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6?,15?-Diacet-oxy-1?,7?,13?-trihydr-oxy-7?,20-ep-oxy-ent-kaur-16-ene.

ABSTRACT: The title compound, C(24)H(34)O(8), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans junctions. The crystal structure is stabilized by inter-molecular O-H?O hydrogen bonds. In addition, an intra-molecular O-H?O hydrogen bond occurs.

SUBMITTER: Di XM

PROVIDER: S-EPMC2979703 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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6β,15β-Diacet-oxy-1β,7β,13α-trihydr-oxy-7α,20-ep-oxy-ent-kaur-16-ene.

Di Xue-Mei XM Yan Fu-Lin FL Feng Chuang C Cui Jian-Min JM

Acta crystallographica. Section E, Structure reports online 20100116 Pt 2

The title compound, C(24)H(34)O(8), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans junctions. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds. In addition, an intra-molecular O-H⋯O hydrogen bond occurs. ...[more]

PMID: 21579784

Similar Datasets

1?,6?,7?,14?,15?-Penta-hydr-oxy-7?,20-ep-oxy-ent-kaur-16-ene.

Project description:The title compound, enmenol, C(20)H(30)O(6), a natural ent-kaurane diterpenoid, comprises five fused rings, four of which are six-membered. Cyclo-hexane ring A adopts a chair conformation, rings B and C adopt boat conformations, while ring D has an envelope conformation, and two intramolecular O-H?O interactions occur. In the crystal, inter-molecular O-H?O hydrogen bonds generate a two dimensional network.

| S-EPMC2980239 | biostudies-literature

1α,6β,7β,11α,15β-Penta-hydr-oxy-7α,20-ep-oxy-ent-kaur-16-ene.

Project description:The title compound, C(20)H(30)O(6), a natural ent-kaurane diterpenoid, named nervosanin B, was obtained from the medicinal plant Isodon serra. It is composed of four rings with the expected trans and cis junctions. One of the six-membered rings is in a chair conformation, the other two are in boat conformations and the five-membered ring adopts an evenlope conformation. The mol-ecules stack along the a axis and are linked together by inter-molecular O-H⋯O hydrogen bonds. Two intramolecular O-H⋯O interactions also occur.

| S-EPMC2979982 | biostudies-literature

6β-Acet-oxy-1α,7β,11β,15β-tetra-hydr-oxy-7α,20-ep-oxy-ent-kaur-16-ene.

Project description:The title compound, C(22)H(32)O(7), a natural ent-kaurane diterpenoid also referred to as Maoyecrystal F, was obtained from the medicinal plant Isodon nervosa. There are four rings with the expected cis and trans junctions. Cyclohexane ring A adopts a chair conformation, rings B and C adopt boat conformations, while the five-membered ring has an envelope conformation. The mol-ecules stack along the a axis in the crystal and are linked together by inter-molecular O-H⋯O hydrogen bonds.

| S-EPMC2979918 | biostudies-literature

15?,20?-Dihydr-oxy-6?-meth-oxy-6,7-seco-6,20-ep-oxy-1,7-olide-ent-kaur-16-ene.

Project description:The title compound, C(21)H(30)O(6), a natural ent-kaurane diterpenoid, was obtained from the medicinal plant Isodon serra. The five rings in the mol-ecule exhibit the expected cis and trans junctions. The three six-membered rings adopt chair, twist-boat and boat conformations, while two five-membered rings adopt envelope conformations. There are two mol-ecules in the asymmetric unit, related by a non-crystallographic twofold screw axis; the main difference is in the different degrees of distortion of ring B. In the crystal, the mol-ecules are linked by inter-molecular O-H?O hydrogen bonds, forming chains along the b axis.

| S-EPMC2984011 | biostudies-other

1?,11?,15?-Triacet-oxy-7?-hydroxy-7?,20-ep-oxy-ent-kaur-16-en-6-one.

Project description:The title compound, C(26)H(34)O(9), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans junctions. In the crystal structure, the mol-ecules stack along the a axis and are linked together by inter-molecular O-H?O hydrogen bonds.

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16?,17?-Ep-oxy-5?-hydr-oxy-6?-nitrooxy-20-oxopregnan-3?-yl acetate.

Project description:The title steroid, C(23)H(33)NO(8), is a pregnane derivative obtained regio-, stereo- and chemoselectively from the ring opening of the corresponding 5?,6?;16?,17?-diepoxide with bis-muth(III) nitrate. There are two symmetry-independent mol-ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. All rings are trans-fused. The conformations of the six-membered rings are close to chair forms, while the five-membered ring adopts an envelope conformation. The mol-ecules are held together by an extensive O-H?O hydrogen-bonding network of chains runnning along the a axis.

| S-EPMC2969566 | biostudies-literature

1?,15?-Dihy-droxy-16?,17-ep-oxy-pregn-4-ene-3,20-dione.

Project description:The title mol-ecule, C21H28O5, is composed of three six-membered rings (A/B/C) and a five-membered ring (D). Ring A adopts a 1?-sofa conformation, while rings B and C adopt chair conformations. Cyclo-pentane ring D adopts a 14?-envelope conformation. In the crystal, O-H?O hydrogen bonds lead to the formation of ribbons running along the a axis. The structure is further consolidated by C-H?O inter-actions, which link the molecules head-to-tail into ribbons along the a axis.

| S-EPMC3588417 | biostudies-literature

Tetra-glucopyranosyl Diterpene ent-Kaur-16-en-19-oic Acid and ent-13(S)-Hydroxyatisenoic Acid Derivatives from a Commercial Extract of Stevia rebaudiana (Bertoni) Bertoni.

Project description:Stevia rebaudiana and its diterpene glycosides are one of the main focuses of food companies interested in developing novel zero calorie sugar substitutes since the recognition of steviol glycosides as Generally Recognized as Safe (GRAS) by the United States Food and Drug Administration. Rebaudioside A, one of the major steviol glycosides of the leaves is more than 200 times sweeter than sucrose. However, its lingering aftertaste makes it less attractive as a table-top sweetener, despite its human health benefits. Herein, we report the purification of two novel tetra-glucopyranosyl diterpene glycosides 1 and 3 (rebaudioside A isomers) from a commercial Stevia rebaudiana leaf extract compounds, their saponification products compounds 2 and 4, together with three known compounds isolated in gram quantities. Compound 1 was determined to be 13-[(2-O-?-d-glucopyranosyl-6-O-?-d-glucopyranosyl-?-d-glucopyranosyl) oxy]ent-kaur-16-en-19-oic acid-?-d-glucopyranosy ester (rebaudioside Z), whereas compound 3 was found to be 13-[(2-O-?-d-glucopyranosyl-3-O-?-d-glucopyranosyl-?-d-glucopyranosyl) oxy]ent-hydroxyatis-16-en-19-oic acid -?-d-glucopyranosy ester. Two new tetracyclic derivatives with no sugar at position C-19 were prepared from rebaudiosides 1 and 3 under mild alkaline hydrolysis to afford compounds 2 13-[(2-O-?-d-glucopyranosyl-6-O-?-d-glucopyranosyl-?-d-glucopyranosyl) oxy]ent-kaur-16-en-19-oic acid (rebaudioside Z?) and 4 13-[(2-O-?-d-glucopyranosyl-3-O-?-d-glucopyranosyl-?-d-glucopyranosyl) oxy]ent-hydroxyatis-16-en-19-oic acid. Three known compounds were purified in gram quantities and identified as rebaudiosides A (5), H (6) and J (7). Chemical structures were unambiguously elucidated using different approaches, namely HRESIMS, HRESI-MS/MS, and 1D-and 2D-NMR spectroscopic data. Additionally, a high-quality crystal of iso-stevioside was grown in methanol and its structure confirmed by X-ray diffraction.

| S-EPMC6321316 | biostudies-literature

Ethyl ent-15?-[(2-meth-oxy-benz-yloxy)meth-yl]-16-oxobeyeran-20-oate.

Project description:The title compound, C(31)H(44)O(5), was synthesized from isostev-iol (systematic name: ent-16-ketobeyeran-19-oic acid). In the mol-ecule, the three six-membered rings adopt chair conformations and the stereochemistry of the A/B and B/C ring junctions are trans. The five-membered ring D adopts an envelope conformation with the methyl-ene C atom as the flap.

| S-EPMC3275241 | biostudies-literature

4?-Hy-droxy-12,13-ep-oxy-trichothec-9-ene.

Project description:The asymmetric unit in the crystal of the title compound, C(15)H(22)O(3), contains two independent mol-ecules with similar structures. Each mol-ecule contains two six-membered rings and one five-membered ring. The five-membered ring displays an envelope conformation with the C atom linking the epoxy group as the flap, while the two six-membered rings show half-chair conformations. The two independent mol-ecules are linked by an O-H?O hydrogen bond. These dimers are further linked by O-H?O hydrogen bonds, forming supra-molecular chains running along the a axis.

| S-EPMC3344132 | biostudies-literature

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