Five new cucurbitane triterpenoids with cytotoxic activity from Hemsleya jinfushanensis

Five new cucurbitane triterpenoids (hemslepenside B–E (1–3 and 5)), one new cucurbitane (16,25-O-diacetyl-cucurbitane F (4)), and six analogues (6–11) were isolated from the roots of Hemsleya jinfushanensis. The structures of 1–5 were elucidated using infrared absorption spectroscopy (IR), high resolution electrospray ionization mass spectrometry (HR-ESI-MS), and nuclear magnetic resonance spectroscopy (NMR). These five new compounds exhibited cytotoxic effects against lung adenocarcinoma (H460), colon cancer (SW620) and human prostate cancer cells (DU145), and compound 4 showed significant cytotoxic activity, with IC₅₀ values of 0.046, 0.18 and 0.87 μg/mL. This finding suggests that cucurbitane triterpenoids isolated from H. jinfushanensis should be studied further as potential anti-cancer drugs.     

Bioactive cucurbitane triterpenoids from the tubers of Hemsleya penxianensis

Four new cucurbitacins, jinfushanencins C-F (1–4) and three known analogues (5–7) were isolated from the tubers of Hemsleya penxianensis by Silica gel column, ODS column, pre-HPLC techniques. The structures of 1–7 were establishhed on the basis of extensive spectroscopic. The isolated compounds were tested for their cytotoxic activity against Hela human cancer cell line and compounds 1, 5, and 7 showed significant cytotoxicity with IC₅₀ values at 5.1, 8.7, and 1.2 μM, respectively. None of the compounds had active anti-HIV activity.     

Purine-containing cucurbitane triterpenoids from Cucurbita pepo cv dayangua

Phytochemical investigation of the fruits of Cucurbita pepo cv dayangua led to the isolation of cucurbitaglycosides A (1) and B (2). This is the first report of cucurbitane triterpenoids with a purine unit. Their structures were elucidated mainly based on interpretation of HRESIMS results, as well as 1D and 2D NMR spectra. Cucurbitaglycosides A and B showed cytotoxic activity against the human epithelial carcinoma cell line HeLa with IC50 of 17.2 and 28.4 microg/mL, respectively.     

New iridal-type triterpenoid derivatives with cytotoxic activities from Belamcanda chinensis

Eight new iridal-type triterpenoid derivatives, including two noriridals with ether bridge (1–2); two iridals lactone (3–4), four monocyclic iridals (5–8), together with five known iridals (9–14) were identified from the rhizome of Belamcanda chinensis. Their structures were elucidated on the basis of comprehensive spectroscopic methods and electronic circular dichroism (ECD) calculations. Bioassay results showed that belamcanoxide B (1) exhibited moderated cytotoxic activities against HCT-116 and MCF-7 cell lines with IC₅₀ values of 5.58 and 3.35 μM.     

Kuguacins F-S, cucurbitane triterpenoids from Momordica charantia

Chemical investigation of the vines and leaves of Momordica charantia resulted in isolation of fourteen cucurbitane triterpenoids, kuguacins F-S (1-14), including two pentanorcucurbitacins (6 and 7), one octanorcucurbitacin (8), and two trinorcucurbitacins (11 and 12), along with six known analogues. Their structures were elucidated on the basis of extensive spectroscopic and single-crystal X-ray diffraction analyses. Compounds 1-14 exhibited weak anti-HIV-1 activities in vitro.     

Cytotoxic polyhydroxy serratene triterpenoids from Lycopodium complanatum

Phytochemical investigation of the 70% aqueous EtOH extract of Lycopodium complanatum led to six new polyhydroxy serratene triterpenoids (serrat A-F, 1–6), along with a known analogue (7). Their structures and configurations were elucidated by data analysis of HRESIMS, 1D and 2D NMR, in combination with comparisons of reported experimental spectroscopic data. All the isolates were evaluated cytotoxic activities against HepG2 cells, MCF-7 cells and series human lung cancer cell lines A549, Calu-6, NCI-H441, NCI-H226 and NCI-H1975. The results indicated that certain compounds inhibited proliferation of human cancer cells. Moreover, all compounds possessed selective cytotoxic activities on MCF-7 cells. Further, possible biosynthesis pathways of these compounds were proposed.     

Four new triterpenoidal saponins from Ilex cornuta and their cytotoxic activities

Four new triterpenoidal saponins (1–4), oleanolic acid 3β-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucuronopyranoside-6-O-butyl ester (1), oleanolic acid 3β-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-glucuronopyranoside-6-O-butyl ester]-28-O-β-d-glucopyranoside (2), 19α-hydroxy oleanolic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (3), and 19α-hydroxy urs-12-en-28-oic acid 3β-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucuronopyranoside-6-O-methyl ester (4) were isolated from the roots of Ilex cornuta. Their structures were determined by means of extensive spectroscopic analyses (IR, ESIMS, HRESIMS, 1D and 2D NMR). Compounds 1–9 were tested for their cytotoxic activities by MTT assay, and 1, 3, 5 and 6 showed moderate cytotoxic activities against HeLa, SMMC-7721, and HL-60 human tumor cell lines.     

Iridoids and lignans from Valeriana officinalis L. and their cytotoxic activities

Two new iridoids (1 and 2), one new lignan (3) together with one known iridoid (4) and twelve known lignans (5－16) were obtained from the roots of Valeriana officinalis L. (V. officinalis). The structures were determined using IR, MS, ¹D and ²D NMR spectroscopy and the absolute configurations of the new structures were deduced by ECD experiments. All of the isolated compounds were assayed for their cytotoxic activities against three tumour cell lines (A549, HCT116 and SW620) and the results showed that compounds 9 and 10 showed cytotoxicities against A549 cells, compounds 9 and 11 showed cytotoxicities against SW620 cells and compound 10 showed cytotoxicities against HCT116 cells.     

Three new sesquiterpenoids from Solanum septemlobum with cytotoxic activities

Three new sesquiterpenoids, attributable to eudesmane-related (1–2, named septemlobins A–B) and vetispirane-type (3, named septemlobin C), respectively, were isolated from the whole plant of Solanum septemlobum. Their structures were elucidated on the basis of integrated spectroscopic techniques. In vitro, compounds 1–3 were found to show significant cytotoxicities against three cancer cell lines (P-388, HONE-1, and HT-29), and gave IC₅₀ values in the range 3.8–7.5 μM.     

Three new cytotoxic aryltetralin lignans from Sinopodophyllum emodi

Three new aryltetralin lignans, 4-acetyl-4-demethyl-podophyllotoxin (1) and sinolignans A, B (2-3), and two new natural products (4-5), were isolated from the roots and rhizomes of Sinopodophyllum emodi together with twelve known lignans (6-17). Their structures and stereochemistry were elucidated on the basis of spectroscopic evidence, and circular dichroism (CD) method. The cytotoxic activities of all isolated compounds were evaluated against HeLa and KB cell lines. Compared with etoposide, compounds 1, 6-9, and 13 showed more potent cytotoxicities against two tumor cell lines. On the basis of IC₅₀ values, deoxypodophyllotoxin (7) was about 579 and 1123 times more toxic than etoposide in HeLa and KB cell lines, respectively. The preliminary SAR study indicated that an oxygenated group at C-7′ might decrease cytotoxicity against two cell lines, which was different from most previous studies. However, this needs to be systematically verified by extensive pharmacological experiments.     

Three new triterpenoids from Potentilla multicaulis

Three new triterpenoids, 19-hydroxy-2,3-secours-12-ene-2,3,28-trioic acid 3- methyl ester (1), 19-hydroxy-1-oxo-2-nor-2,3-secours-12-ene-3,28-dioic acid (2), and (3beta,18alpha,19alpha)-3,28-dihydroxy-20,28-epoxyursan-24-oic acid (3), were isolated from the roots of Potentilla multicaulis. Their structures were elucidated on the basis of spectroscopic methods (IR, HR-ESI-MS, and 1D- and 2D-NMR). Compound 2b exhibited moderate cytotoxic activity against human promyelocytic leukemia (HL-60) cells.     

Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia

Five cucurbitacins, kuguacins A-E (1-5), together with three known analogues, 3beta,7beta,25-trihydroxycucurbita-5,(23E)-diene-19-al (6), 3beta,25-dihydroxy-5beta,19-epoxycucurbita-6,(23E)-diene (7), and momordicine I (8), were isolated from roots of Momordica charantia. Structures of 1-5 were elucidated by NMR and MS spectroscopic analysis. Among them, compounds 3-5 possess an unprecedented 25,26,27-trinorcucurbitane backbone. Compounds 3 and 5 showed moderate anti-HIV-1 activity with EC(50) values of 8.45 and 25.62 microg/ml, and exerted minimal cytotoxicity against C8166 cells (IC(50)>200 microg/ml), with a selectivity index more than 23.68 and 7.81, respectively.     

Five new triterpenoid saponins from the Roots of Camellia oleifera C. Abel with cytotoxic activities

Five new triterpenoid saponins, oleiferosides P–T (1–5) were isolated from the EtOH extract of the roots of Camellia oleifera C. Abel. The structures of saponins 1–5 were elucidated on the basis of integrated spectroscopic techniques. All the compounds were characterized to be oleanane-type saponins with sugar moieties linked to the C-3 of the aglycone. By using the MTT assay, an in vitro analysis of the cytotoxic activities of these saponins on the human tumor cell lines (lung adenocarcinoma A549 cells, hepatic carcinoma SMMC-7721 cells and breast cancer MCF-7 cells). Among them, compound 4 showed a certain cytotoxic activity against all the tested cell lines.     

Two new flavonol derivatives from the whole plants of Centella asiatica and their cytotoxic activities

Centella asiatica is well known as an important medicinal plant because of its various pharmacological effects. However, most investigations on C. asiatica focused on the pharmacological activity of its extract or asiatic acid. In the present work, we aimed to explore the bioactive compounds of the whole plants of C. asiatica. As a result, seven compounds including two new flavonol derivates named 4′-hydroxyl-7-methoxyl-6-prenyl-3-O-trans-p-coumaroyl-flavonol (1) and (2R,3R,2″S)-3-furanoyl-brosimacutin E (2), and five known compounds (3-7) were isolated. Their chemical structures were elucidated on the basis of spectroscopic analyses. All the isolates were evaluated for in vitro cytotoxic effects on four human cancer cells including A549, HepG2, SGC-7901 and MCF-7. Among them, compounds 1 and 2 exhibited higher cytotoxic activities on HepG2 and SGC-7901 cells compared with 3-7. And compound 2 showed potential cytotoxic activities on HepG2 and SGC-7901 cells with IC₅₀ values of 4.52 and 7.03 μM, respectively.     

Six new dihydrobenzofuran lignans from the branches and leaves of Illicium wardii and their cytotoxic activities

Six new dihydrobenzofuran lignans, named illiciumlignans A⿿F (compounds 1⿿6), along with 15 known compounds (7⿿21) were isolated from the branches and leaves of Illicium wardii. The structures of 1⿿6 were determined using a combination of 1D and 2D NMR, HR-ESI⿿-MS, and CD spectroscopic data. Illiciumlignan D (4) is the first reported dihydrobenzofuran lignan arabinofuranoside that is derivatized with the arabinofuranose moiety on C-9⿲. Compounds 1⿿21 were evaluated for cytotoxic activity against four human cancer cell lines. Compounds 8, 12 and 20 exhibited significant activity against human cancer cell lines (A549, SKOV3, HepG2 and HCT116), with IC₅₀ values ranging from 2.7 to 14.9 μM.     

Four new steroidal glycosides from Solanum torvum and their cytotoxic activities

Two novel C-22 steroidal lactone saponins, namely solanolactosides A, B (1, 2) and two new spirostanol glycosides, namely torvosides M, N (3, 4) were isolated from ethanol extract of aerial parts of Solanum torvum. Their structures were characterized as solanolide 6-O-[α-l-rhamnopyranosyl-(1 → 3)-O-β-d-quinovopyranoside] (1), solanolide 6-O-[β-d-xylopyranosyl-(1 → 3)-O-β-d-quinovopyranoside] (2), yamogenin 3-O-[β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside] (3) and neochlorogenin 3-O-[β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside] (4) on the basis of spectroscopic analysis. The cytotoxicities of the saponins (1-4) were evaluated in vitro against a panel of human cancer cell lines. Compounds 3 and 4 showed significant cytotoxic activity with the cell lines.     

New tirucallane triterpenoids from Picrasma quassioides with their potential antiproliferative activities on hepatoma cells

Seven new tirucallane-type triterpenoids (1–7), kumuquassin A-G, along with 20 known analogues (8–27) were isolated from the stems of Picrasma quassioides. The structures and the absolute configurations of new compounds were elucidated by spectroscopic data, electronic circular dichroism (ECD) spectroscopic analyses and quantum ECD calculations. Notably, kumuquassin A (1) contains a rare Δ^{17, 20} double bond, kumuquassin B (2) is the first example of tirucallane triterpenoid possessing a 5/3 biheterocyclic ring system at the side chain. All the compounds were screened for the cytotoxicity against two human hepatoma cell lines, HepG2 and Hep3B, and several compounds exhibited promising activity. The most potential compound 3 was selected for cell cycle analysis, which showed that 3 could cause an accumulation of HepG2 cells at subG1 peak. Annexin V-FITC/PI staining further confirmed that compound 3 caused death of hepatoma cells through apoptosis induction.     

古蔺雪胆中的新三萜皂苷

从采自四川汉源县的古蔺雪胆(Hemsleya penxianensis var.gulinensiks)中分到9个三萜皂苷化合物,通过化学反应和光谱方法鉴定了它们的结构。其中7个为已知化合物,分别为齐墩果酸-28-O-β-D-比喃葡萄糖苷(1),3-O-β-D-吡喃葡萄糖醛基齐墩果酸苷(3),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-吡喃阿拉伯糖苷(4),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(5),3-O-α-L-阿拉伯糖基—(1→3)—β—D-吡喃葡萄糖醛基—齐墩果酸—28—O—β—D—吡喃葡萄糖苷(6),3—O—(6′—丁酯)—β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-阿拉伯糖苷(7),3-O-(6′-丁酯)—β—D吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(8)。两个新化合物,即雪胆皂苷A(2)和雪胆皂苷B(9)。     

New Triterpenoid Glycosides from Hemsleya penxianensis var. gulinensis

Two new triterpenoid saponins were isolated from the rools of Hemsleya penxianensis var. gulinensis together with seven known saponins oleanolic acid 28-O-β-D-glucopyranoside (1), oleanolic acid 3-O-β-D-glucuropyranoside(3), 3-O-β-D-glucuropyranosyl-oleanolic acid-28-O-α-L-arabinopyranoside(4).     

Three new cytotoxic sesquiterpenoids from Solanum lyratum

In our continuing effort to discover more new cytotoxic sesquiterpenoid from Solanum lyratum collected from different districts of China, three new sesquiterpenoids, attributable to eudesmane-type (1, named solajiangxin D) and vetispirane-type (2–3, named solajiangxins E and 2-hydroxysolajiangxin E), respectively, were isolated. Their structures were elucidated on the basis of integrated spectroscopic techniques, mainly HR-FABMS, 1D and 2D NMR (¹H–¹H COSY, HMQC, HMBC and ROESY). In vitro, compounds 1–3 were found to show significant cytotoxicities against three human cancer lines (P-388, HONE-1, and HT-29), and gave ED₅₀ values in the range 2.1–3.7 μg/ml.