Literature DB >> 21265556

Stereochemical investigations of isochromenones and isobenzofuranones isolated from Leptosphaeria sp. KTC 727.

Wilanfranco C Tayone1, Miho Honma, Saki Kanamaru, Shogo Noguchi, Kazuaki Tanaka, Tatsuo Nehira, Masaru Hashimoto.   

Abstract

Two new metabolites, (R)-3,4-dihydro-4,6,8-trihydroxy-4,5-dimethyl-3-methyleneisochromen-1-one (1) and (R)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (2), were isolated along with two structurally known related compounds (3 and 4) from the culture broth of Leptosphaeria sp. KTC 727 (JCM 13076 = MAFF 239586). These structures were disclosed mainly with (1)H and (13)C NMR spectroscopic analyses. The relative configuration of 2 was established by NOE studies. The absolute configuration of this molecule was determined by a combination of the modified Mosher's method and CD spectra after derivatizations. The theoretical CD profiles also supported these assignments. Structural correlations enabled us to establish the absolute configurations of metabolites 1, 3, and 4, in which configurations of the latter two had not been established. Compound 2 exhibited the strongest antifungal activity among them, inhibiting the hyphal growth of Cochliobolus miyabeanus at about 0.5 μg/mL.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21265556     DOI: 10.1021/np100838j

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  9 in total

1.  Identification of GABA A receptor modulators in Kadsura longipedunculata and assignment of absolute configurations by quantum-chemical ECD calculations.

Authors:  Janine Zaugg; Samad Nejad Ebrahimi; Martin Smiesko; Igor Baburin; Steffen Hering; Matthias Hamburger
Journal:  Phytochemistry       Date:  2011-08-31       Impact factor: 4.072

2.  Secondary metabolites produced by fungi derived from a microbial mat encountered in an iron-rich natural spring.

Authors:  Alexandra L Gerea; Katie M Branscum; Jarrod B King; Jianlan You; Douglas R Powell; Andrew N Miller; John R Spear; Robert H Cichewicz
Journal:  Tetrahedron Lett       Date:  2012-06-08       Impact factor: 2.415

Review 3.  Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products.

Authors:  Amardeep Awasthi; Mandeep Singh; Garima Rathee; Ramesh Chandra
Journal:  RSC Adv       Date:  2020-03-27       Impact factor: 4.036

4.  Phylogenetic and chemical diversity of fungal endophytes isolated from Silybum marianum (L) Gaertn. (milk thistle).

Authors:  Huzefa A Raja; Amninder Kaur; Tamam El-Elimat; Mario Figueroa; Rahul Kumar; Gagan Deep; Rajesh Agarwal; Stanley H Faeth; Nadja B Cech; Nicholas H Oberlies
Journal:  Mycology       Date:  2015-02-23

5.  Pseudaboydins A and B: novel isobenzofuranone derivatives from marine fungus Pseudallescheria boydii associated with starfish Acanthaster planci.

Authors:  Wen-Jian Lan; Wei Liu; Wan-Ling Liang; Zeng Xu; Xiu Le; Jun Xu; Chi-Keung Lam; De-Po Yang; Hou-Jin Li; Lai-You Wang
Journal:  Mar Drugs       Date:  2014-07-14       Impact factor: 5.118

6.  Isobenzofuranones and Isochromenones from the Deep-Sea Derived Fungus Leptosphaeria sp. SCSIO 41005.

Authors:  Xiaowei Luo; Xiuping Lin; Limbadri Salendra; Xiaoyan Pang; Yu Dai; Bin Yang; Juan Liu; Junfeng Wang; Xuefeng Zhou; Yonghong Liu
Journal:  Mar Drugs       Date:  2017-06-29       Impact factor: 5.118

7.  Secondary metabolites from the endolichenic fungus Ophiosphaerella korrae.

Authors:  Yue-Lan Li; Rong-Xiu Zhu; Gang Li; Ning-Ning Wang; Chun-Yu Liu; Zun-Tian Zhao; Hong-Xiang Lou
Journal:  RSC Adv       Date:  2019-01-31       Impact factor: 3.361

8.  Anti-inflammatory Polyketides from the Marine-Derived Fungus Eutypella scoparia.

Authors:  Ya-Hui Zhang; Hui-Fang Du; Wen-Bin Gao; Wan Li; Fei Cao; Chang-Yun Wang
Journal:  Mar Drugs       Date:  2022-07-28       Impact factor: 6.085

9.  An anticonvulsive drug, valproic acid (valproate), has effects on the biosynthesis of fatty acids and polyketides in microorganisms.

Authors:  Prapassorn Poolchanuan; Panida Unagul; Sanit Thongnest; Suthep Wiyakrutta; Nattaya Ngamrojanavanich; Chulabhorn Mahidol; Somsak Ruchirawat; Prasat Kittakoop
Journal:  Sci Rep       Date:  2020-06-09       Impact factor: 4.379

  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.