Li-she Gan

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Organization: Zhejiang University

Department: College of Pharmaceutical Sciences

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Chemicals
References

Terpenoids from Curcuma wenyujin increased glucose consumption on HepG2 cells

Co-reporter:Chang-Xin Zhou, Li-Sha Zhang, Fei-Fei Chen, Hao-Shu Wu, Jian-Xia Mo, Li-She Gan

Fitoterapia 2017 Volume 121(Volume 121) pp:

Publication Date(Web):1 September 2017

DOI:10.1016/j.fitote.2017.06.011

Thirty four terpenoids, including two new cadinane-type sesquiterpenoids containing conjugated aromatic-ketone moieties, curcujinone A (1) and curcujinone B (2), were isolated from 95% ethanol extract of the root tubers of Curcuma wenyujin. Their structures were determined by spectroscopic methods, especially 2D NMR and HRMS techniques. The relative and absolute configurations of 1 and 2 were identified by quantum chemical DFT and TDDFT calculations of the 13C NMR chemical shifts, ECD spectra, and specific optical rotations. All compounds and extracts were evaluated for their anti-diabetic activities with a glucose consumption model on HepG2 Cells. The petroleum fraction CWP (10 μg/mL) and compounds curcumenol (4), 7α,11α-epoxy-5β-hydroxy-9-guaiaen-8-one (5), curdione (17), (1S, 4S, 5S 10S)-germacrone (18), zederone (20), a mixture of curcumanolide A (25) and curcumanolide B (26), gajutsulactone B (27), and wenyujinin C (30) showed promising activities with over 45% increasing of glucose consumption at 10 μM.Download high-res image (237KB)Download full-size image

Corroborating study on the absolute configurations of trigochinins A–C

Co-reporter:Yao-Yue Fan, Shi-Xin Chen, Qun-Fang Liu, Li-She Gan, Jian-Min Yue

Tetrahedron Letters 2017 Volume 58, Issue 50(Issue 50) pp:

Publication Date(Web):13 December 2017

DOI:10.1016/j.tetlet.2017.11.012

•Trigochinins A–C (1–3) are three highly oxygenated daphnane-type diterpenes.•The absolute configuration of 1 was confirmed by X-ray crystallography study.•The absolute configurations of 2 and 3 were confirmed by theoretical ECD study.Trigochinins A–C (1–3) are three highly oxygenated daphnane-type diterpenes isolated from Trigonostemon chinensis. Their structures with the absolute configurations were initially assigned by a combination of spectroscopic data, X-ray crystallography (Mo Kα radiation) study and CD analysis. In the current study, the absolute configurations of trigochinins A–C were confirmed by single crystal X-ray diffraction (Cu Kα radiation) study, CD spectral analogy, and theoretical ECD study by using quantum chemical TDDFT calculations.Download high-res image (86KB)Download full-size image

Antibacterial Biphenanthrenes from the Fibrous Roots of Bletilla striata

Co-reporter:Chao-Dong Qian; Fu-Sheng Jiang; Hang-Su Yu; Yong Shen; Yu-Hang Fu; Dong-Qing Cheng; Li-She Gan;Zhi-Shan Ding

Journal of Natural Products 2015 Volume 78(Issue 4) pp:939-943

Publication Date(Web):March 11, 2015

DOI:10.1021/np501012n

Four new 9′,10′-dihydro-biphenanthrenes, including an unprecedented 1,2′-linked biphenanthrene, 4,7,3′,5′-tetramethoxy-9′,10′-dihydro(1,2′-biphenanthrene)-2,7′-diol (1), a new 1,3′-linked biphenanthrene, 4,7,7′-trimethoxy-9′,10′-dihydro(1,3′-biphenanthrene)-2,2′,5′-triol (2), and two new 1,1′-linked biphenanthrenes, 4,7,4′-trimethoxy-9′,10′-dihydro(1,1′-biphenanthrene)-2,2′,7′-triol (3) and 4,7,3′,5′-tetramethoxy-9′,10′-dihydro(1,1′-biphenanthrene)-2,2′,7′-triol (4), as well as two known biphenanthrenes (5, 6), were isolated from a 95% ethanol extract of the fibrous roots of Bletilla striata. Their structures were determined by spectroscopic and spectrometric methods. Atropisomerism of these compounds was considered based on their chiral optical properties and potential energy surface scans at the ab initio HF/3-21G level, which revealed their racemic mixture form. Compounds 2–6 showed potent antibacterial activities against six Gram-positive bacterial strains.

(±)-Torreyunlignans A–D, Rare 8–9′ Linked Neolignan Enantiomers as Phosphodiesterase-9A Inhibitors from Torreya yunnanensis

Co-reporter:Zhong-Bin Cheng ; Xiao Lu ; Jing-Mei Bao ; Qing-Hua Han ; Zhen Dong ; Gui-Hua Tang ; Li-She Gan ; Hai-Bin Luo ;Sheng Yin

Journal of Natural Products 2014 Volume 77(Issue 12) pp:2651-2657

Publication Date(Web):December 12, 2014

DOI:10.1021/np500528u

(±)-Torreyunlignans A–D (1a/1b–4a/4b), four pairs of new 8–9′ linked neolignan enantiomers featuring a rare (E)-2-styryl-1,3-dioxane moiety, were isolated from the trunk of Torreya yunnanensis. The structures were determined by combined spectroscopic and chemical methods, and the absolute configurations were elucidated by ECD calculations. The compounds were screened by using tritium-labeled adenosine 3′,5′-cyclic monophosphate ([3H]-cGMP) as a substrate for inhibitory affinities against phosphodiesterase-9A (PDE9A), which is a potential target for the treatment of diabetes and Alzheimer’s disease. All of the enantiomers exhibited inhibition against PDE9A with IC50 values ranging from 5.6 to 15.0 μM. This is the first report of PDE9A inhibitors from nature.

Two New Cycloartane Triterpenoids from Kleinhovia hospita

Co-reporter:Jian-Xia Mo;Yang Bai;Bo Liu;Chang-Xin Zhou;Li Zou

Helvetica Chimica Acta 2014 Volume 97( Issue 6) pp:887-894

Publication Date(Web):

DOI:10.1002/hlca.201300331

Abstract

Two new cycloartane triterpenoids, (23R)-21,23:23,27-diepoxycycloarta-1,24-diene-3,27-dione (1) and (3α)-(α-L-arabinopyranosyloxy)-1α-hydroxy-23-oxocycloartan-28-oic acid (2), together with six known pentacyclic triterpenoids, 3–8, and five known C₂₉ steroids, 9–13, were isolated from Kleinhovia hospita. The structures of these compounds were determined by analysis of their spectroscopic data. Moreover, the absolute configuration of 1 was confirmed by quantum-chemical TDDFT calculation of its ECD spectrum. All compounds were evaluated for their cytotoxic activities against human colon carcinoma (HCT116) and gastric carcinoma (SGC7901) cell lines, and compounds 6, 7, 8, 11, and 12 exhibited antiproliferative activities with IC₅₀ values ranging from 23.0 to 91.8 μM.

Kleinhospitines A–D, New Cycloartane Triterpenoid Alkaloids from Kleinhovia hospita

Co-reporter:Chang-Xin Zhou, Li Zou, Li-She Gan, and Yue-Lan Cao

Organic Letters 2013 Volume 15(Issue 11) pp:2734-2737

Publication Date(Web):May 24, 2013

DOI:10.1021/ol401066j

Kleinhospitines A–D, four unprecedented cycloartane triterpenoid alkaloids possessing a spiro α,β-unsaturated γ-lactamlactone side chain, were isolated as two mixtures of C-23 epimers from Kleinhovia hospita. Kleinhospitines C and D represent the first examples of naturally occurring cycloartane triterpenoids with a 9α,10α-cyclopropyl ring. The structures and absolute configurations were determined on the basis of spectroscopic analyses and comprehensive quantum chemical calculations. The two mixtures showed hepatoprotective activity against H2O2-induced oxidative damages on primary cultured rat hepatocytes with EC50 values of 167.0 and 126.5 μM.

Cytotoxic Diterpenoids from the Stem Bark of Annona squamosa L.

Co-reporter:Chang-Xin Zhou;Li-Rui Sun;Feng Feng;Jian-Xia Mo;Hong Zhu;Bo Yang;Qiao-Jun He

Helvetica Chimica Acta 2013 Volume 96( Issue 4) pp:656-662

Publication Date(Web):

DOI:10.1002/hlca.201200249

Abstract

Three new ent-kaurane diterpenoids, (4α)-19-nor-ent-kaurane-4,16,17-triol (1), (4α,16α)-17-(acetyloxy)-19-nor-ent-kaurane-4,16-diol (2), and 17-hydroxy-ent-kaur-15-en-19-al (3), together with 11 known compounds, were isolated from the stem bark of Annona squamosa L. The structures of 1–3 were identified by analysis of their spectroscopic data. All compounds were evaluated for cytotoxic activity against human lung cancer (95-D) and ovarian cancer (A2780) cell lines, and compounds 3, 5, 7, 11–14 exhibited promising antiproliferative activities with IC₅₀ values ranging from 0.38 to 34.66 μM.

Homoisoflavonoids from Ophiopogon japonicus

Co-reporter:Chang-Xin Zhou;Li Zou;Jian-Xia Mo;Xue-Yao Wang;Bo Yang;Qiao-Jun He

Helvetica Chimica Acta 2013 Volume 96( Issue 7) pp:1397-1405

Publication Date(Web):

DOI:10.1002/hlca.201200493

Abstract

Phytochemical study on the root tubers of Ophiopogon japonicus resulted in the isolation and identification of 13 homoisoflavonoids, including three new compounds, 8-formyl-7-hydroxy-5,4′-dimethoxy-6-methylhomoisoflavone (1), 6-formylisoophiopogonone B (2), and 8-formylophiopogonanone B (4), and the ten known homoisoflavonoids 3, and 5–13. The absolute configurations of 8-formylophiopogonanone B (4) and 8-formyl-7-hydroxy-5,4′-dimethoxy-6-methylhomoisoflavanone (5) were confirmed by time-dependent density-functional-theory (TD DFT) calculations of their theoretical electronic circular dichroism (ECD) spectra. The structure of the formerly reported ‘6-aldehydoisoophiopogonone B’ was revised to 8-formylophiopogonone B (3). All compounds were evaluated for their cytotoxic activities against the human-lung-tumor A549 cell line, and compounds 3, 9, 10, and 13 exhibited promising antiproliferative activities with IC₅₀ values of 10.01, 6.40, 0.84, and 1.66 μM, respectively.

A new anti-diabetic sesquiterpenoid from Acorus calamus

Co-reporter:Chang Xin Zhou, Di Qiao, You You Yan, Hao Shu Wu, Jian Xia Mo, Li She Gan

Chinese Chemical Letters 2012 Volume 23(Issue 10) pp:1165-1168

Publication Date(Web):October 2012

DOI:10.1016/j.cclet.2012.08.004

A new sesquiterpenoid, 1β,5α-guaiane-4β,10α-diol-6-one (1), was isolated from 70% EtOH extract of the rhizomes of Acorus calamus. The structure was determined on spectroscopic methods, especially 2D NMR techniques. The absolute configuration of 1 was confirmed by TDDFT quantum chemical calculation of its ECD spectrum. Compound 1 showed promising anti-diabetic activity on a insulin-mediated glucose consumption model of HepG2 cells.

Theoretical study on flueggenines A and B: A comparison of calculated spectroscopic properties with IR, UV and ECD experimental data

Co-reporter:Chang-Xin Zhou, Jian-Xia Mo, Xue-Yao Wang, Jian Zhang, Li-She Gan

Journal of Molecular Structure 2011 Volume 989(1–3) pp:131-135

Publication Date(Web):15 March 2011

DOI:10.1016/j.molstruc.2010.12.051

Using DFT at the B3LYP/6-31+G (d) level, DFT-D at the wb97xd/tzvpp level and TD-DFT at the B3LYP/aug-cc-pVDZ level, computational analysis of the first examples of naturally occurring dimeric indolizidine alkaloids, flueggenines A and B, accomplished the simulation and interpretation of their IR, UV and ECD spectra. Compared with the experimental ones, the calculated IR and UV spectra allowed the reinforcement of the carbon skeletons and functional groups. Calculation of the ECD spectra assured the formerly assigned absolute configurations for flueggenines A and B.

Optical Resolution and Structure Determination of New Indolizidine Alkaloids from Elaeocarpus sphaericus

Co-reporter:Chang-Xin Zhou;Xue-Yao Wang;Jian-Xia Mo;Jian Zhang

Helvetica Chimica Acta 2011 Volume 94( Issue 2) pp:347-354

Publication Date(Web):

DOI:10.1002/hlca.201000200

Abstract

Two new indolizidine alkaloids, (±)-3-oxoisoelaeocarpine (1) and (±)-elaeocarpine N-oxide (2), along with three known alkaloids, (±)-isoelaeocarpine (3), (±)-elaeocarpine (4), and (−)-isoelaeocarpiline (5), were isolated from an EtOH extract of the branches and leaves of Elaeocarpus sphaericus. The structures of these compounds were determined by spectroscopic and chemical methods. Furthermore, enantiomers of compounds 1 and 3 were separated on a chiral CD-Ph column, and their absolute configurations were determined by TD-DFT (=time-dependent density-functional theory) quantum-chemical calculations of their electronic circular dichroism (ECD) spectra.