MingHua Qiu

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Name: 邱明华

Organization: Kunming Institute of Botany, Chinese Academy of Sciences , China

Department: Department of Chemistry

Title: NULL(PhD)

TOPICS

Material Chemistry

Graphene & Graphite

Analytical Chemistry

Chemicals
References

Rare Hybrid Dimers with Anti-Acetylcholinesterase Activities from a Safflower (Carthamus tinctorius L.) Seed Oil Cake

Co-reporter:Xing-Rong Peng, Xia Wang, Jin-Run Dong, Xu-Jie Qin, Zhong-Rong Li, Han Yang, Lin Zhou, and Ming-Hua Qiu

Journal of Agricultural and Food Chemistry November 1, 2017 Volume 65(Issue 43) pp:9453-9453

Publication Date(Web):October 10, 2017

DOI:10.1021/acs.jafc.7b03431

Safflower (Carthamus tinctorius) is commercially cultivated for vegetable oil extracted from the seeds. However, during the production process of seed oil, a large amount of the oil cake is thrown away or fermented as fertilizer to improve the homing rate of pigeons. Therefore, to solve the ecological problem and develop its new function, we investigated the chemical constituents of a safflower seed oil cake, and six new hybrid dimers, (±)-carthatins A–F (1–6, respectively), with a phenylpropanoid and a feruloylserotonin fused via a dihydrofuran ring, together with four known compounds, including sinapyl alcohol (7), coniferyl alcohol (8), serotobenine (9), and feruloylserotonin (10), were isolated. The extensive nuclear magnetic resonance spectra, combined with electronic circular dichroism analysis and chiral high-performance liquid chromatography, allowed the complete structural assignments of (±)-carthatins A–F. Moreover, we evaluated their anti-acetylcholinesterase activities. Racemic carthatins A and B (1 and 2, respectively) showed anti-acetylcholinesterase effects with IC50 values of 17.96 and 66.83 μM, respectively. To some extent, our findings provide a new scaffold of acetylcholinesterase inhibitors, which could be beneficial for developing therapeutic molecules for the treatment of Alzheimer’s disease and supporting folk application of a safflower seed oil cake.Keywords: anti-AChE activity; Carthamus tinctorius L.; chiral HPLC; ECD analysis; safflower seed oil cake;

Macahydantoins A and B, two new thiohydantoin derivatives from Maca (Lepidium meyenii): Structural elucidation and concise synthesis of macahydantoin A

Co-reporter:Mu-Yuan Yu, Xu-Jie Qin, Li-Dong Shao, Xing-Rong Peng, Lei Li, Han Yang, Ming-Hua Qiu

Tetrahedron Letters 2017 Volume 58, Issue 17(Issue 17) pp:

Publication Date(Web):26 April 2017

DOI:10.1016/j.tetlet.2017.03.038

•Macahydantoins A and B, two novel thiohydantoin derivatives, were isolated from Lepidium meyenii.•Stereochemistries were determined by ECD calculation.•The chemical synthesis of macahydantoin A was achieved.Macahydantoins A (1) and B (2), two new thiohydantoin derivatives with an unprecedented skeleton, were isolated from maca (Lepidium meyenii). Their structures and absolute configurations were fully established by extensive spectroscopic and computational methods. The totally chemical synthesis of macahydantoin A was achieved via benzylamine and methyl piperidine-3-carboxylate hydrochloride through nucleophilic addition and intramolecular dehydration condensation.Download high-res image (110KB)Download full-size image

Withanolides from aerial parts of Nicandra physalodes

Co-reporter:Mu-Yuan Yu, Gao-Ting Zhao, Jie-Qing Liu, Afsar Khan, Xing-Rong Peng, Lin Zhou, Jin-Run Dong, Hai-Zhou Li, Ming-Hua Qiu

Phytochemistry 2017 Volume 137(Volume 137) pp:

Publication Date(Web):1 May 2017

DOI:10.1016/j.phytochem.2017.02.009

•Twenty withanolides were obtained from Nicandra physalodes, thirteen previously unknown.•Nicanlodes A and B withanolides with an unusual aromatic amine moiety.•None of the isolates displayed cytotoxicity against five cancer cell lines.Twenty withanolides, including previously unknown nicanlodes A–M, were isolated from aerial parts of Nicandra physalodes. Their structural elucidations were unambiguously achieved through interpretation of extensive spectroscopic data (NMR and HRMS) and by comparison with literature data. Nicanlodes A and B have an unusual aromatic amine moiety. The isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines.Twenty withanolides, including 13 previously unknown and named nicanlodes A–M, were isolated from aerial parts of Nicandra physalodes. Nicanlodes A and B have a rare aromatic amine moiety.Download high-res image (320KB)Download full-size image

Cimifrigines A–G, cytotoxic triterpenes with an oxime group from the flowers of Cimicifuga frigida

Co-reporter:Yin Nian;Hui Yan;Xiao-Nian Li;Lin Zhou;Ming-Hua Qiu

RSC Advances (2011-Present) 2017 vol. 7(Issue 61) pp:38557-38564

Publication Date(Web):2017/08/02

DOI:10.1039/C7RA07275A

Seven new dahurinol-type triterpene derivatives, including three aglycones, cimifrigines A–C (1–3), and four glycosides, cimifrigines D–G (4–7), were purified from the flowers of Cimicifuga frigida. These triterpenoids are characterized by an oxime group at C-15. Spectroscopic analyses and X-ray crystallography were used to determine the new structures. In the in vitro cytotoxicity screening, glycosides (4–7) exhibited more noticeable activities than the aglycones (1–3) against human HL-60, SMMC-7721, A549, MCF-7, and SW-480 cell lines. Interestingly, compounds 5 and 7, bearing a 2′-O-acetyl moiety on the sugar unit, showed comparable cytotoxicities to the positive control, cisplatin (IC50: 0.5 to 5.4 μM). Whereas, analogues 4 and 6, without the 2′-O-acetyl group, indicated weaker activities with IC50 values ranging from 8.9 to 14.3 μM.

Macathiohydantoins B–K, novel thiohydantoin derivatives from Lepidium meyenii

Co-reporter:Mu-Yuan Yu, Xu-Jie Qin, Xing-Rong Peng, Xia Wang, Xiao-Xue Tian, Zhong-Rong Li, Ming-Hua Qiu

Tetrahedron 2017 Volume 73, Issue 30(Issue 30) pp:

Publication Date(Web):27 July 2017

DOI:10.1016/j.tet.2017.05.096

Macathiohydantoins B–K (1–10), two new group of naturally occurring thiohydantoin derivatives, together with one known analogues (11), were isolated from the rhizomes of Lepidium meyenii (Maca). Compounds 1–11 were all initially obtained as racemic mixtures and further separated by chiral HPLC chromatography to afford the eleven pairs of enantiomers. The structures of 1–10 including their absolute configurations were fully established by the comprehensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. All isolates were evaluated for their cytotoxic and antimicrobial activities.Download high-res image (294KB)Download full-size image

Three Minor Diterpenoids with Three Carbon Skeletons from Euphorbia peplus

Co-reporter:Luo-Sheng Wan, Yin Nian, Chen-Jun Ye, Li-Dong Shao, Xing-Rong Peng, Chang-An Geng, Zhi-Li Zuo, Xiao-Nian Li, Jian Yang, Ming Zhou, and Ming-Hua Qiu

Organic Letters 2016 Volume 18(Issue 9) pp:2166-2169

Publication Date(Web):April 14, 2016

DOI:10.1021/acs.orglett.6b00787

Euphorbia peplus has been used in traditional medicine to treat asthma and psoriasis. Three highly modified diterpenoids, namely, pepluacetal (1) and pepluanol A–B (2–3), have been isolated and identified from this plant. Compounds 1–3 exhibit unprecedented 5/4/7/3, 5/6/7/3, and 5/5/8/3 ring systems, respectively. Their structures with absolute configurations were determined by spectroscopic analyses, X-ray crystallography, and electronic circular dichroism calculations. Since Kv1.3 is a validated target for the treatment of autoimmune diseases, such as multiple sclerosis, type-1 diabetes, asthma, and psoriasis, Kv1.3 was studied in terms of its response to the new compounds. All three compounds inhibit Kv1.3, with compound 3 being the most effective with an IC50 value of 9.50 μM.

(±)-Ganoapplanin, a Pair of Polycyclic Meroterpenoid Enantiomers from Ganoderma applanatum

Co-reporter:Lei Li, Huan Li, Xing-Rong Peng, Bo Hou, Mu-Yuan Yu, Jin-Run Dong, Xiao-Nian Li, Lin Zhou, Jian Yang, and Ming-Hua Qiu

Organic Letters 2016 Volume 18(Issue 23) pp:6078-6081

Publication Date(Web):November 18, 2016

DOI:10.1021/acs.orglett.6b03064

(±)-Ganoapplanin (1), a pair of novel meroterpenoid enantiomers featuring an unprecedented dioxaspirocyclic skeleton constructed from a 6/6/6/6 tetracyclic system and an unusual tricyclo[4.3.3.03′,7′]dodecane motif, were isolated from Ganoderma applanatum. Its structure and absolute configurations were determined by spectroscopic analyses, X-ray crystallography, and ECD (electronic circular dichroism calculations). A plausible biogenetic pathway, involving a key Gomberg–Bachmann reaction, was also proposed for (±)-1. Biological studies showed that (±)-1 and its enantiomers exhibited different inhibitory activities on T-type voltage-gated calcium channels.

One-Step Semisynthesis of a Segetane Diterpenoid from a Jatrophane Precursor via a Diels–Alder Reaction

Co-reporter:Luo-Sheng Wan, Li-Dong Shao, Liangbing Fu, Jun Xu, Guo-Lei Zhu, Xing-Rong Peng, Xiao-Nian Li, Yan Li, and Ming-Hua Qiu

Organic Letters 2016 Volume 18(Issue 3) pp:496-499

Publication Date(Web):January 19, 2016

DOI:10.1021/acs.orglett.5b03473

A novel segetane diterpenoid (1) and four jatrophane diterpenoids (2–5) were isolated from an acetone extract of Euphorbia peplus. Due to quantity limitations, we prepared 1 via a Diels–Alder reaction, an approach motivated by this compound’s biosynthetic pathway and successfully performed X-ray analysis of 1. Furthermore, in an in vitro activity test, 1 exhibited moderate anti-inflammatory activity, whereas both its precursor (2) and the relevant intermediate (2a, IC50 = 1.56 μM) exhibited significant anti-inflammatory activity.

Pepluane and Paraliane Diterpenoids from Euphorbia peplus with Potential Anti-inflammatory Activity

Co-reporter:Luo-Sheng Wan; Rui Chu; Xing-Rong Peng; Guo-Lei Zhu; Mu-Yuan Yu; Lei Li; Lin Zhou; Shuang-Yang Lu; Jin-Run Dong; Zhi-Run Zhang; Yan Li;Ming-Hua Qiu

Journal of Natural Products 2016 Volume 79(Issue 6) pp:1628-1634

Publication Date(Web):May 20, 2016

DOI:10.1021/acs.jnatprod.6b00206

Twelve new diterpenoids based on two rare skeletal types, namely, paralianones A–D (1–4) and pepluanols A–H (5–12), along with five known compounds, were isolated from an acetone extract of Euphorbia peplus. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. These diterpenoids were evaluated for potential anti-inflammatory activity in a lipopolysaccharide-stimulated mouse macrophage cellular model. Compounds 3, 4, 11, 13, and 16 displayed moderate inhibitory effects on NO inhibition, with IC50 values ranging from 29.9 to 38.3 μM.

Cucurbitane-type triterpenoids from the aerial parts of Momordica charantia L.

Co-reporter:Ying Jiang, Xing-Rong Peng, Mu-Yuan Yu, Luo-Sheng Wan, Guo-Lei Zhu, Gao-Ting Zhao, Lin Zhou, Ming-Hua Qiu, Jian Liu

Phytochemistry Letters 2016 Volume 16() pp:164-168

Publication Date(Web):June 2016

DOI:10.1016/j.phytol.2016.04.007

•Six new cucurbitane-type triterpenoids were isolated from the stems and leaves of Momordica charantia L.•Compounds 2 and 3 were a pair of 19-isomers.•The structures of new compounds were successfully determined by extensive MS, 1D, 2D NMR spectroscopic technologies.Six new cucurbitane-type triterpenoids (1–6), together with two known analogues (7 and 8) were isolated from the aerial parts of Momordica charantia L. The structures of new compounds were identified as cucurbita-6,24-dien-3β,23-diol-19,5β-olide (1), (19R)-5β,19-epoxy-19-methoxycucurbita-6,24-dien-3β,23-diol (2), (19S)-5β,19-epoxy-19-methoxycucurbita-6,24-dien-3β,23-diol (3), (19R)-5β,19-epoxy-19-isopropoxycucurbita-6,24-dien-3β,23-diol (4), 3β,23-dihydroxy-5-methoxycucurbita-6,24-dien-19-al (5) and (19R)-7β,19-epoxy-19-methoxycucurbita-5,24-dien-3β,23-diol (6), by extensive MS, 1D and 2D NMR spectroscopic technologies. This is the first report of the isolation of tetracyclic triterpenoids possessing a 7β,19-epoxy system, viz., 6, from M. charantia L.

Cytotoxic 9,19-cycloartane triterpenoids from the roots of Cimicifuga foetida L.

Co-reporter:Guo-Lei Zhu, Yin Nian, Di-Fan Zhu, Luo-Sheng Wan, Ni-Man Bao, Wei-Hua Wang, Lin Zhou, Ming-Hua Qiu

Phytochemistry Letters 2016 Volume 18() pp:105-112

Publication Date(Web):December 2016

DOI:10.1016/j.phytol.2016.06.002

•Eight new 9,19-cycloartane triterpenoids (1–8) were isolated from the roots of Cimicifuga foetida L.•The structures of the isolated new compounds were clearly elucidated by extensive MS, 1D, 2D NMR spectroscopic technologies.•Compound 2 showed significant cytotoxic activity against five cancer cell lines with IC50 value from 2.61 to 3.32 μM.Eight new cycloartane triterpenoids (1–8), along with eight known analogues (9–16), were isolated from the roots of Cimicifuga foetida L. Their structures were elucidated by spectroscopic analysis and acidic hydrolysis. All of the new compounds were evaluated for their in vitro cytotoxicity against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compound 2 showed inhibitory activities with IC50 values raging from 2.61 to 3.32 μM.

Three New Pregnane Alkaloids from Pachysandra terminalis

Co-reporter:Yun Sun;Jin-Xiong Chen;Jian-Chao Chen;Zhong-Rong Li;Lin Zhou;Yan Li ;Ming-Hua Qiu

Helvetica Chimica Acta 2016 Volume 99( Issue 7) pp:513-517

Publication Date(Web):

DOI:10.1002/hlca.201600016

Three new pregnane alkaloids, pachystermine C (1), pachysanamine A (2), and pachysanamine B (3), together with four known ones, pachystermine B (4), pachysamine A (5), (20S)-20-(dimethylamino)-16α-hydroxy-3β-(3′α-isopropyl)lactam-5α-pregnan-4-one (6), and E-salignone (7), were isolated from Pachysandra terminalis. The chemical structures of the new alkaloids were elucidated by spectroscopic methods. All the compounds were evaluated for their inhibitory activities against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines, some of the compounds showed stronger cytotoxicity for the test cell lines, especially compounds 2, 3, and 7.

Six New 9,19-Cycloartane Triterpenoids from Cimicifuga foetida L.

Co-reporter:Guo-Lei Zhu;Di-Fan Zhu;Luo-Sheng Wan

Natural Products and Bioprospecting 2016 Volume 6( Issue 4) pp:187-193

Publication Date(Web):2016 August

DOI:10.1007/s13659-016-0097-3

Six new 9,19-cycloartane triterpene derivatives, as well as 3 known analogues (7–9), were isolated from the roots of Cimicifuga foetida L. Their structures were established on the basis of extensive spectroscopic analyses (IR, UV, ORD, HRESIMS, 1D and 2D NMR).

Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

Co-reporter:Rui Chu;Luo-Sheng Wan;Xing-Rong Peng;Mu-Yuan Yu

Natural Products and Bioprospecting 2016 Volume 6( Issue 4) pp:217-223

Publication Date(Web):2016 August

DOI:10.1007/s13659-016-0099-1

Five new ent-kaurane diterpenoids, named mascaroside III–V (1–3), and 20-nor-cofaryloside I–II (4–5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

Lactam Triterpenoids from the Bark of Toona sinensis

Co-reporter:Qian-Qian Meng;Xing-Rong Peng;Shuang-Yang Lu

Natural Products and Bioprospecting 2016 Volume 6( Issue 5) pp:239-245

Publication Date(Web):2016 October

DOI:10.1007/s13659-016-0108-4

Three new limonoid-type triterpenoids, namely toonasins A–C (1–3) with a rare lactam E ring, along with six known compounds (4–9) were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compounds 3 and 5 showed weak cytotoxicities.

Unusual prenylated phenols with antioxidant activities from Ganoderma cochlear

Co-reporter:XingRong Peng, JieQing Liu, CuiFang Wang, ZhongHui Han, Yi Shu, XuYang Li, Lin Zhou, MingHua Qiu

Food Chemistry 2015 Volume 171() pp:251-257

Publication Date(Web):15 March 2015

DOI:10.1016/j.foodchem.2014.08.127

•Five novel polycyclic prenylated phenols were isolated from G. cochlear.•Compounds 1–5 were a series of enantiomers.•Compounds 1–8 showed significant antioxidant activities.Seven new prenylated phenols, five novel phenols (1–5) with polycyclic skeleton and two new phenols (6 and 7) with a carbon chain, along with one known compound (8) were isolated from the fruiting bodies of Ganoderma cochlear. The structures of new compounds were elucidated by the spectroscopic technologies, X-ray crystallography analysis and chiral HPLC chromatography. All compounds showed antioxidant effect in radical scavenging assays and a plausible biosynthetic pathway for 1–8 was proposed.

Ganocochlearic acid A, a rearranged hexanorlanostane triterpenoid, and cytotoxic triterpenoids from the fruiting bodies of Ganoderma cochlear

Co-reporter:Xing-Rong Peng, Xia Wang, Lin Zhou, Bo Hou, Zhi-Li Zuo and Ming-Hua Qiu

RSC Advances 2015 vol. 5(Issue 115) pp:95212-95222

Publication Date(Web):29 Oct 2015

DOI:10.1039/C5RA16796E

Ganocochlearic acid A (1), a rearranged hexanorlanostane triterpenoid featuring a γ-lactone ring and a five-membered carbon ring, and eleven new lanostane triterpenoids (2–12), along with six known analogues (13–18) were isolated from the fruiting bodies of Ganoderma cochlear. Their structures, including absolute configurations, were established on the basis of the MS, NMR, X-ray crystallographic, and ECD analysis. A plausible biosynthetic pathway for 1 was proposed. Compounds 7–9, 11–13 showed moderate cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) with IC50 values ranging from 8 to 30 μM. Compound 4 exhibited relatively potent cytotoxic activity against MCF-7 cells (IC50: 9.15 μM), compared to the positive control (cisplatin, IC50: 12.7 μM).

Identification and Antifeedant Activities of Limonoids from Azadirachta indica

Co-reporter:Yu-Xin Yan;Jie-Qing Liu;Hong-Wei Wang;Jin-Xiong Chen;Jian-Chao Chen;Li Chen;Lin Zhou;Ming-Hua Qiu

Chemistry & Biodiversity 2015 Volume 12( Issue 7) pp:1040-1046

Publication Date(Web):

DOI:10.1002/cbdv.201400282

Abstract

Four new limonoids, azadiraindins A–D (1–4, resp.), together with seven known analogs, were isolated from the MeOH extract of Azadirachta indica. The structures of 1–4 were elucidated by NMR and MS spectroscopic analyses, and the relative configuration of 1 was determined by single-crystal X-ray crystallography. The compounds isolated in comparatively large amount were evaluated for their antifeedant activities against Plutella xylostella; the antifeedant rate of 10 was 90.6% and the corrected mortality of 8 was 79.2%.

Two new penterpenoid saponins and a new diterpenoid glycoside from Hemsleya chinensis

Co-reporter:Na-Li Song, Zhen-Jie Li, Jian-Chao Chen, Yuan-Yuan Deng, Mu-Yuan Yu, Lin Zhou, Ming-Hua Qiu

Phytochemistry Letters 2015 Volume 13() pp:103-107

Publication Date(Web):September 2015

DOI:10.1016/j.phytol.2015.05.021

•Triterpenoid-type compounds 1 and 2 were isolated from Hemsleya chinensis.•Diterpenoid-type compound 3 was isolated from Hemsleya genus for the first time.•The paper described the structural identifications of three new compounds.Two new penterpenoid saponins, hemsloside-Ma4 (1) hemsloside-Ma5 (2), and a new diterpenoid glycoside, hemsloside-Ma6 (3), were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra and chemical methods, the structures of new compounds were determined to be 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside (1), 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopy-ranoside (2), and 13ϵ-hydroxylabda-8(17), 14-dien-18-oic acid-18-O-α-l-rhamnopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-O-α-l-rhamnopyranoside (3). Diterpenoid-type compound (3) was isolated from Hemsleya genus for the first time.Two new penterpenoid saponins, hemsloside-Ma4 (1) hemsloside-Ma5 (2), and a new diterpenoid glycoside, hemsloside-Ma6 (3), were isolated from the rhizomes of Hemsleya chinensis.

Two New Cucurbitane Triterpenoids from Immature Fruits of Momordica charantia

Co-reporter:Zhen-Jie Li;Jian-Chao Chen;Yuan-Yuan Deng;Na-Li Song;Mu-Yuan Yu;Lin Zhou;Ming-Hua Qiu

Helvetica Chimica Acta 2015 Volume 98( Issue 10) pp:1456-1461

Publication Date(Web):

DOI:10.1002/hlca.201500096

Abstract

Two new cucurbitane triterpenoids, kuguacin X (1) and kuguaglycoside I (2), together with three known analogs, were isolated from immature fruits of Momordica charantia. By detailed analysis of IR, NMR, and MS data, acid hydrolysis, and comparison with spectroscopic data of known compounds, the new compounds were determined to be (23E)-5β,19-epoxycucurbita-6,23-diene-3β,22ξ,25-triol (1) and (23E)-5β,19-epoxycucurbita-6,23-dien-19-on-3β,25-diol 3-O-β-D-allopyranoside (2).

Cycloartane Glycosides from the Roots of Cimicifuga foetida with Wnt Signaling Pathway Inhibitory Activity

Co-reporter:Di-Fan Zhu;Guo-Lei Zhu;Ling-Mei Kong;Ni-Man Bao

Natural Products and Bioprospecting 2015 Volume 5( Issue 2) pp:61-67

Publication Date(Web):2015 April

DOI:10.1007/s13659-015-0053-7

Four new 9,19-cycloartane triterpenoids, cimilactone E (1), cimilactone F (2), 2′-O-(E)-butenoyl-23-epi-26-deoxyactein (3), and 2′,12β-O-diacetylcimiracemonol-3-O-β-d-xylopyranoside (4), together with four known constituents (5–8) were isolated from the roots of Cimicifuga foetida. The new structures were elucidated by extensive spectroscopic analysis. In addition, compounds 7 and 8 showed significant Wnt signaling pathway inhibitory activity, with IC50 values of 3.33 and 13.34 μM, respectively, using the luciferase reporter gene assay.

Cytotoxic diterpenoids from Jatropha curcas cv. nigroviensrugosus CY Yang Roots

Co-reporter:JieQing Liu, YuanFeng Yang, JianJun Xia, XuYang Li, ZhongRong Li, Lin Zhou, MingHua Qiu

Phytochemistry 2015 Volume 117() pp:462-468

Publication Date(Web):September 2015

DOI:10.1016/j.phytochem.2015.07.002

•Ten diterpenoids were identified from the roots of Jatropha curcas.•Lathyranlactone is a diterpenoid lactone possessing a 5/13/3 tricyclic skeleton.•Two previously known diterpenoids showed potent cytotoxicity against SMMC-7721, MCF-7, and SW480.An investigation of phytochemicals from the roots of Jatropha curcas cv. nigroviensrugosus resulted in the isolation of twenty diterpenoids, including lathyranlactone, an unusual diterpenoid lactone possessing a 5/13/3 tricyclic skeleton, jatrocurcasenones A–E and jatrophodiones B–E, as well as 10 known analogues. All isolates were evaluated for cytotoxicity against the HL-60, SMMC-772, A-549, MCF-7 and SW480 human tumor cell lines using the MTS viability assay. Four of the known analogues showed cytotoxic activity in these cell lines, with IC50 values ranging from 2.0 to 23.0 μM. Moreover, the assessment of their cytotoxic structure–activity relationships showed the epoxy ring between C-5 and C-6 and the hydroxyl group at C-2 were the key functionalities for cytotoxicity.Twenty diterpenoids were isolated from Jatropha curcas cv. nigroviensrugosus, one of them, lathyranlactone is an unusual diterpenoid lactone possessing a 5/13/3 tricyclic skeleton. Two of the previously known diterpenoids showed more potent cytotoxic activity against the SMMC-772, MCF-7 and SW480 human tumor cell lines than the positive control (cisplatin).

Lanostane triterpenoids from Ganoderma hainanense J. D. Zhao

Co-reporter:XingRong Peng, JieQing Liu, JianJun Xia, CuiFang Wang, XuYang Li, YuanYuan Deng, NiMan Bao, ZhiRun Zhang, MingHua Qiu

Phytochemistry 2015 Volume 114() pp:137-145

Publication Date(Web):June 2015

DOI:10.1016/j.phytochem.2014.10.009

•Fourteen lanostane triterpenoids were identified from Ganoderma hainanense.•X-ray single crystal diffraction analysis determined the 25S configuration in ganoderma acids from G. hainanense.•One of the triterpenoids has a 29-norlanostane structure.Chemical investigation of the fruiting bodies of Ganoderma hainanense resulted in isolation of fourteen lanostane triterpenoids, including nine ganoderma acids and five ganoderma alcohols, together with five known compounds. Structural elucidation was determined using extensive spectroscopic technologies, Mosher’s method and X-ray single crystal diffraction. Three of the compounds showed inhibitory activities against HL-60, SMMC-7721, A-549 and MCF-7 cells with IC50 values of 15.0–40.0 μM.Fourteen lanostane triterpenoids were identified from Ganoderma hainanense, of which one possesses a 29-norlanostane structure. X-ray single crystal diffraction analysis determined the absolute configuration of ganoderma acids from G. hainanense to be 25S.

New cycloartane triterpenes from the aerial parts of Cimicifuga heracleifolia

Co-reporter:Wei-Hua Wang, Yin Nian, Yu-Jiao He, Luo-Sheng Wan, Ni-Man Bao, Guo-Lei Zhu, Fei Wang, Ming-hua Qiu

Tetrahedron 2015 Volume 71(Issue 42) pp:8018-8025

Publication Date(Web):21 October 2015

DOI:10.1016/j.tet.2015.08.057

Twelve new cycloartane triterpenes (1–12), as well as five known constituents (13–17), were isolated from the aerial parts of Cimicifuga heracleifolia. Their structures were elucidated on the basis of extensive spectroscopic methods. Selected compounds were evaluated for their in vitro cytotoxicity against human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) and inhibitory activity with STAT 3 signaling pathway.

Hydroxyshengmanol-type triterpenoids from the aerial parts of Cimicifuga simplex Wormsk

Co-reporter:Ni-Man Bao, Yin Nian, Wei-Hua Wang, Xiao-Ling Liu, Zhong-Tao Ding, Ming-Hua Qiu

Phytochemistry Letters 2015 12() pp: 200-202

Publication Date(Web):

DOI:10.1016/j.phytol.2015.04.005

One-Step Semisynthesis Method of Spirocurcasone and Pyracurcasone from Curcusones A and B

Co-reporter:Xu-Yang Li, Yuan-Feng Yang, Xing-Rong Peng, Ming-Ming Li, Liang-Qun Li, Xu Deng, Hong-Bo Qin, Jie-Qing Liu, and Ming-Hua Qiu

Organic Letters 2014 Volume 16(Issue 8) pp:2196-2199

Publication Date(Web):April 3, 2014

DOI:10.1021/ol500692j

High contents of curcusones A and B and trace amounts of spirocurcasone exist in the roots of Jatropha curcas. Here, a one-step semisynthesis method of spirocurcasone and pyracurcasone was built, not only resulted an increased yield of spirocurcasone but also produced pyracurcasone, which exhibited greater cytotoxicity compared to curcusones A and B. The plausible mechanism of the formation of pyracurcasone was proposed, and the proposed biogenetic origin for spirocurcasone by Taglialatela-Scafati was confirmed.

Four New Polycyclic Meroterpenoids from Ganoderma cochlear

Co-reporter:Xing-Rong Peng, Jie-Qing Liu, Luo-Sheng Wan, Xiao-Nian Li, Yu-Xin Yan, and Ming-Hua Qiu

Organic Letters 2014 Volume 16(Issue 20) pp:5262-5265

Publication Date(Web):September 5, 2014

DOI:10.1021/ol5023189

Four pairs of new polycyclic-meroterpenoid enantiomers, ganocins A–C (1–3) possessing a spiro[4,5]decane ring system, along with ganocin D (4) with an eight-membered ring, were isolated from the fruiting bodies of Ganoderma cochlear. Their structures were determined by spectroscopic data and X-ray diffraction crystallography. Their anti-AChE activities were evaluated, and a possible biogenetic pathway was also proposed.

Hepatoprotective Effects of Triterpenoids from Ganoderma cochlear

Co-reporter:Xing-Rong Peng ; Jie-Qing Liu ; Cui-Fang Wang ; Xu-Yang Li ; Yi Shu ; Lin Zhou ;Ming-Hua Qiu

Journal of Natural Products 2014 Volume 77(Issue 4) pp:737-743

Publication Date(Web):February 21, 2014

DOI:10.1021/np400323u

Two novel trinorlanostanes, cochlates A and B (1 and 2), with a 3,4-seco-9,10-seco-9,19-cyclo skeleton, as well as six new triterpenoids, fornicatins D–F (3–5) and ganodercochlearins A–C (6–8), together with five known triterpenoids (9–13), were obtained from the fruiting bodies of Ganoderma cochlear. The structural elucidation was achieved by interpretation of spectroscopic data, and compounds 2 and 7a were further characterized by X-ray crystallographic analysis. Fornicatins A, D, and F (10, 3, and 5) and fredelin (13) lowered the ALT and AST levels in HepG2 cells treated with H2O2, suggesting that they could display in vivo hepatoprotective activities.

Characterization of Diterpenoid Glucosides in Roasted Puer Coffee Beans

Co-reporter:Yi Shu, Jie-Qing Liu, Xing-Rong Peng, Luo-Sheng Wan, Lin Zhou, Tao Zhang, and Ming-hua Qiu

Journal of Agricultural and Food Chemistry 2014 Volume 62(Issue 12) pp:2631-2637

Publication Date(Web):March 8, 2014

DOI:10.1021/jf500788t

Five new diterpenoid glucosides, named mascaroside I (1), mascaroside II (2), paniculoside VI (3), cofaryloside I (4), and villanovane I (5), along with seven known ent-kaurane diterpenoid glucosides (6–12) were isolated from acetone extracts of the roasted coffee beans of Coffea arabica var. yunnanensis. Their structures were established by extensive spectroscopic analysis including 1D and 2D NMR (HSQC, HMBC, COSY, and ROESY) and by comparison with published data. Cytotoxicities evaluation of the isolates showed that they were inactive against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cells.

An unusual 9,11-seco limonoid from Toona ciliata

Co-reporter:Jian-Jun Xia, Xu-Yang Li, Shao-Zhi Zhang, Jie-Qing Liu, Wei-Ming Zhang, Yu-xin Yan, Zhong-Tao Ding, Ming-Hua Qiu

Tetrahedron Letters 2014 Volume 55(Issue 13) pp:2104-2106

Publication Date(Web):26 March 2014

DOI:10.1016/j.tetlet.2014.02.057

An unusual 9,11-seco limonoid, toonasecone A (1), had been isolated from the bark of Toona ciliata. The structure was elucidated on the basis of extensive spectroscopic data analysis. This is the first time the 9,11-seco limonoid has been isolated from the Meliaceae family.

Four New Cucurbitacins from the Fruit of Momordica charantia

Co-reporter:Jian-Chao Chen;Xiao-Xi Yuan;Lin Zhou;Jie-Qing Liu;Yin Nian;Zhong-Rong Li;Yan Li;Ming-Jin Xie;Ming-Hua Qiu

Helvetica Chimica Acta 2014 Volume 97( Issue 11) pp:1546-1554

Publication Date(Web):

DOI:10.1002/hlca.201400051

Abstract

Four new 5β,19-epoxycucurbitacins, kuguacins T–W (1–4, resp.), along with nine known cucurbitane derivatives, 5–13, were obtained from the fresh fruit of Momordica chrantia. Structures of the new metabolites were elucidated as 5β,19-epoxy-25-hydroxycucurbitane-3,7,23-trione (1), 5β,19-epoxy-3,7-dioxo-23,24,25,26,27-pentanorcucurbitan-22-oic acid (2), 5β,19-epoxy-3β-hydroxycucurbit-24-ene-7,23-dione (3), and 5β,19-epoxy-25-hydroxycucurbit-23-ene-3,7-dione (4), by extensive spectroscopic investigations, which were confirmed by a single-crystal X-ray diffraction analyses in the case of compound 4.

Triterpenoids and Sterols from the Leaves and Twigs of Melia azedarach

Co-reporter:Wei-Ming Zhang;Jie-Qing Liu;Xing-Rong Peng

Natural Products and Bioprospecting 2014 Volume 4( Issue 3) pp:157-162

Publication Date(Web):2014 June

DOI:10.1007/s13659-014-0019-1

Two new triterpenoids (1 and 2) and a new sterol (3), together with six known constituents (4–9), were isolated from the leaves and twigs of Melia azedarach. Their chemical structures were elucidated on the basis of spectroscopic analysis.

Diterpenoids and Limonoids from the Leaves and Twigs of Swietenia mahagoni

Co-reporter:Wei-Ming Zhang;Jie-Qing Liu;Yuan-Yuan Deng

Natural Products and Bioprospecting 2014 Volume 4( Issue 1) pp:53-57

Publication Date(Web):2014 February

DOI:10.1007/s13659-014-0006-6

Three new compounds, including two diterpenoids, nemoralisins H and I (1 and 2), and a limonoid, 2-methoxy khayseneganin E (3), along with four known constituents (4–7), were isolated from the leaves and twigs of Swietenia mahagoni. Their chemical structures were elucidated by means of spectroscopic analysis. The cytotoxities of these isolated constituents were assayed.

Norfriedelins A–C with Acetylcholinesterase Inhibitory Activity from Acerola Tree (Malpighia emarginata)

Co-reporter:Jie-Qing Liu, Xing-Rong Peng, Xu-Yang Li, Ting-Zhao Li, Wei-Ming Zhang, Lei Shi, Jiang Han, and Ming-Hua Qiu

Organic Letters 2013 Volume 15(Issue 7) pp:1580-1583

Publication Date(Web):March 13, 2013

DOI:10.1021/ol4003702

Three novel norfriedelanes, A–C (1–3), were isolated from the branches and roots of Malpighia emarginata. Their structures and absolute configurations were determined by 1D and 2D NMR techniques and X-ray crystallographic analysis. Norfriedelin A (possessing an α-oxo-β-lactone group) and norfriedelin B (with a keto-lactone group) showed acetylcholinesterase inhibitory effects with the IC50 values of 10.3 and 28.7 μM, respectively.

Chukfuransins A–D, Four New Phragmalin Limonoids with β-Furan Ring Involved in Skeleton Reconstruction from Chukrasia tabularis

Co-reporter:Kun Hu, Jie-Qing Liu, Xiao-nian Li, Jian-Chao Chen, Wei-Ming Zhang, Yan Li, Liang-qun Li, Lin-lin Guo, Wei-guang Ma, and Ming-Hua Qiu

Organic Letters 2013 Volume 15(Issue 15) pp:3902-3905

Publication Date(Web):July 23, 2013

DOI:10.1021/ol401650m

Four new phragmalin limonoids (chukfuransins A–D) were isolated from the twigs and leaves of Chukrasia tabularis. Chukfuransins A (1) and B (2) feature a unique C-15/C-20 linkage proposed to be built by a biogenetic pathway involving Michael addition. Chukfuransins C (3) and D (4) feature the C-15/C-21 linkage. Their structures and absolute configurations were established by NMR techniques and X-ray crystallographic analysis.

Triterpenes from the Aerial Parts of Cimicifuga yunnanensis and Their Antiproliferative Effects on p53N236S Mouse Embryonic Fibroblasts

Co-reporter:Yin Nian ; Hui Zhu ; Wen-Ru Tang ; Yin Luo ; Jiang; Du ;Ming-Hua Qiu

Journal of Natural Products 2013 Volume 76(Issue 5) pp:896-902

Publication Date(Web):April 26, 2013

DOI:10.1021/np4000262

Nine new triterpene derivatives, yunnanterpenes A–F (1–6), 15,16-seco-cimiterpenes A and B (7, 8), and cimilactone C (9), and 15 known analogues (10–24) were isolated from the aerial parts of Cimicifuga yunnanensis. The new structures were established using a combination of MS, NMR, and single-crystal X-ray diffraction techniques. WT MEFs (wild-type mouse embryonic fibroblasts) and tumorigenic cell lines p53–/–+H-RasV12 and p53–/–+p53N236S+H-RasV12 were used for evaluating active structures, targeting p53N236S (corresponding to p53N239S in humans) mutation. Compound 5 showed nonselective activities against these cell lines, with IC50 values of 5.8, 8.6, and 6.0 μM, respectively. Compound 4 exhibited greater selectivity against the p53–/–+p53N236S+H-RasV12 cells (IC50 5.5 μM) than against the WT MEFs cells (IC50 14.3 μM).

Swietemahalactone, a rearranged phragmalin-type limonoid with anti-bacterial effect, from Swietenia mahagoni

Co-reporter:Jie-Qing Liu, Xing-Rong Peng, Wei-Ming Zhang, Lei Shi, Xu-Yang Li, Jian-Chao Chen and Ming-Hua Qiu

RSC Advances 2013 vol. 3(Issue 15) pp:4890-4893

Publication Date(Web):14 Feb 2013

DOI:10.1039/C3RA23401K

Swietemahalactone (1), a novel rearranged phragmalin-type limonoid, was isolated from Swietenia mahagoni. The structure of 1 was established on the basis of extensive spectroscopic and X-ray crystallographic methods. Swietemahalactone exhibited antibacterial activity using the agar diffusion method. The key biogenetic pathway of 1 is the semipinacol rearrangement.

Cucurbitane-Type Triterpenoids from Momordica charantia

Co-reporter:Bao-Hui Cheng;Jian-Chao Chen;Jie-Qing Liu;Lin Zhou ;Ming-Hua Qiu

Helvetica Chimica Acta 2013 Volume 96( Issue 6) pp:1111-1120

Publication Date(Web):

DOI:10.1002/hlca.201200329

Abstract

The six new cucurbitane-type triterpenoids 1–6, along with the ten known triterpenoids 7–16, were isolated from the vines and leaves of Momordica charantia. The structures of the new compounds were elucidated as (3β,7β,15β,23E)-3,7,15,25-tetrahydroxycucurbita-5,23-dien-19-al (1), (3β,7β)-3,7,22,23-tetrahydroxycucurbita-5,24-dien-19-al (2), (3β,7β)-3,7,23,24-tetrahydroxycucurbita-5,25-dien-19-al (3), (3β,7β,23S)-3,7,23-trihydroxycucurbita-5,24-dien-19-al 7-β-D-glucopyranoside (4), (3β,7β,23E)-cucurbita-5,23-diene-3,7,19,25-tetrol 7-β-D-glucopyranoside (5), and (3β,7β,23E)-3,7-dihydroxy-25-methoxy-cucurbita-5,23-dien-19-al 3-β-D-allopyranoside (6), by extensive analyses of their spectral data, as well as by chemical methods.

New triterpenoids from the kernels of Azadirachta indica

Co-reporter:Hong-Wei Wang;Jie-Qing Liu;Jin-Xiong Chen

Natural Products and Bioprospecting 2013 Volume 3( Issue 1) pp:33-37

Publication Date(Web):2013 February

DOI:10.1007/s13659-013-0005-z

Three new limonoids (1–3) and a new intact triterpenoid (4), along with three known constituents (5–7), were isolated from the dried kernels (after extracting azadirachtin) of Azadirachta indica. The structures of the new compounds 1-benzoyl-3-deacetyl-1-detigloyl salannin (1), 7-tigloyl-12-oxo vilasini (2), azadiralactone (3) and azadirahemiacetal (4) were elucidated by means of spectroscopic analysis. The cytotoxities of these isolated constituents were assayed.

Cytotoxicity of naturally occurring rhamnofolane diterpenes from Jatropha curcas

Co-reporter:Jie-Qing Liu, Yuan-Feng Yang, Xu-Yang Li, En-Qian Liu, Zhong-Rong Li, Lin Zhou, Yan Li, Ming-Hua Qiu

Phytochemistry 2013 Volume 96() pp:265-272

Publication Date(Web):December 2013

DOI:10.1016/j.phytochem.2013.09.008

Highlights•Nineteen diterpenoids were identified, of which 12 were previously unknown.•Curcusecons A–E have unusual secorhamnofolane skeletons.•Among the isolates, seven compounds had cytotoxic activity.•The dienone system in ring B is essential for cytotoxic activity.Twelve rhamnofolane diterpenoids, including curcusecons A–E with unusual seco-rhamnofolane skeletons, curcusones F–J, 4-epi-curcusone E, and 3-dehydroxy-2-epi-caniojane, together with seven known analogues, curcusones A–E, jatrogrossidione, and 2-epi-jatrogrossidione, were isolated from the roots of Jatropha curcas. Their structures were determined by extensive spectroscopic methods, and the relative stereochemistry of curcusecon B was further confirmed by X-ray crystallographic data. Their cytotoxity against five human cancer cells was studied and the results indicated that the dienone system in ring B was essential for cytotoxicity of these compounds.Twelve rhamnofolane diterpenoids, together with seven known analogues, were isolated from the roots of Jatropha curcas. The dienone system in ring B was essential for cytotoxicity of these compounds.

Three new physalins from Physalis alkekengi var. franchetii

Co-reporter:Wan-Xuan Xu;Jian-Chao Chen;Jie-Qing Liu;Lin Zhou

Natural Products and Bioprospecting 2013 Volume 3( Issue 3) pp:103-106

Publication Date(Web):2013 June

DOI:10.1007/s13659-013-0021-z

New jatropholane-type diterpenes from Jatropha curcas cv. Multiflorum CY Yang

Co-reporter:Yuan-Feng Yang;Jie-Qing Liu;Lei Shi;Zhong-Rong Li

Natural Products and Bioprospecting 2013 Volume 3( Issue 3) pp:99-102

Publication Date(Web):2013 June

DOI:10.1007/s13659-013-0031-x

New terpenoids from the roots of Jatropha curcas

Co-reporter:YuanFeng Yang;JieQing Liu;XuYang Li;EnQian Liu;ZhongRong Li

Science Bulletin 2013 Volume 58( Issue 10) pp:1115-1119

Publication Date(Web):2013 April

DOI:10.1007/s11434-012-5655-4

Two new sesquiterpenoids, (1S,2R)-dihydroxycycloax-4(15)-ene (1), 14-dehydroxyl daucucarotol (2), and one new rhamnofalane diterpenoid, 2-hydroxy-3-dehydroxycaniojane (3), together with two known compounds, curcusone D (4) and curcusone C (5), were isolated from the roots of Jatropha curcas. The chemical structures of these compounds were established by chemical methods and extensive 1D- and 2D-NMR spectroscopic data analyses.

Four New 9,19-Cyclolanostane Triterpenes from the Rhizomes of Cimicifuga foetida Collected in Yulong

Co-reporter:Haiyan Wang;Yin Nian;Chengyou Ma;Jieqing Liu;Yanbo Song;Lin Zhou

Chinese Journal of Chemistry 2012 Volume 30( Issue 6) pp:1265-1268

Publication Date(Web):

DOI:10.1002/cjoc.201200193

Abstract

Four new 9,19-cyclolanostane-type triterpenes (1–4), were isolated from the rhizomes of Cimicifuga foetida. On the basis of spectroscopic analysis, their chemical structures were elucidated as 1,7-dien-cimigenol-3,12-dione (1), 1-en-cimigenol-3,11-dione (2), 11(-hydroxy-7-en-cimigenol-3-one (3), and (20R,24R)-24,25-epoxy-11(-hydroxy-7-en-9,19-cyclolanost-3,16,23-trione (4).

Three New Pregnane Alkaloids from Veratrum taliense

Co-reporter:Yun Sun;Jin-Xiong Chen;Lin Zhou;Jia Su;Yan Li;Ming-Hua Qiu

Helvetica Chimica Acta 2012 Volume 95( Issue 7) pp:1114-1120

Publication Date(Web):

DOI:10.1002/hlca.201100461

Abstract

Three new alkaloids, 3-O-acetylveralkamine (1), veralkamine 3-(β-D-glucopyranoside) (2), and 6,7-epoxyverdine (3), together with five known alkaloids, veramitaline, veralkamine (4), angeloylzygadenine, veratroylzygadenine, and veramiline 3-(β-D-glucopyranoside), were isolated from the whole plants of Veratrum taliense. Their structures were elucidated on the basis of spectroscopic analysis, and the NMR data of veralkamine (4) are given for the first time. In addition, the cytotoxic activities of all isolated compounds, except for veramitaline, were tested.

Five New Tetranortriterpenoids from the Seeds of Toona ciliata

Co-reporter:Si-Yuan Jiang;Jie-Qing Liu;Jian-Jun Xia;Yu-Xin Yan;Ming-Hua Qiu

Helvetica Chimica Acta 2012 Volume 95( Issue 2) pp:301-307

Publication Date(Web):

DOI:10.1002/hlca.201100325

Abstract

Five new tetranortriterpenoids, toonaciliatones B–F (1–5, resp.), together with four known compounds, dihydrocedrelone (6), cedrelone (7), 6α-acetoxyazadirone (8), and 6α-acetoxy-14β,15β-epoxyazadirone (9), were isolated from the seeds of Toona ciliata. Their structures were elucidated by spectroscopic methods, including 1D- and 2D-NMR spectroscopy.

Three new diterpenes from Jatropha curcas

Co-reporter:Jie-Qing Liu, Yuan-Feng Yang, Cui-Fang Wang, Yan Li, Ming-Hua Qiu

Tetrahedron 2012 68(4) pp: 972-976

Publication Date(Web):

DOI:10.1016/j.tet.2011.12.006

Cytotoxic cycloartane triterpenes from the roots of Cimicifuga heracleifolia

Co-reporter:Yin Nian, Hai-Yan Wang, Jia Su, Lin Zhou, Gang Feng, Yan Li, Ming-Hua Qiu

Tetrahedron 2012 68(32) pp: 6521-6527

Publication Date(Web):

DOI:10.1016/j.tet.2012.05.083

Cucurbitane triterpenoids from Hemsleya penxianensis

Co-reporter:Jian-Chao Chen;Lin Zhou;Yun-Hua Wang

Natural Products and Bioprospecting 2012 Volume 2( Issue 4) pp:138-144

Publication Date(Web):2012 August

DOI:10.1007/s13659-011-0044-2

Limonoids from the leaves of Toona ciliata var. yunnanensis

Co-reporter:Jie-Qing Liu, Cui-Fang Wang, Yan Li, Jian-Chao Chen, Lin Zhou, Ming-Hua Qiu

Phytochemistry 2012 Volume 76() pp:141-149

Publication Date(Web):April 2012

DOI:10.1016/j.phytochem.2012.01.002

Twelve limonoids, toonayunnanins A–L (1–12) and eleven known compounds (13–23) were isolated from the leaves of Toona ciliata var. yunnanensis, and their structures were elucidated by means of extensive spectroscopic analyses, particularly 1D and 2D NMR techniques. The inhibitory effects of all the isolated compounds were evaluated on human tumor cell lines, such as HL-60, SMMC-7721, A-549, MCF-7 and SW480. Cedrelone (13) and dysobinin (18) showed significant cytotoxicity, and toonayunnanin B (2) and epoxyazadiradione (14), were found to be slightly cytotoxic against the above cell lines. Furthermore, this study provides valuable information for the chemotaxonomy of T. ciliata varieties.Graphical abstractLimonoids, toonayunnanins A–L and eleven known compounds (13–23) were isolated from leaves of Toona ciliata var. yunnanensis, and the cytotoxicity of all isolated compounds were evaluated. Cedrelone and dysobinin were cytotoxic, whereas toonayunnin B and epoxyazadiradione were slightly cytotoxic against the cell lines studied.Highlights► Twenty-three triterpenoids were identified, among them, twelve were previously unknown. ► Among the isolates, four compounds showed cytotoxic activities. ► A possible biogenetic pathway was discussed.

Three New Cycloartane (=9,19-Cyclolanostane) Glycosides from Cimicifuga foetida

Co-reporter:Da-Shan Li;Yin Nian;Yun Sun;Ming-Hua Qiu

Helvetica Chimica Acta 2011 Volume 94( Issue 4) pp:632-638

Publication Date(Web):

DOI:10.1002/hlca.201000226

Abstract

Three new cycloartane glycosides, 24-epicimigenol 3-(α-L-arabinopyranoside) (1), (3β,16β)-cycloartane-3,16,22,24,25-pentol 3-(β-D-xylopyranoside) (2), and (3β,15α,16β)-cycloartane-3,15,16,24,25-pentol 3-(β-D-xylopyranoside) (3), together with five known compounds, including four cycloartane glycosides and bergenin, were isolated from the rhizomes of Cimicifuga foetida. Their structures were elucidated by spectroscopic methods.

Cycloartane triterpenoids from the aerial parts of Cimicifuga foetida Linnaeus

Co-reporter:Yin Nian, Xian-Min Zhang, Yan Li, Yuan-Yuan Wang, Jian-Chao Chen, Lu Lu, Lin Zhou, Ming-Hua Qiu

Phytochemistry 2011 Volume 72(11–12) pp:1473-1481

Publication Date(Web):August 2011

DOI:10.1016/j.phytochem.2011.03.022

Cycloartane triterpenoids, 2′,24-O-diacetylisodahurinol-3-O-α-l-arabinopyranoside, 24-O-acetylisodahurinol-3-O-α-l-arabinopyranoside, 12β-hydroxy-25-anhydrocimigenol, cimigenol-12-one, 12β-hydroxy-15-deoxycimigenol, 2′-O-acetyl-24-epi-cimigenol-3-O-α-l-arabinopyranoside, 2′-O-acetylcimigenol-3-O-β-d-xylopyranoside, 25-anhydrocimigenol-3-O-α-l-arabinopyranoside, 2′,23-O-diacetylshengmanol-3-O-α-l-arabinopyranoside, and 2′,24-O-diacetyl-25-anhydrohydroshengmanol-3-O-α-l-arabinopyranoside, together with eight known compounds, were isolated from aerial parts of Cimicifuga foetida. Their structures were determined by application of spectroscopic analyses and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, SK-BR-3, and PANC-1 cell lines indicated that three of these compounds exhibited broad-spectrum and moderate cytotoxic activities, with IC50 values ranging from 6.20 to 22.74 μM. By comparing previous cytotoxic testing data and bioassay results from this study, preliminary structure–activity relationships of compounds with a cimigenol-skeleton can be proposed.Graphical abstractPhytochemical investigation of the aerial parts of Cimicifuga foetida led to isolation and identification of ten new 9,19-cycloartane triterpenes together with eight known compounds. Further pharmacological study showed that some of these compounds inhibited human tumor cell proliferation.Highlights► Eighteen 9,19-cycloartane triterpenes, including ten new analogues were isolated and identified from Cimicifuga foetida. ► Three isolated triterpenoids exhibited moderate and broad-spectrum cytotoxicities against the testing human tumor cell lines. ► Based on the analysis of reported bioassay results, Preliminary structure–activity relationships for active compounds with a cimigenol-skeleton were proposed.

New alkaloids from the fruiting bodies of Ganoderma sinense

Co-reporter:Jie-Qing Liu;Cui-Fang Wang;Xing-Rong Peng

Natural Products and Bioprospecting 2011 Volume 1( Issue 2) pp:93-96

Publication Date(Web):2011 October

DOI:10.1007/s13659-011-0026-4

Triterpenoid alkaloid derivatives from Buxus rugulosa

Co-reporter:Yu-Xin Yan;Lin Zhou;Yun Sun;Jian-Chao Chen

Natural Products and Bioprospecting 2011 Volume 1( Issue 2) pp:71-74

Publication Date(Web):2011 October

DOI:10.1007/s13659-011-0010-z

Three New Triterpenoids Containing Four-Membered Ring from the Fruiting Body of Ganoderma sinense

Co-reporter:Cui-Fang Wang, Jie-Qing Liu, Yu-Xin Yan, Jian-Chao Chen, Yang Lu, Yong-Hui Guo and Ming-Hua Qiu

Organic Letters 2010 Volume 12(Issue 8) pp:1656-1659

Publication Date(Web):March 16, 2010

DOI:10.1021/ol100062b

Methyl ganosinensate A (1), ganosinensic acid A (1a), and ganosinensic acid B (2), three new triterpenoids with an unusual four-membered ring skeleton produced by a bond across C-1 to C-11, were isolated from the fruiting body of Ganoderma sinense. Their structures were established on the basis of extensive spectroscopic methods, including 1D and 2D NMR techniques, and methyl ganosinensate A was confirmed by X-ray crystallographic analysis.

Cytotoxic Chemical Constituents from the Roots of Cimicifuga fetida

Co-reporter:Yin Nian, Yan-Li Zhang, Jian-Chao Chen, Lu Lu, Ming-Hua Qiu and Chen Qing

Journal of Natural Products 2010 Volume 73(Issue 2) pp:93-98

Publication Date(Web):February 2, 2010

DOI:10.1021/np9003855

Seven new 9,19-cycloartane triterpene glycosides, 25-O-acetylcimigenol-3-O-[2′-O-(E)-2-butenoyl]-β-d-xylopyranoside (1), 25-O-acetylcimigenol-3-O-[4′-O-(E)-2-butenoyl]-β-d-xylopyranoside (2), 25-O-acetylcimigenol-3-O-[3′-O-acetyl]-β-d-xylopyranoside (3), 25-O-acetylcimigenol-3-O-[4′-O-acetyl]-β-d-xylopyranoside (4), 25-O-acetyl-12β-acetoxycimigenol-3-O-β-d-xylopyranoside (5), 3′-O-acetylactein (6), and 3′-O-acetyl-23-epi-26-deoxyactein (7), together with eight known compounds (8−15), were isolated from the roots of Cimicifuga fetida. Their structures were established by spectroscopic and chemical methods. Most of these compounds showed more selective and higher cytotoxicity against the human HepG2 cell line than against the MCF7, HT29, and MKN28 cell lines. Compounds 2, 3, and 7 exhibited significant cytotoxicity against HepG2 cells, with IC50 values of 1.29, 0.71, and 1.41 μM, respectively.

Triterpenoid Alkaloids from Buxus microphylla

Co-reporter:Yu-Xin Yan;Jian-Chao Chen;Yun Sun;Yuan-Yuan Wang;Jia Su;Yan Li;Ming-Hua Qiu

Chemistry & Biodiversity 2010 Volume 7( Issue 7) pp:1822-1827

Publication Date(Web):

DOI:10.1002/cbdv.200900259

Abstract

Two new triterpenoid alkaloids, buxmicrophyllines J and K (1 and 2, resp.), together with four analogues, 3–6, were isolated from the leaves and stems of Buxus microphylla. The structures of the new compounds were elucidated by NMR and MS spectroscopic analyses. The partial assignments of the NMR spectra of 3 were also revised. Compounds 1 and 3–6 were evaluated for their growth inhibitory activity against human cell lines HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1. Compound 6 showed significant cytotoxicity against HL-60, SK-BR-3, and PANC-1 cell lines, with IC₅₀ values of 6.46, 19.61, and 28.57 μM, respectively.

Cytotoxic Triterpenoid Alkaloids from Buxus microphylla

Co-reporter:Yu-Xin Yan, Xiao-Dong Hu, Jian-Chao Chen, Yun Sun, Xian-Min Zhang, Chen Qing and Ming-Hua Qiu

Journal of Natural Products 2009 Volume 72(Issue 2) pp:308-311

Publication Date(Web):January 9, 2009

DOI:10.1021/np800719h

Five new triterpenoid alkaloids, buxmicrophyllines E−I (1−5), and six known ones (6−11) were isolated from the leaves and stems of Buxus microphylla. The structures of compounds 1−5 were elucidated by NMR and MS spectroscopic analysis, and the relative stereochemistry of 5 was determined by single-crystal X-ray crystallography. Compounds 3 and 9 were cytotoxic against HepG2 cells, with IC50 values of 0.89 and 0.78 μM, and compounds 2, 3, 7, 8, and 9 were cytotoxic against K562 cells, with IC50 values of 2.95, 4.44, 1.70, 5.61, and 0.37 μM, respectively.

Rational design and synthesis of highly potent anti-acetylcholinesterase activity huperzine A derivatives

Co-reporter:Jian Yan, Lirong Sun, Guisheng Wu, Ping Yi, Fumei Yang, Lin Zhou, Xianmin Zhang, Zhongrong Li, Xiaosheng Yang, Huairong Luo, Minghua Qiu

Bioorganic & Medicinal Chemistry 2009 Volume 17(Issue 19) pp:6937-6941

Publication Date(Web):1 October 2009

DOI:10.1016/j.bmc.2009.08.017

By targeting multi-active sites of acetylcholinesterase (AChE), a series of huperzine A (Hup A) derivatives with various aromatic ring groups were designed and synthesized by Schiff reaction. They were evaluated as AChE and butyrylcholinesterase (BChE) inhibitors. Results showed very significant specificity that the group of imine derivatives could inhibit TcAChE and hAChE, but no inhibitory effect on hBChE was detected. The experiment was explained by a docking study. In the docking model, we confirmed that aromatic ring of Hup A derivatives played the π–π stacking against aminophenol residues of AChE, and the structure–activity relationship (SAR) was discussed.

A new monoterpenoid indole alkaloid from Rauvolfia yunnanensis

Co-reporter:Bao Hui Cheng, Jian Chao Chen, Ming Hua Qiu

Chinese Chemical Letters 2009 Volume 20(Issue 10) pp:1221-1223

Publication Date(Web):October 2009

DOI:10.1016/j.cclet.2009.05.032

One new monoterpenoid indole alkaloid, 11-methoxyburnamine-17-O-3′,4′,5′-trimethoxybenzoate (1), was isolated from Rauvolfia yunnanensis Tsiang. Its structure was identified by spectroscopic evidences.

Three New Triterpene Saponins from Hemsleya chinensis

Co-reporter:Zhen-Jie Li;Jian-Chao Chen;Yun Sun;Na-Li Song;Bao-Hui Cheng;Lu Lu;Wei-Guang Ma;Lin Zhou;Xian-Min Zhang;Zhong-Rong Li;Ming-Hua Qiu

Helvetica Chimica Acta 2009 Volume 92( Issue 9) pp:1853-1859

Publication Date(Web):

DOI:10.1002/hlca.200900060

Abstract

Three new triterpenoid saponins, xuedanglycosides A–C (1–3, resp.), along with six known ones, were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra, by chemical methods, and by comparison with spectral data of known compounds, the structures of new compounds were determined to be 16α,23α-epoxy-2β,3α,20β-trihydroxy-10α,23α-cucurbita-5,24-dien-11-on-2-yl β-D-glucopyranoside (1), 2β,3α,16α,20β-tetrahydroxycucurbita-5,25-diene-11,22-dion-2-yl β-D-glucopyranoside (2), and oleanolic acid 28-O-β-xylopyranosyl-(16)-O-β-glucopyranoside (3). In addition, hemslecin A 2-O-β-D-glucopyranoside (6), hemsamabilinin B (7), and hemslonin A (9) were obtained for the first time from this plant.

Four New 9,19-Cyclolanostane Derivatives from the Rhizomes of Cimicifuga yunnanensisHsiao

Co-reporter:Yin Nian;Jian-Chao Chen;Lu Lu;Xian-Ming Zhang;Lin Zhou;Ming-Hua Qiu

Helvetica Chimica Acta 2009 Volume 92( Issue 1) pp:

Publication Date(Web):

DOI:10.1002/hlca.200800231

Six New Triterpenoid Glycosides from Gynostemma pentaphyllum

Co-reporter:Jie-Qing Liu;Cui-Fang Wang;Jian-Chao Chen;Shang-Hui Tu;Hong-Fei Gu;Wen-Xiang Hu;Ming-Hua Qiu

Helvetica Chimica Acta 2009 Volume 92( Issue 12) pp:2737-2745

Publication Date(Web):

DOI:10.1002/hlca.200900100

Abstract

Six new triterpenoid glycosides, gynosaponins I–VI (1–6, resp.), together with three known compounds, ginseng Rb₁ (7), gypenoside XLIX (8), and gylongiposide I (9), were isolated from the aerial parts of Gynostemma pentaphyllum. Based on ESI-MS, IR, 1D- and 2D-NMR data (HMQC, HMBC, COSY, and TOCSY), the structures of the new compounds were determined as (3β,12β,20S)-trihydroxydammar-24-ene 20-O-[α-rhamnopyranosyl-(12)]-β-glucopyranoside (1), (3β,12β,20S)-trihydroxydammar-24-ene 20-O-[α-rhamnopyranosyl-(12)] [α-rhamnopyranosyl-(13)]-β-glucopyranoside (2), (3β,12β,20S)-trihydroxydammar-24-ene 3-O-β-glucopyranosyl-20-O-[α-rhamnopyranosyl-(12)]-β-glucopyranoside (3), (3β,12β,20S)-trihydroxydammar-24-ene 3-O-β-glucopyranosyl-20-O-[α-rhamnopyranosyl-(12)] [α-rhamnopyranosyl-(13)]-β-glucopyranoside (4), (3β,12β,20S)-trihydroxydammar-24-ene 3-O-{[β-glucopyranosyl-(12)]-β-glucopyranosyl}-20-O-[α-rhamnopyranosyl-(12)]-β-glucopyranoside (5), and (3β,12β,20S)-trihydroxydammar-24-ene 3-O-{[β-glucopyranosyl-(12)]-β-glucopyranosyl}-20-O-[α-rhamnopyranosyl-(12)] [α-rhamnopyranosyl-(13)]-β-glucopyranoside (6).

Kuguacins F–S, cucurbitane triterpenoids from Momordica charantia

Co-reporter:Jian-Chao Chen, Wu-Qing Liu, Lu Lu, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Xian-Min Zhang, Lin Zhou, Zhong-Rong Li

Phytochemistry 2009 Volume 70(Issue 1) pp:133-140

Publication Date(Web):January 2009

DOI:10.1016/j.phytochem.2008.10.011

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.Fourteen cucurbitane derivatives, including two pentanorcucurbitacins, one octanorcucurbitacin, and two trinorcucurbitacins, were isolated from the vines and leaves of Momordica charantia.

Octanorcucurbitane and Cucurbitane Triterpenoids from the Tubers of Hemsleya endecaphylla with HIV-1 Inhibitory Activity

Co-reporter:Jian-Chao Chen, Gao-Hong Zhang, Zhong-Quan Zhang, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang and Kai-Bei Yu

Journal of Natural Products 2008 Volume 71(Issue 1) pp:153-155

Publication Date(Web):December 19, 2007

DOI:10.1021/np0704396

Two new cucurbitacins, endecaphyllacins A (1) and B (2), together with six known analogues (3−8), were isolated from the tubers of Hemsleya endecaphylla. The structures of 1 and 2 were elucidated by NMR and MS spectroscopic analysis. The relative stereochemistry of 1 was determined by single-crystal X-ray diffraction. Compound 4 (cucurbitacin B) showed potent anti-HIV-1 in C8166 cells (EC = 0.09 µg/mL) with a selectivity index of 16.7.

3D-QSAR studies of Checkpoint Kinase Weel inhibitors based on molecular docking, CoMFA and CoMSIA

Co-reporter:Ping Yi, Xin Fang, Minghua Qiu

European Journal of Medicinal Chemistry 2008 Volume 43(Issue 5) pp:925-938

Publication Date(Web):May 2008

DOI:10.1016/j.ejmech.2007.06.021

Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies were performed on 97 4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione inhibitors, based on molecular docking scores obtained by using GOLD 3.1, comparative molecular field analysis (CoMFA) and comparative molecular similarity indices (CoMSIA). The docking results provided a reliable conformational alignment scheme for the 3D-QSAR model. Based on the docking conformations and alignments, highly predictive CoMFA and CoMSIA were obtained with cross-validated q2 value of 0.828 and 0.796, respectively, and non-cross-validated partial least-squares (PLS) analysis with the optimum components of five showed a conventional r2 of 0.962 and 0.949, respectively. The predictive ability was validated by compounds that were not included in the training set. Furthermore, the CoMFA and CoMSIA model plots were mapped back to the binding sites of Checkpoint Kinase Weel, to get a better understanding of vital interactions between the inhibitors and Weel kinase. As a result, we have identified some key features in the 4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones responsible for the Weel inhibitory activity that may be used to design more potent 4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones and predict their activity prior to synthesis.Molecular docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA were applied to a set of novel 4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Checkpoint Kinase Weel inhibitors.

3D-QSAR and docking studies of aminopyridine carboxamide inhibitors of c-Jun N-terminal kinase-1

Co-reporter:Ping Yi, Minghua Qiu

European Journal of Medicinal Chemistry 2008 Volume 43(Issue 3) pp:604-613

Publication Date(Web):March 2008

DOI:10.1016/j.ejmech.2007.04.020

In order to better understand the structural and chemical features of c-Jun N-terminal kinase-1 (JNK-1), which is a member of the mitogen activated protein kinase (MAP kinase) family of enzymes responsible for the serine/threonine phosphorylation of intracellular targets, 3D-QSAR studies of some aminopyridine carboxamides as c-Jun N-terminal kinase inhibitors were performed by comparative molecular field analysis (CoMFA) to rationalize the structural requirements responsible for the inhibitory activity of these compounds. The genetic algorithm of GOLD3.1 has been employed to position 54 aminopyridine carboxamides in the active sites of JNK-1 to determine the probable binding conformation. The docking results provided a reliable conformational alignment scheme for 3D-QSAR model. Based on the docking conformations, highly predictive comparative molecular field analysis (CoMFA) was performed with a cross-validated q2 of 0.585. The non-cross-validated analysis with six optimum components revealed a conventional r2 value of 0.988, F = 510.200, and an estimated standard error of 0.071. Furthermore, the CoMFA model was mapped back to the binding sites of JNK-1, to get a better understanding of vital interactions between the aminopyridine carboxamides and the kinase. Based on the docking and CoMFA analyses, we have identified some key features in the aminopyridine carboxamides that are responsible for JNK-1 inhibitory activity. The analyses may be used to design more potent aminopyridine carboxamides and predict their activity prior to synthesis.Molecular docking and three-dimensional quantitative structure–activity relationship (3D-QSAR) methods, CoMFA, were applied to a set of novel aminopyridine carboxamide c-Jun N-terminal kinase inhibitors.

Eight New Cucurbitane Glycosides, Kuguaglycosides AH, from the Root of Momordica charantia L.

Co-reporter:Jian-Chao Chen;Lu Lu;Xian-Ming Zhang;Lin Zhou;Zhong-Rong Li;Ming-Hua Qiu

Helvetica Chimica Acta 2008 Volume 91( Issue 5) pp:920-929

Publication Date(Web):

DOI:10.1002/hlca.200890097

Abstract

Eight new cucurbitane glycosides, kuguaglycosides A–H (1–8, resp.), together with five known analogues, 3β,23-dihydroxycucurbita-5,24-dien-7β-yl β-D-glucopyranoside (9), karaviloside III (10), karaviloside V (11), karaviloside XI (12), and momordicoside K (13), were isolated from the root of Momordica charantia L. The structures of the new compounds were determined on the basis of spectroscopic and chemical methods.

Two New Spirostanol Saponins from Reineckia carnea

Co-reporter:Zhong-Quan Zhang;Jian-Chao Chen;Xian-Ming Zhang;Zhong-Rong Li;Ming-Hua Qiu

Helvetica Chimica Acta 2008 Volume 91( Issue 8) pp:1494-1499

Publication Date(Web):

DOI:10.1002/hlca.200890162

Abstract

Two new spirostanol saponins, (1β,3β,5β,25S)-spirostan-1,3-diol 1-(β-D-xylopyranoside) (1) and (1β,3β,5β,25S)-spirostan-1,3-diol 1-[α-L-rhamnopyranosyl-(12)-β-D-fucopyranoside] (2), along with two known compounds, (1β,3β,5β,25S)-spirostan-1,3-diol 1-[α-L-rhamnopyranosyl-(12)-β-D-xylopyranoside] (3) and (1β,3β,4β,5β,25S)-spirostan-1,3,4,5-tetrol 5-(β-D-glucopyranoside) (4) were isolated from the whole plant of Reineckia carnea. The structures of the new steroids were determined by detailed analysis of their 1D- and 2D-NMR spectra and chemical methods, and by comparison with spectral data of known compounds. Compounds 3 and 4 were isolated from the genus Reineckia for the first time.

A New Alkaloid from Lycopodium japonicumThunb.

Co-reporter:Yun Sun;Jian Yan;Hao Meng;Chun-Lin He;Ping Yi;Ying Qiao;Ming-Hua Qiu

Helvetica Chimica Acta 2008 Volume 91( Issue 11) pp:

Publication Date(Web):

DOI:10.1002/hlca.200890225

Abstract

A new alkaloid, miyoshianine C (1), was isolated from the whole plants of Lycopodium japonicumThunb., together with the known four compounds α-obscurine (2), lycodoline (3), miyoshianine A (4), and lucidioline (5). Their structures were elucidated on the basis of in-depth spectroscopic analysis.

Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia

Co-reporter:Jianchao Chen, Renrong Tian, Minghua Qiu, Lu Lu, Yongtang Zheng, Zhongquan Zhang

Phytochemistry 2008 Volume 69(Issue 4) pp:1043-1048

Publication Date(Web):February 2008

DOI:10.1016/j.phytochem.2007.10.020

Five cucurbitacins, kuguacins A–E (1–5), together with three known analogues, 3β,7β,25-trihydroxycucurbita-5,(23E)-diene-19-al (6), 3β,25-dihydroxy-5β,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 EC50 values of 8.45 and 25.62 μg/ml, and exerted minimal cytotoxicity against C8166 cells (IC50 > 200 μg/ml), with a selectivity index more than 23.68 and 7.81, respectively.Cucurbitacins, kuguacins A–E (1–5), were isolated from the roots of Momordica charantia together with three known analogues. Compounds (3–5) possess an unprecedented 25,26,27-trinorcucurbitane backbone. Kuguacin C (3) showed moderate anti-HIV-1 activity with a selectivity index more than 23.68.

Polyhydroxyserratane triterpenoids from Diphasiastrum complanatum

Co-reporter:Jian Yan, Ping Yi, Baohui Chen, Lu Lu, Zhongrong Li, Xianmin Zhang, Lin Zhou, Minghua Qiu

Phytochemistry 2008 Volume 69(Issue 2) pp:506-510

Publication Date(Web):January 2008

DOI:10.1016/j.phytochem.2007.07.024

Serratane triterpenoids were identified from Diphasiastrum complanatum (L.) Holub, including serratane-3α,14α,15α,20β,21β,24,29-heptol (1), 3α,20β,21β-trihydroxyserrat-14-en-24-oic acid (2), 3β,20β,21β-trihydroxyserrat-14-en-24-oic acid (3), 3α,20β,21β-trihydroxy-16-oxoserrat-14-en-24-oic acid (4), and 16-oxolyclanitin-29-yl E-4′-hydroxyl-3′-methoxycinnamate (5) on the basis of their spectroscopic data as well as nine known analogs.Five polyhydroxyserratane triterpenoids was isolated from Diphasiastrum complanatum including serratane-3α,14α,15α,20β,21β,24, 29-heptol (1), given the trivial name diphasiastrol.

Two New Cholestane Bisdesmosides from Reineckia carnea

Co-reporter:Zhong-Quan Zhang;Jian-Chao Chen;Ming-Hua Qiu;Lin Zhou

Helvetica Chimica Acta 2007 Volume 90(Issue 3) pp:616-622

Publication Date(Web):19 MAR 2007

DOI:10.1002/hlca.200790063

Three cholestane bisdesmosides, together with the corresponding aglycone, were isolated from the whole plant of Reineckia carnea. By detailed analysis of the 1D- and 2D-NMR spectra, chemical methods, and comparison with spectral data of known compounds, the structures were determined to be (1β,3β,16β,22S)-cholest-5-ene-1,3,16,22-tetrol (1), (1β,3β,16β,22S)-cholest-5-ene-1,3,16,22-tetrol 1,16-di(β-D-glucopyranoside) (2), (1β,3β,16β,22S)-cholest-5-ene-1,3,16,22-tetrol 1-[O-α-L-rhamnopyranosyl-(12)-β-D-glucopyranoside] 16-(β-D-glucopyranoside) (3), (1β,3β,16β,22S)-cholest-5-ene-1,3,16,22-tetrol 1-(β-D-glucopyranoside) 16-(3-O-acetyl-β-D-glucopyranoside) (4). Compounds 3 and 4 appeared to be new compounds, while compound 1 was isolated for the first from a natural source. Compound 2 was isolated from the genus Reineckia for the first time.

Cimicifine A: A Novel Triterpene Alkaloid from the Rhizomes of Cimicifuga foetida

Co-reporter:Li-Rong Sun;Jian Yan;Zhong-Rong Li;Sheng-Ji Pei;Lu Lu;Lin Zhou;Xian-Min Zhang;Ming-Hua Qiu

Helvetica Chimica Acta 2007 Volume 90(Issue 7) pp:1313-1318

Publication Date(Web):16 JUL 2007

DOI:10.1002/hlca.200790132

Cimicifine A (1), the first cycloartane triterpene alkaloid, was isolated from the rhizomes of Cimicifuga foetida, together with the known compound cimicifugoside H-1 (2). Their chemical structures were established by extensive NMR and MS analyses and by comparison with literature.

Chemical Constituents from Craibiodendron yunnanense

Co-reporter:Sheng-Xiang Yang;Jian-Chun Qin;Lin Zhou;Lei Wang;Jin-Ming Gao;Ming-Hua Chiu

Helvetica Chimica Acta 2007 Volume 90(Issue 8) pp:1477-1481

Publication Date(Web):21 AUG 2007

DOI:10.1002/hlca.200790153

A new triterpene, (3β,12β)-taraxast-20(30)-ene-3,12-diol (=(3β,12β,18α,19α)-urs-20(30)-ene-3,12-diol; 1), together with the known compounds ursolic acid, α-amyrin, β-amyrin, (2α,3β)-2,3-dihydroxyursa-5,12-dien-28-oic acid, (2α,3β)-2,3,23-trihydroxyurs-12-en-28-oic acid, (2S,3S,4R,8Z)-1-O-(β-D-glucopyranosyl)-2-{[(2R)-2-hydroxydocosanoyl]amino}octadec-8-ene-1,3,4-triol, and (2S,3S,4R,8Z)-1-O-(β-D-glucopyranosyl)-2-[(palmitoyl)amino]octadec-8-ene-1,3,4-triol, and quercetin 3-(β-D-glucopyranoside) were isolated from the leaves of Craibiodendron yunnanense. Their structures were established on the basis of spectral evidence. The last four compounds were identified for the first time in this plant.

A New 18(13 12β)-abeo-Lanostadiene Triterpenoid from Ganoderma fornicatum

Co-reporter:Ying Qiao;Xue-Chang Dong;Xian-Min Zhang;Ming-Hua Qiu

Helvetica Chimica Acta 2006 Volume 89(Issue 5) pp:1038-1041

Publication Date(Web):24 MAY 2006

DOI:10.1002/hlca.200690081

A new triterpenoid, fornicatin C (= (3β)-3-hydroxy-18(13 12β)-abeo-lanosta-13(17),24-dien-18-oic acid; 1), was isolated from the fruiting bodies of Ganoderma fornicatum, together with the known compounds fornicatin A (2) and fornicatin B (3), among other constituents. The structure of 1 was elucidated by means of spectroscopic techniques, and those of 2 and 3 were identified by comparing their spectroscopic data with those reported in the literature.

Three New Serratane Triterpenoids from Phlegmariurus squarrosus

Co-reporter:Jian Yan;Bao-Hui Cheng;Xian-Min Zhang;Ming-Hua Qiu

Helvetica Chimica Acta 2006 Volume 89(Issue 12) pp:2975-2980

Publication Date(Web):15 DEC 2006

DOI:10.1002/hlca.200690266

Three new serratane triterpenoids, (3α,14α,15α,21α)-3,14,15,21,29-pentahydroxyserratan-24-oic acid (1), (3α,21β)-serrat-14-ene-3,21,24,30-tetraol (2), and (3α,21α)-serrat-14-ene-3,21,24,29-tetraol (3), were isolated from Phlegmariurus squarrosus, together with eight known compounds. Their chemical structures were elucidated on the basis of in-depth spectroscopic analyses.

Three New Triterpenoids from Lycopodium japonicumThunb

Co-reporter:Jian Yan;Zhong-Rong Li;Xiang-Ming Zhang;Lin Zhou;Li-Rong Sun;Jian-Chao Chen;Ming-Hua Qiu

Helvetica Chimica Acta 2005 Volume 88(Issue 2) pp:240-244

Publication Date(Web):18 FEB 2005

DOI:10.1002/hlca.200590004

Three new triterpenoids, (3β,8β,14α,21α)-26,27-dinoronocerane-3,8,14,21-tetrol (1), (3β,8β,14α,21β)-26,27-dinoronocerane-3,8,14,21-tetrol (2), and lycopodiin A (3), together with four known compounds, lycoclavanol (4), lycoclaninol (5), α-onocerin (6), and 3-epilycoclavanol (7), were isolated from Lycopodium japonicum Thunb (Lycopodiaceae). Their structures were established by means of spectroscopic analyses. Compounds 3 and 7 showed moderate antitumor activity. Compounds 4 and 6 exhibited acetylcholinesterase inhibition activity.

Two New Pregnanone Derivatives with Strong Cytotoxic Activity from Pachysandra axillaris

Co-reporter:Ming-Hua Qiu;Masao Hattori;Byung-Sun Min;Norio Nakamura

Chemistry & Biodiversity 2005 Volume 2(Issue 7) pp:866-871

Publication Date(Web):18 JUL 2005

DOI:10.1002/cbdv.200590063

Two new, bioactive, pregnane-based natural products, pachysanonin (=3β,11α,12β)-12-acetoxy-3-(dimethylamino)-11-[(3,4-dimethylpent-3-enoyl)oxy]pregnan-20-one; 1) and pachysanone (=(11α,12β)-12-acetoxy-11-[(3,4-dimethylpent-3-enoyl)oxy]pregnan-3,20-dion; 2) have been isolated from Pachysandra axillaris. Their structures were determined by spectroscopic methods, and, in the case of 2, by single-crystal X-ray crystallography (Figure). Compound 2 showed significant antitumor activity against Lewis lung carcinoma (LCC) tumor cells, with an IC₅₀ value of 0.020±0.006 μg/ml, which is equal or even lower than those of the well-known natural antitumor agents harringtonine (0.02), homoharringtonine (0.15), and adriamycin (0.06 μg/ml; positive control).

Antioxidant farnesylated hydroquinones from Ganoderma capense

Co-reporter:Xingrong Peng, Lei Li, Xia Wang, Guolei Zhu, Zhongrong Li, Minghua Qiu

Fitoterapia (June 2016) Volume 111() pp:18-23

Publication Date(Web):1 June 2016

DOI:10.1016/j.fitote.2016.04.006

Phytochemical investigation of the fruiting bodies of Ganoderma capense led to isolation of eight aromatic meroterpenoids (1–8). Ganocapensins A and B (1, 2) possessed a thirteen-membered and a fourteen-membered ether rings, respectively. The structures of new isolates including absolute configuration were elucidated on the basis of extensive spectroscopic technologies and Mosher's method. All isolated compounds showed significant antioxidant effects with IC50 values ranging from 6.00 ± 0.11 to 8.20 ± 0.30 μg/ml in the DPPH radical scavenging assay.Download high-res image (298KB)Download full-size image

Hydroxyshengmanol-type triterpenoids from the aerial parts of Cimicifuga simplex Wormsk

Co-reporter:Ni-Man Bao, Yin Nian, Wei-Hua Wang, Xiao-Ling Liu, Zhong-Tao Ding, Ming-Hua Qiu

Phytochemistry Letters (June 2015) Volume 12() pp:200-202

Publication Date(Web):1 June 2015

DOI:10.1016/j.phytol.2015.04.005

•New hydroxyshengmanol-type triterpenoids with a carbonyl group at C-15 are rare in cimicifuga spp.•The absolute configuration of hydroxyshengmanol was initially determined through X-ray diffraction.•Compounds 7 and 8 showed inhibitory activity on AchE.New hydroxyshengmanol-type triterpenoids (1–8) were identified from the aerial parts of cimicifuga simplex Wormsk by comprehensive 1D and 2D NMR, MS, and single-crystal X-ray diffraction analyses. The absolute configuration of the himeketal carbon (C-16) in hydroxyshengmanol-type constituents from cimicifuga spp. was initially determined as R using X-ray diffraction. All compounds were evaluated for their cytotoxicity in a panel of cancer cell lines and acetylcholinesterase inhibitory activity.Download full-size image

Six new physalins from Physalis alkekengi var. franchetii and their cytotoxicity and antibacterial activity

Co-reporter:Ye-Kun Yang, Si-da Xie, Wan-xuan Xu, Yin Nian, Xiao-Ling Liu, Xing-Rong Peng, Zhong-Tao Ding, Ming-Hua Qiu

Fitoterapia (July 2016) Volume 112() pp:144-152

Publication Date(Web):1 July 2016

DOI:10.1016/j.fitote.2016.05.010

Six new physalin steroids, 7β-methoxylisophysalin B (1), 7β-methoxylphysalin C (2), physalin V (3), physalin VI (4), physalin VII (5), isophysalin I (6), together with 20 known physalins (7–26) were isolated from calyces of Physalis alkekengi var. franchetii. Structures of the new compounds were revealed through 1D and 2D NMR and mass spectroscopic methods. Compounds 1–26 were evaluated for cytotoxicity against human HL-60, SMMC-7721, A-549, MCF-7 and SW-480, and the results indicated that compounds 8, 11, and 14 displayed potent cytotoxicities (IC50 < 5 μM) in vitro. Further antibacterial assay indicated that compounds 8, 14, and 19 showed high antibacterial activities against Bacillus subtilis and Escherichia coli.Download high-res image (233KB)Download full-size image

Pregnane alkaloids from Pachysandra axillaris

Co-reporter:Yun Sun, Yu-Xin Yan, Jian-Chao Chen, Lu Lu, Xian-Min Zhang, Yan Li, Ming-Hua Qiu

Steroids (December 2010) Volume 75(Issue 12) pp:818-824

Publication Date(Web):1 December 2010

DOI:10.1016/j.steroids.2010.05.005

Nine new pregnane alkaloids, pachysamines J–R (1–9), together with seven known ones, were isolated from Pachysandra axillaris. The chemical structures of the new alkaloids were elucidated by spectroscopic methods. All the compounds were evaluated for their inhibitory activities against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Compound 15 possessed moderate activities against A-549, SK-BR-3, and PANC-1 cells, with the IC50 values of 11.17, 4.17, and 10.76 μM, respectively. Besides, compound 11 showed cytotoxicities against A-549 cell, with the IC50 values as 24.94 μM.Research highlights▶ Nine new pregnane alkaloids were isolated from Pachysandra axillaris. ▶ All the compounds evaluated for their inhibitory activities against human tumor cell lines of HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1. ▶ Compounds 15 and 11 showed cytotoxicities.