Botanical, Pharmacological, Phytochemical, and Toxicological Aspects of the Antidiabetic Plant Bidens pilosa L.

Table 4

Polyynes isolated from 𝐵. pilosa [32].

S. number	IUPAC names	Common names	Structure	Plant part (country)	References
1	1,7𝐸,9𝐸,15𝐸-Heptadecatetraene-11,13-diyne	Heptadeca-2𝐸,8𝐸,10𝐸,16-tetraen-4,6-diyne		Not found (China)	[33]
2	1,11-tridecadiene-3,5,7,9-tetrayne			Roots (not stated)	[34]
3	1-Tridecene-3,5,7,9,11-pentayne	Pentadiene		Leaves (not stated) and not found (Egypt)	[34, 35]
4	5-Tridecene-7,9,11-triyne-3-ol			Not found (Egypt)	[35]
5	2,10,12-Tridecatriene-4,6,8-triyn-1-ol			Part not specified (not stated)	[36]
6	2,12-Tridecadiene-4,6,8,10-tetrayn-1-ol	1,11-Tridecadiene-3,5,7,9-tetrayn-13-ol		Roots (not stated) and not found (Egypt)	[34, 35]
7	2,12-Tridecadiene-4,6,8,10-tetraynal	1,11-Tridecadiene-3,5,7,9-tetrayn-13-al		Roots (Germany)	[37]
8	2,12-Tridecadiene-4,6,8,10-tetrayn-1-ol,1-acetate	1,11-Tridecadiene-3,5,7,9-tetrayn-13-acetate		Roots (not stated)	[34]
9	(5𝐸)-1,5-Tridecadiene-7,9-diyn-3,4,13-triol			Aerial (China)	[38]
10	(6𝐸,12𝐸)-3-oxo-tetradeca-6,12-dien-8,10-diyn-1-ol			Aerial (China)	[38]
11	(𝐸)-5-Tridecene-7,9,11-triyne-1,2-diol	1,2-Dihydroxy-5(𝐸)-tridecene-7,9,11-triyne		Whole (Taiwan)	[39]
12	(𝐸)-6-Tetradecene-8,10,12-triyne-1,3-diol	1,3-Dihydroxy-6(𝐸)-tetradecene-8,10,12-triyne		Whole (Taiwan)	[39–41]
13	(2𝑅,3𝐸,11𝐸)-3,11-Tridecadiene-5,7,9-triyne-1,2-diol	Safynol		Not found (Egypt and China)	[33, 35]
14	5,7,9,11-Tridecatetrayne-1,2-diol	1,2-Dihydroxytrideca-5,7,9,11-tetrayne		Whole (Taiwan)	[39, 40, 42]
15	(𝑅)-3,5,7,9,11-Tridecapentayne-1,2-diol	(𝑅)-1,2-Dihydroxytrideca-3,5,7,9,11-pentayne		Aerial (Japan)	[43]
16	(4𝐸)-1-(Hydroxymethyl)-4-dodecene-6,8,10-triyn-1-yl-𝛽-𝐷-glucopyranoside	2-𝛽-𝐷-Glucopyranose-1-hydroxy-5(𝐸)-tridecene-7,9,11-triyne		Aerial (USA); whole (Taiwan); leaves (Taiwan)	[15, 23, 24, 30, 41]
17	(4𝐸)-1-(2-Hydroxylethyl)-4-dodecene-6,8,10-triyn-1-yl-𝛽-𝐷-glucopyranoside	3-𝛽-𝐷-Glucopyranose-1-hydroxy-6(𝐸)-tridecene-8,10,12-triyne		Aerial (USA and China); whole (Taiwan); leaves (Taiwan)	[15, 23, 24, 30, 41, 44]
18	3-Hydroxy-6-tetradecene-8,10,12-triynyl-𝛽-D-glucopyranoside	𝛽-𝐷-Glucopyranoyloxy-3-hydroxy-6𝐸-tetradecene-8,10,12-triyne		Whole (Mexico)	[45]
19	1-(Hydroxymethyl)-4,6,8,10-dodecatetrayne-1-yl-𝛽-𝐷-glucopyranoside	Cytopiloyne, 2-𝛽-𝐷-Glucopyranose-1-hydroxytrideca-5,7,9,11-tetrayne		Whole (Taiwan); leaves (Taiwan)	[15, 20, 24]
20	2-𝑂-𝐷-Glucosyltrideca-11𝐸-en-3,5,7,9-tetrayn-1,2-diol			Leaves (Brazil)	[46]
21	(𝑅)-1-(Hydroxymethyl)-2,4,6,8,10-dodecapentayn-1-yl-â-𝐷-glucopyranoside	2-𝛽-𝐷-Glucopyranose-1-hydroxytrideca-3,5,7,9,11-pentayne		Aerial (China and Japan)	[43, 44]
22	1-[[(Carboxyacetyl)oxy]methyl]4,6,8,10-dodecatetraynyl-â-𝐷-glucopyranoside			Aerial (Japan)	[47]
23	(4𝐸)-1-[[(Carboxyacetyl)oxy]-methyl]-4-dodecene-6,8,10-triynyl-â-D-glucopyranoside			Aerial (Japan)	[47]
24	(4𝐸)-1-[[(Carboxyacetyl)oxy]-ethyl]-4-dodecene-6,8,10-triynyl-â-𝐷-glucopyranoside			Aerial (Japan)	[47]
25	(5𝐸)-5-Heptene-1,3-diyn-1-yl-benzene	1-Phenylhepta-1,3-diyn-5en		Whole (Taiwan)	[48]
26	7-Phenyl-2(𝐸)-heptene-4,6-diyn-1-ol			Roots (not stated); aerial (China)	[34, 38]
27	7-Phenyl-2(𝐸)-heptene-4,6-diyn-1-ol-acetate			Roots not stated and brazil	[34, 49, 50]
28	7-Phenyl-4,6-heptadiyn-2-ol	Pilosol A		Whole (Taiwan); aerial (China)	[38, 48]
29	7-Phenylhepta-4,6-diyn-1,2-diol			Aerial (China)	[38]
30	1,3,5-Heptatriyn-1-yl-benzene	1-Phenylhepta-1,3,5-triyne		Leaves (not stated); leaves of tissue culture (not stated); aerial (Tanzania and China); whole (Taiwan); roots (Brazil)	[34, 38, 48, 50–53]
31	7-Phenyl-2,4,6-heptatriyn-1-ol			Leaves (not stated) and aerial (China)	[34, 38]
32	7-Phenyl-2,4,6-heptatriyn-1-ol-acetate			Leaves (not stated)	[34]
33	5-(2-Phenylethynyl)-2-thiophene methanol			Aerial (China)	[38]
34	5-(2-Phenylethynyl)-2𝛽-glucosylmethyl-thiophene			Aerial (China)	[38]
35	3-𝛽-𝐷-Glucopyranosyl-1-hydroxy-6(𝐸)-tetradecene-8,10,12-triyne			Leaves (Cameroon)	[54]
36	1-Phenyl-1,3-diyn-5-en-7-ol-acetate			Leaves (Brazil)	[46]