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The New Steroids from Silene montbretiana

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Presentation on theme: "The New Steroids from Silene montbretiana"— Presentation transcript:

1 The New Steroids from Silene montbretiana
Hilal KILINÇ 6th World Congress on Medicinal Chemistry and Drug Design 7-8th June 2017, Milano/Italy

2 NATURAL PRODUCTS Natural product chemistry is examining the chemical compounds and substances obtained by a living organism which found in the nature. Compounds that occur naturally in plants and animals. Natural products are unique to only one species or family or organisms.

3 Examples of Primary Metabolites
NATURAL PRODUCTS Primary metabolites are vital importance to life functions. They can be found in all plants. They are the subject of biochemistry. The plants synthesize sugars, fats and proteins. Examples of Primary Metabolites

4 They have been served as drugs, herbal medicine, making perfumes.
Secondary metabolites are humans life source and they are immensely various. Each plant family, genus and species produces a characteristic chemical class. They have been served as drugs, herbal medicine, making perfumes. Aspirin from the Salix spirea Morphine and codeine from the Papaver somniferum

5 Secondary metabolites subject of Natural Product Chemistry.
Natural Product Chemistry, including isolation, identification for chemical reactions and spectroscopic methods.

6 Natural products chemistry is at the intersection of many fields
Pharmaceutical sciences Taxonomy Biochemistry Natural Products Chemistry Entomology Biotechnology Chemical synthesis Molecular biology Microbiology

7 CLASSIFICATION OF SECONDARY METABOLITES
There are many different classifications and classified based on common biosynthetic pathways where a chemical is derived. Biosynthetic classification divides these compounds into three major groups; the phenolics, terpenoids and alkaloids. Each of the 3 major classes can be subdivided into subclasses.

8 BIOSYNTHETIC PATHWAY CO2+H2O Photosynthesis Primary metabolism
Secondary metabolism Terpenoids Phenolics Alkaloids Polyphenols Simple Phenols Flavonoids Tannins Coumarins Phenolic acids Isoflavones Flavonols Anthocyanins

9 PHENOLICS Plant substances, which posses an aromatic ring with one or more hydroxyl substituents, are classified as phenolic compounds. Major classes of phenolics are the simple phenols, the flavonoids, the phenylpropanoids, the phenolic quinones and phenolic polymers. Phenolic compounds are classified according to the number of carbon atoms in their skeletons.

10 Examples to Phenolics

11 FLAVONOIDS Flavonoids are the largest class of phenolic compounds.
The name of the flavone come from the root of the word flavone is flavus. It means a yellow in Latin. They are found in all organs of plants, in fruits, pollen, roots, bark, resins.

12 Examples to Flavonoids
The most widespread flavonoids are flavone and flavonols but isoflavones found in only a few plant families. Flavonoids generally consist of in plants as glycosides. The sugar free part of the glycoside is called aglycone. More than 80 different sugars have been found attached to flavonoids.

13 TERPENOIDS Terpenoids are the largest class of natural products.
They are classified according to the number of isoprene units in the molecule. Terpenes are usually found in every part of the higher plants like a flower, root and wood. Also algaes and lichens are included the terpenes. They are used cosmetics, detergents, soaps, vitamin supplements.

14 Examples to Terpenoids

15 STEROIDS They are subclass of triterpenoids.
These compounds possess significant biological activities. Plant sterols are frequently in the family of Caryophyllaceae and Cucurbitaceae.

16 Caryophyllaceae FAMILY
The Caryophyllaceae family is a large family which is species rich family of approximately 104 genera and more than species. In Turkey, there are 32 genus and 500 species. This family mainly temperate and warm- temperate region of Mediterranean with the centre of distribution is the, a part of Europe and Asia.

17 TRADITIONAL USE Silene vulgaris used in urinary infection, sedative, stomach ache, skin problem (juice) Silene flos-cuculi used in malaria and stomach ache (flower) Silene ciliata used in renal antiseptic (“for kidney”), administered internally as an herb-flavoured tea (aerial part) Silene gonosperma used in eye trouble, skin problem (whole plant) juice

18 Biological Properties
The leaf extracts of Silene armeria species showed high antifungal activity. Silene swertiifolia methanolic extracts possess a good antioxidant activity. Silene viridiflora showed antitumour activity. Whole plant extract of Silene multifida has antimicrobial activity.

19 In conclusion; Silene species are known to be a source of biological active compounds. Phytochemical analysis indicated that their richness in belonging to different structural types, such as phytoecdysteroids, terpenoids, flavonoids, N-containing compounds, sterols, vitamins. The most important compounds in Silene species are the phytoecdysteroids which is the same chemical structure to molting hormones of insects. Some species of this genus are used as ornamental plants and in traditional medicine to treat some of diseases.

20 Silene montbretiana BOISS
Silene montbretiana BOISS. was collected from Sivas, 2012, and identified by Assoc. Prof. Dr. Serdar G. ŞENOL. The voucher specimen has been deposited in Ege University Botanical Garden.

21 Distribution of the Taxon over Turkey
Adana, Kars, Erzincan, Erzurum, Gümüşhane, Muş, Sivas, Tunceli

22 Isolation procedure of Silene montbretiana
Powdered dry plant 670g n-hexane extract 2.67g Dichloromethane extract 4.5g Filtered plant Resolving in H2O Extraction with n-hexane (2.5L2) Extraction with dichloromethane (2.5L2) Extraction with methanol (2.5L2) A-H 8 main fraction RP-VLC 350g Methanol extract 51.4g n-BuOH phase 19.46g

23 A-H 8 main fraction Fr-A 2.77g Si-gel 150g Fr-3 35mg Fr-B 5.4g 500g
SM 1 Fr-B 5.4g 500g Fr-2 20mg 5mg SM 6 Fr-3 21 mg 6mg SM 7 20 mg 5.4mg SM9 Fr-D 634mg 70g Fr-2 53 mg 24mg SM 4 30mg SM 2 Fr-F 1.634g 160g Fr-2 30mg 1mg SM 23 Fr-G 2.164g 200g Fr mg 2mg SM 39 SM mg SM mg Fr-H 388mg 98mg Fr-5 SM 16

24 RESULTS SM 2 SM 1 6,8-dihydroxy-kaempherol-3-O-α-L-rhamnopyranoside
2β,3β,5β-14,20,22R,25-heptahydroxy-cholest-7-en-6-one. SM 4 (2β,3β,14α,20R,25-pentahydroxy-cholest-7-en-6-one)

25 2β,3β,14α-trihydroxy-5β-pregn-7-ene,6,20-dione SM 7
2β,3β,14α-trihydroxy-5β-androst-7-ene,6,17-dione SM 9 2β,3β,14,20,22R,25-hexahydroxy-cholest-7-en-6-one

26 SM 15 (1-O-β-D-glucopyranosyl-(2S,3R,4E,8E)-2-[(2'R)-2-hydroxyhexadecanoylamino]-4,8-octadecadiene-1,3-diol) SM 16 (3-O-β-D-glucopyranosyl,25-O-β-D-glucopyranosyl-3β,25-dihydroxycholest-7-en-6-one)

27 2β,3β,14α,20S,25-pentahydroxy-cholest-7-en-6-one
SM 23 (2-O-β-D-glucopyranosyl-3β,14,20,22R,25-hexahydroxy-cholest-7-en-6-one) SM 39 2β,3β,14α,20S,25-pentahydroxy-cholest-7-en-6-one

28 1H-NMR spectrum of SM 2 (600 MHz, CD3OD)

29 HSQC spectrum of SM 2

30 HMBC spectrum of SM 2

31 1H-NMR spectrum of SM 4 (600 MHz, CD3OD)

32 HSQC spectrum of SM 4 H-7 V C-7 H-2 H-3 H-5 H-17 C-5 C-17 C-3 C-2 C-18

33 HMBC spectrum of SM 4 H-19 H-18 H-21 H-26 H-27 C-12 C-13 C-17 C-25

34 1H-NMR spectrum of SM 16 (600 MHz, CD3OD)

35 HSQC spectrum of SM 16 H-1' H-1'' C-1'' C-1' H-3 C-3 H-7 C-7 H-21 H-18

36 HMBC spectrum of SM 16 H-1'' H-1' H-21 C-3 C-25 C-25 H-19 H-26 H-27

37 COSY spectrum of SM 16

38 In conclusion; Their structures were established by the extensive use of 1D- and 2D-NMR experiments along with ESI-MS analyses. Two new steroid-type together with six known steroid-type, one flavonoid and one cerebroside compounds, in total ten compounds were isolated from Silene montbretiana.

39 This study was granted by
TÜBİTAK (Project #: 114Z226) Ege University Research Foundation (Project #: 2012 FEN 047) Also thanks again to TÜBİTAK 2214/A International Doctoral Research Fellowship Programme (Application #: 1059B )

40 THANK YOU FOR YOUR ATTENTION

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45 Subkingdom Tracheobionta Division Magnoliophyta Class Magnoliopsida
Family : Caryophyllaceae Genus Silene L. Taxon Silene montbretiana BOISS.  Kingdom Plantae  Subkingdom Tracheobionta  Division Magnoliophyta  Class Magnoliopsida  Subclass Caryophyllidae  Order Caryophyllales  Family Caryophyllaceae  Genus Silene  Species Silene montbretiana BOISS.

46 1H-NMR spectrum of SM 1 (600 MHz, CD3OD)

47 HSQC spectrum of SM 1 HSQC spectrum of SM 1 H-7 H-17 C-22 H-22 H-9

48 HMBC spectrum of SM 1 H-9 C-8 H-19 H-18 C-13 C-14 H-26 H-27 C-10 C-25

49 1H-NMR spectrum of SM 6 (600 MHz, CD3OD)

50 HSQC spectrum of SM 6 H-18 H-19 H-21 H-7 C-7 H-5 H-2 H-3 C-19 C-21 C-2

51 HMBC spectrum of SM 6 H-21 H-19 H-18 H-5 C-12 C-10 C-13 C-17 C-14 C-6

52 1H-NMR spectrum of SM 7 (600 MHz, CD3OD)

53 HSQC spectrum of SM 7 H-19 H-5 H-18 H-7 C-3 C-2 C-7 H-2 H-3 C-18 C-19

54 HMBC spectrum of SM 7 H-19 C-10 H-18 C-13 C-17 C-14 H-5 C-6

55 1H-NMR spectrum of SM 9 (600 MHz, CD3OD)

56 HSQC spectrum of SM 9

57 HMBC spectrum of SM 9

58 1H-NMR spectrum of SM 15 (600 MHz, CD3OD)

59 HSQC spectrum of SM 15

60 HMBC spectrum of SM 15

61 1H-NMR spectrum of SM 23 (600 MHz, CD3OD)

62 HSQC spectrum of SM 23

63 HMBC spectrum of SM 23

64 1H-NMR spectrum of SM 39 (600 MHz, CD3OD)

65 HSQC spectrum of SM 39

66 HMBC spectrum of SM 39

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