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Structure of tinosporide, a diterpenoid furanolactone from Tinospora cordifolia Miers

Structure of tinosporide, a diterpenoid furanolactone from Tinospora cordifolia Miers

Acta Crystallographica. Section C, Crystal Structure Communications 45: 134-136

(1S,2S,3R,4R,5R,8S,10R,12S)-4-Hydroxy-2,3:15,16-diepoxycleroda-13( 16),14- dieno-17,12:18,1-biscarbolactone, C20H22O7, Mr = 374, m.p. = 509-511 K, orthorhombic, P2(1)2(1)2(1), a = 9.191 (2), b = 13.8230 (6), c = 26.956 (2) A, V = 3424.50 A3, Z = 8, Dx = 1.450, Dm (by flotation) = 1.446 g cm-3, lambda (Cu K alpha) = 1.5418 A, mu = 8.20 cm-1, F(000) = 1584, T = 295 K, R = 0.0464, wR = 0.0579 for 3437 observed reflections. The asymmetric unit contains two molecules. The structure resembles that of a similar compound [Swaminathan, Sinha, Bhatt & Sabata (1988). Acta Cryst. C44, 1421-1424] with atom H(15) replacing the tertiary hydroxyl group at C(8). Atoms H(4) and H(15) are alpha- and beta-oriented respectively at sites C(12) and C(8). The terpene ring A is locked into a boat conformation by the C(1)-C(4) lactone bridge. The hydroxyl at C(4) is involved in hydrogen bonding.

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Accession: 041451986

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PMID: 2610955

DOI: 10.1107/s0108270188009953

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