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51. Aspergilolide, a steroid lactone produced by an endophytic fungus . MBL1612 isolated from

Author

Zhang, Pei-Liang, Wang, Gang, Xu, Feng-Qing, Liu, Jin-Song, Wang, Ju-Tao, Zhang, Rui, Liu, Hai-Tao, Hu, Jiang-Miao, Wang, Guo-Kai, and Wu, Pei-Yun

Subjects
chemistry.chemical_classification, Aspergillus, biology, 010405 organic chemistry, Chemistry, Stereochemistry, medicine.medical_treatment, Organic Chemistry, Plant Science, Endophytic fungus, biology.organism_classification, 01 natural sciences, Biochemistry, 0104 chemical sciences, Analytical Chemistry, Steroid, 010404 medicinal & biomolecular chemistry, Paeonia ostii, Cell culture, medicine, Helvolic acid, Cytotoxicity, Lactone
Abstract

A new steroid lactone aspergilolide (1), and nine known compounds helvolic acid (2), verruculogen (3), tryprostatin B (4), 13-oxofumitremorgin B (5), fumitremorgin C (6), demethoxy fumitremorgin C (7), terezine D (8), aszonalenin (9), 12, 13-dihydroxy-fumitremorgin C (10) from cultures of the endophytic fungus Aspergillus sp. MBL1612. Their chemical structures were determined by a series of extensive spectroscopic methods. All of the compounds were isolated from this genus for the first time. The cytotoxicity against five human cancer cell lines of new compound were detected.

Published
2018
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52. Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity

Author

Zi,Cheng-Ting, Yang,Liu, Kong,Qing-Hua, Li,Hong-Mei, Yang,Xing-Zhi, Ding,Zhong-Tao, Jiang,Zi-Hua, Hu,Jiang-Miao, Zhou,Jun, Zi,Cheng-Ting, Yang,Liu, Kong,Qing-Hua, Li,Hong-Mei, Yang,Xing-Zhi, Ding,Zhong-Tao, Jiang,Zi-Hua, Hu,Jiang-Miao, and Zhou,Jun

Abstract

Cheng-Ting Zi,1,2,* Liu Yang,2,* Qing-Hua Kong,2 Hong-Mei Li,2 Xing-Zhi Yang,2 Zhong-Tao Ding,3 Zi-Hua Jiang,4 Jiang-Miao Hu,2 Jun Zhou2 1Key Laboratory of Pu-Er Tea Science, Ministry of Education, College of Science, Yunnan Agricultural University, Kunming, 650201, People’s Republic of China; 2State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China; 3Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People’s Republic of China; 4Department of Chemistry, Lakehead University, Thunder Bay ON P7B 5E1, Canada*These authors contributed equally to this workCorrespondence: Zi-Hua JiangDepartment of Chemistry, Lakehead University, 955 Oliver Road, Thunder Bay ON P7B 5EI, CanadaTel +1 807 766 7171Fax +1 807 346 7775Email zjiang@lakeheadu.caJiang-Miao HuState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, No. 132, Lanhei Road, Kunming 650201, People’s Republic of ChinaTel +86 871 6522 3264Fax +86 871 6522 3261Email hujiangmiao@mail.kib.ac.cnBackground: Widespread concern of the side effects and the broad-spectrum anticancer property of podophyllotoxin as an antitumor agent highlight the need for the development of new podophyllotoxin derivatives. Although some per-butyrylated glucosides of podophyllotoxin and 4β-triazolyl-podophyllotoxin glycosides show good anticancer activity, the per-acetylated/free of podophyllotoxin glucosides and their per-acetylated are not well studied.Methods: A few glucoside derivatives of PPT were synthesized and evaluated for their in vitro cytotoxic activities against five human cancer cell lines, HL-60 (leukemia), SMMC-7721 (hepatoma), A-549 (lung cancer), MCF-7 (breast cancer), and SW480 (colon

Published
2019

53. Two new acetoisovanillone glycosides from the water-soluble fraction of Paeonia ostii.

Author

Sun, Lei, Hu, Hua-Ping, Chen, Xiao-Xiao, Xu, Guo-Yong, Liu, Jin-Song, Hu, Jiang-Miao, Wu, De-Ling, and Xu, Feng-Qing

Subjects
GLYCOSIDES, CHINESE medicine
Abstract

The cortex root of Paeonia ostii, is used as a traditional Chinese medicine for treating female diseases. Phytochemical investigation of the water-soluble fraction of the plant led to the isolation of two new acetoisovanillone glycosides: acetoisovanillone-3-O-β-D-glucopyranoside (1) and 2-hydroxy-acetoisovanillone-3-O-β-D-glucopyranoside (2). Their structures were elucidated by extensive spectroscopic methods. [ABSTRACT FROM AUTHOR]

Published
2021
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59. Design, Synthesis, and Biological Evaluation of Novel Biotinylated Podophyllotoxin Derivatives as Potential Antitumor Agents

Author

Zi, Cheng-Ting, primary, Gao, Ying-Sheng, additional, Yang, Liu, additional, Feng, Shu-Yun, additional, Huang, Yue, additional, Sun, Li, additional, Jin, Yi, additional, Xu, Feng-Qing, additional, Dong, Fa-Wu, additional, Li, Yan, additional, Ding, Zhong-Tao, additional, Zhou, Jun, additional, Jiang, Zi-Hua, additional, Yuan, Sheng-Tao, additional, and Hu, Jiang-Miao, additional

Published
2019
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66. Sesquiterpenoids from the roots and rhizomes of Valeriana amurensis and their effects on NGF-induced neurite outgrowth in PC12 cells.

Author

Dong, Fa-Wu, Li, Fang, Ren, Jia-Jia, Zhao, Cheng-Mei, Diao, Hong-Li, Li, Bao-Jing, Li, Yan-Ping, Hu, Jiang-Miao, and He, Hong-Ping

Subjects
SESQUITERPENES, NERVE growth factor, VALERIANA, CELL differentiation
Abstract

Two new sesquiterpenoids, including a kessane-type sesquiterpenoid (1) and one bisabolane derivative (2), together with fourteen known sesquiterpenoids (3–16), were isolated from the roots and rhizomes of Valeriana amurensis. The structures of new compounds were established on the basis of extensive spectroscopic analysis. All isolates were evaluated for their effects on nerve growth factor (NGF)-mediated neurite outgrowth in pheochromocytoma (PC12) cells. As a results, four compounds including 10–12 and 15 showed potent promoting effects at the concentration of 10 µM on NGF-induced neurite outgrowth in PC12 cells with the differentiation rate of 11.84%, 12.21%, 13.77% and 12.16%, respectively. [ABSTRACT FROM AUTHOR]

Published
2021
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67. Synthesis and anticancer activity of dimeric podophyllotoxin derivatives

Author

Zi,Cheng-Ting, Yang,Liu, Xu,Feng-Qing, Dong,Fa-Wu, Yang,Dan, Li,Yan, Ding,Zhong-Tao, Zhou,Jun, Jiang,Zi-Hua, Hu,Jiang-Miao, Zi,Cheng-Ting, Yang,Liu, Xu,Feng-Qing, Dong,Fa-Wu, Yang,Dan, Li,Yan, Ding,Zhong-Tao, Zhou,Jun, Jiang,Zi-Hua, and Hu,Jiang-Miao

Abstract

Cheng-Ting Zi,1–3,* Liu Yang,2,* Feng-Qing Xu,2 Fa-Wu Dong,2 Dan Yang,2 Yan Li,2 Zhong-Tao Ding,3 Jun Zhou,2 Zi-Hua Jiang,4 Jiang-Miao Hu2 1Key Laboratory of Pu-er Tea Science, Ministry of Education, College of Science, Yunnan Agricultural University, Kunming 650201, China; 2State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; 3Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China; 4Department of Chemistry, Lakehead University, Thunder Bay, ON P7B 5E1, Canada *These authors contributed equally to this work Background: Podophyllotoxin is a potent cytotoxic agent and serves as a useful lead compound for the development of antitumor drugs. Several podophyllotoxin-derived antitumor agents, including etoposide, are currently in clinical use; however, their therapeutic efficacy is often limited due to side effects and the development of resistance by cancer cells. Previous studies have shown that 4β-1,2,3-triazole derivatives of podophyllotoxin exhibit more potent anticancer activity and better binding to topoisomerase-II than etoposide. The effect of dimerization of such derivatives on the anticancer activity has not been studied. Methods: Two moieties of podophyllotoxin were linked at the C-4 position via 1,2,3-triazole rings to give a series of novel dimeric podophyllotoxin derivatives. 4β-Azido-substituted podophyllotoxin derivatives (23 and 24) were coupled with various dipropargyl functionalized linkers by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction to provide dimeric products in very good yield. The in vitro anticancer activity of the synthesized compounds was evaluated by MTT assay against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480). The normal BEAS-2B (lun

Published
2018

69. Structure Revision of Four Classes of Prenylated Aromatic Natural Products Based on a Rule for Diagnostic 13C NMR Chemical Shifts

Author

Ren, Fu-Cai, Wang, Li-Xia, Lv, Yong-Feng, Hu, Jiang-Miao, and Zhou, Jun

Abstract

Errors in elucidating the structures of four natural classes of prenylated aromatic compounds with 2,3-epoxy, 2,3-dihydroxy, and cyclization with an ortho-phenolic hydroxyl to give a pyran or furan ring moiety are frequent and inevitable. Based on rigorous literature research and a series of chemical transformation experiments, a rule for the rapid determination of these four classes of prenylated derivates based on 13C NMR data was formulated, and 57 corrections featuring these fragments were accordingly reported.

Published
2021
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70. Synthesis and antitumor activity of camptothecin- 4β-triazolopodophyllotoxin conjugates.

Author

Zi, Cheng-Ting, Yang, Liu, Dong, Fa-Wu, Kong, Qing-Hua, Ding, Zhong-Tao, Zhou, Jun, Jiang, Zi-Hua, and Hu, Jiang-Miao

Subjects
CELL lines, ANTINEOPLASTIC agents, CANCER cells, CAMPTOTHECIN
Abstract

Two new compounds (9 and 10) having a camptothecin (CPT) analog conjugated to the 4β-azido-4-deoxypodophyllotixin analog by untilizing the copper-catalyzed azide-alkyne cycloadditon (CuAAC) reaction, and were evaluated for their cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) using the MTT (3-(4,5-dimethyl-thiahiazo-2-yl)-2,5-diphenyltetrazolium bromide) assay. Two novel conjugates shown weak cytotoxicity, compound 10 showed highly potent against HL-60 cell line tested, with IC50 value 17.69 ± 0.19 μM. This compound suggested its potential as anticancer agents for further development. [ABSTRACT FROM AUTHOR]

Published
2020
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71. Design, synthesis and cholinesterase inhibitory activity of α-mangostin derivatives.

Author

Chi, Xiao-Qian, Hou, Bo, Yang, Liu, Zi, Cheng-Ting, Lv, Yong-Feng, Li, Jin-Yu, Ren, Fu-Cai, Yuan, Ming-Yan, Hu, Jiang-Miao, and Zhou, Jun

Subjects
ACETYLCHOLINESTERASE, MANGOSTEEN, CHALCONE, CHOLINESTERASE inhibitors
Abstract

α-mangostin, a polyphenol xanthone derivative, was mainly isolated from pericarps of the mangosteen fruit (Garcinia mangostana L.). In present investigation, a series of derivatives were designed, synthesised and evaluated in vitro for their inhibitory activity of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among the synthesised xanthones, compounds 1, 9, 13 and 16 showed AChE selective inhibitory activity, 15 was a BuChE selective inhibitor while 2, 3, 5, 6, 7, 12 and 14 were dual inhibitors. The most potent inhibitor of AChE was 16 while 5 was the most potent inhibitor of BuChE with IC50 values of 5.26 μM and 7.55 μM respectively. [ABSTRACT FROM AUTHOR]

Published
2020
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72. Dendrobium officinale kimura et migo improved dry eye symptoms via promoting tear production in an experimental dry eye rat model.

Author

Zeng, Qiang, Siu, Wing-Sum, Ko, Chun-Hay, Wong, Chun-Wai, Lau, Clara, Wu, Zheng-Zhi, Hu, Jiang-Miao, and Leung, Ping-Chung

Subjects
DRY eye syndromes, MEIBOMIAN glands, LACRIMAL apparatus, DENDROBIUM, CONJUNCTIVITIS, IMMUNOSTAINING
Abstract

Objectives: To evaluate the ameliorative effect of Dendrobium officinale Kimura et Migo (DO) on a desiccated environment-induced experimental dry eye rat model and elucidate its underlying mechanisms. Materials and Methods: The Sprague-Dawley rats were kept in low-humidity environment and received constant airflow for 8 weeks to establish the experimental dry eye model. DO water extract (DOW, 372 mg/kg/day) was orally administered daily for 8 weeks. Schirmer's test was used to measure the tear fluid production at days 0, 14, 28, 42, and 56. At the end of experiment, lacrimal gland tissues and eyeballs were collected for hematoxylin and eosin staining, PAS staining, and immunohistochemical staining. Inflammatory cytokines in conjunctiva including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6, and matrix metalloproteinase 9 were measured by real-time PCR. The aquaporin 5 (AQP5) expression in lacrimal gland was also determined using Western blot assay. Results: DOW treatment (DOWT) increased the tear production of rats significantly in the desiccated environment at day 42. Histological analysis revealed that DOW could reverse destruction of conjunctiva and increase goblet cell number and mucin expression in the experimental dry eye rats. In dry eye rats, desiccated environment and constant airflow induced TNF-α and IL-1β production in the conjunctiva, whereas DOWT reversed the upregulation of proinflammatory cytokines. Moreover, DOWT increased the expression of AQP5 at protein level in the lacrimal gland tissues in both desiccated and normal environmental conditions. Conclusion: The present study suggests that DO has therapeutic potential on dry eye symptoms through upregulating AQP5 expression, increasing tear production, inhibiting conjunctiva destruction and inflammation, as well as promoting mucin production. [ABSTRACT FROM AUTHOR]

Published
2020
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83. Antibacterial Prenylated p-Hydroxybenzoic Acid Derivatives from Oberonia myosurusand Identification of Putative Prenyltransferases

Author

Ren, Fu-Cai, Liu, Li, Lv, Yong-Feng, Bai, Xue, Kang, Qian-Jin, Hu, Xiao-Jing, Zhuang, Hong-Dan, Yang, Liu, Hu, Jiang-Miao, and Zhou, Jun

Abstract

Twelve hitherto unknown tandem prenylated p-hydroxybenzoic acid derivatives, namely, oberoniamyosurusins A–L, together with five known derivatives, were isolated from an EtOH extract of the whole parts of the plant Oberonia myosurus. Compounds 10, 13, and 17exhibited moderate inhibitory activity against Staphylococcus aureussubsp. aureusATCC29213 with MIC50values ranging from 7.6 to 23 μg/mL. To determine the biosynthetic pathway of this class of tandem prenyl-substituted compounds, the full-length transcriptome of O. myosuruswas sequenced, yielding 19.09 Gb of clean data and 10 949 nonredundant sequences. Two isoforms of p-hydroxybenzoic acid prenyltransferases were annotated and functionally characterized as the enzymes that might be involved in the biosynthesis of nervogenic acid (13) in Pichia pastoris.

Published
2021
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91. Aspergilolide, a steroid lactone produced by an endophytic fungus Aspergillus sp. MBL1612 isolated from Paeonia ostii.

Author

Zhang, Pei-Liang, Wang, Gang, Xu, Feng-Qing, Liu, Jin-Song, Wang, Ju-Tao, Zhang, Rui, Liu, Hai-Tao, Hu, Jiang-Miao, Wang, Guo-Kai, and Wu, Pei-Yun

Subjects
ENDOPHYTIC fungi, ASPERGILLUS, STEROIDS, CHEMICAL structure, CELL lines, CANCER cells
Abstract

A new steroid lactone aspergilolide (1), and nine known compounds helvolic acid (2), verruculogen (3), tryprostatin B (4), 13-oxofumitremorgin B (5), fumitremorgin C (6), demethoxy fumitremorgin C (7), terezine D (8), aszonalenin (9), 12, 13-dihydroxy-fumitremorgin C (10) from cultures of the endophytic fungus Aspergillus sp. MBL1612. Their chemical structures were determined by a series of extensive spectroscopic methods. All of the compounds were isolated from this genus for the first time. The cytotoxicity against five human cancer cell lines of new compound were detected. [ABSTRACT FROM AUTHOR]

Published
2019
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93. Seco-Dendrobine-Type Alkaloids and Bioactive Phenolics from Dendrobium findlayanum

Author

Yang, Dan, Cheng, Zhong-Quan, Yang, Liu, Hou, Bo, Yang, Jing, Li, Xiao-Nian, Zi, Cheng-Ting, Dong, Fa-Wu, Liu, Zheng-Hua, Zhou, Jun, Ding, Zhong-Tao, and Hu, Jiang-Miao

Abstract

Investigation of the 95% EtOH extract of stems of Dendrobium findlayanumafforded four new seco-dendrobines, findlayines A–D (1–4); two known dendrobines, dendrobine (5) and 2-hydroxydendrobine (6); and four new phenolic compounds, dendrofindlaphenols A–C (7, 9, and 10) and 6″-de-O-methyldendrofindlaphenol A (8). Compounds 1and 2are the first seco-dendrobines possessing a seven-membered lactam moiety, with 3and 4derived from the oxidative cleavage of the C-2–C-3 bond of dendrobine. The structures were established using spectroscopic methods and by comparison with literature data. The absolute configurations of 1–4were confirmed via single-crystal X-ray diffraction data. Cytotoxic activity assays against HL-60, SMMC-7721, A-549, MCF-7, and SW480 human cancer cell lines revealed IC50values ranging from 2.3 to 5.3 μM for compound 7, from 19.4 to 34.4 μM for 8, and from 49.4 to 96.8 μg/mL for the EtOAc extract. An assay of the inhibition of NO production with RAW 264.7 cells indicated that 8had an IC50value of 21.4 μM, and the EtOAc extract, 10.5 μg/mL. The EtOAc extract possessed DPPH radical scavenging activity of 69.93% at 100 μg/mL.

Published
2024
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