Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.

نویسندگان

  • Curtis C Barnes
  • Mary K Smalley
  • Kirk P Manfredi
  • Kelly Kindscher
  • Hillary Loring
  • Douglas M Sheeley
چکیده

The organic soluble extract from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory) showed in vitro activity against M. tuberculosis. Bioassay-guided fractionation of this extract resulted in the identification of two new resin glycosides (6, 7). Base-catalyzed hydrolysis of these glycosides gave operculinic acid (1) as the glycosidic acid component as well as trans-cinnamic acid, propanoic acid, and lauric acid. The complete structure elucidation was accomplished through derivatization, 1D and 2D NMR spectroscopy (TOCSY, ROESY, HSQC, HMBC), and MS/MS experiments on 6 and 7 as well as the permethylated derivative 8.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Isolation of secondary products from Ipomoea digitata – a medicinally important plant

The paper reports the isolation and characterization of β-sitosterol, t-cinnamic acid [undecyl (E)-3-(4hydroxyphenyl)-2-propenoate], an unknown coumarin and a lignan type resin glycoside from the tuberous roots of Ipomoea digitata. The structures of the compounds were elucidated on the basis of extensive chemical and spectroscopic data. Importantly, one of the compounds exhibited significant an...

متن کامل

Ether-soluble resin glycosides from the roots of Ipomoea batatas.

Two new resin glycosides, batataosides I (1) and II (2), and five known compounds, friedelin (3), scopoletin (4), octadecyl caffeate (5), beta-sistosterol (6) and daucosterol (7), were isolated from the roots of Ipomoea batatas. Their structures have been determined based on the chemical and spectral data. Batataosides I and II have novel structures because the core simonic acid B was esterised...

متن کامل

Three new pentasaccharide resin glycosides from the roots of sweet potato (Ipomoea batatas).

Three new pentasaccharide resin glycosides, batatosides III-V (1-3), were isolated from the roots of Sweet potato (Ipomoea batatas). Saponification of the crude resin glycoside mixture yielded substituents and simonic acid B. The structures of the isolated compounds (1-3) were established through spectroscopic analyses, including high field NMR spectroscopy and HR-ESI-MS, and chemical correlati...

متن کامل

Components of ether-insoluble resin glycoside (convolvulin) from seeds of Quamoclit pennata.

Alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction of the seeds of Quamoclit pennata BOJER (Convolvulaceae) provided five new glycosidic acids, quamoclinic acids B, C, D, E, and F, along with six organic acids, isobutyric, 2S-methylbutyric, tiglic, 2R,3R-nilic, 7S-hydroxydecanoic, and 7S-hydroxydodecanoic acids. These new compounds were characterized on the basis ...

متن کامل

08 BR ERCISLI.indd

Methanolic extracts of diff erent parts of fi ve medicinal plants, Ferula assafoetida L. resin, Grewia asiatica L. leaves, Ipomoea hederacea Jacq. seeds, Lepidium sativum L. seeds and Terminalia chebula Retz. fruits were tested in vitro for their cytotoxic, phytotoxic, insecticidal, nematicidal and anthelmintic activities. Ipomoea hederacea showed very signifi cant phytotoxic and cytotoxic acti...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Journal of natural products

دوره 66 11  شماره 

صفحات  -

تاریخ انتشار 2003