Tinocrisposid, ein neues Furanoditerpenglykosid aus Tinospora crispa Miers

Abstract

Aus Stengeln vonAus dem Methanolextrakt der Stengel isolierten wir nach Abtrennung der N-Acylaporphine als neues, Dragendorflpositives Furanoditerpenglykosid Tinocrisposid (l), uber dessen Strukturaufklarung hier berichtet werden soll. Furanoditerpene wurden schon haufiger als bittere Inhaltsstoffe in anderen Menispermaceen, besonders aber in der Gattung Tinospora g e f~n d e n~?~.~) .Aus Tinospora tuberculata Beumee (syn. T. crispa) wurde Borapetosid A beschrieben*), das sich von 1 u.a. durch eine zusatzliche OH-Gruppe sowie durch 2 Lactonringe und Glukosidierung in Position 3 unterscheidet.Das in Wasser schwer losliche 1 hat laut FAB-MS die gleiche Summenformel C27H3601 wie Tinophyllolosid (31, das vor einiger Zeit als Inhaltsstoff von Fibraurea tinctoria beschrieben wurdeg). Auf Grund der ersten spektroskopischen Ergebnisse hatten wir fur Tinocrisposid zunachst Struktur 2 vorgeschlagen"), erst die intensive Auswertung von 600 MHz-'H-NMR-Spektren ermoglichte die genaue Zuordnung der in 300 MHz-Spektren sich vielfach uberlagemden Protonensignale, die dann zu Struktur

Anti-Inflammatory Activity of Tinocrisposide by Inhibiting Nitric Oxide Production in Lipopolysaccharides-Stimulated Raw 264.7 Cells

“…In this study, we used tinocrisposide as a test compound which was isolated from methylene chloride fractions of T. crispa stems. The isolation process was conducted according to our previous method by Pachaly and Adnan [8]. The structure of the compound was identified spectroscopically and confirmed with previous data in our publication.…”

“…From methanol extract of dried pulvered T. crispa stems, we have isolated tinocrisposide (C 27 H 36 O 11 ), a furano diterpene glycoside with very bitter taste. This work has been reported in Arch Pharm [8]. An antiinflammatory effect of tinocrisposide has been investigated in vivo in our previous study and reported in 43 rd GA-Congress in Halle, Germany [9].…”

Amritosides A, B, C and D: clerodane furano diterpene glucosides from Tinospora cordifolia

“…(Menispermaceae) popularly known as Amrita in Sanskrit, has been used for several centuries in Ayurvedic medicine for the treatment of various ailments (Chadha, 1976). This species is rich in clerodane derived diterpenes (Pachaly and Adnan, 1992;Rahman et al, 1992;Fukuda et al, 1993;Gangan et al, 1995;Maurya, 1996;Martin et al, 1996). Previously, we reported on the isolation and characterization of several new furanoditerpene glucosides Maurya et al, 1995) from T. cordifolia.…”

Antihyperglycemic Activity of Tinocrisposide by Stimulating 3t3-L1 Adipocyte Cell Differentiation

“…This hypoglycemic effect was likely due to by insulinotropic mechanism [2]. From methanol extract of dried pulverized T. crispa stems, tinocrisposide (C 27 H 36 O 11 ) has been isolated, a furanoditerpene glycoside with a very bitter taste [4]. It is considered that tinocrisposide is responsible for some biological activity of T. crispa stem extracts so that it has been used as an antidiabetic treatment in traditional medicine (Fig.…”