Studies On Chemical Constituents From The Seed Of Cuminum Cyminum L.(?)

Cuminum cyminum L.belongs to Cuminum Genus of the Umbelliferae family.It is native to North Africa and Mediterranean coastal areas and now is largely distributed in Xinjiang,Inner Mongolia and Gansu in China.The seeds of C.cyminum are also known as cumin or Sabbath fennel in Uyghur,and fragrant celery in Tibetan.In addition to being an important seasoning in barbecue or cooking,the seeds of C.cyminum are often used by different ethnic groups in China to treat digestive diseases,such as indigestion,stomachache,hernia,anorexia,distention of stomach,etc.The extract of the seeds is one of the important raw materials in the Formula of Carly Cumin Tincture,which is recently used to treat vitiligo in clinic.The current reports on the chemical compositions of the seeds of C.cyminum focus on the extraction and separation of volatile oil,and found that cumalaldehyde was the most abundant ingredient in the oil.In vivo and in vitro bioactivity test results show that cumalaldehyde has middle insecticidal,antibacterial,and antioxidant activities,and is one of the main active ingredients in this herb.In addition to volatile oil,some flavonoids and their glycosides,polyphenols,and terpenoids that are common in other plants have also been little reported in cumin seeds.In our previous study,some cuminaldehyde derivatives and polyphenols with novel structures and significant anti-inflammatory activities we were found.In order to find more new cuminaldehyde derivatives or polyphenols,and provide compounds for subsequent biological activity screening,we continue to conduct a systematic phytochemical study on the unfinished subfractions of Lu Huang.From this phytochemical study,31 pure compounds were acquired,and the structures of which were elucidated to be apigenin(WZ-1),luteolin(WZ-2),apigenin-7-O-?-D-glucopyranoside(WZ-3),apigenin-4'-O-?-D-glucopyranoside(WZ-4),luteolin-7-O-?-D-glucopyranoside(WZ-5),luteoin-4'-O-?-D-glucopyranoside(WZ-6),luteoin-3'-O-?-D-glucopyranoside(WZ-7),chrysoeriod-7-O-?-D-glucopyranoside(WZ-8),luteolin-3',4'-dimethoxy-7-O-?-D-glucopyranoside(WZ-9),acacetin-7-rutinoside(WZ-10),diosmin(WZ-11),apigenin-7-O-?-D-(6"-O-acetyl)-glucopyranoside(WZ-12),agriflavone(WZ-13),narirutin(WZ-14),hesperidin(WZ-15),(R)-p-(2-hydroxy-1-methyl ethy)-benzoic acid(WZ-16),(R)-p-cymen-9-yl-O-?-D-glucopyranoside(WZ-17),(4-isopropylbenzyl)-proline(WZ-18),(4-isopropylbenzyl)-valine(WZ-19),salicylic acid(WZ-20),polydatin(WZ-21),torachrysone-8-O-?-D-glucopyranoside(WZ-22),emodin-8-O-?-D-glucopyranoside(WZ-23),cuminoid E(WZ-24),cuminoid E1(WZ-25),cuminoid E2(WZ-26),[1,4-bis(4-hydroxyphenyl)butane-1,4-dione]-4-O-?-D-glucopyranoside(WZ-27),cuminoside A(WZ-28),Byzantionoside B(WZ-29),(6R,7E,9R)-9-hydroxymegastigman-4,7-dien-3-one-9-O-?-D-glucopyranoside(WZ-30),blumenol C-9-O-?-D-apiofuranosyl-(1?6)-?-D-glucopyranoside(WZ-31).Among them,the compounds WZ-25,WZ-26,WZ-27 were the new phenols;WZ-18,WZ-19 were firstly isolated as new natural compounds;and compounds WZ-4,WZ-7,WZ-8,WZ-9,WZ-13,WZ-17,WZ-20,WZ-22,WZ-23,WZ-29,WZ-30,WZ-31 were isolated for the first time from the Cuminum genus.In this paper,the chemical constituents in the seeds of C.cyminum were further investigated,which enriched the amount of compounds in this herb,and provided a material basis for the further biological activity evaluation and quality standard improvement.