Chang-heng Tan

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Organization: Shanghai Institute of Materia Medica
Department: Department of Natural Medicinal Chemistry
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Co-reporter:Li-Jun Yang;Kun Jiang;Jun-Jie Tan;Shi-Jin Qu;Hong-Feng Luo;Da-Yuan Zhu
Helvetica Chimica Acta 2013 Volume 96( Issue 1) pp:119-123
Publication Date(Web):
DOI:10.1002/hlca.201200211

Abstract

Chemical investigation on the stem and root of Melicope pteleifolia afforded three new prenylated benzene metabolites as racemic mixtures, named pteleifolins A–C (13, resp.). Their gross structures were elucidated on the basis of spectroscopic analysis, especially 2D-NMR experiments. An enantiomer resolution of (±)-1 using chiral HPLC was performed, and the absolute configuration of the enantiomers were determined to be (+)-(S)-1 and (−)-(R)-1 by means of circular-dichroism analysis.

Co-reporter:Yang Zhang, Li-Jun Yang, Kun Jiang, Chang-Heng Tan, Jun-Jie Tan, Pei-Ming Yang, Da-Yuan Zhu
Carbohydrate Research 2012 Volume 361() pp:114-119
Publication Date(Web):1 November 2012
DOI:10.1016/j.carres.2012.08.011
Seven new diglycosidic constituents, named pteleifosides A–G (1–7), along with ten known glycosides, were isolated from the roots and rhizomes of Melicope pteleifolia (Champ. ex Benth.) T. Hartley. The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry.Graphical abstractHighlights► Water-soluble constituents of Melicope pteleifolia were investigated. ► Seven new and ten known glycosidic constituents were isolated. ► The β-d-glucosylation-induced shift-trend rule was applied. ► Atropisomerism in megastigmene diglycosides was firstly observed and confirmed.
Co-reporter:Shi-Jin Qu, Gui-Feng Wang, Wen-Hu Duan, Shan-Yan Yao, Jian-Ping Zuo, Chang-Heng Tan, Da-Yuan Zhu
Bioorganic & Medicinal Chemistry 2011 Volume 19(Issue 10) pp:3120-3127
Publication Date(Web):15 May 2011
DOI:10.1016/j.bmc.2011.04.004
A series of tryptamine derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compounds 2e and 4a showed potent antiviral activity (IC50 = 0.4 and <1 μM, respectively) and low cytotoxicity (CC50 = 40.6 and >25 μM, respectively).
Co-reporter:Shi-Jin Qu, Chang-Heng Tan, Zu-Long Liu, Shan-Hao Jiang, Long Yu, Da-Yuan Zhu
Phytochemistry Letters 2011 Volume 4(Issue 2) pp:144-146
Publication Date(Web):15 June 2011
DOI:10.1016/j.phytol.2011.02.003
Tanaconitine (1), a novel Aconitum alkaloid with a C29 skeleton, together with six known diterpenoid alkaloids, was isolated from the roots of Aconitum tanguticum. The structure of 1 was elucidated to be 17-dehydroxyl-3′a(cis-1′-methyl-3′,3′a,7′,7′a-tetrahydro-1H-indol-6′(2H)-one)-naviculine A by spectroscopic analysis.Figure optionsGraphical abstractTanaconitine (1), a novel Aconitum alkaloid with a C29 skeleton, together with six known diterpenoid alkaloids, was isolated from the roots of Aconitum tanguticum.Research highlights► Seven alkaloids were isolated from Aconitum tanguticum. ► Tanaconitine was identified to be a novel Aconitum alkaloid with a C29 skeleton. ► A biogenetic pathway of tanaconitine derived from a diterpenoid skeleton alkaloid was hypothesized.
Co-reporter:Jun-Ming Tan;Yi-Hua Qiu;Xin-Qi Tan
Helvetica Chimica Acta 2011 Volume 94( Issue 9) pp:1697-1702
Publication Date(Web):
DOI:10.1002/hlca.201100166

Abstract

Three new 3(4),9(10)-disecocycloartane peroxy triterpene lactones, named as pseudolarolides Q2, T1, and T2 (13, resp.), along with five known triterpenoids, were isolated from the seeds of Pseudolarix kaempferiGord. Their structures were elucidated to be (9R,10R,16R,23R,25R)-16,23-epoxy-9,10-epidioxy-3,4:9,10-disecocycloart-1(2)-ene-3,4:26,23-diolide (1), (1R,9R,10S,16R,23S,25R)-1,4:16,23-diepoxy-9,10-epidioxy-3,4;9,10-disecocycloartan-26(23)-olid-3-oic acid methyl ester (2), and (1R,9R,10S,16R,23R,25R)-1,4:16,23-diepoxy-9,10-epidioxy-3,4;9,10-disecocycloartan-26(23)-olid-3-oic acid methyl ester (3) on the basis of spectroscopic analysis.

Co-reporter:Qiu-Ling Fan, Chang-Heng Tan, Jing Liu, Ming-Ming Zhao, Fu-Sen Han, Da-Yuan Zhu
Phytochemistry 2011 Volume 72(14–15) pp:1927-1932
Publication Date(Web):October 2011
DOI:10.1016/j.phytochem.2011.04.019
C9-iridoid glycosides, wallichiisides A–C (1–3), and four dimers, wallichiisides D–G (4–7), together with 13 known glycosidic compounds, were isolated from whole plants of Eriophyton wallichii Benth. Their structures were elucidated by spectroscopic methods and comparison with literature values. Four of these compounds showed moderate DPPH free radical scavenging activity.Graphical abstractThree C9-iridoid glycoside monomers (1–3) and four dimers (4–7), together with 13 known glycosidic compounds, were isolated from whole plants of Eriophyton wallichii Benth. Four of the compounds showed moderate DPPH free radical scavenging capacitiy.Highlights► Twenty compounds were isolated from Eriophyton wallichii. ► Wallichiisides A–C were identified as C9-iridoid glycosides whereas Wallichiisides D–G were C9-iridoid glycoside dimers. ► Wallichiisides A, B, and E, and rutin showed moderate antioxidant activity.
Co-reporter:Ming-Sheng Lan;Jian-Xiong Ma;Song Wei;Da-Yuan Zhu
Helvetica Chimica Acta 2010 Volume 93( Issue 11) pp:2276-2280
Publication Date(Web):
DOI:10.1002/hlca.201000168

Abstract

A new purine derivative, 3-(3-methylbut-2-en-1-yl)isoguanine (1), and a new cleistanthane-type diterpenoid glucoside, 19-hydroxyspruceanol 19-O-β-D-glucopyranoside (2), together with eight known compounds were isolated from the whole plant of Phyllanthus reticulatus. The structures were elucidated by chemical and spectroscopic methods.

Co-reporter:Yang Zhang;Jun-Jie Tan;Pei-Ming Yang;Shan-Hao Jiang;Xiang Ni;Da-Yuan Zhu
Helvetica Chimica Acta 2010 Volume 93( Issue 7) pp:1407-1412
Publication Date(Web):
DOI:10.1002/hlca.200900424

Abstract

Three new, 13, and seven known phenolic and terpenic glycosides were isolated from the BuOH-soluble fraction of 95% EtOH extract of the roots and rhizomes of Celastrus orbiculatus. The structures of the new compounds were elucidated as carvacrol 2-O-α-L-rhamnopyranosyl-(16)-β-D-glucopyranoside (1), 5-methoxycarvacrol 2-O-α-L-rhamnopyranosyl-(16)-β-D-glucopyranoside (2), and 15-hydroxytorreyol 10-O-β-D-apiofuranosyl-(16)-β-D-glucopyranoside (3) on the basis of spectroscopic analysis and chemical methods.

Co-reporter:Yi-Lei Chen;Jun-Jie Tan;Xue-Mei Zhao;Shan-Hao Jiang;Da-Yuan Zhu
Helvetica Chimica Acta 2009 Volume 92( Issue 12) pp:2802-2807
Publication Date(Web):
DOI:10.1002/hlca.200900121

Abstract

Two new diterpenoid glucosides, clerodendranthusides B and C (1 and 2, resp.), together with 16 known compounds, comprising four lignans, five miscellaneous phenylpropanoids, two flavonoids, one sesquiterpenoid glycoside, two triterpenoid glycosides, one megastigmane, as well as one anthraquinone, were isolated from the 50% EtOH extract of the whole plants of Clerodendrathus spicatus. Their structures were elucidated by chemical and spectroscopic methods.

Actinidic acid
Shegansu B
(+)-ampelopsin A
Ampelopsin F
Olean-12-en-28-oicacid, 2,3,23,24-tetrahydroxy-, (2a,3b)-
(E)-2-(3,5-Dihydroxystyryl)benzene-1,3-diol
Gnetin C
2'-Hydroxy-Gnetin C
5-METHOXY-1-BENZOTHIOPHENE-2-CARBALDEHYDE
Olean-12-en-28-oicacid, 2,3,19,23-tetrahydroxy-, b-D-glucopyranosyl ester, (2a,3b,4a,19a)-