title: Penicamedine A, a Highly Oxygenated Hexacyclic Indole Alkaloid from Penicillium camemberti.
abstract: A highly oxygenated hexacyclic indole alkaloid, penicamedine A (1), bearing a rare furan ring, was isolated from the culture broth of Penicillium camemberti, together with two known analogs, iso-α-cyclopiazonic acid (2) and cyclopiazonic acid (3). The structure of 1 was elucidated by comprehensive spectroscopic analyses including NMR and HR-ESI-MS. Its absolute configuration was further confirmed unambiguously by single-crystal X-ray diffraction analysis. Compound 1 was evaluated for anti-HIV activity with p24 assays and tested for cytotoxic activities against five human cancer cell lines, including HL-60, SMMC-7721, A-549, MCF-7, SW480, and the immortalized non-cancerous human pulmonary epithelial cell line BEAS-2B by MTS method.
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Hucheng
authors.initials: H
authors.lastname: Zhu
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Chunmei
authors.initials: C
authors.lastname: Chen
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Jianping
authors.initials: J
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China.
authors.forename: Xiao-Nian
authors.initials: XN
authors.lastname: Li
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Guangzheng
authors.initials: G
authors.lastname: Wei
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Yi
authors.initials: Y
authors.lastname: Guo
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Guangmin
authors.initials: G
authors.lastname: Yao
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311).
authors.forename: Zengwei
authors.initials: Z
authors.lastname: Luo
authors.affiliation: Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China.
authors.forename: Jinwen
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311). yongboxue@mail.hust.edu.cn.
authors.forename: Yongbo
authors.initials: Y
authors.lastname: Xue
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, P. R. China, (phone: +86-27-83692311). zhangyh@mails.tjmu.edu.cn.
authors.forename: Yonghui
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010407:Penicillium / Q000737:chemistry*
chemical_list: D019380:Anti-HIV Agents; D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids; C000609800:penicamedine A; D010100:Oxygen
keywords: Anti-HIV activity; Cytotoxic activity; Indole alkaloids; Penicamedine A; Penicillium camemberti; X-Ray crystallography