Gymnopusin

Last updated
Gymnopusin
Gymnopusin.svg
Chemical structure of gymnopusin
Names
Preferred IUPAC name
3,4,9-Trimethoxyphenanthrene-2,7-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C17H16O5/c1-20-14-7-9-6-13(19)16(21-2)17(22-3)15(9)11-5-4-10(18)8-12(11)14/h4-8,18-19H,1-3H3
    Key: GIVSZLKTIBWYRM-UHFFFAOYSA-N
  • InChI=1/C17H16O5/c1-20-14-7-9-6-13(19)16(21-2)17(22-3)15(9)11-5-4-10(18)8-12(11)14/h4-8,18-19H,1-3H3
    Key: GIVSZLKTIBWYRM-UHFFFAOYAJ
  • COC1=CC2=CC(=C(C(=C2C3=C1C=C(C=C3)O)OC)OC)O
Properties
C17H16O5
Molar mass 300.310 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gymnopusin is a phenanthrenediol produced by the orchid Bulbophyllum gymnopus . [1] It is also found in Bulbophyllum reptans [2] and Maxillaria densa . [3]

Related Research Articles

<span class="mw-page-title-main">Orchid</span> Orchid family of flowering plants in the order Asparagales

Orchids are plants that belong to the family Orchidaceae, a diverse and widespread group of flowering plants with blooms that are often colourful and fragrant.

<i>Bulbophyllum</i> Genus of orchids

Bulbophyllum is a genus of mostly epiphytic and lithophytic orchids in the family Orchidaceae. It is the largest genus in the orchid family and one of the largest genera of flowering plants with more than 2,000 species, exceeded in number only by Astragalus. These orchids are found in diverse habitats throughout most of the warmer parts of the world including Africa, southern Asia, Latin America, the West Indies, and various islands in the Indian and Pacific Oceans. Orchids in this genus have thread-like or fibrous roots that creep over the surface of trees or rocks or hang from branches. The stem is divided into a rhizome and a pseudobulb, a feature that distinguished this genus from Dendrobium. There is usually only a single leaf at the top of the pseudobulb and from one to many flowers are arranged along an unbranched flowering stem that arises from the base of the pseudobulb. Several attempts have been made to separate Bulbophyllum into smaller genera, but most have not been accepted by the World Checklist of Selected Plant Families.

<i>Maxillaria</i> Genus of orchids

Maxillaria, abbreviated as Max in the horticultural trade, is a large genus of orchids. This is a diverse genus, with very different morphological forms. Their characteristics can vary widely. They are commonly called spider orchids, flame orchids or tiger orchids. Their scientific name is derived from the Latin word maxilla, meaning jawbone, reflecting on the column and the base of the lip of some species, that may evoke a protruding jaw.

Black orchid or Black Orchid may refer to:

<span class="mw-page-title-main">Phenanthrenoid</span>

Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.

<i>Bulbophyllum vaginatum</i> Species of orchid

Bulbophyllum vaginatum is a species of orchid.

<i>Maxillaria cucullata</i> Species of orchid

Maxillaria cucullata, the cowl-carrying maxillaria, is a species of orchid ranging from Mexico, Belize southward into Panama.

<i>Maxillaria densa</i> Species of orchid

Maxillaria densa, the crowded maxillaria, is a species of orchid ranging from Mexico south to Nicaragua.

<i>Maxillaria sophronitis</i> Species of orchid

Maxillaria sophronitis, the sophronitis-like maxillaria, is a species of orchid found in Venezuela and northeastern Colombia.

Bulbophyllum gymnopus is a species of orchid in the genus Bulbophyllum.

Bulbophyllum reptans is a species of orchid in the genus Bulbophyllum.

Bulbophyllum crabro, commonly called "Kam Pu Ma" in Thai, is a small orchid that grows as an epiphyte or is sometimes found as lithophyte. It grows in rainforests 1,600-2,000 m above sea level. It was formerly known as Monomeria barbata and was the type species of the genus Monomeria, now synonymous with Bulbophyllum. It is used in traditional Chinese medicine for treating coughs, pulmonary tuberculosis and trauma.

<span class="mw-page-title-main">Dihydrostilbenoid</span>

Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.

<span class="mw-page-title-main">Maxillariinae</span> Subtribe of orchids

Maxillariinae is an orchid subtribe in the tribe Cymbidieae. It was formerly treated as the tribe Maxillarieae, and divided into a number of subtribes.

<span class="mw-page-title-main">Plicatol B</span> Chemical compound

Plicatol B is one of the three phenanthrenes that can be isolated from the stems of the orchid Flickingeria fimbriata. It can also be isolated from Dendrobium densiflorum, D. loddigesii, D. moschatum, D. rotundatum and Bulbophyllum kwangtungense

<span class="mw-page-title-main">Nudol</span> Chemical compound

Nudol is a phenanthrenoid of the orchids Eulophia nuda, Eria carinata, Eria stricta and Maxillaria densa.

<span class="mw-page-title-main">Confusarin</span> Chemical compound

Confusarin is a phenanthrenoid found in the orchids Eria confusa and Bulbophyllum reptans. It can also be synthesized.

<i>Heterotaxis sessilis</i> Species of orchid

Heterotaxis sessilis is an epiphytic orchid widespread across the West Indies, Central America, southern Mexico, Florida and northern South America. Hidden orchid is a common name.

<i>Camaridium vestitum</i> Species of orchid

Camaridium vestitum, called purple tiger orchid, is a species of epiphytic orchids native to Florida, the West Indies and through Latin America from Mexico to Bolivia.

References

  1. Structure and synthesis of gymnopusin, a novel phenanthrenediol from the orchid Bulbophyllum gymnopus. Andrew B. Hughes and Melvyn V. Sargent, J. Chem. Soc., 1989, Perkin Trans. 1, pages 1787-1791, doi : 10.1039/P19890001787
  2. Kovacs, Phytochemistry, 69, (2008), 1084
  3. Phytotoxicity and ultrastructural effects of gymnopusin from the orchid Maxillaria densa on duckweed (Lemna pausicostata) frond and root tissues. Valencia-Islas NA, Paul RN, Shier WT, Mata R and Abbas HK, Phytochemistry, 2002, volume 61, issue 2, pages 141-148, PMID   12169307, doi : 10.1016/S0031-9422(02)00220-0