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    Schumannione - Manuscript

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    Mahfuz Rob

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    “earahedron Letters 6 (2020) 152168 Contonts lists available at ScionooDiroct A Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet, Schumannione, a new butenolide derivative isolated from Schumannianthus dichotomus as a potential phytotoxic agent Md Mahfuzur Rob“, Kaori Ozaki, i Toshiaki Teruya‘, Hisashi Kato-Noguchi *" *beporment of Applied Bilal See, Fal of Agicatre, Kagan Univer, Mi Kagawa 761-0795, japan chuduste Schoo! of Eine and cece niesy of he Rul. 1 Seba. Nara, Ona 903-213. Jopan ‘aul of Education, Unversity ofthe Ruts, Senbar star Okinawse 9030213 pan ‘The United Graduate Scho! of Agar Sciences, Ehime Univers, 35-7 Taam, Matsuyama, Eine 790-8565 Jopan ARTICLE INFO ABSTRACT Fre io Rewsed 17 june 2020 ‘Accepted 19 ume 2020 ‘able online 22 Jane 2020 ‘Schumannione, a new butenolide derivative, was isolated from the leaves of Schumannianhus dchotoms ough phytotoxie assay-gukded Traetionation, The structure of the compound was elucidated by ‘etailed spectroscopic analysis including ECD spectra, Schumannione displayed significant phytotoxcity ‘against cimothy and cress with a minimum 10 uM concentration having IC values ranging from 1088 to 160° uM, indicating it might play 2 role in the phytotoxic potential ofS dichotomus a ‘© 2020 Elsevier L.A rights reserved Schomarnanchas chermis Butenode Schumannione hyttosc compound Introduction lation and structural elucidation of a new butenolide compound Exploitation of new plant materials is a way of finding unique sources of diversified secondary metabolites that might possess useful biological activity. We have focused on potential phytotoxic substances from unreported phytotoxic plant materials in Bangla- ddesh [1.2 As part of our continuing research to isolate structurally ‘unique substances, we have investigated the phytotoxic potential ‘of Schumannianthus dichotomus (Roxb.) Gagnep and found strong phytotoxic activity against several model test plant species [3] Schumannianthus dichotomus belongs to the Marantaceae family ‘under the small genus Schumarnianthus (comprising only twa spe- cies) (4), Different members of the Marantaceae family have been investigated for phytochemical constituents and some novel com- pounds with promising biological activities have been reported, ‘but the genus Schumannianthus has not yet been wel investigated [5 Schumannianchus dichocomus is distributed in the northern part fof Bangladesh and in some areas of India and the Malayan penin- sula [6|, Generally, the plant has been grawn without using pest cides and insecticides because ofits hardiness, and itis used as a raw material in the rural cottage industry not only in Bangladesh ‘but also in different states of India. In this study, we report the iso- ® Gorespondng author at: Department of Applied Biological Science, Faculty of ‘Agree Kagawa Universi. i Kagawa 761-0795, apn. Email addresses: mazrobOymailcom, — mahfurobhor@sauacbd on Rob aeps:doiog/10.10165e.2000152168 (040-4039) 2020 sevir Ld Al ihe reserve {rom the leaves ofS, dichotomus and its phytotoxic potential. Results and discussion Air dried leaves of S. dichotomus (1.7 kg) were successively, extracted with aqueous methanol and methanol. The extracts were combined and dried under reduced pressure to produce the crude extract (67 g), which was partitioned with water and EtOAc. The EOAc fraction showed stronger phytotoxic activity than the aque- fous fraction against cress (Lepidium sativum L) considering the ‘growth percentages of treated seedlings (EtOAc and aqueous extract treatment) with parallel control seedlings. (without extract). ‘The EtOAc-soluble material was then subjected to repeated fractionation by column chromatography on silica gel, Sephadex L120, Cys cartridge, and HPLC. A cress phytotoxicty assay was conducted for each fractionation step, leading to isolation of a new active compound 1 obtained as a colorless oil (2.2 mg), and its molecular formula was determined to be Cyst. by HRESIMS, The NMR data for compound 1 is summarized in Table 1. The 'H NMR spectrum of compound 1 revealed three methyl groups: C-methyl (triplet at 3H 0.93, singlet at JH 1.97 and 1.79), The !'C NMR spectrum indicated one carbonyl carbon (3C 17438), ‘two olefatic carbons (aC 159.9 and 126.2), one hemiacetal carbon (6C 109.4), and three methyl carbons (9C 14.3, 11.2, and 8.2). The 2 MM Rob et /Teadron Lets 61 (2020) 152168, NM spectral data for compe in CD00. Position “amu n He)™ a 2 1362, 3 1308 4 14 5 3.68, (104, 1.7) Bo 7 134m 295 5 135m 236 ° gs,¢(72) tas 7 Recorded a 500 Mi ® Assignments for protonated carbons and quaternary carbons were obtained From HSQC and HME spectra respectively remaining carbon signals were assigned to three methylenes and ‘one methine based on the results of an HSQC experiment. ‘The gross structure was determined based on 1D and 2D NMR ‘experiments (Fig, 1). A detailed analysis of the COSY and HSQC spectra of compound 1 allowed one partial structure, C5-C9, to be constructed, as shown in Fig. 1. In the HMBC spectrum, H-10 showed correlations to C-2, C-3, and C-4; and H-11 showed corre- lations to C-1, C-2, and C-3. Although no additional connectivities ‘were obtained from the NMR analysis, the linkage of C-1 t0 C-4 through an oxygen atom was confirmed by the chemical shifts con- sistent with an. f-unsaturated carbonyl-y-lactone ring (Lee etal, 2007), in addition, the linkage of C-4 to C-5 was confirmed by its molecular formula and degree of unsaturation. Thus, the gross structure of compound 1 was determined to be as shown in F121 ‘The ECD spectral data of compound 1 (ECD (MeOH) ex 225 nm, ‘Ae $4.48, 243 nm, Ac 0.24) was similar to those of model com pounds (ECD (MeOH) ice 200 nm, Ac 05, 204 nm, Ac 0, 213 nm, Ae +0.3, 236 nm, Ae 40.13, 255 nm, Ae +0.1, Compound 9: hoy 213 nm, Ac +1.25,221 nm, Ae 0.02, 244 nm, Ae ~ 1.10, si ularone I(13-(2-hydroxy-3.4-dimethyl-5-oxo-2,5-dihydrofuran-2 si) tridecanoic acd ethyl ester) [7,8 Thus, the absolute configura- tion of C-4 in compound 1 was determined to be 4R, and we pro- posed schumannione ((4R)-4,5-dihydroxy-2,3-

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