Isohelianol:  A 3,4-seco-Triterpene Alcohol from Sasanqua Oil

Abstract

The structure of isohelianol isolated from the seeds of Camellia sasanqua Thunb. was established to be 3,4-seco-19(10-->9)-abeo-8alpha,9beta,10alpha-eupha-4,24-dien-3-ol (1) on the basis of spectroscopic methods.

3-Epicabraleahydroxylactone and Other Triterpenoids from Camellia Oil and Their Inhibitory Effects on Epstein-Barr Virus Activation

“…Fraction A acetate contained acetylated triterpene monols of which the isolation and characterization have been reported recently. [1][2][3][4][5] Upon column chromatography on silica gel [silica gel, 70 g; eluant, nhexane-EtOAc (4 : 1)], the fraction B acetate yielded six fractions with the ascending order of polarity: fractions B1 (292 mg), B2 (201 mg), B3 (112 mg), B4 (126 mg), B5 (107 mg), and B6 (212 mg). Fractions B1-B6 were subjected to preparative HPLC which yielded: dammarenediol II 3-acetate (5a; 67.0 mg, t R 28.9 min) from fraction B1; 3-epicabraleadiol 3-acetate (2a; 11.0 mg, t R 31.4 min), ocotillol I 3-acetate (4a; 2.0 mg, t R 33.4 min), 5a (5.0 mg), and lupane-3b,20-diol (7a; 5.4 mg, t R 37.8 min) from fraction B2; 2a (1.0 mg), ocotillol II 3-acetate (3a; 3.3 mg, t R 29.2 min), and 7a (3.2 mg) from fraction B3; 3-epicabraleadiolhydroxylactone 3-acetate (1a; 3.7 mg, t R 12.5 min), 3a (0.5 mg), and (20R)-taraxastane-3b,20-diol 3-acetate (6a; 4.5 mg, t R 48.4 min) from fraction B4; and 1a (12.2 mg) from fraction B5.…”

“…Identification and Characterization Identification of 2 and 5 was performed by spectral (MS, 1 H-, C-NMR), 3,17,18) 4 (MS and 1 H-NMR), 19) and 7 (MS, 1 H-,…”

“…[2][3][4][5] Upon evaluation of the antiinflammatory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice, 14 tetracyclic and pentacyclic triterpenoids were shown to have inhibitory effects. 1) In this paper, we report the isolation and characterization of a triterpenoid, 3-epicabraleahydroxylactone [1; (20S)-3b-hydroxy-25,26,27-trisnordammaran-24, 20-olide], which is known as a semisynthetic compound 6) but is a new natural product, along with six known trieterpenoids, 3-epicabraleadiol (2), ocotillol II (3), ocotillol I (4), dammarenediol II (5), (20R)-taraxastane-3b,20-diol (6), and lupane-3b,20-diol (7), from the dihydroxy triterpenoid (triterpene diol) fraction of the NSL fraction obtained from camellia oil, as well as their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, as a primary screening for antitumor promoters.…”

Molluscicidal Activity of Compounds Isolated from Euphorbia conspicua N. E. Br

“…2 The Me 2 CO fraction was evaporated and redissolved in MeOH/H 2 O (1:1) and subsequently extracted with hexane. The hexane fraction (30 g) was analyzed by 1 H and 13 C NMR and identified as the triterpenic fraction. 17 The metanolic filtrate, obtained from the defrosted latex, was evaporated to dryness and extracted with hexane to yield fraction I (1 g); the insoluble portion was dissolved in MeOH-H 2 O (1:1) and extracted with Et 2 O (fraction II, 2 g).…”

New (9βH)‐Lanostanes and Lanostanes from Mikania aff. jeffreyi (Asteraceae)

“…The olefinic C-atom chemical shifts are very useful in the determination of the Cskeleton of triterpenes [15]. A literature research about with higher intensity for each C-atom, i.e., C, CH, CH 2 , and Me, with those of acetyleuphol, acetyl-tirucallol [12], and acetyl-lanosterol [13] established the structure of 1 as acetyl-lanosterol. On the other hand, the chemical shifts of the olefinic C-atoms of compound 2 were not in agreement with those of lanost-7-en-3b-ol acetate [17].…”