“Withanolide”的意思、由来-开放百科全书

Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton.^[1]^[2] They occur as secondary metabolites primarily in genera of the Nightshade family, for example in the tomatillo.

Structurally, withanolides consist of a steroid backbone bound to a lactone or one of its derivatives; they are produced via oxidation of steroids. It remains unknown to what end withanolides are produced; they may act as a deterrent for feeding insect larvae and other herbivores.

In the laboratory, many withanolides have exhibited medicinally interesting properties.^[3]^[4]

Genera within the nightshade family that have been found to produce withanolides include: Acnistus, Datura, Dunalia, Iochroma, Lycium, Nicandra, Physalis, Salpichroa, Solanum, Withania, and Jaborosa.{{citation needed|date=April 2016}}

This class of steroidal lactones involves an ergostane-type framework in which C-22 and C-26 are appropriately oxidised to form a (delta)-lactone ring. They are subdivided into nine groups: withanolides, withaphysalins, physalins, nicandrenones, jaborols, ixocarpalactones, perulactones, acnistins and miscellaneous withasteroids.{{citation needed|date=April 2016}}

Examples

Salpichrolides A, B and G (isolated from Salpichroa origanifolia) exhibit an inhibitory effect on the growth of larva of the Mediterranean Fruit Fly (Ceratitis capitata). For this reason, potential pesticide uses for the compounds are being explored.^[9]

The nicandrenones of Nicandra physalodes are another group of withanolides with insecticidal effects. 30 years after their discovery, the first total synthesis of nicandrenones was carried out in the year 2000.^[10]

Ixocarpalactone A, isolated from the tomatillo (Physalis philadelphica), shows promise as an anti-tumor agent.^[11]

References

1. ^{{cite journal|last1=Glotter|first1=E.|title=Withanolides and related ergostane-type steroids|journal=Natural Product Reports|volume=8|issue=4|year=1991|pages=415|issn=0265-0568|doi=10.1039/np9910800415}}
2. ^{{cite journal|last1=Kirson|first1=Isaac|last2=Glotter|first2=Erwin|title=Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review|journal=Journal of Natural Products|volume=44|issue=6|year=1981|pages=633–647|issn=0163-3864|doi=10.1021/np50018a001}}
3. ^{{ cite web | url = http://www.qo.fcen.uba.ar/Grupos/burtongrp-en.htm#Withas | work = Synthesis, structure and conformation of natural products and analogues of biological importance | title = Insecticides and feedant deterrants of natural origin related to the withanolides. Isolation, structural elucidation and synthesis | author = Burton, G.| publisher = University of Buenos Aires |display-authors=etal}}
4. ^{{ cite web | url = http://www.qo.fcen.uba.ar/Grupos/burtongrp-en.htm#SAR | work = Synthesis, structure and conformation of natural products and analogues of biological importance | title = Synthesis and structure-activity correlations of steroid hormone analogues | author = Burton, G.| publisher = University of Buenos Aires |display-authors=etal}}
5. ^{{ cite web | url = https://www.drugs.com/npp/ashwaganda.html | publisher = Drugs.com | work = Natural Products | title = Ashwagandha }}
6. ^¹²{{cite journal |author1=Prasanna, K. S. |author2=Shilpa, P. |author3=Salimath, B. P. | title = Withaferin A suppresses the expression of vascular endothelial growth factor in Ehrlich ascites tumor cells via Sp1 transcription factor | journal = Current Trends in Biotechnology and Pharmacy | year = 2009 | volume = 3 | issue = 2 | pages = 138–148 | url = http://www.pharmainfo.net/files/Withaferin%20A_0.pdf}}
7. ^{{cite journal |author1=Mohan, R. |author2=Hammers, H. J. |author3=Bargagna-Mohan, P. |author4=Zhan, X. H. |author5=Herbstritt, C. J. |author6=Ruiz, A. |author7=Zhang, L. |author8=Hanson, A. D. | title = Withaferin a is a potent inhibitor of angiogenesis | journal = Angiogenesis | year = 2004 | volume = 7 | issue = 2 | pages = 115–122 | doi = 10.1007/s10456-004-1026-3 | pmid = 15516832 |display-authors=etal}}
8. ^{{cite journal | last1 = Prabhakaran | first1 = Y. | last2 = Dinakaran | first2 = S. K. | last3 = Macharala | first3 = S. P. | last4 = Ghosh | first4 = S. | last5 = Karanam | first5 = S. R. | last6 = Kanthasamy | first6 = N. | last7 = Avasarala | first7 = H. | title = Molecular docking studies of withanolides against Cox-2 enzyme | journal = Pakistan Journal of Pharmaceutical Sciences | year = 2012 | volume = 25 | issue = 3 | pages = 595–598 | pmid = 22713947 }}
9. ^{{ cite journal | last1 = Bado | first1 = S. | last2 = Mareggiani | first2 = G. | last3 = Amiano | first3 = N. | last4 = Burton | first4 = G. | last5 = Veleiro | first5 = A. S. | title = Lethal and Sublethal Effects of Withanolides from Salpichroa origanifolia and Analogues on Ceratitis capitata | journal = Journal of Agricultural and Food Chemistry | year = 2004 | volume = 52 | issue = 10 | pages = 2875–2878 | doi = 10.1021/jf035508a | pmid = 15137828 }}
10. ^{{ cite journal | last1 = Stoltz | first1 = B. M. | last2 = Kano | first2 = T. | last3 = Corey | first3 = E. J. | authorlink3 = Elias James Corey | title = Enantioselective Total Synthesis of Nicandrenones | journal = Journal of the American Chemical Society | year = 2000 | volume = 122 | issue = 37 | pages = 9044–9045 | doi = 10.1021/ja0024892 }}
11. ^{{ cite journal | first1 = A. D. | last2 = Su | first2 = B. N. | last3 = Lee | first3 = D. | last4 = Gu | first4 = J. Q. | last5 = Pezzuto | first5 = J. M. | title = Cancer Chemopreventive Agents Discovered by Activity-Guided Fractionation: An Update | last1 = Kinghorn | journal = Current Organic Chemistry | year = 2003 | volume = 7 | issue = 3 | pages = 213–226 | doi = 10.2174/1385272033373003 }}