<i>ent</i>-Kaur-16-ene-13,19-diol

Salae, Abdul Wahab; Chantrapromma, Suchada; Fun, Hoong‐Kun; Ponglimanont, Chanita

doi:10.1107/s1600536807012834

Cited by 3 publications

(1 citation statement)

References 8 publications

(8 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In our continuing research on bioactive compounds from mangrove sources, we have studied the chemical constituents from the roots of Bruguiera cylindrica (Rhizophoraceae) to search for the bioactive components. We have previously reported the crystal structure of the entkaur-16-ene-13,19-diol which was isolated from this plant (Salae et al, 2007). We herein report the crystal structure of the title compound which has an inhibitory activity on vascular smooth muscle contraction (Müller et al, 2003).…”

Section: S1 Commentmentioning

confidence: 85%

ent-Kaur-16-en-19-al

et al. 2007

Self Cite

View full text Add to dashboard Cite

Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.035; wR factor = 0.097; data-to-parameter ratio = 14.1.The title ent-kaurane diterpene compound, C 20 H 30 O, was isolated from the roots of Bruguiera cylindrica (Rhizophoraceae), a mangrove plant. The molecule contains a fused fourring system, with the three cyclohexane rings in standard chair conformations and the cyclopentane ring adopting an envelope conformation. The aldehyde is bisectionally attached to the cyclohexane ring. The methylene group is coplanar with the attached cyclopentane ring. In the crystal structure, molecules are packed by van der Waals interactions. Related literatureFor the values of bond lengths, see Allen et al. (1987). For literature on ring conformations, see Cremer & Pople (1975). For further details of ent-kaurane diterpenes and their bioactive properties, see, for example: Karle (1972); Mü ller et al. (2003); Salae et al. (2007). Experimental Crystal data C 20 H 30 O M r = 286.44 Orthorhombic, P2 1 2 1 2 1 a = 6.3126 (2) Å b = 11.2823 (4) Å c = 22.8044 (7) Å V = 1624.14 (9) Å 3 Z = 4 Mo K radiation = 0.07 mm À1 T = 100.0 (1) K 0.56 Â 0.40 Â 0.13 mm Data collection Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) T min = 0.952, T max = 0.991 20475 measured reflections 2709 independent reflections 2571 reflections with I > 2(I) R int = 0.029 Refinement R[F 2 > 2(F 2 )] = 0.035 wR(F 2 ) = 0.097 S = 1.07 2709 reflections 192 parameters H-atom parameters constrained Á max = 0.31 e Å À3 Á min = À0.17 e Å À3 Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

show abstract

Section: S1 Commentmentioning

confidence: 85%

ent-Kaur-16-en-19-al

et al. 2007

Self Cite

View full text Add to dashboard Cite

show abstract

Metabolites and bioactivities of Rhizophoraceae mangroves

Murukesh

Harisankar

Chandramohanakumar

2013

Nat. Prod. Bioprospect.

View full text Add to dashboard Cite

This review examines the chemical compositions and bioactivities of mangrove plants belonging to the Rhizophoraceae family. The Rhizophoraceae family of true mangrove plants is the most common and is also widely distributed species. It consists of 24 species across four genera. Of the 24 species, 12 species remain unexamined for their phytochemical constituents. There have been 268 metabolites reported from 16 species. The key phytochemical constituents identified across the family are the diterpenoids and triterpenoids. The major diterpenoids include pimaranes, beyeranes, kaurenes, dolabranes and labdanes whereas the significant triterpenoids are lupanes, dammaranes and oleananes. Disulphides, dolabranes and labdanes are considered to be the chemotaxonomic markers of the genera Bruguiera, Ceriops and Rhizophora respectively.

show abstract