fitikimia

BAB II

Pembahasan

2.1 Stuktur Kimia

Flavonoid merupakan suatu senyawa-senyawa polifenol yang mempunyai 15 atom karbon, terdiri dari dua cincin benzena yang dihubungkan menjadi satu oleh rantai linier yang terdiri dari tiga atom karbon. Senyawa-senyawa flavonoid adalah senyawa 1,3 diaril propana, senyawa isoflavonoid adalah senyawa 1,2 diaril propana, sedangkan senyawa-senyawa neoflavonoid adalah 1,1 diaril propane.

Senyawa flavonoid sebenarnya terdapat pada semua bagian tumbuhan termasuk daun, akar, kayu, kulit, tepung sari, bunga, buah, dan biji. Kebanyakan flavonoid ini berada di dalam tumbuh-tumbuhan, kecuali alga. Namun ada juga flavonoid yng terdapat pada hewan, misalnya dalam kelenjar bau berang-berang dan sekresi lebah. Senyawa flavonoid adalah senyawa yang mengandung C15 terdiri atas dua inti fenolat yang dihubungkan dengan tiga satuan karbon. Struktur dasar flavonoid dapat digambarkan sebagai berikut :

Flavonoid mengandung sistem aromatik yang terkonjugasi sehingga menunjukkan pita serapan kuat pada daerah spektrum sinar ultraviolet dan spektrum sinar tampak, umumnya dalam tumbuhan terikat pada gula yang disebut dengan glikosida.

(Harborne, 1996)

Pada flavonoida O-glikosida, satu gugus hidroksil flavonoid (atau lebih) terikat pada satu gula (lebih) dengan ikatan yang tahan asam. Glukosa merupakan gula yang paling umum terlibat dan gula lain yang sering juga terdapat adalah galaktosa, ramnosa, silosa, arabinosa, dan rutinosa. Waktu yang diperlukan untuk memutuskan suatu gula dari suatu flavonoid O-glukosida dengan hidrolisis asam ditentukan oleh sifat gula tersebut. Pada flavonoid C-glikosida, gula terikat pada atom karbon flavonoid dan dalam hal ini gula tersebut terikat langsung pada inti benzena dengan suatu ikatan karbon-karbon yang tahan asam. Gula yang terikat pada atom C hanya ditemukan pada atom C nomor 6 dan 8 dalam inti flavonoid, misalnya pada orientin.

(Markham, 1988)

Menurut Robinson (1995), flavonoid dapat dikelompokkan berdasarkan keragaman pada rantai C3 yaitu:

1. Flavonol

Flavonol paling sering terdapat sebagai glikosida, biasanya 3-glikosida, dan aglikon flavonol yang umum yaitu kamferol, kuersetin, dan mirisetin yang berkhasiat sebagai antioksidan dan antiimflamasi. Flavonol lain yang terdapat di alam bebas kebanyakan merupakan variasi struktur sederhana dari flavonol. Larutan flavonol dalam suasana basa dioksidasi oleh udara tetapi tidak begitu cepat sehingga penggunaan basa pada pengerjaannya masih dapat dilakukan.

2. Flavon

Flavon berbeda dengan flavonol dimana pada flavon tidak terdapat gugusan 3-hidroksi. Hal ini mempunyai serapan UV-nya, gerakan kromatografi, serta reaksi warnanya. Flavon terdapat juga sebagai glikosidanya lebih sedikit daripada jenis glikosida pada flavonol. Flavon yang paling umum dijumpai adalah apigenin dan luteolin. Luteolin merupakan zat warna yang pertama kali dipakai di Eropa. Jenis yang paling umum adalah 7-glukosida dan terdapat juga flavon yang terikat pada gula melalui ikatan karbon-karbon. Contohnya luteolin 8-C-glikosida. Flavon dianggap sebagai induk dalam nomenklatur kelompok senyawa flavonoid.

3. Isoflavon

Isoflavon merupakan isomer flavon, tetapi jumlahnya sangat sedikit dan sebagai fitoaleksin yaitu senyawa pelindung yang terbentuk dalam tumbuhan sebagai pertahanan terhadap serangan penyakit. Isoflavon sukar dicirikan karena reaksinya tidak khas dengan pereaksi warna manapun. Beberapa isoflavon (misalnya daidzein) memberikan warna biru muda cemerlang dengan sinar UV bila diuapi amonia, tetapi kebanyakan yang lain tampak sebagai bercak lembayung yang pudar dengan amonia berubah menjadi coklat.

4. Flavanon

Flavanon terdistribusi luas di alam. Flavanon terdapat di dalam kayu, daun dan bunga. Flavanon glikosida merupakan konstituen utama dari tanaman genus prenus dan buah jeruk, dua glikosida yang paling lazim adalah neringenin dan hesperitin, terdapat dalam buah anggur dan jeruk.

5. Flavanonol

Senyawa ini berkhasiat sebagai antioksidan dan hanya terdapat sedikit sekali jika dibandingkan dengan flavonoid lain. Sebagian besar senyawa ini diabaikan karena konsentrasinya rendah dan tidak berwarna.

6. Katekin

Katekin terdapat pada seluruh dunia tumbuhan, terutama pada tumbuhan berkayu. Senyawa ini mudah diperoleh dalam jumlah besar dari ekstrak kental Uncaria gambir dan daun teh kering yang mengandung kira-kira 30% senyawa ini. Katekin berkhasiat sebagai antioksidan.

7. Leukoantosianidin

Leukoantosianidin merupakan senyawa tan warna, terutama terdapat pada tumbuhan berkayu. Senyawa ini jarang terdapat sebagai glikosida, contohnya melaksidin, apiferol.

8. Antosianin

Antosianin merupakan pewarna yang paling penting dan paling tersebar luas dalam tumbuhan. Pigmen yang berwarna kuat dan larut dalam air ini adalah penyebab hampir semua warna merah jambu, merah marak , ungu, dan biru dalam daun, bunga, dan buah pada tumbuhan tinggi. Secara kimia semua antosianin merupakan turunan suatu struktur aromatik tunggal yaitu sianidin, dan semuanya terbentuk

dari pigmen sianidin ini dengan penambahan atau pengurangan gugus hidroksil atau dengan metilasi atau glikosilasi.

9.Khalkon

Khalkon adalah pigmen fenol kuning yang berwarna coklat kuat dengan sinar UV bila dikromatografi kertas. Aglikon flavon dapat dibedakan dari glikosidanya, karena hanya pigmen dalam bentuk glikosida yang dapat bergerak pada kromatografi kertas dalam pengembang air. (Harborne, 1996)

10. Auron

Auron berupa pigmen kuning emas yang terdapat dalam bunga tertentu dan briofita. Dalam larutan basa senyawa ini berwarna merah ros dan tampak pada kromatografi kertas berupa bercak kuning, dengan sinar ultraviolet warna kuning kuat berubah menjadi merah jingga bila diberi uap amonia. (Robinson, 1995)

JanglotSaccopetalum horsfieldii Benn.

Nama umumIndonesia: Janglot

KlasifikasiKingdom: Plantae (Tumbuhan)Subkingdom: Tracheobionta (Tumbuhan berpembuluh)Super Divisi: Spermatophyta (Menghasilkan biji)Divisi: Magnoliophyta (Tumbuhan berbunga)Kelas: Magnoliopsida (berkeping dua / dikotil)Sub Kelas: MagnoliidaeOrdo: MagnolialesFamili: Annonaceae Genus: SaccopetalumSpesies: Saccopetalum horsfieldii Benn.

Biosintesis [sunting ]

Fenilalanin dikonversi ke 4 - coumaroyl - CoA dalam serangkaian langkah-langkah yang dikenal sebagai jalur fenilpropanoid umum menggunakan fenilalanin amonia - liase , sinamat - 4 - hidroksilase , dan 4 - coumaroyl - CoA - ligase . 4 - Coumaroyl - CoA ditambahkan ke tiga molekul malonil - CoA untuk membentuk tetrahydroxychalcone menggunakan 7,2 ' - dihidroksi- 4' - methoxyisoflavanol synthase . Tetrahydroxychalcone kemudian diubah menjadi naringenin chalcone isomerase menggunakan . Naringenin kemudian diubah menjadi eriodictyol menggunakan flavanoid 3' - hidroksilase . Eriodictyol kemudian diubah menjadi dihydroquercetin dengan flavanone 3 - hidroksilase , yang kemudian diubah menjadi quercetin menggunakan flavonol sintase . [ 14 ]

Quercetin rilis di jalur degradasi rutin [sunting ]

Enzim quercitrinase dapat ditemukan di Aspergillus flavus . [ 15 ] substrat Its quercitrin dan H2O dan rilis quercetin dan L - rhamnosa . Ini adalah enzim dalam jalur katabolik rutin [ 16 ]

Konjugasi [sunting ]

Quercetin 3 - O - sulfat adalah plasma quercetin metabolit manusia .

Glikosida [sunting ]

Quercetin adalah bentuk aglikon dari sejumlah flavonoid glikosida lainnya , seperti rutin dan quercitrin , ditemukan dalam buah jeruk , soba dan bawang . Quercetin membentuk glikosida quercitrin dan rutin bersama dengan rhamnose dan rutinose , masing-masing. Demikian juga guaijaverin adalah 3 - O - arabinoside , hyperoside adalah 3 - O - galactoside , isoquercitin adalah 3 - O - glukosida dan spiraeoside adalah 4' - O - glukosida . CTN - 986 merupakan turunan quercetin ditemukan di cottonseeds dan minyak biji kapas . Miquelianin adalah quercetin 3 - o - β - d - glucuronopyranoside . [ 17 ]

Studi metabolisme menggunakan Cunninghamella elegans [ sunting]

Cunninghamella elegans adalah model jamur metabolisme obat mamalia . Hal ini dapat digunakan untuk mempelajari biodegradasi quercetin . [ 18 ]

Efek dari konsumsi oleh manusia dan hewan lainnya [sunting ]

Quercetin sendiri ( aglikon quercetin ) , sebagai lawan kuersetin glikosida , bukan komponen diet normal. Dalam sebuah studi bioavailabilitas pada tikus , radiolabelled quercetin - 4' - glukosida dikonversi menjadi asam fenolik saat melewati saluran pencernaan , memproduksi senyawa tidak dimonitor dalam studi hewan sebelumnya aglikon kuersetin [ 19 ] Semua kecuali 4 % itu pulih dalam waktu 72 . jam ( 69 % dalam urin ) , menunjukkan retensi rendah dan ekskresi yang tinggi , karakteristik polifenol tertelan . Quercetin juga dapat menginduksi sekresi insulin oleh aktivasi L - jenis saluran kalsium dalam β - sel pankreas . [ 20 ] Quercetin belum dikonfirmasi secara ilmiah sebagai terapi spesifik untuk kondisi apapun atau disetujui oleh badan pengawas apapun. US Food and Drug Administration tidak menyetujui klaim kesehatan untuk quercetin . [ 21 ]

Quercetin / ̍ k w ɜr s ɨ t ɨ n / , flavonol, adalah flavonoid, dengan kata lain, pigmen tanaman dengan struktur

molekul seperti atau berasal dari flavon. [2] Hal ini ditemukan dalam buah-buahan, sayuran, daun dan biji-

bijian. Hal ini dapat digunakan sebagai bahan dalam suplemen, minuman, atau makanan.

Contents

[hide]

1 Occurrence

2 Metabolism

o 2.1 Biosynthesis

o 2.2 Quercetin release in the rutin degradation pathway

o 2.3 Conjugates

o 2.4 Glycosides

o 2.5 Study of metabolism using Cunninghamella elegans

3 Effects of consumption by humans and other animals

4 Preliminary research

o 4.1 Antiviral

o 4.2 Asthma

o 4.3 Cancer

o 4.4 Eczema

o 4.5 Inflammation

o 4.6 Fibromyalgia

o 4.7 Metabolic syndrome

o 4.8 Monoamine-oxidase inhibitor

o 4.9 Prostatitis

5 Drug interactions

6 See also

7 References

8 External links

Occurrence[edit]

Quercetin is a flavonoid widely distributed in nature. The name has been used since 1857, and is derived

from quercetum (oak forest), after Quercus.[3][4] It is a naturally occurring polar auxin transport inhibitor.[5]

Foods containing quercetin Quercetin (mg/100g of edible portion)

capers, raw 234[6]

capers, canned 173[6]

lovage 170[6]

dock like sorrel 86[6]

radish leaves 70[6]

carob fiber 58[6]

dill 55[7] (48-110)[8]

cilantro 53[6]

Hungarian wax pepper 51[6]

fennel leaves 48.8[6]

onion, red 32[9]

radicchio 31.5[6]

watercress 30[9]

buckwheat 23[10]


kale 23[9]

chokeberry 19[9]

cranberry 15[9]

lingonberry 13[9]

plums, black 12[9]

cow peas 11[9]

sweet potato 10[9]

blueberry, cultivated 8[9]

sea buckthorn berry 8[9]

rowanberry 7[9]

crowberry 5[9]

prickly pear cactus fruits 5[9]

apples, Red Delicious 4[9]

broccoli 3[9]


bilberry 3[9]

tea, black or green Camellia sinensis

2[9]

In red onions, higher concentrations of quercetin occur in the outermost rings and in the part closest to the root,

the latter being the part of the plant with the highest concentration.[11] One study found that organically

grown tomatoes had 79% more quercetin than chemically grown fruit.[12] Quercetin is present in various kinds

of honey from different plant sources.[13]

Metabolism[edit]

Biosynthesis[edit]

Phenylalanine is converted to 4-coumaroyl-CoA in a series of steps known as the

general phenylpropanoid pathway usingphenylalanine ammonia-lyase, cinnamate-4-hydroxylase, and 4-

coumaroyl-CoA-ligase. 4-Coumaroyl-CoA is added to three molecules of malonyl-CoA to

form tetrahydroxychalcone using 7,2’-dihydroxy-4’-methoxyisoflavanol synthase. Tetrahydroxychalcone is

then converted into naringenin using chalcone isomerase. Naringenin is then converted

intoeriodictyol using flavanoid 3’-hydroxylase. Eriodictyol is then converted

into dihydroquercetin with flavanone 3-hydroxylase, which is then converted into quercetin using flavonol

synthase.[14]

Quercetin release in the rutin degradation pathway[edit]

The enzyme quercitrinase can be found in Aspergillus flavus.[15] Its substrates are quercitrin and H2O and

releases quercetin and L-rhamnose. It is an enzyme in the rutin catabolic pathway[16]

Conjugates[edit]

Quercetin 3-O-sulfate is a human plasma quercetin metabolite.

Glycosides[edit]

Quercetin is the aglycone form of a number of other flavonoid glycosides, such as rutin and quercitrin, found

in citrus fruit,buckwheat and onions. Quercetin forms the glycosides quercitrin and rutin together

with rhamnose and rutinose, respectively. Likewise guaijaverin is the 3-O-arabinoside, hyperoside is the 3-O-

galactoside, isoquercitin is the 3-O-glucoside and spiraeoside is the 4'-O-glucoside. CTN-986 is a quercetin

derivative found in cottonseeds and cottonseed oil. Miquelianin is the quercetin 3-o-β-d-glucuronopyranoside.[17]

Study of metabolism using Cunninghamella elegans[edit]

Cunninghamella elegans is a fungal model of mammalian drug metabolism. It can be used to study the

quercetin biodegradation.[18]

Effects of consumption by humans and other animals[edit]

Efek dari konsumsi oleh manusia dan hewan lainnya [sunting]

Quercetin sendiri (aglikon quercetin), sebagai lawan kuersetin glikosida, bukan komponen diet normal. Dalam sebuah studi bioavailabilitas pada tikus, radiolabelled quercetin-4'-glukosida dikonversi menjadi asam fenolik saat melewati saluran pencernaan, memproduksi senyawa tidak dimonitor dalam studi hewan sebelumnya aglikon kuersetin [19] Semua kecuali 4% itu pulih dalam waktu 72. jam (69% dalam urin), menunjukkan retensi rendah dan ekskresi yang tinggi, karakteristik polifenol tertelan. Quercetin juga dapat menginduksi sekresi insulin oleh aktivasi L-jenis saluran kalsium dalam β-sel pankreas. [20] Quercetin belum dikonfirmasi secara ilmiah sebagai terapi spesifik untuk kondisi apapun atau disetujui oleh badan pengawas apapun. US

Food and Drug Administration tidak menyetujui klaim kesehatan untuk quercetin. [21]Preliminary research[edit]

Antiviral[edit]

Hyperoside (which is the 3-O-galactoside of quercetin) is a strong inhibitor of HBsAg and HBeAg secretion in

2.2.15 cells.[22]

Quercitrin and myricetin 3-O-beta-D-galactopyranoside inhibit HIV-1 reverse transcriptase, all with

IC50 values of 60 μM.[23]

Quercetin can also inhibit reverse transcriptase, part of the replication process of retroviruses.[24] The

therapeutic relevance of this inhibition has not been established.

Asthma[edit]

Quercetin is an effective bronchodilator and helps reduce the release of histamine and other allergic or

inflammatory chemicals in the body.[25]

Quercetin has demonstrated significant anti-inflammatory activity because of direct inhibition of several initial

processes of inflammation.[26]

Cancer[edit]

Laboratory studies have investigated Quercetin's potential for use in anti-cancer applications.[27] The American

Cancer Society says while quercetin "has been promoted as being effective against a wide variety of diseases,

including cancer," and "some early lab results appear promising, as of yet there is no reliable clinical evidence

that quercetin can prevent or treat cancer in humans." In the amounts consumed in a healthy diet, quercetin "is

unlikely to cause any major problems or benefits."[28]

Eczema[edit]

Serum IgE levels are highly elevated in eczema patients, and virtually all eczema patients are positive for

allergy testing. Excessive histamine release can be minimized by the use of antioxidants. Quercetin has been

shown to be effective in reducing IgE levels in rodent models.[29]

Inflammation[edit]

Several laboratory studies show quercetin may have anti-inflammatory properties,[30][31] and it is being

investigated for a wide range of potential health benefits.[31][32]

Quercetin has been reported to be of use in alleviating symptoms of pollinosis.[33] An enzymatically modified

derivative was found to alleviate ocular but not nasal symptoms of pollinosis.[34][35][36]

Studies done in test tubes have shown quercetin may prevent immune cells from releasing histamines which

might influence symptoms of allergies.[37][38]

A study with rats showed that quercetin effectively reduced immediate-release niacin (vitamin B3) flush, in

part by means of reducing prostaglandin D2 production.[39] A pilot clinical study of four humans gave

preliminary data supporting this.[40]

Quercetin may have properties of a calcineurin inhibitor, similar to cyclosporin A and tacrolimus, according to

one laboratory study.[41]

Fibromyalgia[edit]

Quercetin may be effective in the treatment of fibromyalgia because of its potential anti-inflammatory or mast

cell inhibitory properties shown in laboratory studies.[42]

Metabolic syndrome[edit]

Quercetin has been shown to increase energy expenditure in rats, but only for short periods (fewer than 8

weeks).[30]Effects of quercetin on exercise tolerance in mice have been associated with increased mitochondrial

biogenesis.[31] In mice, an oral quercetin dose of 12.5 to 25 mg/kg increased gene

expression of mitochondrial biomarkers and improved exercise endurance.[31]

It has also been claimed that quercetin reduces blood pressure in hypertensive[43] and obese subjects in

whom LDL cholesterol levels were also reduced.[44]

In vitro studies showed quercetin and resveratrol combined inhibited production of fat cells[45] and vascular

smooth muscle cell proliferation.[46]

Supplements of quercetin with vitamin C and niacin does not cause any significant difference in body mass or

composition[47] and has no significant effect on inflammatory markers, diagnostic blood chemistries, blood

pressure, and blood lipid profiles.[48]

Monoamine-oxidase inhibitor[edit]

Possibly an active component of heather (Calluna vulgaris), quercetin was suspected from a bioassay test on

crude extracts to selectively inhibit monoamine oxidase, possibly indicating pharmacological properties.[49]

Prostatitis[edit]

Quercetin has been found to provides significant symptomatic improvement in most men with

chronic prostatitis, a condition also known as male chronic pelvic pain syndrome.[50]

Drug interactions[edit]

Quercetin is contraindicated with some antibiotics; it may interact with fluoroquinolones (an antibiotic), as

quercetin competitively binds to bacterial DNA gyrase. Whether this inhibits or enhances the effect of

fluoroquinolones is not certain.[51]

AHFS Drug Information (2010)[52] identifies quercetin as an inhibitor of CYP2C8, and specifically names it as

a drug with potential to have harmful interactions with taxol/paclitaxel. As paclitaxel is metabolized primarily

by CYP2C8, its bioavailabilitymay be increased unpredictably, potentially leading to harmful side-effects.[53][54]

Quercetin is described as an inhibitor of CYP2C9.[55] Quercetin is an inhibitor[56] and inducer [57] of CYP3A4 (in

other words, it reduces the enzyme's activity in the short term, but the body responds by producing more of it).

CYP2C9 and CYP3A4 are members of the cytochrome P450 mixed-function oxidase system, and as such

are enzymes involved in the metabolism ofxenobiotics in the body. In either case, quercetin may alter serum

levels and, therefore, effects of drugs metabolized by these enzymes.

See also[edit]

Flavonol 3-sulfotransferase

Phenolic compounds in wine

Phytochemical

Quercetin 2,3-dioxygenase

Quercetin 3-O-methyltransferase

Quercetin-3-sulfate 3'-sulfotransferase

Quercetin-3-sulfate 4'-sulfotransferase

Quercetin-3,3'-bissulfate 7-

sulfotransferase

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External links[edit]

UMM Complementary and Alternative Medicine Guide:

Quercetin (University of Maryland Medical Center Website)

Russo, Maria; Spagnuolo, Carmela; Tedesco, Idolo; Bilotto, Stefania;

Russo, Gian Luigi (2012). "The flavonoid quercetin in disease prevention

and therapy: Facts and fancies". Biochemical Pharmacology 83 (1): 6–

15.doi:10.1016/j.bcp.2011.08.010. PMID 21856292.

Loke, Wai Mun; Hodgson, Jonathan M; Proudfoot, Julie M; McKinley,

Allan J; Puddey, Ian B; Croft, Kevin D (2008). "Pure dietary flavonoids

quercetin and (−)-epicatechin augment nitric oxide products and reduce

endothelin-1 acutely in healthy men". The American Journal of Clinical

Nutrition 88 (4): 1018–25. PMID 18842789.

Murota, Kaeko; Terao, Junji (2003). "Antioxidative flavonoid quercetin:

Implication of its intestinal absorption and metabolism". Archives of

Biochemistry and Biophysics 417 (1): 12–7. doi:10.1016/S0003-

9861(03)00284-4.PMID 12921774.

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