The Crystal Structure of Biatractylolide, an 8,8' (C-C) Linked Dimeric 12,8-Eudesmanolide from the Resin of Trattinickia rhoifolia WILLD.

Abstract

In previous papers 1,2) we have described several compounds, mainly sesquiterpenoids, isolated from the resin of Trattinickia rhoifolia WILLD. (Burseraceae). In this paper we report the isolation and structure elucidation by spectroscopic methods and X-ray diffraction analysis of biatractylolide (1). Results and DiscussionTo the solution of resin of T. rhoifolia in methylene chloride, n-hexane was added to selectively precipitate and separate the insoluble material; the soluble part was taken to dryness and redissolved in diethyl ether, then washed with aqueous sodium bicarbonate (5% w/v) to remove the acidic compounds. Elimination of the solvent yielded an oily mixture, which was resolved by silica gel column chromatography using increasing gradient n-hexane-ethyl acetate mixtures as eluent. After column rechromatography on silica gel using an increasing gradient of n-hexane-methylene chloride as eluent, low polarity fractions afforded, along with other previously reported compounds, 3) the bis [8-eudesma-4(15)

Gastroprotective activity of atractylenolide III from Atractylodes ovata on ethanol-induced gastric ulcer in vitro and in vivo

“…A voucher specimen of A. ovata (AO‐1013) was deposited in the Graduate Institute of Pharmacognosy Science, Taipei Medical University. The isolation procedure was modified from a previous study 20,21 . Evidence has shown that the major active components of A. ovata were sesquiterpenoids.…”

Natural disesquiterpenoids

“…153 It was interesting that biatractylolide 152 was also found to be present in the resin of Trattinickia rhoifolia. 154 Biologically, biatractylolide possesses negative inotropic and chronotropic actions on isolated guinea pig hearts -specifically, it significantly inhibited the contractile force and decreased the heart rate of the isolated right atrium, making it a potential agent for lowering blood pressure. 155 The biomimetic synthesis of these dimers has been reported.…”

ChemInform Abstract: Naturally Occurring Dimers from Chemical Perspective

“…Scheme 11 Biatractylolide (86) is a symmetrical dimeric sesquiterpenoid from the resin of Trattinickia rhoifolia Willd. [59]. Glochidiolide (87) is a dimeric butenolide isolated from the leaves of Glochidion acuminatum Mˇll.…”