。通过质谱以及一维二维核磁确定了化合物的结构。化合物1和2均为首次从该属植物中分离得到。     

Four new triterpenoid saponins from Ilex Godajam

Four new triterpenoid saponins, godosides A - D ( 1 - 4 ), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam . Structure elucidation of 1 - 4 was based on NMR, MS, IR and chemical analyses.     

Two new triterpenoid saponins from Symplocos Chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21β-O- cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (1) and 21β-O-cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-(3-O-acetyl)-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.     

Two new triterpenoid saponins from Sarcandra glabra

Two new triterpenoid saponins, named sarcandroside A and B, have been isolated from Sarcandra glabra (Thunb) Nakai. Their structures have been established as 3β,19α,20β-trihydroxyurs-11,13 (18)-diene-28,20β-lactone-3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranoside (1) and 3-O-β-d-glucopyranosyl (1 → 3)-[α-l-rhamnopyranosyl(1 → 2)]-β-d-xylopyranosyl-pomolic acid 28-O-β-d-glucopyranosyl ester (2) by means of spectral and chemical methods.     

A new anthraquinone and a new naphthoquinone from the whole plant of Spermacoce latifolia

A phytochemical study on the whole plant of Spermacoce latifolia led to the isolation of a new anthraquinone, 1,2,6-trihydroxy-5-methoxy-9,10-anthraquinone (1), and a new naphthoquinone, (2R)-6-hydroxy-7-methoxy-dehydroiso-α-lapachone (2), together with three known anthraquinones (3–5). Their structures were established on the basis of detailed spectroscopic analysis, including one- and two-dimensional NMR, ESI–MS, and HR–ESI–MS techniques. All the compounds were isolated from S. latifolia for the first time. Compounds 1, 2, 4, and 5 showed significant antibacterial activity toward Bacillus subtilis with MIC values ranging from 0.9 to 31.2 μg/ml, and compound 4 aslo exhibited antibacterial activity against Bacillus cereus with a MIC value 62.5 μg/ml. Compound 1 was further revealed to show significant in vitro α-glucosidase inhibitory activity with IC₅₀ value of 0.653 mM.     

Two new triterpenoid glycosides from Cyclocarya paliurus

Two new dammarane triterpenoid glycosides named cyclocarosides B (1) and C (2) were isolated from the leaves of Cyclocarya paliurus. Based on FAB-MS, HRESI-MS, IR, ¹H NMR, ¹³C NMR, and 2D-NMR (HMQC, HMBC, COSY, ROESY) data, the structures of cyclocarosides B (1) and C (2) were elucidated as (20S,24R)-epoxydammarane (3β,12β)-25-hydroxyl-12-O-β-d-quinovopyranosyl-3-O-β-d-quinovopyranoside (1), and (20S,24R)-epoxydammarane (3β, 12β)-25-hydroxyl-12-O-α-l-arabinopyranosyl-3-O-(5′-O-acetyl)-α-l-arabinofuranoside (2).     

Phenolic acid glucosides from the seeds of Entada phaseoloides Merill

Phytochemical investigation of the defatted seeds of Entada phaseoloides Merill. (Mimosaceae) led to the isolation of three new phenolic acid glucosides, which were characterized as 2-hydroxy-5-methylbenzoyl-β-l-glucopyranoside (p-cresotyl glucoside, 1), 2-hydroxy-5-methylbenzoyl-β-l-glucopyranosyl (2 → 1)-β-l-glucopyranosyl (2 → 1)-β-l-glucopyranoside (p-cresotyl triglucoside, 2), and 2-hydroxybenzoyl-β-l-glucopyranosyl (2 → 1)-β-l-glucopyranosyl (2 → 1)-β-l-glucopyranosyl (2 → 1)-β-l-glucopyranoside (salicylic acid tetraglucoside, 5), along with sucrose and triglucoside. The structures of these phytoconstituents have been established on the basis of spectral data analysis and chemical reactions.     

Three new triterpenoid saponins from the rhizomes of Impatiens pritzellii var. hupehensis

Three new triterpenoid saponins, impatiprins A-C (1-3), together with a known triterpenoid (4) and two known triterpenoid saponins (5, 6), were isolated from the rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. The structures of 1-3 were determined by 1D and 2D NMR, FAB-MS techniques and chemical methods. Compounds 1 and 2 showed weak cytotoxicities against S-180, HeLa and HepG2 cell lines.     

A new periplogenin cardenolide from the seeds of Antiaris toxicaria

A new periplogenin cardenolide, periplogulcoside (1), together with three known cardenolides, was isolated from the seeds of Antiaris toxicaria. The structure of the new compound was characterized as periplogenin-3-O-β-d-glucopyranosyl-(1 → 4)-β-d-glucopyranoside (1) by spectroscopic methods including 1D and 2D NMR, HR-TOF-MS, and CD spectrometry, and the known compounds were identified by comparison of their NMR and HR-TOF-MS data with those reported in the literature. Compound 1 showed significant cytotoxicity against Hela and HepG-2 cell lines.     

Cytotoxic triterpenoid saponins from Vaccaria segetalis

By the guidance of bioassay, one new cytotoxic triterpenoid saponin, 3-O-[β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl] quillaic acid 28-O-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-fucopyranosyl-(1 → 4)]-β-d-fucopyranoside (1), and five known cytotoxic triterpenoid saponins, vaccaroside E (2), vaccaroside G (3), vaccaroside B (4), segetoside H (5) and segetoside I (6), were isolated from Vaccaria segetalis. Their structures were established on the basis of ESI-MS, IR, extensive NMR (¹H NMR, ¹³C NMR, TOCSY, ¹H–¹H COSY, DEPT, HMQC, HMBC and ROESY) analyses, chemical degradation, and by comparing with previously reported data. Compounds 1–6 showed moderate cytotoxic activities against LNcap, P-388 and A-549 cell lines with IC₅₀ values in the range 0.1–12.9 μM.     

A new tetracyclic triterpenoid compound from Mastich

A new tetracyclic triterpenoid compound named as mastichinoic acid A (1) was isolated from Mastich. The structure was established as 3,7-dioxo-11β-hydroxy-5α-tirucalla-8,24(Z)-dien-26-oic acid by various spectroscopic techniques including MS, 1D, and 2D NMR and HRTOFMS.     

Three new triterpenoid saponins from the seeds of Aesculus turbinata

Three new triterpenoid saponins, named isoescins VIIa (1), VIa (2), and VIIIa (3), were isolated from the seeds of Aesculus turbinata and identified by spectroscopic analysis and chemical hydrolysis. Their structures were established as 21β-O-tigloyl-28-O-acetylprotoaescigenin 3β-O-[β-d-galactopyranosyl(1 → 2)][β-d-glucopyranosyl(1 → 4)]-β-d-glucopyranosiduronic acid (Isoescin VIIa, 1), 21β-O-(2-methylbutyryl)-28-O-acetylprotoaescigenin 3β-O-[β-d-glucopyranosyl(1 → 2)] [β-d-glucopyranosyl(1 → 4)]-β-d-glucopyranosiduronic acid (Isoescin VIa, 2), and 21β-O-angeloyl-28-O-acetylbarringtogenol C 3β-O-[β-d-glucopyranosyl(1 → 2)] [β-d-glucopyranosyl(1 → 4)]-β-d-glucopyranosiduronic acid (Isoescin VIIIa, 3).     

Three new triterpenoid saponins from the seeds of Vaccaria segetalis

Three new triterpenoid saponins, named segetoside G(1), H(2) and I(3), have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reaction and spectral data, their structures have been established as: 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinofuranosyl (1-->3)]-beta-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-(6-O-butyl ester)-glucuronopyranoside (1), 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-(5-O-acetyl)-arabinofuranosyl-(1-->3)]-beta-D-(4-O-acetyl)-fucopyranosyl-gypsogenin-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (2) and 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-(5-O-acetyl)-arabinofuranosyl-(1-->3)]-beta-D-(4-O-acetyl)-fucopyranosyl-quillaic acid-3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (3).     

Three new triterpenoid saponins from the seeds of Aesculus turbinata

Three new triterpenoid saponins, named isoescins VIIa (1), VIa (2), and VIIIa (3), were isolated from the seeds of Aesculus turbinata and identified by spectroscopic analysis and chemical hydrolysis. Their structures were established as 21beta-O-tigloyl-28-O-acetylprotoaescigenin 3beta-O-[beta-d-galactopyranosyl(1 --> 2)][beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIIa, 1), 21beta-O-(2-methylbutyryl)-28-O-acetylprotoaescigenin 3beta-O-[beta-d-glucopyranosyl(1 --> 2)] [beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIa, 2), and 21beta-O-angeloyl-28-O-acetylbarringtogenol C 3beta-O-[beta-d-glucopyranosyl(1 --> 2)] [beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIIIa, 3).     

Cytotoxic protobassic acid saponins from the kernels of Palaquium formosanum

Bioassay guided fractionation and separation of the EtOH extract of the kernels of Palaquium formosanum against PC-3 cells via Sephadex LH-20 and reverse phase C-18 columns led to the isolation of 13 protobassic saponins. One of these saponins is new and was characterized as 3‴-O-rhamnopyranosyl-arganin C, a bisdesmoside of 16α-hydroxyprotobassic acid at the C-3 and C-28 positions. The structures of these compounds were determined on the basis of 1D NMR (¹H, ¹³C), 2D NMR (¹H–¹H COSY, HSQC, HMBC, and NOESY), and selectively excited 1D TOCSY spectroscopic analyses and MS data, and comparison with literature data. Bioassay of these compounds and five additional compounds, isolated from Planchonella obovata leaf, against PC-3 prostate cancer cells indicated arganin C to be the most potent one with the IC₅₀ value of 13.8 μM. Some structure and activity relationships were also drawn.     

Aceriphyllic acid A,A new ACAT inhibitory triterpenoid,from Aceriphyllum rossii

Two new triterpenoids along with three known ones, 3-oxoolean-12-en-27-oic acid (1), 3alpha-hydroxyolean-12-en-27-oic acid (2) and 3beta-hydroxyolean-12-en-27-oic acid (3), were isolated from Aceriphyllum rossii. The structures of the new compounds were determined to be a 3alpha,23-dihydroxyolean-12-en-27-oic acid (4) and a 3alpha,23-dihydroxyolean-12-en-29-oic acid (5) by spectroscopic and chemical methods; they were designated aceriphyllic acids A and B, respectively. Compounds 2, 3 and 4 remarkably inhibited the activity of ACAT.     

茯苓皮中三萜酸类成分的研究

目的 研究茯苓皮中的三萜酸类化合物.方法 采用柱色谱法和制备液相色谱法,从茯苓皮的二氯甲烷及乙酸乙酯提取物中分离纯化单体化合物,并通过光谱方法鉴定其结构.结果 从茯苓皮的提取物中分离并鉴定了11个三萜酸,分别为茯苓酸A(Ⅰ)、茯苓酸B(Ⅱ)、茯苓酸AM(Ⅲ)、茯苓酸(Ⅳ)、dehydroeburiconic acid(Ⅴ)、dehydrotrametenonic acid(Ⅵ)、dehydrotrametenolic acid(Ⅶ)、eburicoic acid(Ⅷ)、3-O-acetyl-16α-hydroxytrametenolic acid(Ⅸ)、3-O-formyl-dehydrotrametenolic acid(X)、3-O-formyl-eburicoic acid(Ⅺ),其中化合物Ⅹ、Ⅺ为新化合物.结论 通过验证实验证明:化合物Ⅹ、Ⅺ为分离过程中产生的人工产物.     

Three new lignans from the seeds of Saussurea involucrata

Three new lignans, arctigenin-4-O-(6″-O-acetyl-β-d-glucoside) (1), arctigenin-4-O-(2″-O-acetyl-β-d-glucoside) (2), and arctigenin-4-O-(3″-O-acetyl-β-d-glucoside) (3), together with two known lignans, were isolated from the seeds of Saussurea involucrata. Their structures were established by spectroscopic methods, mainly 1D and 2D NMR, and mass spectral analysis.